Fortschritte der Chemie organischer Naturstoffe

Author(s)

• Zechmeister, L. (László)
• Herz, W.
• Achenbach, H.

Bibliographic Information

Fortschritte der Chemie organischer Naturstoffe

herausgegeben von L. Zechmeister ... [et al.]

Springer, 1938-

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Other Title

Progress in the chemistry of organic natural products

Progrès dans la chimie des substances organiques naturelles

Note

42:Authors, Y. Asakawa, M. Heidelberger

43:Authors, J. L. Ingham, A. Koskinen, M. Lounasmaa

52: Authors, H. Achenbach ... [et al.]

57: Authors, E. Casadevall ... [et al.]

59: Authors, A.-M. Eklund, S.-I. Hatanaka, I. Wahlberg

61: Authors, D.G.I. Kingston ... [et al.]

65: Author, Y. Asakawa

86: Author, A. Gossauer

87: Authors, H. Budzikiewicz ... [et al.]

88: Authors, J.F. Grove, E. Reimann, S. Roy

89: Authors, B. Kräutler ... [et al.]

90: The epothilones : an outstanding family of anti-tumor agents : from soil to the clinic / Authors, K.-H. Altmann ... [et al.]

91: Naturally occurring organohalogen compounds : a comprehensive update / Author: G. W. Gribble

92: Authors, H. Budzikiewicz ... [et al.]

93: Authors, S.A. Begum ... [et al.]

子書誌あり

Description and Table of Contents

Volume

87 ISBN 9783211027806

Table of Contents

Cephalostatin Analogues - Synthesis and Biological Activity (Timo Flessner/Rolf Jautelat/Ulrich Scholz/Ekkehard Winterfeldt) Introduction * Synthesis of Bissteroidal Pyrazines * A-D-Ring Functionalization * The Spiroketal Area of Cephalostatins, Summary * Acknowledgements * References Siderophores of the Pseudomonadaceae sensu stricto (Fluorescent and Non-Fluorescent Pseudomonas spp.) (Herbert Budzikiewicz) Introduction * The Typical Siderophores of the Fluorescent Pseudomonads - the Pyoverdins * Other Siderophores of Fluorescent Pseudomonads * Iron Sequestering * Pseudomonas and Health * Pseudomonas and Agriculture * Pseudomonas and Environmental Problems * Acknowledgements * Abbreviations * Appendices: Bacterial Species, Bacterial Culture Collections * References: Books, Chapters and Review Articles, Original Publications Author Index Subject Index

Volume

88 ISBN 9783211206881

Description

The volumes contain contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a recognized authority in his field and provides a comprehensive and up-to-date review of the topic in question.

Table of Contents

Synthesis Pathways to Erythrina Alkaloids and Erythrina Type Compounds.- The Trichothecenes and Their Biosynthesis.- Melanin, Melanogenesis, and Vitiligo.

Volume

89 ISBN 9783211740187

Description

The volumes of this classic series have appeared under the Springer Imprint ever since the series' inauguration in 1938. The volumes contain contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a recognized authority to provide an up-to-date review of the topic in question.

Table of Contents

Chlorophyll Catabolites.- Steroidal Saponins.

Volume

28 : Wien ISBN 9783211809754

Description

The cyanogenic glycosides, here defined as glycosidic derivatives of iX-hydroxynitriles, represent a rather limited class of natural products, which are widely distributed in the plant kingdom and, to a small ex- tent, even in animals. A characteristic feature of these glycosides is their ability to release hydrocyanic acid on treatment with dilute acids or appropriate enzymes. The term "cyanogenic" is used to designate this property, regardless of whether pure substances, plants, or animals, are serving as the source. In the latter cases the term "cyanophoric" is occasionally employed synonymously. Cyanogenesis in plants was probably first discovered by SCHRADER in 1803 (Io3) working with bitter almonds. In 1830, ROBIQUET and BOUTRON-CHARLARD (IOO) succeeded in isolating the parent glycoside, namely amygdalin. Over the years, a total of 18 cyanogenic glycosides have been isolated and characterized more or less completely (Table I, p. 76). It will be noted that the majority of these compounds has been isolated in the era of classical organic chemistry and that progress in .discovering new compounds, not to mention new structural types, has been surprisingly slow. It is worth remembering here that the mechanism *of cyanogenesis has been established only in the minority of known cyanogenic species. The cyanogenic glycosides have last been reviewed in 1958 by DILLE- MANN (36). Since then, no complete reviews in this field have appeared. It is the purpose of the present article to survey the more recent ad- vances and, hopefully, to stimulate continued interest in these interesting .compounds.

Table of Contents

Structural and Biogenetic Relationships of Isoflavonoids.- I. Introduction.- II. Isoflavones.- 1. Simple Isoflavones.- 2. Complex Isoflavones.- 3. Isoflavone Glycosides.- 4. Synthesis of Isoflavones.- III. Isoflavanones.- IV. Rotenoids.- V. Pterocarpans.- 1. Natural Pterocarpans.- 2. Stereochemistry of Pterocarpans.- 3. Reactions and Synthesis of Pterocarpans.- VI. Isoflavans.- VII. 3-Aryl-4-hydroxycoumarins.- 1. Structure Elucidation.- 2. Synthesis of 3-Aryl-4-hydroxycoumarins.- VIII. Coumestans.- 1. Natural Coumestans.- 2. Structure Elucidation and Synthesis.- IX. Other Types of Isoflavonoids.- X. Biogenesis of Isoflavonoids.- 1. 1,2-Aryl Migration as a Common Feature.- 2. Branching Point from the Flavonoid Pathway.- 3. Nature of the Primary Isoflavonoid Product.- 4. Biogenetic Relationships among the Isoflavonoid Classes.- a) Direct Experimental Evidence.- b) Co-occurrence of Classes of Isoflavonoids.- c) Isoflavanones - Dehydropterocarpans - Pterocarpans - Isoflavans - Coumestans.- d) Isoflavones - 2-Hydroxyisoflavones - 3-Aryl-4-hydroxycoumarins.- e) Isoflavones - Rotenoids - Coumaronochromones.- f) Summary of Biogenetic Interrelationships.- References.- Recent Advances in the Chemistry of Cyanogenic Glycosides.- I. Introduction.- II. General Chemical Considerations.- Structural Relationships.- Chemical Properties.- Enzymic Degradation.- III. Detection.- Detection in Fresh Plant Specimens.- Detection on Chromatograms.- IV. Isolation.- Column Chromatography.- Preparative Paper Chromatography.- Preparative Thin Layer Chromatography.- Gas Liquid Chromatography.- V. Structure Elucidation.- Gynocardin.- Triglochinin.- Dhurrin and Taxiphyllin.- Linamarin.- Lotaustralin.- Proteacin.- Nandinaglucoside.- VI. Synthesis.- VII. Distribution.- Cyanogenesis in Higher Plants.- Cyanogenesis in Bacteria.- Cyanogenesis in Fungi.- Cyanogenesis in Animals.- VIII. Biosynthesis.- IX. Metabolic Aspects.- The Fate of Cyanogenic Glycosides in Living Organisms.- Cyanide Metabolism.- References.- Naturstoffe mit Pyridinstruktur und ihre Biosynthese.- Einfuhrung.- I. Naturlich vorkommende Pyridinverbindungen.- 1. Carbonsauren und einfache Pyridinderivate.- 2. Alkaloide.- a) Nicotin und verwandte Alkaloide.- b) Pyridonalkaloide.- c) Terpenoide Alkaloide.- d) Verschiedenartige Pyridinalkaloide.- 3. Aminosauren mit Pyridinstruktur.- 4. Mikrobielle Stoffwechselprodukte.- II. Biosynthese des Pyridinringes.- 1. Entstehung der Nicotinsaure.- a) Oxydativer Tryptophanabbau.- b) C3- + C4-Kondensation.- c) Pyridinnucleotid-Cyclus.- 2. Biosynthese von Fusarinsaure und 2,6-Dipicolinsaure.- 3. Lysin als Pyridinvorstufe.- a) Biosynthese von Mimosin sowie Desmosin und Isodesmosin.- b) In vitro-Biosynthese von Anabasin.- 4. Entstehung des Pyridinringes auf dem Monoterpenweg.- 5. Biosynthese der Piericidine A und B.- III. Hypothesen zur Biogenese weiterer Pyridinverbindungen.- Schlussbetrachtung.- Peptide Alkaloids.- I. Introduction.- II. General Properties of Peptide Alkaloids.- III. General Methods and Techniques of Structural Determination.- IV. Structure and Properties of Peptide Alkaloids.- 1. Pandamine.- 2. Zizyphine.- 3. Ceanothine-B.- 4. Scutianine.- 5. Integerrine.- 6. Lunarine.- 7. Homaline.- 8. Adouetine-X.- 9. Americine.- 10. Aralionine.- 11. Ceanothine-A.- 12. Franganine, Frangufoline, and Frangulanine.- 13. Hymenocardine.- 14. Integerrenine and Integerressine.- 15. LBX and LBZ.- 16. Lasiodine-A.- V. Ultraviolet Spectra of Peptide Alkaloids.- VI. NMR Spectra of Peptide Alkaloids.- VII. Mass Spectra of Aryloxy Macrocyclic Peptide Alkaloids.- VIII. Pharmacological Properties of Peptide Alkaloids.- IX. Tables.- 1. Basicity of Peptide Alkaloids.- 2. Peptide Alkaloids.- 3. Sources of Peptide Alkaloids.- References.- Insektensexuallockstoffe.- I. Einleitung.- II. Insektensexuallockstoffe.- a) Olefinische Verbindungen.- b) Aliphatische Verbindungen.- c) Terpenartige Verbindungen.- d) Heterocyclische Verbindungen.- III. Weitere Pheromone.- IV. Insektenhormone.- a) Juvenilhormon (JH).- b) Hautungshormon (MH = moulting-Hormon).- c) Sterilisantien (Juvenilhormonartige Substanzen).- d) Synthetische Produkte.- Arthropod Molting Hormones.- I. Introduction.- II. Hormonal Regulation of Growth of Insects and Crustaceans.- III. Occurrence in Animals.- IV. Occurrence in Plants.- V. Isolation and Assay.- VI. Structure Determination and Chemistry.- 1. ?-Ecdysone (Ecdysone).- 2. ?-Ecdysone (Crustecdysone, 20-Hydroxyecdysone, Ecdysterone).- 3. Tobacco Hornworm Ecdysone III (20,26-Dihydroxyecdysone).- 4. Deoxycrustecdysone.- 5. Ponasterone A.- 6. Ponasterone B.- 7. Ponasterone C.- 8. Inokosterone.- 9. Cyasterone, Isocyasterone, Sengosterone and Capitasterone.- 10. Polypodine B.- 11. Rubrosterone.- 12. Ponasteroside A.- 13. Shidasterone.- 14. Ajugasterone C.- 15. Pterosterone, Makisterone A, Makisterone B, Lemmasterone (Makisterone C, Podecdysone A), Amarasterone A, Makisterone D and Amarasterone B.- 16. Viticosterone E, Stachysterone C, Stachysterone A, Stachysterone B, Podecdysone B and Stachysterone D.- 17. Ajugasterone B.- VII. Synthesis.- 1. ?-Ecdysone.- 2. ?-Ecdysone and Ponasterone A.- 3. Rubrosterone.- 4. Miscellaneous.- VIII. Biosynthesis and Catabolism.- IX. Tables.- 1. Animals Known to Contain Ecdysterols.- 2. Plant Families Containing Ecdysterols.- 3. Plants Known to Contain Ecdysterols.- 4. Properties of Ecdysterols.- 5. NMR Data of some Ecdysterols.- 6. ORD and CD Data of Ecdysterols.- References.- Total Synthesis of Prostaglandins.- I. Introduction.- II. Structure and Chemical Transformations of the Prostaglandins.- III. General Approaches to Prostaglandin Synthesis.- A. Initial Corey Synthesis of dl-PGE1.- B. Corey's Second Synthesis of dl-PGE1.- C. A Stereocontrolled Synthesis of Prostaglandins E2 and F2? (Corey).- D. Bicyclohexane Route to Prostaglandins.- E. Non-Enzymic Cyclization of Fatty Acids.- IV. Synthetic Routes to Structurally Simplified Prostaglandins.- A. Synthesis of dl-13,14-Dihydro-PGE1, Ethyl Ester.- B. Synthesis of dl-15-Dehydro-PGE1.- C. Synthesis of dl-PGB1.- V. Synthetic Routes to Prostaglandin Analogs.- A. 11-Deoxy-Prostaglandins.- B. 7-Oxa-Prostaglandins.- VI. Miscellaneous Synthetic Approaches.- VII. Resolution of Racemic Prostaglandins.- References.- Chemistry of Cephalosporin Antibiotics.- I. Introduction.- II. Isolation and Structure of Cephalosporin Antibiotics.- A. Historical.- B. Cephalosporin P.- C. Cephalosporin N (Penicillin N).- D. Cephalosporin C.- III. Chemical Transformations of Cephalosporin C.- A. Nomenclature.- B. Sidechain Amido Functions.- 1. Reactions of the 7,? Aminoadipamoyl Group.- 2. Reactions of the 7-Amino Group.- C. Reactions of the ?-Lactam Ring System.- D. Reactions of the Dihydrothiazine Ring System.- 1. Reactions of the Double Bond.- a) Formation of ?2-Isomers.- b) Other Reactions of the Double Bond.- 2. Reactions of the C-3 Substituents.- a) Formation of Desacetyl Derivatives.- b) Nucleophilic Displacement of the Acetate.- c) Hydrogenolysis of the Acetate.- 3. Reactions of the Carboxyl Group.- 4. Formation of Sulfoxides.- E. Conformation of Cephalosporanates.- IV. Physicochemical Properties of Cephalosporanates.- V. Syntheses of Cephalosporins.- A. Total Synthesis.- B. Partial Synthesis.- VI. Biosynthesis.- VII. Biological Activity of Cephalosporanates.- References.- Oligosaccharide der Frauenmilch.- I. Einleitung.- II. Isolierung und Analyse der Oligosaccharide.- 1. Isolierung.- 2. Analytische Methoden.- III. Beschreibung der Zucker.- IV. Vergleich der freien Kohlenhydrate der Milch und des Urins mit den konjugierten Oligosacchariden der Glykosphingolipide.- V. Biosynthese und Blutgruppenmerkmale.- Glucagon: Chemistry and Action.- I. Introduction.- II. Assay.- 1. Physicochemical Methods.- 2. Bioassay.- a) Measurement of the Hyperglycemic Action of Glucagon.- b) Measurement of the Glycogenolytic Effect of Glucagon.- 3. Radioimmune Assays.- III. Chemical Aspects.- 1. Isolation, Properties, and Primary Structure.- 2. Synthesis.- 3. Conformation.- 4. Relationships of Structure and Function.- IV. Site of Formation and Release.- 1. Pancreas.- 2. Intestine.- 3. Release.- V. Glucagon in Blood.- 1. Concentration.- 2. Catabolism.- VI. Glucagon Action.- 1. On Adenyl Cyclase.- 2. In Pancreatic ?-cells.- 3. In Liver.- 4. In Adipose Tissue.- 5. In Heart.- 6. In the Gastrointestinal System.- 7. On Plasma Electrolytes and Renal Function.- VII. Physiologic Role.- References.- Namenverzeichnis. Author Index.- Sachverzeichnis. Subject Index.

Volume

29 : Wien ISBN 9783211810248

Description

Eine grosse Anzahl heterocyclischer Naturstoffe leitet sich vom Ring- system des Piperidins (1) ab. Als Substituenten einfach oder mehrfach substituierter Piperidinbasen finden sich Methyl-, Carboxyl-, Hydroxyl- und Aminogruppen sowie aliphatische Seitenketten unterschiedlicher Lange. Die Substitution erfolgt bevorzugt an den C-Atomen 2, 3 und 6 sowie am Heteroatom. In zahlreichen Fallen ist der Piperidinring in a- oder ss-Stellung direkt oder uber eine C-Brucke mit einem weiteren Heterocyclus verbunden, z. B. einem Piperidin-, Piperidein-, Pyridin-, Indol-, Chinolizidin- oder Furanrest. Daruber hinaus kann der Piperidin- ring zum 2,6-Dioxopiperidin (Glutarimid) oxydiert oder zum Pipendein dehydriert sein. Wahrend Naturstoffe mit Pyridinstruktur im Tier- und Pflanzenreich weit verbreitet sind und einzelnen von ihnen wie NAD oder Pyridoxal- phosphat als Coenzymen des Primarstoffwechsels besondere Bedeutung zukommt, handelt es sich bei den naturlichen Piperidinverbindungen im allgemeinen um sekundare Pflanzenstoffe (vgl. I8, I9I). Dabei sind einige wie z. B. die Pipecolinsaure (7) sporadisch auf verschiedene Pflanzen- familien verteilt. Andere Piperidinbasen wie die Conium- oder Piper- Alkaloide weisen dagegen eine ausgesprochene Artspezifitat auf. Im Gegensatz zu den meisten Pyridinalkaloiden finden sich die Piperidin- basen oft mit strukturell andersartig gebauten Alkaloiden vom Chino- lizidin- oder Trepantyp vergesellschaftet, was in den meisten Fallen durch eine enge biogenetische Verwandtschaft bedingt sein durfte.

Table of Contents

/ Contents.- Vorkommen, Struktur und Biosynthese naturlicher Piperidinverbindungen.- Gallenfarbstoffe und Biliproteide.- The Chemistry of Glutarimide Antibiotics.- Chemie und Biosynthese der Flechtenstoffe.- The Cucurbitanes, a Group of Tetracyclic Triterpenes.- Biogenetic-type Synthesis of Terpenoid Systems.- The Biosynthesis of the Diterpenes.- Chemistry of Natural Products Derived from Marine Sources.- Namenverzeichnis. Author Index.- Sachverzeichnis. Subject Index.

Volume

30 : Wien ISBN 9783211810620

Table of Contents

Bioluminescence: Chemical Aspects.- I. Introduction.- II. Renilla (Sea Pansy) Bioluminescence.- 1. General Comments.- 2. Chemical Requirements for Light Emission.- 3. Mechanism of the Light Reaction.- 4. Related Bioluminescent Systems.- III. Firefly Bioluminescence.- 1. General Comments.- 2. Chemical Requirements for Light Emission.- 3. Mechanism of the Light Reaction.- IV. Cypridina Bioluminescence.- 1. General Comments.- 2. Chemical Requirements for Light Emission.- 3. Mechanism of the Luminescent Reaction.- 4. Related Bioluminescent Systems.- V. Bacterial Bioluminescence.- 1. General Comments.- 2. Chemical Requirements for the Light Reaction.- 3. Mechanism of the Light Reaction.- VI. Latia Bioluminescence.- 1. General Comments.- 2. Chemical Requirements for Light Emission.- 3. Mechanism of the Light Reaction.- VII. Earthworm Bioluminescence.- 1. General Comments.- 2. Chemical Requirements for Light Emission.- VIII. Comments on General Mechanisms Involved in Bioluminescence.- References.- Gametenlockstoffe bei niederen Pflanzen und Tieren.- I. Einleitung.- II. Verbreitung der Gameten-Lockstoffe.- III. Spezifitat chemotaktisch wirksamer Substanzen.- IV. Topo- und phobotaktische Reaktion.- V. Sirenin.- a) Vorkommen, Funktion und Bestimmung.- b) Isolierung.- c) Strukturaufklarung.- d) Biosynthese.- e) Total-Synthesen von Sirenin.- VI. Ectocarpen.- a) Vorkommen und Wirkung.- b) Gewinnung und Nachweis.- c) Strukturbeweis.- d) Synthese.- e) Biosynthese.- VII. Dictyopteren und andere Inhaltsstoffe von Dictyopteris.- VIII. Einige weitere Falle von Gameten-Chemotaxis.- a) Fucus.- b) Chlamydomonas.- c) Sphaerocarpos.- d) Campanularia calceolifera.- IX. Betrachtungen zum Wirkungsmechanismus der Gametenlockstoffe.- Quassinoid Bitter Principles.- I. Introduction.- II. Quassinoid General Features.- 1. Chemical Properties.- 2. Spectral Properties.- III. Structure Determination of Quassinoids.- 1. Quassin and Neoquassin.- 2. Nigakilactones A, B, C, E, F, H, Simalikalactone C, Picrasin D, E and F, and Nigakihemiacetals A and C.- 3. Amarolide, 11-Acetylamarolide,Chaparrolide,Castelanolide, Klaineanone, 11- Dehydroklaineanone, 15-Hydroxyklaineanone, Picrasin B, and 6-Hydroxy-picrasin B, Picrasin C.- 4. Glaucarubin, Glaucarubinone, Glaucarubol, Glaucarubolone, 15-Isovaleryl-glaucarubol, 15-Acetoxyglaucarubolone (Holocanthone), ?-Methyl-?-acetoxy-butyric Ester of Glaucarubolone, Ailanthinone.- 5. Chaparrin, Chaparrinone, and Ailanthone.- 6. Bruceins A-G, Brusatol, and Simalikalactone D.- 7. Samaderins B, C and D, 3,4-Dihydrosamaderin B, Cedronin, Cedronolin, and Eurycomalactone.- 8. Simarolide and Picrasin A ( = Nigakilactone G).- IV. The Biogenetic Isoprene Rule and the Biosynthesis of the Quassinoids.- V. Tetracyclic Triterpenes from Simaroubaceae.- VI. Physiological Activity.- VII. Tables.- 1. Quassinoids of Type A.- 2. Quassinoids of Type B.- 3. Quassinoids of Type C.- References.- Die Ergochrome (Physiologie, Isolierung, Struktur und Biosynthese).- I. Einleitung.- II. Allgemeine Informationen uber Ergochrome.- 1. Strukturvariation und Nomenklatur der Ergochrysine A und B.- 2. Isolierung und Trennung der Ergochrome.- a) Aus Mutterkorn.- b) Aus Flechten.- c) Aus Schimmelpilzen.- d) Ubersicht uber das Vorkommen der Ergochrome.- e) Trennungsmethoden.- 3. Biologische Aktivitat der Ergochrome.- III. Struktur und Konfiguration der Ergochrome.- 1. Methoden zur Strukturbestimmung.- a) Das aromatische Grundgerust.- b) Struktur von Ring C.- c) Verknupfung der Molekulhalften.- 2. Methoden zur Konfigurationsbestimmung und Struktur der Secalonsauren A, B und D sowie des Ergoflavins.- a) Konfiguration der C-Methylgruppe an C-6.- b) Konfiguration der sekundaren Hydroxygruppe an C-5.- c) Konfiguration am Ringverknupfungszentrum C-10.- 3. Struktur der Secalonsaure C sowie der Ergochrysine A und B.- 4. Strukturen der Ergochrome AD, BD, CD und DD.- 5. Struktur des Ergoxanthins.- IV. Biosynthese der Ergochrome.- 1. Hypothesen.- 2. Futterungsversuche.- 3. Modellreaktionen.- The Chemistry of Biflavanoid Compounds.- I. Introduction.- II. Nomenclature for Biflavanoids.- III. Chemistry of Biflavones of the Amentoflavone (1) Family-Structures of Ginkgetin (13), Isoginkgetin (23), and Sciadopitysin (14).- IV. Biflavones of the Hinokiflavone (2) Family.- V. Biflavones of the Cupressuflavone (3) Family.- VI. Biflavones of the Agathisflavone (4) Family.- VII. Methods for the Location of O-Methyl Groups in Biflavones.- VIII. Chiral Properties of Biflavones.- IX. Reduced Forms of Amentoflavone and Hinokiflavone.- X. The C-3/C-8 Biflavanones.- XI Flavanone-flavones Possessing a C-3/C-8 Interflavanoid Linkage.- XII. Natural Glycosides of Biflavanoids.- XIII. Synthesis of Biflavanoids.- 1. Ullmann Coupling of Flavones.- 2. Ullmann Synthesis of Biflavones via Biphenyl Precursors.- 3. Wesseley-Moser Rearrangements.- 4. Partial Demethylation and Methylation of Natural and Synthetic Biflavones.- 5. Phenol Oxidative Coupling of Flavones as a Route to Biflavones.- XIV. Pharmacology.- XV. Tables.- 1. Biflavones of the Amentoflavone Series.- 2. Biflavones of the Hinokiflavone Series.- 3. Biflavones of the Cupressuflavone Series.- 4. Biflavones of the Agathisflavone Series.- 5. Natural Distribution of Biflavanoids.- 6. 1H NMR Spectral Data for Biflavanones (9)-(12).- 7. Optical Rotatory Dispersion Data for Biflavanones (9)-(12).- References.- Addendum.- Chemie der Makrolid-Antibiotica.- I. Einleitung.- II. Antibakterielle Makrolid-Glykoside aus Actinomyceten.- 1. Die Erythromycin-Gruppe.- a) Die Konstitution des Erythromycins.- b) Konfiguration und Konformation des Erythromycins.- c) Weitere Antibiotica der Erythromycin-Gruppe.- 2. Die Carbomycin-Gruppe.- a) Carbomycine, Leucomycine und Spiramycine.- b) Weitere Antibiotica der Carbomycingruppe.- III. Polyen-Makrolide.- 1. Allgemeines.- 2. Konstitutionsaufklarung von Polyen-Makroliden.- a) Die Konstitution des Lucensomycins.- b) Weitere Polyen-Makrolide mit bekannter Struktur.- IV. Primycin, Borrelidin, die Venturicidine und das Chlorothricin.- a) Primycin.- b) Borrelidin.- c) Die Konstitutionsaufklarung der Venturicidine.- d) Chlorothricin.- V. Makrolide aus Pilzen.- 1. Zearalenon.- 2. Weitere Makrolide aus Pilzen.- VI. Die Zuckerbausteine der Makrolide.- 1. Die Aminozucker der Erythromycin- und Carbomycin-Gruppe.- a) Die Struktur der Mycaminose.- b) Weitere Aminozucker aus antibakteriellen Makrolid-Glykosiden.- 2. Mycosamin und Perosamin.- 3. Lankavose (Chalcose).- 4. Die verzweigten Zucker aus Makroliden.- 5. Weitere Zucker aus Makroliden.- VII. Schlussbemerkungen.- Chemie und Biologie der Saponine.- I. Einleitung.- II. Die Reindarstellung und Strukturermittlung der Saponine.- 1. Isolierung und Reindarstellung.- a) Allgemeines.- b) Die Gewinnung des Rohsaponins.- c) Auftrennung von Saponingemischen.- 2. Strukturermittlung.- a) Allgemeines.- b) Vollstandige Hydrolyse.- ?) Aglykone.- ?) Zucker.- ?) Sauren.- c) Methylierung.- d) Partialhydrolysen.- e) Konfiguration der glykosidischen Bindung.- III. Die Struktur der neutralen Steroidsaponine.- 1. Allgemeine Bemerkungen.- 2. Tabellen der neutralen Steroidsapogenine.- 3. Furostanolglykoside.- 4. Nuatigeninglykoside.- 5. Spirostanolglykoside.- a) Allgemeines.- b) Glykoside mit Zuckern am OH an C-3 des Aglykons.- c) Glykoside mit einem Zuckeranteil, der nicht an das OH am C-3 des Aglykons gebunden ist.- d) Glykoside mit mehr als einer Zuckerkette am Spirostanol-Aglykon.- 6. Polypodosaponin-Typ.- IV. Die Struktur der Triterpensaponine.- 1. Allgemeines.- 2. Tabellen der Triterpenaglykone.- 3. Neutrale, monodesmosidische Glykoside.- 4. Estersaponine.- 5. Durch Uronsaure saure Monodesmoside.- 6. Durch das Aglykon saure Monodesmoside.- 7. Neutrale Bisdesmoside.- 8. Monodesmosidische Acylglykosen.- 9. Durch Aglykon und Zuckeranteil saure Monodesmoside.- 10. Saure Bisdesmoside.- 11. Tierische Saponine.- V. Biosynthese der Saponine.- 1. Die Biogenese der Steroidsapogenine.- 2. Die Biogenese der pentacyclischen Triterpensapogenine.- VI. Eigenschaften der Saponine.- 1. Allgemeines.- 2. Hamolyse und Saponinbegriff.- 3. Die antibiotische Wirksamkeit.- 4. Wirksamkeit gegen Insekten.- 5. Toxizitat der Saponine.- 6. Pharmakologie der Saponine.- 7. Quantitative Bestimmung der Saponine.- Namenverzeichnis. Author Index.- Sachverzeichnis. Subject Index.

Volume

31 : Wien ISBN 9783211811726

Description

Mit Beitragen zahlreicher Fachwissenschaftler

Table of Contents

/ Contents.- Recent Developments in the Chemistry of Penicillins.- I. Introduction.- II. Nomenclature.- III. Reactions at the ?-Lactam Ring.- A. Acylation of the 6-Amino Group.- B. Alkylation of the 6-Amino Group.- C. Hydrolysis of the 6-Amido Group.- D. Epimerization at the 6-Position.- E. Diazotization of the 6-Amino Group.- F. Substitution at the 6-Position.- G. Cleavage of the C-7-N-4 Bond.- IV. Reactions at the Thiazolidine Ring.- A. Rearrangements of Penicillin Sulfoxides.- B. Other Thiazolidine Ring Cleavages.- C. Miscellaneous Nuclear Transformations.- D. Modification of the 3-Carboxylic Acid.- V. Conclusion.- References.- The Antibiotic Complex of the Verrucarins and Roridins.- I. Introduction.- II. Production and Isolation.- III. Structure and Chemical Transformations.- 1. Sterols.- 2. Chromane Derivatives.- 2.1. Myrochromanol and Myrochromanone.- 3. Pyrrole Derivatives.- 3.1. Verrucarin E.- 3.2. Verrucarin G.- 4. Macrocyclic Trichothecane Esters.- 4.1. Verrucarol and Roridin C (Trichodermol).- 4.2. Verrucarin A and 2?-Dehydroverrucarin A.- 4.3. Verrucarin B.- 4.4. Verrucarin J.- 4.5. Roridin A.- 4.6. Roridin D.- 4.7. Roridin E.- 4.8. Roridin H.- 5. Wortmannin.- IV. Total Synthesis.- V. Methods of Assay.- VI. Biosynthesis.- 1. Pyrrole Derivatives.- 2. Trichothecane Esters.- VII. Biological Activity.- 1. Antibiotic Activity.- 2. Cytostatic Activity.- 3. Toxicity.- 4. Structure and Biological Activity.- Acknowledgement.- References.- Aflatoxins and Sterigmatocystins.- I. Introduction.- II. Isolation and Characterisation of the Mycotoxins.- III. Structural Elucidation of the Mycotoxins.- 1. Sterigmatocystin.- 2. Other Metabolites Closely Related to Sterigmatocystin.- 3. Aspertoxin.- 4. Aflatoxin-B1, -B2, -Gl, and -G2.- 5. Aflatoxin-M1 and -M2.- 6. Aflatoxin-B2a and -G2a.- IV. Synthesis of the (+-)-Forms of the Mycotoxins and of Related Compounds.- 1. Tetrahydro-4-hydroxy-6-methoxyfuro[2,3-b]benzofuran.- 2. Tetrahydrodeoxoaflatoxin-B1.- 3. Aflatoxin-B1.- 4. Aflatoxin-B2.- 5. Aflatoxin-G1.- 6. Aflatoxin-M1.- 7. Dihydro-O-methylsterigmatocystin.- 8. O-methylsterigmatocystin.- V. Biogenesis of the Mycotoxins.- 1. Sterigmatocystin.- 2. Aflatoxin-B1.- VI. Conclusion.- References.- Flavonoid-Glykoside.- I. Strukturtypen von Flavonoid-O-Glykosiden und ihre Verbreitung.- 1. Glykosidierungsmuster.- 2. O-Monoside.- 3. O-Bioside.- 4. O-Trioside, Tri-, Tetra- und Poly-O-Glykoside.- 5.O-Glykuronide.- 6. Acyl-O-Glykoside.- II. Flavonoid-C-Glykoside.- III. Synthese von Flavonoidglykosiden.- 1. Darstellung von Acetobromzuckern.- 2. Synthese von O-Monosiden und O-Biosiden.- a) Glykosidierung der C7-OH-Gruppe.- b) Glykosidierung der C3-OH-Gruppe.- c) Glykosidierung der C4?-C2?-C3?-C5-OH-Gruppen.- 3. Synthese von Flavonoid-O-Bisglykosiden.- 4. Synthese von Flavonoid-C-Glykosiden.- Addenda.- Biogenetic-Type Syntheses of Polyketide Metabolites.- I. Introduction.- II. Early Studies.- III. Modern Concepts of Polyketide Biosynthesis.- IV. Experimental Support for the Polyketide Theory.- V. Syntheses of ?-Polycarbonyl Compounds.- 1. 3,5-Diketo Acids and Esters.- 2. 1,3,5-Triketones.- 3. 3,5,7-Triketo Acids and Esters.- 4. 1,3,5,7-Tetraketones.- 5. 3,5,7,9-Tetraketo Acids and Esters.- 6. 1,3,5,7,9-Pentaketones.- 7. 3,5,7,9,11-Pentaketo Acids and Esters.- 8. 1,3,5,7,9,11-Hexaketones.- 9. ?-Heptacarbonyl Compounds.- 10. ?-Octacarbonyl Compounds.- 11. ?-Nonacarbonyl Compounds.- 12. Reduced Polycarbonyl Compounds.- VI. Cyclizations of ?-Polycarbonyl Compounds.- 1. Using Several Ketide Fragments.- 2. Using a Single Polycarbonyl Compound.- a) With 3,5-Diketo Acids.- b) With 1,3,5-Triketones.- c) With 3,5,7-Triketo Acids and Esters.- d) With 1,3,5,7-Tetraketones.- e) With 3,5,7,9-Tetraketo Acids and Esters.- f) With 1,3,5,7,9-Pentaketones.- g) With ?-Hexacarbonyl Compounds.- h) With ?-Heptacarbonyl Compounds.- i) With ?-Octacarbonyl Compounds.- j) With ?-Nonacarbonyl Compounds.- k) With Reduced ?-Polycarbonyl Compounds.- 3. Using Partially Cyclized Polycarbonyl Compounds.- VII. Conclusions.- References.- The Chemistry of Spiro[4.5]Decane Sesquiterpenes.- A. Introduction.- B. The Acoranes and Alaskanes.- 1. Structure Elucidation of the Acorus Spiranes.- 2. The Alaskanes, Precursors of Cedrene.- 3. Mass Spectral Considerations.- 4. Synthesis.- C. The Spirovetivanes.- 1. Structure.- a) Agarospirol.- b) ?-Vetivone and Related Compounds.- 2. Synthesis.- D. Biogenetic Considerations.- 1. The Relationship between Spirovetivanes and Hydronaphthalenic Sesquiterpenes.- 2. Alaskane-Acorane Spiranes as Precursors of Tricyclic Sesquiterpenes.- 3. Chemical Simulation of Biogenetic Pathways involving Spiro[4.5]Decanes.- E. Tables of Naturally Occurring Spiro[4.5]Decanes.- Addendum.- References.- Phorbolesters - the Irritants and Cocarcinogens of Croton Tiglium L..- 1. Introduction.- 2. Fractionation of Croton Oil.- 2.1. General Analytical Chemical Procedures and Biological Assays.- 2.1.1. Methods of Separation and Criteria of Purity.- 2.1.2. Monitoring of Fractionation Steps.- 2.2. Preparation of the Hydrophilic and the Hydrophobic Portions.- 2.3. Phorbol Diesters from the Hydrophilic Portion.- 2.3.1. Isolation and Resolution of Croton Oil Factor Groups A and B.- 2.3.2. Chemical Characterization of the Croton Oil Factors from Groups A and B as Diesters of Phorbol.- 2.4. Higher Phorbol Esters from the Hydrophobic Portion.- 2.4.1. Isolation and Resolution of Croton Oil Factor Groups A' and B'.- 2.4.2. Separation and Chemical Characterization of the Croton Oil Factors from Groups A' and B'.- 3. Chemistry of Phorbol and of the Croton Oil Factors.- 3.1. Structure and Stereochemistry of Phorbol.- 3.2. Reactions Altering the Functional Groups of Phorbol.- 3.2.1. Functional Derivatives of the Carbonyl Group.- Reaction with Carbonyl Reagents.- Reduction of the Carbonyl Group.- 3.2.2. Functional Derivatives of the Hydroxyl Groups.- Phorbol Esters.- Phorbol Ethers.- Oxidation of Single Hydroxyl Groups.- Substitution and Elimination of Hydroxyl Groups.- 3.2.3. Functional Derivatives Involving the C = C-Bonds.- Catalytic Hydrogenation.- Bromination and Hydrobromination.- Oxidation.- 3.3. Structure of the Croton Oil Factors.- 3.3.1. Phorbol Diesters from the Hydrophilic Portion.- 3.3.2. Phorbol Triesters from the Hydrophobic Portion.- 3.4. Reactions Altering the Tigliane Skeleton of Phorbol and of Neophorbol.- 3.4.1. Dehydrogenation of Phorbol and 3-Deoxo-3?-hydroxyphorbol.- 3.4.2. Oxidative Ring Opening of Phorbol and Derivatives.- Ring A.- Ring B.- Rings C and D (Bicyclo[4.1.0]heptane System).- 3.4.3. Rearrangements in Phorbol and Neophorbol involving the Bicyclo[4.1.0]-heptane System.- Crotophorbolone-enol-13,20-diacetate and Acetoxycrotophorbolone-20-acetate.- Phorbobutanone and Phorboisobutanone.- The "Flaschentrager Reaction".- 12,13-Ketol Rearrangement in Neophorbol.- 4. Further Diterpenes and Diterpene Esters from Croton Oil.- 4.1. Chemistry of 4?-Phorbol.- 4.2. Chemistry of 4-Deoxy-4?-phorbol and 4-Deoxyphorbol.- 4.3. Compound Groups D, E, D' and E' from Croton Oil.- 4.4. Composition of Croton Oil with Regard to Diterpenes and their Esters.- 5. On the Biological Activities of the Isolated Diterpenes and their Esters.- 6. Conclusions and Perspectives.- References.- Stereoselektive Totalsynthese von Indolalkaloiden..- Structure, Chemistry, and Biosynthesis of the Melanins..- I. Introduction.- II. Enzymic Nature of Melanogenesis.- 1. Melanogenesis in Invertebrates and Plants.- 2. Melanogenesis in Vertebrates.- 3. The Enzyme.- III. Allomelanins.- 1. Catechol-Melanin.- 2. Natural Allomelanins.- IV. Eumelanins.- 1. Chemical Investigations on Dopa-Melanin and 5,6-Dihydroxyindole-Melanin.- 1.1. Introduction.- 1.2. Studies on Model Compounds.- 1.3. Isotopic and Degradative Studies.- 1.4. Conclusion Regarding the Structure of Melanin.- 1.5. Studies Relevant to the Structure of the Melanoproteins.- 2. Chemical and Biochemical Investigations on Natural Eumelanins.- 2.1. Introduction.- 2.2. Sepiomelanin.- 2.3. Melanin from Melanoma.- 2.4. Melanin from Hair.- 2.5. Melanin from the Eye.- 2.6. Other Melanins.- 3. Investigations on Melanins by Spectroscopic and other Physical Methods.- 3.1. Ultraviolet and Infrared Spectra.- 3.2. X-Ray Diffraction.- 3.3. Electron Spin Resonance.- 4. Adrenochrome-Melanin.- 5. Dopamine-Melanin.- V. Phaeomelanins.- VI. Conclusions.- References.- Addendum.- Mechanisms of Corrin Dependent Enzymatic Reactions..- I. Introduction.- II. Nomenclature.- III. Properties and Reactions of Corrins and Related Compounds.- 1. Vitamin B12 Chemistry.- 2. Vitamin B12 Model Compounds.- 3. Coenzyme B12 Reactions.- IV. Coenzyme B12 Dependent Enzymatic Reactions.- 1. Dioldehydrases.- 2. Ethanolamine Deaminase.- 3. Ribonucleotide Reductase.- 4. Mutases.- 5. Aminomutases.- V. Corrin Dependent Enzymatic Reactions.- 1. Methane Biosynthesis.- 2. Acetate Biosynthesis.- 3. Methylarsine Biosynthesis.- 4. Methylmercury Formation.- 5. Methionine Biosynthesis.- References.- Namenverzeichnis. Author Index.- Sachverzeichnis. Subject Index.

Volume

32 : Wien ISBN 9783211812556

Table of Contents

Carboxylic Acids in Petroleum and Sediments..- I. General.- 1. Introduction.- 2. Occurrence.- 3. Derivatization.- II. Paraffinic Acids.- 1. Linear Fatty Acids.- 2. Unsaturated Fatty Acids.- 3. Iso and Anteiso Acids.- 4. Isoprenoid Acids.- 5. "Pseudo" Isoprenoid Acids.- III. Cyclic Saturated Acids.- 1. Monocyclic Acids.- 2. Bi- and Polycyclic Naphthenic Acids.- 3. Tricyclic Terpenoid Acids.- 4. Steroid Acids.- 5. Pentacyclic Triterpenoid Acids.- IV. Aromatic Acids.- 1. Mono- and Diaromatic Acids.- 2. Polynuclear Aromatic and Heterocyclic Carboxylic Acids.- V. The Origin of Petroleum Carboxylic Acids.- VI. Bifunctional Acids.- 1. Dicarboxylic Acids.- 2. Hydroxy- and Ketoacids.- 3. Amino Acids.- 4. Miscellaneous.- References.- Naturally Occurring 2,5-Dioxopiperazines and Related Compounds..- I. Introduction.- II. Synthesis of 2,5-Dioxopiperazines.- III. Conformations of Dioxopiperazines.- IV. Simple Dioxopiperazines.- V. The Echinulins and Related Derivatives.- VI. Hydroxypyrazine Derivatives.- VII. Sulphur-bridged Dioxopiperazines.- VIII. Bicyclomycin and Dibromophakellin.- References.- Structural Investigations of Natural Products by Newer Methods of NMR Spectroscopy..- I. Introduction.- II. Solvent Effects.- III. Derivatives and In Situ Reactions.- IV. Coupling Constants.- V. Superconducting Magnets.- VI. Lanthanide Induced Shifts.- VII. Computer-Aided Interpretation of Spectra.- VIII. INDOR.- IX. The Nuclear Overhauser Effect.- X. Fourier Transform Techniques.- 1. Instrumentation.- 2. Proton Spectra from Small Samples.- XI. 13C Satellites.- XII. Other Nuclei.- XIII. 13C NMR Spectra.- 1. General Discussion.- 2. Sample Size and Acquisition Times.- 3. Chemical Shifts of Alkyl Residues.- 4. Functional Group Recognition.- 5. Substituent and Stereochemical Effects.- 6. Biogenetic Studies.- 7. Relaxation Studies.- XIV. Complementary Studies.- References.- Applications of the Chiroptical Techniques to the Study of Natural Products..- I. Introduction.- 1. Units and Definitions.- 2. Logic of Applications.- II. Allocation of Configuration.- 1. Carbonyl Chromophores in Steroids and Terpenes: Empirical Correlations.- a) Hexahydroindan-l- and 2-ones.- b) Bicyclo-[5,3,0]-octanones.- c) Decalones.- d) 4,4-Dimethyl-3-oxo-Steroids and Triterpenes.- e) Orientation of the Steroidal Side Chain.- f) Monocyclic and Acyclic Ketones.- g) Difference Curves in Dicarbonyl Compounds.- h) Epoxyketones.- 2. Carbonyl Chromophores: Application of the Octant Rule.- a) trans-Decalones.- b) cis-Decalones.- c) Flexible Monocyclic Cyclohexanones.- d) Cyclopentanones.- e) Cycloheptanones and Cyclobutanones.- f) Epoxy- and Cyclopropyl Ketones.- 3. Unsaturated Ketones.- a) Empirical Correlations.- b) Helicity Rule.- 4. Dienes and Polyenes.- a) Helicity Rules for Dienes.- b) Carotenoids and Related Compounds.- 5. Aromatic Chromophores.- a) Tetrahydroisoquinoline Alkaloids.- b) Indole Alkaloids.- c) Oxindole and Isoindole Alkaloids.- d) Aryltetralins Including Lignans.- e) Aryltetrahydroisoquinolines.- f) Flavans: Isoflavans and Related Compounds.- g) Other Aromatic Correlations.- h) Biphenyls.- i) Purine and Pyrimidine Chromophores in Nucleosides.- 6. The Carboxyl Chromophore.- a) Correlations Involving Acids or Modified Groups as Principal Chromophore.- b) Correlations Involving Degradation to a Carboxylic Acid Fragment.- c) Empirical Correlations in Complex Lactones and Lactams.- d) Saturated Lactones: Correlations by Semi-Empirical Rules.- e) ?, ?-Unsaturated Lactones.- 7. Chromophoric Derivatives.- III. Studies of Conformation.- IV. Position of Functional Groups.- VI Inhaltsverzeichnis. Contents.- V. Detection of Optical Activity.- VI. Identity of Two Samples.- VII. Reaction Kinetics and Equilibria.- Acknowledgement.- References.- Chemistry and Biosynthesis of Plant Galactolipids..- I. Introduction.- II. Occurrence and Localization.- III. Structure Determination and Synthesis.- 1. Fractionation.- 2. Identification and Structure Determination.- 3. Synthesis of Galactosyl Glycerol and Galactosyl Diglycerides.- 4. Semi-Synthesis.- 5. Fatty Acid Content.- IV. Biosynthesis.- V. Enzymatic Hydrolysis.- VI. Function.- 1. Galactolipids in Chloroplast Membrane Structure.- 2. Galactolipids and the Synthesis of Fatty Acids.- 3. Galactolipids and Electron Transport.- 4. Other Functions.- References.- Recent Advances in Polynucleotide Synthesis..- Abbreviations and Symbols.- 1. Protecting Groups.- 1.1. General Considerations.- 1.2. Choice of Blocking and Deblocking Conditions.- 1.3. Survey of Blocking Groups.- 1.3.1. Protecting Groups for the Phosphate Moiety.- 1.3.2. Protecting Groups for the Hydroxyl and Amino Functions of the Sugar and Base Moieties.- 1.3.3. Protecting Groups for the Vicinal Diol Group of Ribonucleic Acid Constituents.- 1.4. Protecting Groups with Special Applications.- 1.4.1. Protecting Groups for Solvent Extraction.- 1.4.2. Protecting Groups for Separations by Affinity Chromatography.- 1.4.3. Activable Protecting Groups.- 1.5. Strategy of Consecutive Blocking or Deblocking of Several Functions.- 1.6. General Blocking Schemes for Intermediates of Polynucleotide Synthesis.- 2. Phosphorylation Methods in the Synthesis of Mono- and Oligonucleotides.- 2.1. Transfer of a Phosphoryl Group.- 2.2. Transfer of a Phosphate Group.- 2.3. Miscellaneous Chemical Phosphorylation Reactions.- 2.3.1. Phosphorylation by Oxidation of Nucleoside Phosphites.- 2.3.2. "Thermal" Phosphorylation.- 2.3.3. Prebiotic Phosphorylations.- 2.4. Enzymic Phosphorylation.- 3. Separation Techniques.- 3.1. Column Procedures.- 3.1.1. Column Chromatography on Conventional Adsorbent Types.- 3.1.2. Column Chromatography on Newly Developed Adsorbent Types.- 3.2. Extraction Procedures.- 3.3. Miscellaneous Techniques.- 4. Formation of Internucleotide Linkages by Chemical Synthesis.- 4.1. Conventional Methods.- 4.1.1. Synthesis in the Deoxy Series.- 4.1.2. Synthesis in the Ribo Series.- 4.1.3. Modified Oligonucleotides.- 4.2. Polymer-Support Synthesis of Oligonucleotides.- 4.2.1. General Reaction Principle.- 4.2.2. Requirements for Supports and Reactants.- 4.2.3. Chemical Synthesis of Oligonucleotides on Supports.- 4.2.4. Enzymatic Synthesis of Oligo- and Polynucleotides on Supports.- 4.2.5. Miscellaneous Uses of Supports in Nucleotide Chemistry.- 4.3. Miscellaneous Methods in Chemical Oligonucleotide Synthesis.- 4.3.1. Chemical Synthesis via Activation of Hydroxyl Functions.- 4.3.2. Chemical Synthesis via Preactivated Phosphate Derivatives.- 4.3.3. Chemical Synthesis Using Unprotected Nucleotides.- 4.3.4. Chemical Synthesis on Complementary Templates.- 5. Formation of Internucleotide Linkages by Enzymic Reactions.- 5.1. Reactions Catalyzed by Polymerizing Enzymes.- 5.2. Reactions Catalyzed by Polynucleotide Ligases.- 5.3. Synthetic Reactions Catalyzed by Ribonucleases.- References.- Namenverzeichnis. Author Index.- Sachverzeichnis. Subject Index.

Volume

33 : Wien ISBN 9783211813577

Table of Contents

/ Contents.- Natural Products from Porifera.- Biogenetic-Type Rearrangements of Terpenes.- Chemistry of the Ansamycin Antibiotics.- The Chemistry of Tryptophan in Peptides and Proteins.- The Present Status of Flavin and Flavocoenzyme Chemistry.- Namenverzeichnis. Author Index.- Sachverzeichnis. Subject Index.

Volume

34 : Wien ISBN 9783211814154

Table of Contents

Inhaltsverzeichnis, Contents.- Isoprenoids and Alkaloids of Tobacco.- I. Introduction.- II. Carotenoids and Acyclic Isoprenoids.- 1. Carotenoid.- 2. Acyclic Isoprenoids.- 3. Meroterpenoids.- 4. Nor-Compounds Derived from Cyclic Carotenoids.- a) General Considerations.- b) C15 Constituent.- c) C13 Constituents.- d) C12 Constituent.- e) C9 Constituents.- f) C10 Constituents.- g) C9 Constituents.- 5. Nor-Compounds Derived from Acyclic Isoprenoids.- III. Diterpenoids.- 1. Thunberganoids.- 2. Nor-Thunberganoids.- 3. Labdanoids and Nor-Labdanoids.- IV. Triterpenoids and Steroids.- V. Cyclic Sesqui- and Monoterpenoids.- VI. Pyridine Derivatives.- 1. Nicotine.- a) Structure and Synthesis.- b) Biosynthesis.- c) Metabolism in the Growing Plant.- d) Post-Harvest Reactions.- e) Bacterial Degradation.- 2. Anabasine and Structurally Related Compounds.- 3. Others.- VII. Pyrrole and Pyrrolidine Derivatives.- VIII. Pyrazine Derivatives.- IX. Miscellaneous Nitrogen-Containing Constituents.- References.- The Chemistry of the Eremophilane and Related Sesquiterpenes.- I. Introduction.- II. Bicyclic Eremophilanes.- 1. Hydrocarbons.- 2. Alcohols.- 3. Ketones.- 4. Keto Alcohols.- 5. Acids.- 6. Esters.- III. Furanoeremophilanes.- 1. Butenolactones.- 2. Furanoeremophilanes.- a) Monohydric Alcohols and Their Ethers and Esters.- b) Monoketones.- c) Epoxides.- d) Di- and Trihydric Alcohols and Their Esters and Ethers.- e) Keto Alcohols and Keto Esters.- f) Miscellaneous Furanoeremophilanes.- g) Furanoeremophilanes from South African Plants.- IV. 4-epi-Eremophilanes.- V. Bicyclic 7-epi-Eremophilanes (Nootkatanes).- 1. Hydrocarbons.- 2. Alcohols.- 3. Ketones.- 4. Esters.- VI. Tricyclic 7-epi-Eremophilanes.- 1. Hydrocarbons.- 2. Alcohols.- 3. Ketones.- VII. Ishwaranes.- VIII. B-Noreremophilanes.- 1. The Bakkenolides.- 2. Other Noreremophilanes.- IX. Biogenetic Considerations.- References.- Phytoalexine und verwandte Pflanzenstoffe.- I. Einfuhrung.- II. Prainfektionelle Abwehrstoffe.- III. Postinfektionelle Abwehrstoffe.- IV. Phytoalexine und phytoalexinahnliche Verbindungen.- 1. Polyacetylene.- a) Safinol und Dehydrosafinol.- b) Wyeron.- c) Wyeronsaure.- 2. Dihydrophenanthrene.- a) Orchinol.- b) Hircinol.- c) Loroglossol.- d) Strukturverwandte Pflanzeninhaltsstoffe.- 3. Isoflavonoide.- a) Isoflavane.- b) Isoflavanone.- c) Pterocarpane.- 4. Sesquiterpene.- a) Rishitin.- b) Rishitinol.- c) Glutinoson.- d) Capsidiol.- e) Lubimin, 4-Hydroxylubimin und Isolubimin.- f) Strukturverwandte Sesquiterpene.- g) Gossypol.- h) Hemigossypol und strukturverwandte Verbindungen.- 5. Furanoterpenoide.- a) Ipomeamaron.- b) Ipomeamaronol.- c) Dehydroipomeamaron und 4-Hydroxymyoporon.- 6. Verschiedenes.- V. Schlussbetrachtung.- Literatur.- Studies in Secondary Metabolism with Plant Tissue Cultures.- I. Introduction.- II. The Chemical Potential of Plant Tissue Cultures.- III. Biosynthesis of Polyisoprenoids.- 1. Plant Sterol Metabolism.- 2. Mechanism of Side Chain Ethylation in Stigmasterol Biosynthesis.- 3. Biosynthesis of Steroidal Sapogenins.- 4. Biosynthesis of Triterpenoids.- 5. Isomerisation of trans, trans- and eis, trans-Fzmesol and the Biosynthesis of ?-Bisabolene.- 6. Biosynthesis of ent-Kaurene.- IV. Biosynthesis of Polyketides.- 1. Biosynthesis of Cyclopropane and Cyclopropene Fatty Acids in Higher Plants.- V. Metabolism of Aromatic Plant Constituents.- 1. Flavonoid Biosynthesis.- 2. Anthocyanidin Biosynthesis.- 3. Retrochalcone Biosynthesis.- 4. Anthraquinone Biosynthesis.- 5. Coumarin Biosynthesis.- 6. Catabolism of Aromatic Plant Constituents.- 6.1 General.- 6.2 Flavonoid Catabolism.- 6.3 Degradation of Tyrosine by the Homogentisate Pathway.- VI. Biosynthesis of Alkaloids.- 1. General.- 2. Indole Alkaloids.- 3. Berberine Alkaloids.- 4. ?-Carboline Alkaloids.- 5. Furoquinoline Alkaloids.- 6. Tropane Alkaloids.- References.- Carbazole Alkaloids.- I. Introduction.- A. Nomenclature and Electronic Characteristics.- B. Occurrence.- C. Isolation.- D. Detection of Carbazoles by Chromatographic Methods.- II. Methods of Structure Elucidation.- A. Physical Methods.- 1. Ultraviolet Absorption Spectra.- 2. IR Spectra.- 3. NMR Spectra.- 4. Mass Spectra.- 5. X-Ray Crystallographic Methods.- B. Chemical Methods.- Degradative Reactions.- a) Zinc Dust Distillation.- b) Decarbonylation and Decarboxylation.- c) Demethylation.- d) Ozonisation.- e) Permanganate Oxidation.- C. Synthesis of Carbazoles.- 1. Graebe-Ullmann Synthesis.- 2. Borsche Synthesis.- 3. Watermann and Vivian's Method.- 4. Nenitzescu Synthesis.- 5. Thermal Synthesis of Carbazoles.- 6. Photocyclisation of Diphenylamine to Carbazole.- 7. Anodic Oxidation.- III. Biogenesis of Carbazole Alkaloids.- IV. Biochemical Properties of Carbazole Alkaloids.- V. Chemistry of Carbazole Alkaloids.- A. Members of the C13-Skeleton Group.- 1. Murrayanine.- 2. Glycozoline.- 3. Glycozolidine.- 4. Mukoeic Acid.- 5. Mukonine.- 6. 3-Methylcarbazole.- 7. Mukonidine.- B. Members of the C18-Skeleton Group.- 1. Indizoline.- 2. Heptaphylline.- 3. 6-Methoxyheptaphylline.- 4. Heptazoline.- 5. Girinimbine.- 6. Koenimbine.- 7. Heptazolidine.- 8. Murrayacine.- 9. Koenigine and Koenidine.- 10. Koenine.- C. Members of the C23-Skeleton Group.- 1. Mahanimbine.- 2. dl-Mahanimbine.- 3. Mahanimbicine and Isomahanimbine.- 4. Mahanine.- 5. Mahanimbinine.- 6. Murrayazoline.- 7. Murrayazolinine.- 8. Murrayazolidine.- 9. Cyclomahanimbine.- 10. Bicyclomahanimbine.- 11. Murrayacinine.- 12. Bicyclomahanimbicine.- References.- Burzeldriisenlipide.- I. Einleitung.- II. Anatomie und Histologie der Burzeldruse.- III. Burzeldrusensekrete.- 1. Analytische Methoden.- a) Isolierung und Reinigung.- b) Gaschromatographie (GLC).- c) Massenspektrometrie (MS).- 2. Zusammensetzung der Burzellipide bei Arten unterschiedlicher Ordnungen.- a) Systematik.- b) Einzelne Ordnungen.- 1. Sphenisciformes.- 2. Procellariiformes.- 3. Ciconiiformes.- 4. Phoenicopteriformes.- 5. Anseriformes.- 6. Falconiformes.- 7. Galliformes.- 8. Gruiformes.- 9. Charadriiformes.- 10. Lariformes.- 11. Columbiformes.- 12. Psittaciformes.- 13. Cuculiformes.- 14. Strigiformes.- 15. Piciformes.- 16. Passeriformes.- 16.1. Corvidae.- 16.2. Sylviidae.- 16.3. Paridae.- 16.4. Fringillidae und Emberizidae.- 16.5. Ploceidae.- 16.6. Certhiidae und andere.- IV. Andere Vogellipide.- 1. Depotfette.- 2. Magenole.- V. Biosynthese.- VI. Physiologische Funktion.- VII. Chemotaxonomie und Systematik.- Literatur.- Hypothalamus-Regulationshormone..- I. Einfuhrung.- II. Thyreotropin-freisetzendes Hormon.- A. Strukturaufklarung.- B. Synthesen vom Thyreotropin-freisetzenden Hormon.- C. Synthesen von TRH-Analoga. Struktur-Aktivitatsbeziehungen beim Thyreotropin-freisetzenden Hormon.- D. Spektroskopische Untersuchungen von TRH und seinen Derivaten.- D 1. Infrarotspektroskopie.- D 2. Massenspektroskopie.- D 3. 1-NMR-Spektroskopie.- D 4. 13C-NMR-Spektroskopie.- D 5. Circulardichroismus.- III. Luteinisierendes/Follikel-stimulierendes Hormon-freisetzendes Hormon.- A. Strukturaufklarung.- B. Synthesen vom luteinisierenden/Follikel-stimulierenden Hormon-freisetzenden Hormon.- C. Synthesen von LH/FSH-RH-Analoga. Struktur-Aktivitatsbeziehungen beim luteinisierenden/Follikel-stimulierenden Hormon-freisetzenden Hormon.- IV. Somatostatin.- Literatur.- Namenverzeichnis. Author Index.- Sachverzeichnis. Subject Index.

Volume

35 : Wien ISBN 9783211814604

Description

This volume is part of a series, inaugurated in 1938, now referred to simply as "Zechmeister" after its founder, L. Zechmeister. It contains contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a reconized authority in his field, and provides a comprehensive and up-to-date review of the topic in question. This title looks at the chemistry of organic natural products. It is addressed to biologists, technologists and chemists alike. The series can be used by the expert as a source of information and literature citations, and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

Neolignans.- I. Introduction.- II. 8.8'-Neolignans.- 1. l,4-Diaryl-2,3-dimethyl-butene and butanes.- 2. 2,5-Diaryl-3,4-dimethyl-tetrahydrofurans and furans.- III. 8.8',7.2'-Neolignans.- 1. l-Aryl-2,3-dimethyl-tetralins and naphthalene.- 2. l,2-Dimethyl-l,2,4,6a,llb,llc-hexahydro-7-oxa-4-oxobenz?de? anthracene.- IV. 8.8',2.2'-Neolignans.- 1. 6,7-Dimethyl-l,2,3,4-dibenzocycloocta-l,3-dienes.- V. 3.3'-, 5.1',2.2'- and 5.1',2.2,,1.5,,6.6,-Neolignans.- 1. 3,3'-Dipropenylbiphenyl.- 2. 3,3/-Diallylbiphenyls.- 3. 8a-Allyl-l,2,3,4,5,6,5a,8a-octahydro-1.4-(2'-allylethyleno)-2,6-dioxonaphthalene and internal cycloaddition product.- VI. 8.3'-Neolignans.- 1. 2-Aryl-3-methyl-5-propenyl-2,3-dihydrobenzofurans.- 2. 2-Aryl-3-methyl-5-propenylbenzofurans.- 3. 5-Allyl-2-aryl-3-methyl-2,3,3a,6-tetrahydro-6-oxobenzofurans and 2,3,3a,6,7,7a-hexahydro-6-oxobenzofuran.- 4. 2-Allyl-4-(?-methyl- ? -styryl)-cyclohexa-2,6-dienone.- VII. 8.1'-Neolignans.- 1. 3a-Allyl-2-aryl-3-methyl-2,3,3a,6-tetrahydro-6-oxobenzofurans.- 2. 3a-Allyl-2-aryl-3-methyl-2,3,3a,4,5,6-hexahydro-6-oxobenzofurans.- VIII. Rearranged 8.1'-Neolignans.- 1. 5-Allyl-2-aryl-3-methyl-2,3,5,6-tetrahydro-6-oxobenzofurans, 7-allyl-2-aryl-3- methyl-2,3,6,7-tetrahydro-6-oxobenzofurans, 6-0-allyl-2-aryl-3-methyl-2,3-di- hydrobenzofurans, 7-allyl-2-aryl-3-methyl-2,3-dihydrobenzofurans and 7- allyl-2-aryl-3-methylbenzofurans.- 2. 1-Aryl-2-(p-allyloxyphenyl)-propane.- IX. 13C NMR Spectroscopy of Neolignans.- X. 8.1',7.3'- and 8.5',7.3'-Neolignans.- 1. 1 - Allyl-6-aryl-7-methyl-4-oxobicyclo[3,2, 1]oct-2-enes.- 2. 1 - Allyl-6-aryl-7-methylbicyclo[3,2,1]octanes.- 3. 3-Allyl-6-aryl-7-methyl-4-(and 8)-oxobicyclo[3,2,1]oct-2-enes.- XI. 8.1',7.9'-Neolignan.- 1. 2-Aryl-l-methyl-4,7-epoxy-9-oxo-?7,10-spiro[5,5]undecane.- XII. 8. 0.4'-Neolignans.- 1. 1 - Aryl-1 -hydroxy-2-(p-E-propenylphenoxy)-propane.- 2. 7-Allyl-2-aryl-3-methylbenzodioxans.- XIII. Function and Use of Neolignans.- XIV. Biogenesis of Neolignans.- XV. Conclusion.- Addendum.- References.- Hydroxyzimtsauren und Hydroxybenzoesauren enthaltende Naturstoffe in Pflanzen.- I. Einleitung.- II. Hydroxyzimtsauren und Hydroxybenzoesauren.- III. Ester der Hydroxyzimtsauren und der Gallussaure mit anderen Hydroxycarbonsauren.- 1. Caffeyl-D-chinasauren (Chlorogensauren).- 2. Dicaffeyl-D-chinasauren.- 3. Ester der p-Cumarsaure, Ferulasaure, Sinapinsaure und Gallussaure mit Chinasaure.- 4. Ester der Hydroxyzimtsauren mit Weinsaure.- 5. Ester der Hydroxyzimtsauren mit anderen Hydroxycarbonsauren.- IV. Verbindungen der Phenolsauren mit Kohlenhydraten.- 1. Ester der Hydroxyzimtsauren mit Mono- und Disacchariden.- 2. Weitere Ester der Hydroxyzimtsauren.- 3. Ester der Hydroxybenzoesauren mit Mono- und Disacchariden.- 4. Ester der Ferulasauren mit Polysacchariden.- 5. Glykoside der Phenolsauren.- V. Ester der Hydroxyzimtsauren und Hydroxybenzoesauren mit n-Alkoholen, n-?-Alkandiolen, Glycerin und ?-Hydroxyfettsauren.- 1. Ester mit Methanol und Athanol.- 2. Ester mit langkettigen n-Alkoholen und n-?-Alkandiolen.- 3. Ester mit Glycerin.- 4. Verbindungen der Hydroxyzimtsauren mit Hydroxyfettsauren.- VI. Ester der Hydroxyzimtsauren und Hydroxybenzoesauren mit Naturstoffen ausser Flavonoiden und Glucosiden.- 1. Ester mit Cholin.- 2. Phenolsauren mit Lignin.- 3. Ester der Ferulasaure mit Sterinen und Triterpenen.- 4. Ester mit Terpenalkoholen.- 5. Ester mit Catalpol.- 6. Ester mit weiteren Naturstoffen und einige acylierte Glykoside.- VII. Ester der Hydroxyzimtsauren und Hydroxybenzoesauren mit Phenolglucosiden, Cyclohexanolglucosiden und ahnlichen Naturstoffen.- 1. Ester mit Arbutin (4-Hydroxyphenyl-?-D-glucopyranosid).- 2. Ester mit Calleryanin (3-Hydroxy-4-O- ? -D-glucopyranosyl-benzylalkohol).- 3. Ester mit Salicin (2-O- ? -D-Glucopyranosyl-benzylalkohol).- 4. Ester mit Grandidentin (cis-2-Hydroxycyclohexyl- ?-D-glucopyranosid).- 5. Acylierte 3,4-Dihydroxy-?-phenylathyl-?-D-glucopyranoside.- VIII. Ester der Hydroxyzimtsauren und Hydroxybenzoesauren mit Flavonoiden.- 1. Ester mit Catechinen.- 2. Ester mit Flavonen.- IX. Mit Hydroxyzimtsauren oder Hydroxybenzoesauren acylierte Flavonoidglykoside.- 1. Acylierte Anthocyanidinglykoside.- 2. Acylierte Flavon(ol)glykoside.- 3. Acylierte Flavanonglykoside.- X. Amide der Hydroxyzimtsauren und Hydroxybenzoesauren.- 1. Verbindungen mit Aminosauren bzw. Proteinen.- 2. Amide mit Putrescin (1,4-Butandiamin).- 3. Weitere Hydroxyzimtsaureamide.- XI. Isolierung, qualitativer Nachweis und quantitative Bestimmung.- XII. Biologische Eigenschaften und Bedeutung.- Natural 4-Ylidenebutenolides and 4-Ylidenetetronic Acids.- I. Introduction.- II. Structure and Distribution.- 1. 4-Ylidenebutenolides.- 2. 4-Ylidenetetronic Acids.- III. Synthesis.- 1. From 4-Oxo-2-enoic Acids.- 2. From Z-2-En-4-ynoic Acids.- 3. From But-2-enolides.- 4. From Substituted Maleic Anhydrides.- 5. Miscellaneous Syntheses.- IV. Biosynthesis.- 1. Fungal Metabolites.- 2. Pulvinic Acids and Pulvinones.- 3. Acetylenic Ylidenebutenolides in Compositae.- 4. Terpenoid Butenolides.- 5. Other Metabolites.- V. Biological Activity.- References.- Naturally Occurring Plant Coumarins.- I. Introduction: Scope of Review.- II. Structural Types.- 1. Coumarins With Acyclic Substituents.- 2. Furano- and Pyrano-Coumarins.- III. Nomenclature.- IV. Isolation and Identification.- 1. Isolation.- 2. Identification of Known Coumarins.- 2.1 Paper and Thin-Layer Chromatography.- 2.2 Gas-Liquid Chromatography.- 2.3 High-Pressure Liquid Chromatography.- V. Structure Determination.- 1. Use of Spectroscopy.- 1.1 Nuclear Magnetic Resonance Spectroscopy.- 1.2 Mass Spectrometry.- 1.3 Ultraviolet and Infrared Spectroscopy.- 2. Stereochemistry.- VI. Synthesis and Biosynthesis.- 1. Synthesis.- 2. Biosynthesis.- VII. Introduction to Tables.- Table 1 Coumarin and 7-Oxygenated Coumarins.- 1.1 6-Substituted-7-Oxygenated Coumarins.- 1.2 8-Substituted-7-Oxygenated Coumarins.- 1.3 6,8-Disubstituted-7-Oxygenated Coumarins.- Table 2 5,7-Dioxygenated Coumarins.- Table 3 6,7-Dioxygenated Coumarins.- Table 4 7,8-Dioxygenated Coumarins.- Table 5 5,6,7-Trioxygenated Coumarins.- Table 6 5,7,8-Trioxygenated Coumarins.- Table 7 6,7,8-Trioxygenated Coumarins.- Table 8 5,6,7,8-Tetraoxygenated Coumarins.- Table 9 3-Substituted Coumarins.- Table 10 4-Substituted Coumarins.- Table 11 Miscellaneous Coumarins.- Formula Index.- Trivial Name Index.- References.- Recent Developments in the Field of Naturally-Occurring Aroma Components.- I. Occurrence and Implication of Flavors.- II. Oxygen-Containing Aliphatic Aroma Compounds.- 1. Alcohols and Carbonyl Compounds.- 2. Lactones.- III. Isoprenoid Aroma Compounds.- 1. Monoterpenoids.- 2. Monoterpenoid Ethers and Lactones.- 3. Sesquiterpenes.- 4. Sesquiterpenoid Ethers.- 5. Norsesquiterpenoids.- 6. Metabolites From Higher Terpene Precursors.- References.- Namenverzeichnis. Author Index.- Sachverzeichnis. Subject Index.

Volume

36 : Wien ISBN 9783211814727

Description

Since the late 1950's when proton n. m. r. spectroscopy was first used in organic natural products studies the technique has increasingly con of this important area of chemistry. tributed to the rapid advancement Although the potential utility of 13C n. m. r. was recognized very early, essentially no application of 13C n. m. r. appeared in the literature prior to 1966 and 95% of the existing data are less than five years old. The initially slow growth had its cause in inadequate instrumentation, insufficient sensitivity being the main obstacle. This situation drastically changed with the advent and commercial availability of broadband ex citation and Fourier transform methods, giving natural-abundance 13C n. m. r. and its numerous chemical applications a tremendous impetus. Today BC spectra can be recorded on sample quantities down to the submilligram level, which until recently even withstood proton n. m. r. Paralleling the development of experimental techniques considerable progress has also been made on an understanding of spectral parameters, in particular their stereochemical implications on natural products. Although the large majority of data present up to now deals with known structures, an adequate basis now exists which allows the chemist to use the technique for tackling real problems on unknown molecules.

Table of Contents

The Use of Carbon-13 Nuclear Magnetic Resonance Spectroscopy in Natural Products Chemistry.- The Role of Heteroatomic Substances in the Aroma Compounds of Foodstuffs.- Naturally Occurring Cerubranes.- Namenverzeichnis. Author Index.- Sachverzeichnis. Subject Index.

Volume

37 : Wien ISBN 9783211815281

Description

This volume is part of a series, inaugurated in 1938, now referred to simply as "Zechmeister" after its founder, L. Zechmeister. It contains contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a reconized authority in his field, and provides a comprehensive and up-to-date review of the topic in question. This title looks at the chemistry of organic natural products. It is addressed to biologists, technologists and chemists alike. The series can be used by the expert as a source of information and literature citations, and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

Insect Pheromones: A Critical Review of Recent Advances in Their Chemistry, Biology, and Application.- I. Introduction.- II. Structure Elucidation.- A. Isolation.- B. Identification.- III. Synthesis.- A. Coleoptera.- B. Diptera.- C. Homoptera.- D. Hymenoptera.- E. Isoptera.- F. Lepidoptera.- G. Orthoptera.- IV. Stereobiology.- A. Geometric Isomers.- B. Enantiomers.- C. Chemorecognition.- V. Biosynthesis.- A. Exposure of Bark Beetles to Pheromone Precursors.- B. Hormonal Influence on Pheromone Production.- C. Possible Role of Mixed-Function Oxidases.- D. Possible Involvement of Microorganisms in Pheromone Synthesis.- E. Biosynthesis of the Bicyclic Ketals.- F. Boll Weevil Sex Attractant.- G. Miscellaneous Labelling Studies.- H. Dietary Origin of Pheromones.- VI. Chemosystematics and Speciation.- VII. Practical Applications: Status and Projections.- A. Plea for Sanity and Integrated Pest Management.- B. Forest and Shade-Tree Insect Pests.- C. Orchard and Vineyard Insect Pests.- D. Field Crops Insect Pests.- E. Stored Products Insect Pests.- F. Pests That Directly Afflict Humans or Animals.- G. Pheromone Formulations.- VIII. Conclusion.- Addendum.- References.- The Structural Polymers of the Primary Cell Walls of Dicots.- I. Introduction.- A. Why Study the Structure of Cell Walls?.- B. Availability of Homogeneous Cell Wall Preparations.- C. Goals of Cell Wall Structural Research.- D. Problems Associated With Cell Wall Structural Research.- E. Types of Cell Wall Polysaccharides.- II. Sugar Nomenclature and Abbreviations Used in this Review.- A. Glycosyl Residues.- B. Abbreviations.- C. Absolute Configuration.- D. Anomeric Configuration.- E. Ring Size.- F. Linkage Analysis.- G. Polymer Names.- III. Methods Used in the Structural Analysis of Cell Wall Polysaccharides.- A. Introduction.- B. Solubilization and Fractionation of Cell Wall Polysaccharides.- C. Quantitative Analysis of the Glycosyl Residues of Oligo- or Polysaccharides.- D. Uronic Acid Quantitation.- E. Glycosyl-Linkage Composition Analysis.- F. Sequencing the Glycosyl Residues in Polysaccharides.- IV. The Pectic Polysaccharides.- A. Introduction.- B. Rhamnogalacturonan I.- C. Homogalacturonan.- D. Araban..- E. Galactan.- F. Arabinogalactan.- G. Rhamnogalacturonan II.- H. Apiogalacturonan.- V. The Hemicelluloses.- A. Xyloglucan.- B. Xylan.- VI. Non-Cellulosic Glucan.- VII. Cellulose.- VIII. Cell Wall Protein.- A. Hydroxyproline-Rich Proteins.- B. Hydroxyproline-Rich Glycoproteins With Lectin-Like Properties.- IX. Interconnections Between the Primary Cell Wall Polymers of Dicots.- A. Introduction.- B. The Pectic Polysaccharides are Covalently Interconnected.- C. The Hemicelluloses of Primary Cell Walls Bond Strongly to Cellulose Fibers.- D. Is the Hydroxyproline-Rich Glycoprotein of the Cell Wall Connected to the Other Polymers of the Cell Wall?.- E. Are the Xyloglucan Chains Covalently Linked to the Pectic Polysaccharides.- F. The Current Cell Wall Model.- X. The Future of Primary Cell Wall Research -New Methods.- References.- Dehydroamino Acids, ?-Hydroxy-?-amino Acids and ?-Mercapto-?-amino Acids.- I. Introduction and Scope.- II. Occurrence and Biosynthesis of Dehydroamino Acids, Hydroxy Amino Acids, Mercapto Amino Acids and the Corresponding Dioxopiperazines.- A. Occurrence.- B. Biosynthesis.- III. Determination of Structure and Configuration of Dehydroamino Acid Derivatives.- IV. Synthesis of Dehydroamino Acid Derivatives.- A. Acylenamino Acid Derivatives.- 1. Via Oxazolinones.- 2. By ?-Elimination Reactions.- 2.1 ?-Elimination Reactions of ?-Hydroxy-?-amino Acid Derivatives.- 2.2 ?-Elimination Reactions from Cysteine Derivatives.- 3. By N-Chlorination/Dehydrochlorination.- 4. From N-Hydroxyamino Acid Derivatives.- 5. From Carbonyl Compounds and Isocyanoacetic Ester or Isothiocyanato-acetic Ester.- 6. By Condensation of ?-Keto Acids With Amides or Nitriles.- 7. By Chain Lengthening of ?-Halo-?-acylaminoacrylic Acid Derivatives.- B. Unsaturated Piperazinediones.- 1. By Condensation Reactions.- 2. By Ring Closure Reactions.- 3. By Elimination Reactions.- 4. By Dehydrogenation.- C. Arylidene-enamino Acid Compounds.- D. a-Enaminocarboxylic Acid Compounds.- E. a-Iminocarboxylic Acid Derivatives.- F. a-Acyliminocarboxylic Acid Derivatives.- V. Synthesis of ?-Hydroxy- and ?-Mercapto-?-amino Acids, ?,?-Diamino Acids and the Corresponding Peptides and Piperazinediones.- A. Via Oxazolinones.- B. Direct Oxidation of Amino Acid Derivatives and Piperazinediones.- C. Interconversion of ?-Hydroxy- and ?-Mercapto-?-amino Acids, Hydroxy- and Mercaptopiperazinediones, Pyruvoylamino Acid Amides and Dehydro- peptides.- VI. Reactions of Dehydroamino Acids.- A. Enaminocarboxylic Acid Derivatives.- 1. Reactions of the Amino and Carboxy Groups.- 2. Reactions of the Double Bond.- 2.1 Additions Leading to ?-Substituted Amino Acids.- 2.2 Additions Leading to ?-Substituted Amino Acids.- 2.3 Hydrolysis.- 2.4 Intramolecular Additions.- 2.5 Catalytic Hydrogenation.- B. Addition Reactions to ?-Acylimino- and ?-Iminocarboxylic Acid Derivatives.- Addendum.- References.- Author Index.- Subject Inde.

Volume

38 : Wien ISBN 9783211815298

Description

This volume is part of a series, inaugurated in 1938, now referred to simply as "Zechmeister" after its founder, L. Zechmeister. It contains contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a reconized authority in his field, and provides a comprehensive and up-to-date review of the topic in question. This title looks at the chemistry of organic natural products. It is addressed to biologists, technologists and chemists alike. The series can be used by the expert as a source of information and literature citations, and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

The Mitomycin Antibiotics.- I. Isolation and Structure.- II. Transformation Products.- III. Mechanism of Action.- IV. Biosynthesis of the Mitomycins.- V. Synthetic Studies.- References.- The Biogenesis and Chemistry of Sesquiterpene Lactones.- I. Introduction.- II. Germacradiene-Derived Sesquiterpene Lactones.- 1. Skeletal Types of Sesquiterpene Lactones.- 2. Biogenesis of the Germacradiene and the Lactone Ring.- 3. Common Ester Side Chains in Sesquiterpene Lactones.- III. Germacranolides.- 1. Structural Types of Germacranolides and Biogenetic Considerations.- 2. Physical Methods of Structure Determination.- 2.1 Mass Spectra of Germacranolides.- 2.2 NMR Spectroscopy.- 2.21 Proton Spectroscopy.- 2.22 13C NMR.- 2.23 Conformational Considerations.- 2.3 UV and CD Spectra.- 2.31 UV Spectra.- 2.32 CD of the Lactone Ring.- 2.33 CD of the Cyclodecadiene Ring.- 2.4 X-Ray Diffraction.- 3. Chemical Transformations of Germacranolides.- 3.1 Hydrolysis, Relactonizations, and Esterifications.- 3.2 Reductions and Oxidations.- 3.3 Cyclization Reactions of Germacranolides.- 3.4 Cope Rearrangements of Germacranolides.- 3.5 Photochemical Reactions of Germacranolides.- IV. Eudesmanolides and Biogenetic Derivatives.- 1. Structural, Biosynthetic, and Biogenetic Considerations.- 2. Physical Methods of Structure Determination.- 3. Chemical Transformations of Eudesmanolides.- 3.1 Dehydrogenations, Hydrogenations, and Oxidations of Eudesmanolides.- 3.2 Selected Chemical and Photochemical Modifications and Transformations of Eudesmanolides.- V. Guaianolides and Seco-Guaianolides (Xanthanolides).- 1. Structural Types and Their Biogenesis.- 2. Selected Chemical Transformations of Guaianolides and Xanthanolides.- VI. Elemanolides.- VII. Pseudoguaianolides and Biogenetic Derivatives.- 1. Structural Types of Pseudoguaianolides and Their Biogenesis.- 2. Physical Methods of Structure Elucidation.- 3. Selected Chemical Transformations.- VIII. Eremophilanolides and Bakkenolides.- IX. Special Structural Types and Minor Classes of Sesquiterpene Lactones.- 1. Drimanolides.- 2. Tutinanolides (Picrotoxins).- 3. Special Structural Types.- X. Sesquiterpene Lactones of Unknown Structure.- XI. Addendum.- References.- Index of Major Charts and Tables.- Author Index.

Volume

39 : Wien ISBN 9783211815304

Description

This volume is part of a series, inaugurated in 1938, now referred to simply as "Zechmeister" after its founder, L. Zechmeister. It contains contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a reconized authority in his field, and provides a comprehensive and up-to-date review of the topic in question. This title looks at the chemistry of organic natural products. It is addressed to biologists, technologists and chemists alike. The series can be used by the expert as a source of information and literature citations, and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

Carbohydrate Derivatives in the Asymmetric Synthesis of Natural Products.- I. Introduction.- II. Some Background Information.- III. Some Attributes of Carbohydrate Synthons.- 1. Enantiomeric Purity.- 2. Conformational Bias.- 3. Ready Proof of Structure.- 4. Latent Functionalities.- IV. Syntheses.- 1. Acyclic Transfer.- a) L-erythro-Biopterin.- b) Pyridomycin.- c) (+)- and (-)-Frontalin.- d) (+)- and (-)-exo-Brevicomin.- e) Erythronolide.- 2. Cyclic Transfer of Pyranoids.- a) Thromboxane.- b) Asperlin.- c) ?-Multistriatin.- 3. Cyclic Transfer of Furanoids.- a) (-)-Avenaciolide.- b) (+)-Avenaciolide.- c) (-)-Isoavenaciolide.- d) (-)-Canadensolide.- e) 11-Oxaprostaglandin.- f) d-Oxybiotin.- g) (+)-Biotin.- 4. Transcription.- a) Prostaglandins.- b) An Approach to Tetrodotoxin.- c) Chiral Cycloalkanes from Annulated Pyranosides.- d) Cyclopropano Pyranosides.- e) Cyclobutano Pyranosides.- f) Cyclohexano Pyranosides.- g) Cyclopentano Furanosides.- References.- Recent Advances in the Biology and Chemistry of Vitamin D.- I. Biology and Biochemistry of Vitamin D.- 1. Introduction.- 2. 25-Hydroxyvitamin D3 and l?,25-Dihydroxyvitamin D3.- 3. Calcium.- 4. 24(R) 25-Dihydroxyvitamin D3.- 5. 25,26-Dihydroxyvitamin D3.- 6. Clinical Aspects.- II. Partial and Total Synthesis.- 1. Introduction.- 2. Side Chain Modification.- a) 25-Hydroxycholesterols.- b) 24,25-Dihydroxycholesterol and 25,26-Dihydroxycholesterol.- c) Side Chain Analogs of Vitamin D.- 3. Ring Modified Sterols.- a) l?-Hydroxycholesterols.- b) Other A-Ring Modifications.- c) Reactions in the B-Ring of Sterols.- 4. Analogs Prepared by Modification of Vitamin D and Related Compounds.- 5. Total Synthesis.- a) A-Ring Precursors.- b) C-D Ring and Side Chain Fragments.- c) Other Approaches.- III. Photolytic and Thermal Conversions of the Vitamin D Isomers.- 1. Photolysis of the Provitamin.- 2. Photolysis of the Previtamin.- 3. Photolysis of Vitamin D.- 4. Thermolysis of Previtamin D.- References.- Stereochemistry of Naturally Occurring Carotenoids.- I. General Introduction.- II. Historical.- III. Methods and Application.- 1. X-Ray Crystallography.- 2. Electronic Spectra.- 3. Vibrational Spectra.- 4. Proton Nuclear Magnetic Resonance Spectroscopy.- 5. 13C Nuclear Magnetic Resonance Spectroscopy.- a) Authentic Carotenoids.- b) Use in Structural Elucidation.- 6. Optical Rotatory Dispersion and Circular Dichroism.- 7. Linear Dichroism.- 8. High Pressure Liquid Chromatography.- 9. Horeau Method.- 10. Oxidative Degradation.- 11. Partial Synthesis.- 12. Total Synthesis.- a) Racemic Carotenoids.- b) Optically Active Model Carotenoids.- c) Optically Active Carotenoids.- d) Z-Isomers.- IV. Geometrical Isomerism.- V. Established Chirality.- VI. Chirality and Biogenetic Relationships.- 1. De novo Synthesis.- 2. Metabolic Transformations.- 3. Carotenoproteins.- References.- Chemistry and Biochemistry of ?-Glutamyl Derivatives from Plants Including Mushrooms (Basidiomycetes).- I. Introduction.- II. Nomenclature.- III. Structures and Distribution of ?-Glutamyl Derivatives from Plants.- 1. ?-Glutamyl Derivatives of Protein Amino Acids.- 2. ?-Glutamyl Derivatives of Non-Protein Amino Acids Which Do not Contain Sulphur or Selenium.- 3. ?-Glutamyl Derivatives of Non-Protein Amino Acids Containing Sulphur or Selenium.- 4. ?-Glutamyl Derivatives of Amines.- 5. Distribution Patterns for the ?-Glutamyl Derivatives.- VI. Chemical, Spectroscopic, and Analytical Properties of ?-Glutamyl Derivatives.- 1. pK-Values.- 2. Optical Activity.- 3. Infrared Spectra.- 4. NMR-Spectra.- 5. Gas Chromatography, Mass Spectroscopy, and Combined Gas Chromatography-Mass Spectroscopy.- 6. Paper Chromatography.- 7. Paper Electrophoresis.- 8. Ion-Exchange Chromatography.- 9. Degradation and General Chemical Properties of ?-Glutamyl Derivatives.- 10. Isolation Procedures and Stability of ?-Glutamyl Derivatives.- 11. Establishment of the ?-Linkage.- V. Isolation and Structure Determination of Individual Compounds.- 1. ?-L-Glutamyl-?-cyano-l-alanine.- 2. Linatine (l-[(N-?-l-Glutamyl)amino]-D-proline).- 3. ?-Glutamylvalylglutamic Acid.- 4. ?-L-Glutamyl-l-phenylalanyl-l-willardiine.- 5. ?-L-Glutamyl-?-l-glutamyl-l-phenylalanine.- 6. ?-Glutamylmarasmine (?-l-Glutamyl-3-(methylthiomethylsulphinyl)-l-alanine).- 7. Lentinic Acid (2- ?-l-Glutamylamino-4,6,8,10,10-pentaoxo-4,6,8,10-tetrathiaundecanoic Acid).- 8. N,N-bis-(?-Glutamyl)-3,3?-(1-methylethylene-1,2-dithio)-dialanine.- 9. ?-l-Glutamyl-L-cysteinyl-?-alanine.- 10. ?-l-Glutamyl-S-(prop-1-enyl)-cysteinyl-S-(prop-1-enyl)-l-cysteine sulphoxide.- 11. ?-l-Glutamyl-S-(2-carboxypropyl)-l-cysteinylglycinfe.- 12. ?-Glutamyl-?-glutamylmethionine.- 13. N5-(1-Methyl-2-oxopentyl)-l-glutamine.- 14. N5-(2-Cyanoethyl)-l-glutamine.- 15. Coprine (N5-(l-Hydroxycyclopropyl)-l-glutamine).- 16. N5-(3,4-Dioxocyclohexa-l,5-dien-l-yl)-l-glutamine.- 17. Agaritine (N5-[(4-Hydroxymethylphenyl)amino]-l-glutamine).- VI. Synthesis.- 1. General Discussion.- 2. Linatine (l-[(N- ?-l-Glutamyl)amino]-d-proline).- 3. Hypoglycine B (?-L-Glutamyl-(2S,1?R)-3-methylene-cyclopropyl)-alanine.- 4. Coprine (N5-(l-hydroxycyclopropyl)-l-glutamine).- 5. Agaridoxin (N5-(3,4-Dihydroxyphenyl)-l-glutamine).- 6. Agaritine (N5-[(4-Hydroxymethylphenyl)amino]-l-glutamine).- VII. Biosynthesis and Transformations of ?-Glutamyl Derivatives in Plants.- 1. Glutathione in Plants and Its Relationship to Other Plant ?-Glutamyl Derivatives.- 1.1. Occurrence and Isolation of Glutathione.- 1.2. Biosynthesis of ?-Glutamylcysteine and Glutathione.- 1.3. The Function of Glutathione in Plants.- 1.4. Degradation of Glutathione in Plants.- 2. Biosynthesis of Glutamine in Plants.- 3. ?-Glutamyl Transferases in Plants.- 4. Degradation Systems for ?-Glutamyl Derivatives in Plants.- 5. Occurrence of ?-Glutamyl Derivatives in Different Parts of Plants and During the Life Cycles of Plants.- 6. Specific Systems for Biosynthesis and Degradation of Individual ?-Glutamyl Derivatives.- 6.1. ?-l-Glutamyl-?-cyano-l-alanine.- 6.2. ?-Glutamyl Derivatives of Sulphur-Containing Amino Acids in Allium Species.- 6.3. Lentinic Acid and ?-Glutamylmarasmine.- 6.4. Theanine (N5-Ethyl-l-glutamine) and N5-Methyl-l-glutamine.- 6.5. N5-(4-Hydroxyphenyl)-l-glutamine, Agaridoxin (N5-(3,4-Dihydroxyphenyl)-l-glutamine), and N5-(3,4-Dioxocyclohexa-l,5-dien-l-yl)-l-glutamine.- 7. The ?-Glutamyl Cycle and ?-Glutamyl Derivatives in Plants.- 7.1. The Cycle in Animals and Microorganisms.- 7.2. Evidence for the Presence in Plants of the Enzymes Involved in the ?-Glutamyl Cycle.- 7.3. Transport of Amino Acids Across Cell Membranes in Plants.- 8. Conclusions.- VIII. ?-Glutamyl Derivatives with Toxic or Other Specific Biological Properties.- 1. ?-l-Glutamyl-?-cyano-l-alanine and N5-(2-Cyanoethyl)-l-glutamine.- 2. Linatine (l-[(N- ?-l-Glutamyl)amino]-d-proline).- 3. HypoglycineB(?-L-Glutamyl-(2S,1?R)-3-(methylenecyclopropyl)-alanine).- 4. ?-l-Glutamyl-Se-methylseleno-l-cysteine.- 5. Coprine (N5-(l-Hydroxycyclopropyl)-l-glutamine).- 6. N5-(3,4-Dioxocyclohexa-l,5-dien-l-yl)-l-glutamine.- IX. Compounds Structurally Related to ?-Glutamyl Derivatives from Plants.- X. Summary.- Acknowledgements.- Addendum.- References.- Author Index.

Volume

40 : Wien ISBN 9783211816240

Description

This volume is part of a series, inaugurated in 1938, now referred to simply as "Zechmeister" after its founder, L. Zechmeister. It contains contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a reconized authority in his field, and provides a comprehensive and up-to-date review of the topic in question. This title looks at the chemistry of organic natural products. It is addressed to biologists, technologists and chemists alike. The series can be used by the expert as a source of information and literature citations, and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

Chemistry of Synthetic Immunomodulant Muramyl Peptides.- I. From Freund's Adjuvant to MDP.- II. Synthesis of N-acetyl-muramyl-L-alanyl-D-isoglutamine (MDP).- 1. Protected Dipeptide Derivatives.- 2. Protected N-acetyl-muramyl Derivatives.- 3. Coupling of Protected Muramic Acid and Dipeptide Derivatives.- 4. Deprotecting Procedures.- 5. Synthesis of Labelled MDP.- III. Synthesis of Other N-acetyl-muramyl-dipeptides, Analogues and Derivatives of MDP.- 1. Modifications of the Peptide Moiety.- 2. Modifications of the Carbohydrate Moiety.- IV. Synthesis of N-acetyl-muramyl-tri-, tetra-, and -pentapeptides, and of Some Analogs Bearing a Lipophilic Group at the C-terminal End.- 1. Substitution of the ?-amide Group of MDP by a Free or Amidated Amino Acid.- 2. Lengthening of the Peptide Chain at the Carboxyl Function of MDP.- 3. Lipophilic Derivatives of N-acetyl-muramyl-L-alanyl-D-isoglutaminyl-L-alanine.- V. Synthesis of N-acetyl-?-D-glucosaminyl-(1-4)-N-acetyl-muramyl-peptides.- VI. Synthesis of Oligomers and Conjugates of MDP.- 1. Synthesis of Oligomers of MDP.- 2. Synthesis of Conjugates of MDP.- VII. Mass Spectrometry of MDP and Analogues.- VIII. 13C-NMR Spectrometry of MDP and Derivatives.- IX. Analysis of MDP.- Addendum.- References.- Appendix: Leading References on Biological Activities of MDP and Derivatives.- The Chemistry of Longifolene and Its Derivatives..- I. Introduction.- II. Isolation, Occurrence.- III. Structure.- IV. Synthesis.- V. Isolongifolene.- 1. Structure.- 2. Synthesis.- 3. Mechanism of Rearrangement.- VI. Reactions of Longifolene.- 1. "Normal" Reactions.- a) Addition Reactions.- b) Substitution Reactions.- 2. Skeletal Rearrangements.- a) Simple Wagner-Meerwein Rearrangements.- b) Deep-Seated Rearrangements.- 3. Steric Diversion.- a) Electrophilic Additions.- b) Oxidations.- 4. Transannular Reactions.- a) Radical Reactions.- b) Ionic Reactions.- c) Lead Tetraacetate Oxidation of Longifolols.- 5. Conversions into Other Sesquiterpene Skeletons.- 6. Miscellaneous Transformations.- VII. Reactions of Isolongifolene.- 1. Epoxidation and Reactions of Epoxide.- 2. Addition of Halogens and Pseudo-Halogens.- VIII. Ultraviolet Absorption of Some Longifolene Derivatives.- IX. Biosynthesis.- X. Longifolene in Industry.- References.- Homoisoflavanones and Biogenetically Related Compounds..- 1. Introduction.- 2. Isolation and Identification.- 2.1. Isolation.- 2.2. Chromatography.- 3. Structure and Nomenclature.- 3.1. General Aspects and Nomenclature.- 3.2. Ultraviolet-Visible Spectroscopy.- 3.3. Infrared Spectroscopy.- 3.4. Nuclear Magnetic Resonance Spectroscopy.- 3.4.1. 1H-NMR Spectra.- 3.4.2. 13C-NMR Spectra.- 3.5. Mass Spectrometry.- 3.6. Optical Activity and Absolute Configuration.- 4. Chemical Transformations and Syntheses.- 4.1. Synthesis of the Skeleton.- 4.2. Routes to Eucomol.- 4.3. Isomerization and Hydrogenation Reactions of the 3(9)-Double Bond.- 4.4. Deuterium Exchange Reactions.- 4.5. Acylation and Deacylation Reactions.- 4.6. Alkylation and Dealkylation Reactions.- 4.7. Further Reactions of Eucomol.- 4.8. Chemistry of Brazilin and Hematoxylin.- 5. Biosynthesis.- 6. Biological Activity.- 7. Chemotaxonomy.- References.- Naturally Occurring Phenalenones and Related Compounds..- I. Introduction.- II. Phenalenones and Related Metabolites from Fungi.- A. Occurrence.- B. Structure and Chemistry.- C. Synthesis.- D. Biosynthesis.- E. Biological Activity.- III. Phenalenones and Related Metabolites in Higher Plants.- A. Occurrence.- B. Structure Determination.- C. Spectroscopic Methods.- D. Synthesis.- E. Biological Activity.- F. Biosynthesis.- References.- Molecular Mechanisms of Enzyme-Catalyzed Dioxygenation. (An Interdisciplinary Review.).- I. Introduction.- II. Some Basic Chemistry of Molecular Oxygen.- III. Precedents for Metal-Activation of Dioxygen.- 1. How Would an Iron- or Copper-Protein Interact with Molecular Oxygen?.- 2. Precedents for the Transfer of Dioxygen Within the Co-ordination Sphere.- 3. Precedents for the Reaction of Co-ordinated Dioxygen with Free Substrates.- 4. Free Forms of Activated Dioxygen Generated by Metals.- IV. Precedents for Metal Activation of Organic Substrates.- V. The Double Bond-Cleaving Dioxygenases.- 1. Ene-diol Cleaving Dioxygenases.- 2. Extradiol-Cleaving Dioxygenases.- 3. Other Double Bond-Cleaving Dioxygenases.- VI. The Luciferases.- VII. Peroxidizing Dioxygenases.- VIII. Miscellaneous Dioxygenases.- 1. External Flavoprotein Dioxygenases.- 2. Sulfur Oxidizing Dioxygenases.- 3. Inositol Dioxygenase.- 4. Nitropropane Dioxygenase.- 5. Carotene Dioxygenase.- 6. Ribulose Bisphosphate Carboxylate/Oxygenase.- IX. ?-Keto Carboxylic Acid Decarboxylating Dioxygenases.- X. Summary.- Acknowledgments.- References.- Author Index.

Volume

41 : Wien ISBN 9783211816905

Description

The chemistry of condensed tannins has hitherto represented a relatively unattractive and therefore neglected area of study; one in which the weight of research effort involved is invariably disproportionate to the results achieved, in which the participating schools generally confine their approach to specific molecular species, and in which as yet no consensus has been reached regarding likely precursors. The problems which beset those engaged in this field represent a combined function of the abnormal complexity of the gradational range of oligomers of increasing mass and affinity for substrates which typify most extracts rich in tannins, and the consequent problem of their isolation and purification, the high chirality of tannin oligomers, the need to contend with the phenomenon of dynamic 'rotational isomerism about interflavanoid bonds in the IH n.m.r. spectral interpretation of their derivatives, the lack of precise knowledge regarding the points of bonding at nucleophilic centres, and the obvious limitations of a hitherto predominantly analytical approach. The last of these reflects the need for a general method of synthesis which permits unambiguous proof of both structure and absolute configuration also at higher oligomeric levels. With these objectives in mind we initiated a purely synthetic approach based on the premise that flavan-3,4-diols as source of electrophilic flavanyl-4-carbocations, and flavan-3-0Is as nucleophiles (cf 1,2) represent the prime initiators of a process of repetitive condensation in which the immediate products also represent the sequent nucleophilic substrates.

Table of Contents

The Metabolism of Gallic Acid and Hexahydroxydiphenic Acid in Higher Plants..- 1. Polyphenol Biosynthesis in Higher Plants - An Overview.- 2. Metabolites of Gallic Acid.- 2.1 Simple Esters - Occurrence and Structural Analysis.- 2.2 Depside Metabolites - Group A.- 2.3 Metabolites Formed by Oxidative Coupling of Galloyl Esters - Groups B and C.- 2.3.1 Hexahydroxydiphenoyl Esters.- 2.3.2 Dehydrohexahydroxydiphenoyl and Isohexahydroxydiphenoyl Esters..- 2.3.3 Hexahydroxydiphenoyl Metabolites - Group B.- 2.3.4 Hexahydroxydiphenoyl Metabolites - Group C.- 3. The Ellagitannins.- 4. Postscript.- References.- The Direct Biomimetic Synthesis, Structure and Absolute Configuration of Angular and Linear Condensed Tannins..- I. Introduction.- II. Bonding Positions at Nucleophilic Centres.- III. Conditions for Interflavanoid Bonding. Stereochemical Course of the Reaction. Chiroptical Method for Determining the Absolute Configuration at C-4.- IV. Direct Biomimetic Synthesis of Biflavanoids.- V. Direct Biomimetic Synthesis of "Angular" Triflavanoids.- VI. Biflavanoids and a "Linear" Triflavanoid with Terminal 3,4-Diol Function.- VII. Composition of the Metabolic Pool and Condensation Aptitudes of Tannin Precursors.- References.- Streptonigrin.- I. Introduction.- II. Isolation and Structure.- III. Structure Activity Relationships and Mechanism of Action.- IV. Biosynthesis.- V. Synthetic Studies.- References.- The Pyrrolizidine Alkaloids.- I. Introduction.- II. The Necine Bases.- 1. Structure and Stereochemistry.- a) 1-Hydroxymethylpyrrolizidines.- b) Pyrrolizidine Diols.- c) Pyrrolizidine Triols.- d) Dihydropyrrolizines.- 2. Synthesis of Necine Bases.- III. The Necic Acids.- 1. C6-Acids - Strigosic Acid.- 2. C8-Acids.- a) (-)-Curassavic Acid.- b) Crispatic Acid and Stereoisomers.- c) Monocrotalic Acid.- d) Latifolic Acid.- e) ?- and ?-Retusanecic Acids.- 3. C9-Acids.- 4. C10-Acids.- a) Retusaminic Acid.- b) Syneilesinolides A-C.- c) Ligularidenecic Acid.- d) Crotaverric Acid.- e) Petasinecic Acid.- f) cis-Nemorensic Acid.- 5. Orchid Acids.- IV. The Pyrrolizidine Alkaloids.- 1. Analytical Methods.- 2. Spectroscopy.- 3. Synthesis.- V. Pyrrolizidine Derivatives in the Lepidoptera.- VI. Biosynthesis.- 1. Necine Bases.- 2. Necic Acids.- VII. Pharmacology.- VIII. Table 1. List of Plant Genera Containing Pyrrolidine Alkaloids.- Table 2. Alkaloid Content of Plant Species Which Have Been Investigated.- Table 3. The Structures of the Pyrrolizidine Alkaloids.- References.- Addendum.- Alkaloids of Neotropical Poison Frogs (Dendrobatidae).- I. Introduction.- II. Batrachotoxins.- A. Structures.- B. Syntheses.- C. Biological Activity.- III. Pumiliotoxin-C Class (cis-decahydroquinolines).- A. Structures.- B. Syntheses.- C. Biological Activity.- IV. Histrionicotoxins.- A. Structures.- B. Syntheses.- C. Biological Activity.- V. Gephyrotoxins.- A. Structures.- B. Syntheses.- C. Biological Activity.- VI. Pumiliotoxin-A Class.- A. Structures.- B. Syntheses.- C. Biological Activity.- VII. Other Alkaloids.- A. Structures, Properties, and Occurrence.- References.- Author Index.

Volume

42 : Wien ISBN 9783211817063

Table of Contents

Chemical Constituents of the Hepaticae.- I. Introduction.- II. Chemical Constituents.- 1. Monoterpenoids.- 2. Sesquiterpenoids.- 2.1 Acoranes and Aristolanes.- 2.2 Aromadendranes and 2,3-Secoaromadendranes.- 2.3 Azulenes.- 2.4 Barbatanes (= Gymnomitranes) and Trichothecanes.- 2.5 Bicycloelemanes, Bicyclogermacranes and Vitranes.- 2.6 Bisabolanes.- 2.7 Cadinanes and Calamenanes.- 2.8 Caryophyllanes.- 2.9 Chamigranes, Copaanes and Ylanganes.- 2.10 Cuparanes.- 2.11 Drimanes.- 2.12 Elemanes.- 2.13 Eremophilanes.- 2.14 Eudesmanes.- 2.15 Farnesanes and Monocyclofarnesanes.- 2.16 Germaeranolides.- 2.17 Guaianes and Pseudoguaianes.- 2.18 Himachalanes, Longifolanes and Longipinanes.- 2.19 Humulanes.- 2.20 Maalianes.- 2.21 Pinguisanes.- 2.22 Miscellaneous.- 3. Diterpenoids.- 3.1 Kauranes.- 3.2 Labdanes.- 3.3 Pimaranes.- 3.4 Sacculatanes.- 3.5 Verrucosanes.- 3.6 Miscellaneous.- 4. Triterpenoids and Steroids.- 5. Aromatic Compounds.- 5.1 Benzoic Acid Derivatives.- 5.2 Cinnamic Acid Derivatives.- 5.3 Bibenzyls.- 5.4 Indole Derivatives.- 5.5 Miscellaneous.- 5.6 Flavonoids and Dihydrochalcones.- 6. Lipids.- 6.1 n-Alkanes.- 6.2 Alkanoic Acids.- 7. Miscellaneous.- III. Biologically Active Substances.- 1. Pungency and Bitterness.- 2. Allergenic Contact Dermatitis.- 3. Anticancer Activity.- 4. Tumor Promoting Activity.- 5. Antimicrobial and Antifungal Activity.- 6. Antifeedant Activity.- 7. Plant Growth Regulatory Activity.- 8. Piscicidal Activity and Others.- IV. Chemosystematics of the Hepaticae.- 1. Jungermanniidae.- 2. Marchantiidae.- Index of Major Charts and Tables.- References.- Cross-Reactions of Plant Polysaccharides in Antipneumococcal and Other Antisera, an Update.- 1. Introduction.- 2. Plant Gums of Original Publication.- 3. Discussion of the Data in Table 1.- Author Index.

Volume

43 : Wien ISBN 9783211817414

Description

This volume is part of a series, inaugurated in 1938, now referred to simply as "Zechmeister" after its founder, L. Zechmeister. It contains contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a reconized authority in his field, and provides a comprehensive and up-to-date review of the topic in question. This title looks at the chemistry of organic natural products. It is addressed to biologists, technologists and chemists alike. The series can be used by the expert as a source of information and literature citations, and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

Naturally Occurring Isoflavonoids (1855-1981).- I. Introduction.- II. Distribution.- III. Biological Activity and Uses.- Table 1. Minor Properties and Uses of Some Isoflavonoid Compounds.- IV. Introduction to Tables 2, 3 and 4.- Acknowledgements.- Table 2. Naturally Occurring Isoflavonoid Aglycones.- A. Isoflavones.- a) Simple 5-Deoxy Isoflavones.- b) Complex 5-Deoxy Isoflavones.- c) Simple 5-Oxy Isoflavones.- d) Complex 5-Oxy Isoflavones.- e) Chloro Isoflavones.- B. Isoflavonequinone.- C. Coumaranochromones.- D. Isoflavanones.- a) Simple 5-Deoxy Isoflavanones.- b) Complex 5-Deoxy Isoflavanones.- c) Simple 5-Oxy Isoflavanones.- d) Complex 5-Oxy Isoflavanones.- E. Rotenoids.- a) Simple 12a-Deoxy Rotenoids.- b) Complex 12a-Deoxy Rotenoids.- c) Simple 12a-Oxy Rotenoids.- d) Complex 12a-Oxy Rotenoids.- F. Dehydrorotenoids.- a) Simple Dehydrorotenoids.- b) Complex Dehydrorotenoids.- G. Pterocarpans.- a) Simple 6a-Deoxy Pterocarpans.- b) Complex 6a-Deoxy Pterocarpans.- c) Simple 6a-Oxy Pterocarpans.- d) Complex 6a-Oxy Pterocarpans.- H. Pterocarpanones.- a) Simple Pterocarpanones.- b) Complex Pterocarpanones.- I. Pterocarpenes.- a) Simple Pterocarpenes.- b) Complex Pterocarpenes.- J. Pterocarpenequinones.- K. Isoflavans.- a) Simple Isoflavans.- b) Complex Isoflavans.- c) Isoflavan Dimer.- L. Isoflavanol.- M. Isoflavanquinones.- N. Isoflavenes.- a) Simple Isoflavenes.- b) Complex Isoflavenes.- O. Coumestans.- a) Simple Coumestans.- b) Complex Coumestans.- P. 3-Arylcoumarins.- a) Simple 4-Deoxy 3-Arylcoumarins.- b) Complex 4-Deoxy 3-Arylcoumarins.- c) Simple 4-Oxy 3-Arylcoumarin.- d) Complex 4-Oxy 3-Arylcoumarins.- Q. ?-Methyldeoxybenzoins.- a) Simple ?-Methyldeoxybenzoins.- b) Complex ?-Methyldeoxybenzoins.- R. 2-Arylbenzofurans of Leguminous Origin.- a) Simple 2-Arylbenzofurans.- b) Complex 2-Arylbenzofurans.- S. 2-Arylbenzofuranquinone.- Table 3. Naturally Occurring Isoflavonoid Glycosides.- A. Isoflavone Glycosides.- B. Isoflavanone Glycosides.- C. Rotenoid Glycosides.- D. Pterocarpan Glycosides.- E. Coumestan Glycosides.- F. Deoxybenzoin Glycoside.- Table 4. Partially Identified Isoflavonoids, and Some Substances Possibly of an Isoflavonoid Nature Found in the Family Leguminosae.- Molecular Weight Index.- Trivial Name Index.- Source Index.- References.- Note Added in Proof.- The Sarpagine-Ajmaline Group of Indole Alkaloids.- 1. Introduction.- 2. Skeletal Types.- 2.1. Sarpagine Type Alkaloids.- 2.1.1. Polyneuridine Subgroup.- 2.1.2. Akuammidine Subgroup.- 2.1.3. Voamonine-Voacoline.- 2.1.4. Talpinine.- 2.1.5. Vomifoline Subgroup.- 2.2. Ajmaline Type Alkaloids.- 2.2.1. Perakine Subgroup.- 2.2.2. Quebrachidine Subgroup.- 2.2.3. Indolenine Subgroup.- 2.2.4. Tetraphyllicine Subgroup.- 2.2.5. 17-Keto Alkaloids.- 2.2.6. Ajmaline Subgroup.- 2.3. Bisindole Alkaloids.- 3. Occurrence.- 4. Biogenesis.- 4.1. Barger-Hahn-Robinson Theory.- 4.2. Wenkert-Bringi Hypothesis.- 4.3. Thomas-Wenkert Hypothesis.- 4.4. Leete's Postulate.- 4.5. Battersby's Observations.- 4.6. Mevalonoid Origin of the Non-Tryptophan Unit.- 4.7. Van Tamelen's Theory.- 4.8. Stockigt's Work.- 4.9. Court's Observations.- Interlude: Enzymic Transformations.- 4.10. The Concise Biogenetic Representation.- 4.10.1. Sarpagine Group.- 4.10.2. Ajmaline Group.- 4.10.3. Bisindole Alkaloids.- 5. Chemistry.- 5.1. Conversion of Normacusine B to Macroline.- 5.2. Photochemistry.- 6. Syntheses.- 6.1. Total Syntheses of Ajmaline.- 6.1.1. Masamune Synthesis.- 6.1.2. Mashimo and Sato Synthesis.- 6.1.3. The Biogenetic-Type Synthesis of van Tamelen and Olivier.- 6.2. Partial Synthesis of Talpinine.- 6.3. Synthesis of the Ring Skeleton.- 6.4. Bisindole Alkaloids.- 7. Spectroscopy.- 7.1. Carbon-13 NMR Spectroscopy.- 7.1.1. Sarpagine Group.- 7.1.2. Ajmaline Group.- 7.2. Mass Spectrometry.- 7.2.1. Sarpagine Group.- 7.2.2. Ajmaline Group.- 8. Pharmacology.- References.- Author Index.

Volume

44 : Wien ISBN 9783211817544

Description

This volume is part of a series, inaugurated in 1938, now referred to simply as "Zechmeister" after its founder, L. Zechmeister. It contains contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a reconized authority in his field, and provides a comprehensive and up-to-date review of the topic in question. This title looks at the chemistry of organic natural products. It is addressed to biologists, technologists and chemists alike. The series can be used by the expert as a source of information and literature citations, and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

Pro-Inflammatory, Tumour-Promoting and Anti-Tumour Diterpenes of the Plant Families Euphorbiaceae and Thymelaeaceae.- I. Introduction.- II. Classification of Structural Types.- III. Botanical Considerations.- 1. The Family Euphorbiaceae.- 2. The Family Thymelaeaceae.- IV. Biosynthetic Relationships.- V. Isolation of Diterpenes.- VI. The Macrocyclic Diterpenes.- 1. Casbane Type.- 2. Jatrophane Type.- 3. Lathyrane Type.- 4. Jatropholane and Crotofolane Types.- 5. Rhamnofolane.- VII. Tigliane Diterpenes.- 1. Phorbol and Its Esters.- 2. Distribution of Phorbol Esters in Plants.- 3. Identification of Phorbol Esters.- 4. 4-Deoxyphorbol Esters.- 5. Other 4-Deoxyphorbol Derivatives.- 6. Identification of 4-Deoxyphorbol Esters.- 7. 12-Deoxyphorbol Esters.- 8. Identification of 12-Deoxyphorbol Esters.- 9. 12-Deoxy-16-Hydroxyphorbol Esters.- 10. Other 12-Deoxyphorbol Derivatives.- 11. 16-Hydroxyphorbol Esters.- VIII. Ingenane Derivatives.- 1. Ingenol.- 2. Distribution of Ingenol Esters in Plants.- 3. 5-Deoxyingenol.- 4. 16-Hydroxyingenol.- 5.. 13-Hydroxyingenol.- 6. 13,19-Dihydroxyingenol.- 7. 20-Deoxyingenol.- IX. Daphnane Derivatives.- 1. Daphnetoxin Type.- 2. 12-Hydroxydaphnetoxin Type.- 3. Resiniferonol Type.- 4. 1-Alkyldaphnane Type.- X. Closing Remarks.- Acknowledgements.- References.- Bitter Principles of Cneoraceae.- I. Introduction.- II. Nomenclature and Classification.- III. Constitution and Configuration of Cneorins A, B, C and D.- 1. Structural Studies by Ozonolysis.- 2.. Establishment of Relative and Absolute Configuration.- 3. Carbon Skeleton of Cneorins A -D: Numbering of C-Atoms.- 4. Configuration of Cneorin-CI.- 5. Configuration of Cneorin B, BI and BIII.- a). Elucidation of the Configuration at Carbon Atoms 7 and 9.- b). Elucidation of the Configuration at Carbon Atoms 5, 10, 13 and 17.- c). Hydrogenolysis of Cneorins BIII and CIII.- d). The Steric Series B and C with (17R)- and (17 S)-Configuration.- 6. Intramolecular Cyclisation to Cneorins BII and CII.- 7.. Constitution and Configuration of Cneorins A and D and Pyrolysis of Cneorin-D.- IV. The Series of Stereoisomeric ?8(30)-Olefms.- V. Stereoisomeric Alcohols with an 8-OH Group and (5 S, 10 R)-Configuration.- VI. Cneorins and Tricoccins with a C-7 Carbonyl Group.- 1. Cneorin-F and Tricoccin-S14.- 2. The Tricoccins R9, R12 and Their Epi-compounds.- VII. C-7 Hemiacetals and Methylacetals with (5S, 10R, 17R)-Configuration.- 1. Cneorin K and K1.- 2. Tricoccin R1 and R10.- VIII. C-9 Hemiacetals with (5S, 8S, 10R-Configuration.- IX. Cyclic Peroxides.- X. Bitter Principles with a ?-Lactol Ring (C-15 Hemiacetals).- 1. Precursors of Known Cneoroids.- 2. C-15 Cycloacetals.- 3. ?-Lactols with the Partial Structure of Ring A of Obacunone.- XI. Tetranortriterpenoids from Cneoraceae.- 1. 3,4-seco-Meliacans.- 2. 7,8-seco-Meliacans.- 3. 3,4-16,17-seco-Meliacans (Limonin Group).- 4. 3,4-7,8-16,17-seco-Meliacans.- XII. Protolimonoids.- 1. Tirucallan-(20 S)-Triterpenoids.- 2. Apotirucallan-(20 S)-Triterpenoids.- XIII. Comments on Biosynthesis of Cneorins and Tricoccins.- XIV. Tables of Natural Bitter Principles from Cneoraceae.- 1. Cneorins from Neochamaelea pulverulenta (Vent.) Erdtm. of Known Constitution and Configuration.- 2. Cneorins of Unknown Structure.- 3. Tricoccins from Cneorum tricoccon L. of Known Constitution and Configuration.- 4. Tricoccins of Unknown Structure.- References.- Chemical and Biological Aspects of Marine Monoterpenes.- I. Introduction.- II. Structural Variation.- III. The Role of Halogens in Biogenesis.- 1. Introduction.- 2. Acyclic Structures.- 3. Monocyclic Structures.- IV. Relationships Between Taxonomy and Occurrence of Structural Types.- 1. Introduction.- 2. The Plocamiaceae Family.- 3. The Rhizophyllidaceae Family.- 4. The Ceramiaceae Family.- 5. Degraded and Mixed Biogenetic Monoterpenes.- 6. Conclusion.- V. Metabolite Transfer and Biological Activity.- VI. Spectroscopic and Chemical Properties.- 1. Introduction.- 2. Halogen Content and Regiochemistry.- 3. Stereochemistry.- 4. Artifacts.- 5. Conclusions.- VII. Physical and Spectroscopic Tables.- 1. Table 13 A-H: Summary of Structures and Carbon-13 NMR Chemical Shifts.- 2. Table 14: Physical Properties.- Acknowledgement.- References.- The C-Nucleoside Antibiotics.- I. Introduction.- II. General Aspects of C-Nucleosides.- III. Showdomycin.- IV. The Formycins.- V. Pyrazofurin (Pyrazomycin).- VI. Oxazinomycin (Minimycin).- VII. The Ezomycins.- VIII.. Biosynthesis of C-Nucleoside Antibiotics.- References.- Author Index.

Volume

45 : Wien ISBN 9783211817551

Table of Contents

The Chemistry of the Limonoids from Meliaceae.- I. Introduction.- II. Classes of Limonoids.- 1. Group I. Protolimonoids and Related Triterpenes.- 2. Group II. Havanensin Group.- 3. Group III. Gedunin Group (Ring D Opened).- 4. Group IVa. Limonoids with Rings B and D Opened.- 5. Group IVb. Mexicanolide Group.- 6. Group IVc. Phragmalin Group.- 7. Group V. Methyl Ivorensate Group (Rings A, B and D Opened).- 8. Group VI. Obacunol Group (Rings A and D Opened).- 9. Group VII. Nimbin Group (Ring C Opened).- 10. Group VIII. Toonafolin Group (Ring B Opened).- 11. Group IX. Evodulone Group (Ring A Opened).- 12. Group X. Prieurianin Group (Rings A and B Opened).- III. Outlook for Future Work.- IV. Tables.- Table 1. Group 1.- Table 2. Group II.- Table 3. Group III.- Table 4. Group IV.- Table 5. Group V.- Table 6. Group VI.- Table 7. Group VII.- Table 8. Group VIII.- Table 9. Group IX.- Table 10. Group X.- Table 11. Unknown or Doubtful Structures.- References.- Recent Progress in the Chemistry of Liehen Substances.- 1. Introduction.- 2. Carbohydrates.- 2.1 Mono- and Oligosaccharides.- 2.2 Polysaccharides.- 3. Amino-acid Derivatives.- 4. 4-Ylidenetetronic Acids.- 5. Aliphatic Acids and Related Compounds.- 5.1 Straight Chain Aliphatic Acids and Related Esters, Alcohols and Lactones.- 5.2 Cn + C4 Derived Aliphatic Acids and Lactones.- 5.2.1 Acylic Acids.- 5.2.2 ?-Lactonic Acids.- 5.2.3 ?-Lactonic Acids.- 5.3 Biogenetically Atypical Aliphatic Acids and Esters.- 6. Mononuclear Phenolic Compounds from Lichens.- 6.1 Orsellinic Acid Derivatives.- 6.2 Phloroglucinol Derivatives.- 6.3 Phthalide Derivatives.- 7. Chromones.- 8. Xanthones.- 9. Anthraquinones arid Biogenetically Related Compounds.- 9.1 Anthraquinones.- 9.2 Bisanthraquinones and Bisxanthones.- 9.3 Naphthoquinones.- 10. Depsides.- 10.1 Structural Variation.- 10.1.1 Orcinol Para-Depsides.- 10.1.2 Orcinol ?-Orcinol Para-Depsides.- 10.1.3 ?-Orcinol Para-Depsides and meta-Depsides.- 10.1.4 Orcinol Tridepsides.- 10.1.5 Orcinol meta-Depsides.- 10.2 Separation of Liehen Depsides.- 10.3 Identification of Liehen Depsides.- 10.3.1 The Structure of Isolated Depsides.- 10.3.2 Identification and Detection of Depsides Without Isolation.- 10.4 Partial Synthesis of Depside Derivatives.- 10.5 Total Synthesis of Depsides.- 10.5.1 Para-Orcinol Depsides.- 10.5.2 Olivetoric Acid and Related Depsides.- 10.5.3 Synthesis of ?-Orcinol Para-Depsides, ss-Orcinol raeta-Depsides, meta-Orcinol Depsides and Orcinol Tridepsides.- 11. Depsidones and Related Diphenyl Ethers.- 11.1 Introduction.- 11.2 Orcinol Depsidones.- 11.3 ?-Orcinol Depsidones.- 11.4 Mixed Depsidones.- 11.5 Fungal Depsidones.- 11.6 Biosynthesis of Depsidones.- 12. Dibenzofurans and Biogenetically Related Compounds.- 12.1 Dibenzofurans.- 12.2 Usnic Acids.- 12.3 The Diphenyl Ether Leprolomin.- 13. Mevalonic Acid Derivatives.- 13.1 A Sesterterpene.- 13.2 Triterpenoids.- 13.2.1 Hopanes.- 13.2.2 Dammaranes.- 13.2.3 Stictanes.- 13.3 Steroids.- 13.4 Carotenoids.- 14. Liehen Chemotaxonomy.- 14.1 Replacement Type Compounds and Chemosyndromic Variation.- 14.2 Accessory Metabolites.- References.- Paralytic Shellfish Poisons.- I. Introduction.- II. Occurrence and Isolation.- III. Structure and Chemistry.- A. Saxitoxin.- B. Neosaxitoxin.- C. Gonyautoxin-II and -III.- D. Gonyautoxin-I and -IV.- E. Gonyautoxin-V and -VI (B1 and B 2 Toxins).- F. Gonyautoxin-VII.- G. Gonyautoxin-VIII (C2 Toxin).- H. C3 and C 4 Toxins.- IV. Synthesis.- V. Biosynthesis.- VI. Pharmacology.- References.- Aiithor Index.

Volume

46 : Wien ISBN 9783211818046

Table of Contents

• Saponins of Ginseng and Related Plants.- I. Introduction.- II. Structure and Chemistry of Dammarane Sapogenins.- 1. Panaxadiol, an Artifact.- 2. Acid Catalyzed Reactions of Dammarane Type Triterpenes and the Genuine Sapogenin of Ginseng.- III. Structures of Ginseng Saponins (1).- 1. Structure of the Prosapogenin Common of Ginsenosides-Rb1, -Rb2, -Rb3, -Rc and-Rd.- 2. Ginsenosides-Rb1, -Rb2, -Rb3, -Rc and -Rd, Saponins of 20(S)-Protopanaxadiol.- 3. Panaxatriol and Ginsenosides-Rf, -Rg1, -Rg2 and 20-Gluco-ginsenoside-Rf (glc-Rf), Saponins of 20(S)-Protopanaxatriol.- IV. Modern Techniques Used in Structure Determination.- 1. Enzymatic Hydrolysis of Glycosides.- 2. 13C-NMR Spectroscopy of Dammarane Type Triterpenes.- 3. Glycosylation Shifts in 13C-NMR Spectra.- 4. Mass Spectrometry.- V. Structures of Ginseng Saponins (2).- 1. Minor Saponins of Ginseng, Ginsenosides-Ra1, -Ra2, -Ra3, and -Rh1.- 2. Saponins of Red Ginseng.- VI. Analysis of Ginseng Saponins.- 1. Quantitative Analysis of Panaxadiol and Panaxatriol.- 2. Separative Analysis of Ginsenosides.- 3. Localization of Saponins in Ginseng Roots.- 4. Seasonal Variation of Ginseng Root Constituents.- VII. Production of Saponins by Tissue Culture.- VIII. Saponins of Other Panax spp..- 1. Saponins of American Ginseng and Dwarf Ginseng.- 2. Saponins of Chinese Sanchi-Ginseng.- 3. Saponins of P. japonicus Rhizomes (Japanese Chikusetsu-Ninjin and Chinese Zhujie-Shen).- 4. Saponins of Rhizomes of P. japonicus var. major (Chinese Zu-Tzi-Shen).- 5. Saponins of P. zingiberensis Rhizomes.- 6. Saponins of Rhizomes of Himalayan Panax, P. pseudo-ginseng subsp. himalaicus.- IX. Saponins of Aerial Parts of Panax spp..- 1. Saponins of P. ginseng Leaves and Flower Buds.- 2. Saponins of Leaves of Himalayan and American Panax spp..- 3. Saponins of Aerial Parts of Chinese Panax spp..- 4. Saponins of Leaves of P. japonicus (Japanese Chikusetsu-Ninjin).- X. Syntheses of Dammarane Sapogenins.- XI. Other Constituents of Ginseng Roots.- 1. Ether-Soluble Compounds.- 2. Carbohydrates.- 3. Nitrogen-Containing Compounds.- XII. Pharmaceutical Studies of Ginseng Saponins.- XIII. Biological Activities of Ginseng.- References.- Diterpenoids of Rabdosia Species.- I. Introduction.- II. Isolation and Structure Determination.- 1. Structure Determination of Enmein in Outline.- 2. Listing of Rabdosia Diterpenoids and Their Sources.- 3. Properties and Reactions Important for Structure Determination.- a) Spectral Aspects and Important Reactions for Ring D Structure Determination.- b) Structure Determination of ent-Kaurane-type Diterpenoids.- c) Structure Determination of ent-6,7-Secokaurane-type Diterpenoids.- d) Structure Determination of ent-8,9-Secokaurane-type Diterpenoids.- e) Structure Determination of ent-7,20-Bonded Kaurane-type Diterpenoids.- f) Structure Determination of an ent-Gibberellane-type Diterpenoid.- III. Chemical Conversions.- 1. Conversion of Rabdosia Diterpenoids to ent-Kaurane and ent-Kaurene.- 2. Conversion of Enmein to ent-Abietane.- 3. Conversion of Enmein and Trichokaurin to Aconite Alkaloids.- 4. Conversion of Enmein into Gibberellins.- 5. Interconversions among Rabdosia Diterpenoids.- a) Biogenetic-type Conversion (Kaurene type ? 6,7-Secokaurene-type).- b) Retrobiogenetic-type Conversions.- 6. Other Topics.- a) Stereochemistry of Ring D in Enmein Derivatives.- b) Hypoiodite Reaction of Enmein Derivatives.- c) Isolation of Dihydroenmein and Its Conversion to Enmein.- IV. Total Synthesis of Enmein.- V. Biosynthesis.- VI. Physiological Activity.- 1. Antibacterial Activity.- 2. Antitumor Activity.- 3. Insect Growth Inhibitory Activity.- 4. Bitterness.- References.- The Quinazoline Alkaloids.- I. Introduction.- II. Simple Substituted Quinazolin-4-ones.- 1. General Characteristics.- 2. Arborine.- 3. Glycorine.- 4. Glycosmicine.- 5. Glycosminine.- 6. Glycophymoline.- 7. Pegamine.- 8. Quinazolines of Zanthoxylum arborescens.- 9. Febrifugine and Isofebrifugine.- III. The Pyrroloquinazolines.- 1. Vasicine (Peganine), Vasicinone, 7-Hydroxypeganine, Vasicinolone, Vasicol, Nordine and Deoxyvasicinone.- 2. Anisotine, Anisessine, Aniflorine, Deoxyaniflorine and Sessiflorine.- 3. Vasicoline, Vasicolinone and Adhatodine.- 4. Peganidine, Isopeganidine, Deoxypeganidine, Dipegine and Peganol.- IV. The Pyridoquinazolines.- V. The Indolopyridoquinazolines.- 1. Rutaecarpine and Related Alkaloids.- 2. Evodiamine and Dehydroevodiamine.- 3. Hortiamine and Hortiacine.- 4. Euxylophorine A-D
• Euxylophoricine A-F.- 5. Paraensine.- VI. Quinazolines Produced by Microorganisms.- 1. Tryptanthrin.- 2. Quinazolines of Pseudomonas Species.- 3. Quinazolines of Aspergillus Species.- 4. Quinazolines of Streptomyces.- 5. Chrysogine.- VII. Quinazolines Found in Animals.- 1. Glomerin and Homoglomerin.- 2. Tetrodotoxin.- VIII. Biosynthesis.- 1. Pyrroloquinazolines.- 2. Arborine and Glomerin.- 3. Indolopyridoquinazolines.- 4. Fungal Metabolites.- IX. Biological Activity of Natural and Synthetic Quinazolines.- Acknowledgement.- References.- Author Index.

Volume

47 ISBN 9783211818640

Description

More than ten years have elapsed since the publication of a compre- hensive review on the quassinoids, the bitter principles of the Simaroubaceae family (80). Interest in these terpenoids has increased enormously in recent years due in part to the finding of the American National Cancer Institute in the early 1970s that these compounds display marked antileukemic activity. Furthermore, a wide spectrum of other biological properties for the quassinoids has been discovered and studies on chemical modifications of inactive members to yield biologically active ones were undertaken. New structures have been established also and numerous synthetic approaches have been developed which include the total synthesis of the parent compound, quassin (p. 250) and also that of castelanolide (p. 253). It is intended that this present chapter will be an extension of my first review in this series and will contain references up to September 1984. A short article on some aspects of this subject was published recently (81). II. Quassinoid General Features In reviewing the essential features of the quassinoids, the new structural types discovered during the last decade will be emphasised. The quassinoids can be divided into distinct groups according to their basic skeletons. The five skeletons observed are presented on Chart 1.

Table of Contents

Naturally Occurring ?-Lactams.- I. Introduction.- II. Nocardicins.- III. Monobactams.- IV. Penicillins.- V. Clavulanic Acid.- VI. Olivanic Acids, Thienamycin and Other Carbapenems.- VII. Cephalosporins and Cephamycins.- VIII. Pachystermines, Wild-Fire Toxin and Antimetabolites.- IX. Biosynthesis.- 1. Biosynthesis of Nocardicin A.- 2. Biosynthesis of the Monobactams.- 3. Biosynthesis of the Penicillins.- 4. Biosynthesis of Clavulanic Acid.- 5. Biosynthesis of Carbapenem Antibiotics.- 6. Biosynthesis of the Cephalosporins.- References.- New Techniques for the Mass Spectrometry of Natural Products.- I. Introduction.- II. Methods of Ionization.- II.1. Electron Impact.- II.2. Chemical Ionization.- II.3. Desorption Chemical Ionization.- II.4. Field Desorption.- II.5. Secondary Ion Mass Spectrometry and Fast Atom Bombardment Mass Spectrometry.- II.6. Plasma Desorption Mass Spectrometry.- II.7. Laser Desorption Mass Spectrometry.- II.8. General Comments and Future Prospects.- III. Other Techniques in Mass Spectrometry.- III.1. High-Mass Spectra.- III.2. Tandem Mass Spectrometry.- III.3. Coupled Chromatography.- III.4. Computers.- III.5. Quantitative Measurements.- IV. Applications of the Newer Techniques in Mass Spectrometry to Specific Classes of Natural Product.- IV. 1. Peptides and Proteins.- IV. 2. Carbohydrates.- IV. 3. Nucleotides.- IV. 4. Tetrapyrroles.- IV. 5. Fatty Acids, Alcohols, and Esters.- IV. 6. Complex Lipids.- IV. 7. Eicosanoids.- IV. 8. Steroids.- IV. 9. Antibiotics.- IV. 10. Miscellaneous Natural Products.- References.- Chemical Synthesis of the Trichothecenes.- I. General Introduction.- II. Origin and Biological Activity.- III. Structure.- IV. Synthesis of the Simple Sesquiterpenoid Trichothecenes.- 1. Introduction.- 2. The Aldol Approach.- 3. The Biomimetic Approach.- 4. Miscellaneous Approaches.- V. Synthesis of the Trichoverroids.- 1. Introduction.- 2. Total Syntheses.- VI. Synthesis of the Macrocycles.- 1. Introduction.- 2. Model Systems.- 3. Verrucarin A.- 4. Verrucarin J.- 5. Verrucarin B.- 6. Roridin E and Baccharin B5.- 7. Vertisporin.- References.- Quassinoid Bitter Principles II.- I. Introduction.- II. Quassinoid General Features.- III. Structure Determination of Quassinoids.- 1. C18-Quassinoids.- 2. C19-Quassinoids.- 3. C20-Quassinoids.- 4. C25-Quassinoids.- IV. Physical Methods.- V. Biological Activity.- 1. Antileukemic Activity.- 2. Antiviral Activity.- 3. Antimalarial Activity.- 4. Antifeedant and Insecticidal Properties.- 5. Amebicidal Activity.- 6. Anti-inflammatory Activity.- VI. Chemical Modifications.- VII. Synthetic Studies.- VIII. Total Synthesis of dl-Quassin.- IX. Total Synthesis of dl-Castelanolide.- X. Tables 3-6.- References.- Author Index.

Volume

48 ISBN 9783211818862

Description

The metabolic products of micro-organisms can be classified either as compounds of primary metabolic concern or else as secondary metabolites - substances which are apparently non-essential to the producing or- ganism. Fungi have a remarkable capacity to produce such secondary metabolites, e. g. mycotoxins with a diverse array of structural and pharmacological properties (1). The present resurgence of interest in all aspects of mycotoxin research (2, 3) can be related to the impact of the hepatotoxins (aflatoxin, sporidesmin, and phomopsin), nephrotoxins (ochratoxin and citrinin), and dermal toxins (trichothecenes) on human and animal health. Some of the mycotoxins appear to act at the level of the central nervous system. Ergotism, the earliest known mycotoxicosis, that is a disease caused by mycotoxins, was attributed to the contamination of wheat by the parasitic neurotoxin-producing fungus, C/aviceps purpurea. These neuro- toxins elaborated by C. purpurea are collectively called the ergot toxins (4). The neurotoxin, citreoviridin (1) which causes paralysis in the extremities of laboratory animals, followed sometimes by convulsions and respiratory arrest, has been implicated in acute cardiac beri-beri in Japan (5). Tremoring has not been associated with citreoviridin or the structurally related aurovertins (2) (6) and asteltoxin (3) (7); these compounds are therefore excluded from this review. However, verrucosidin (4) (8), a tremorgenic compound which structurally resembles (1)-(3), will be described later.

Table of Contents

Tremorgenic Mycotoxins.- 1. Introduction.- 2. The Penitrems, Janthitrems, Lolitrems, Aflatrem, Paxilline, Paspaline, Paspalicine, Paspalinine, and Paspalitrems A and B.- 2.1 The Penitrems.- 2.1.1 Producing Organisms.- 2.1.2 Isolation and Chromatography of the Penitrems.- 2.1.3 Structure of the Penitrems.- 2.1.3.1 General Aspects, Ultraviolet and Infrared Spectroscopy.- 2.1.3.2 Nuclear Magnetic Resonance Spectroscopy.- 2.1.3.3 Mass Spectrometry.- 2.1.3.4 Stereochemistry of the Penitrems: Conformation and Absolute Configuration.- 2.2 The Janthitrems.- 2.2.1 Producing Organisms.- 2.2.2 Isolation and Chromatography of the Janthitrems.- 2.2.3 Structure of the Janthitrems.- 2.2.3.1 General Aspects, Ultraviolet and Infrared Spectroscopy.- 2.2.3.2 Nuclear Magnetic Resonance Spectroscopy.- 2.2.3.3 Stereochemistry of the Janthitrems: The Relative Configuration.- 2.3 The Lolitrems.- 2.3.1 Producing Organisms.- 2.3.2 The Structure of Lolitrems B and C.- 2.3.2.1 The Stereochemistry of Lolitrem B.- 2.4 Aflatrem.- 2.4.1 Producing Organism.- 2.4.2 The Structure of Aflatrem.- 2.5 Paxilline.- 2.5.1 Producing Organism.- 2.5.2 Production and Isolation of Paxilline.- 2.5.3 Structure of Paxilline.- 2.6 Paspaline, Paspalicine, Paspalinine and Paspalitrems A and B.- 2.6.1 Producing Organism.- 2.6.2 Structural Studies.- 2.7 Biosynthesis of the Penitrems, Janthitrems, Lolitrems, Aflatrem, Paxilline, Paspaline, Paspalicine, Paspalinine, and Paspalitrems A and B.- 2.8 Mode of Action of the Penitrem Type of Fungal Neurotoxins.- 3. The Territrems.- 3.1 Producing Organisms.- 3.2 Isolation and Chromatography of the Territrems.- 3.3 Structure of the Territrems.- 4. Verrucosidin.- 4.1 Producing Organism.- 4.2 Structure of Verrucosidin.- 5. Verruculotoxin.- 5.1 Producing Organism.- 5.2 Isolation and Chromatography.- 5.3 Structure of Verruculotoxin.- 5.4 Synthesis.- 6. Tremorgens Containing a 6-Methoxyindole Moiety: The Verruculogens and Fumitremorgins.- 6.1 Producing Organisms.- 6.2 Isolation and Chromatography.- 6.3 Structure of Verruculogen.- 6.4 Structure of the Fumitremorgins.- 6.5 Biosynthesis of the Fumitremorgins and Verruculogen.- 7. The Tryptoquivalines.- 7.1 Producing Organisms.- 7.2 Isolation and Chromatography.- 7.3 Structure of Tryptoquivaline A.- 7.4 Structure of Nortryptoquivalone (Tryptoquivaline B or Tryptoqui val one).- 7.5 Structures of Toxic Metabolites Related to Tryptoquivaline A and Nortryptoquivalone.- 7.6 Structures of Nontoxic Metabolites Related to Tryptoquivaline A and Nortryptoquivalone.- 7.7 Synthesis of the Tryptoquivalines.- 7.7.1 Tryptoquivaline A.- 7.7.2 Tryptoquivaline G.- 7.8 Biosynthesis of the Tryptoquivalines.- References.- Structure of Palytoxin.- I. Introduction.- II. Isolation.- III. Characterization.- IV. Gross Structure Determination.- IV.1 Periodate Oxidation.- a) Degradation Products Implying C(1)-C(16) Segment.- b) Degradation Products Implying C(17)-C(27) and C(65)-C(72) Segments.- c) Degradation Products Implying C(73)-C(87) and C(98)-C(108) Segments.- d) Degradation Products Implying C(28)-C(64) Segment.- e) Degradation Products Implying C (89)-C (96) Segment.- f) Degradation Products Implying C(109)-C(123) Segment.- IV.2 Ozonolysis.- a) Degradation Products Implying C(7)-C(14) Segment.- b) Degradation Products Implying C(15)-C(59) Segment.- c) Degradation Products Implying C(60)-C(84) Segment.- d) Degradation Products Implying C(85)-C(91), C(92)-C(106), and C(107)-C(123) Segments.- V. Stereochemistry.- V.1 Methods Used for Relative Stereochemistry.- a) X-Ray Crystallography.- b) 1XH NMR Spectroscopy.- c) Periodate Oxidation.- d) Borate Complexation.- V.2 Methods Used for Absolute Stereochemistry.- a) X-Ray Crystallography.- b) Circular Dichroic Spectroscopy.- c) Synthesis.- VI. Conclusions.- Acknowledgement.- References.- Sesterterpenes: An Emerging Group of Metabolites from Marine and Terrestrial Organisms.- I. Introduction.- II. Summary of Carbon Skeletons and Structural Variations.- 1. Conventions.- Table 1. Sesterterpene Carbon Skeleton Classes.- Table 2. Modified Sesterterpene Carbon Skeleton Classes.- 2. Carbon Skeletons of "Regular" Sesterterpenes.- 3. Carbon Skeletons of Modified Sesterterpenes.- 4. Heteroatom Substituent Patterns.- III. Biosynthetic and Comparative Biochemical Observations.- 1. Introduction.- Table 3. Relationships Between Sesterterpene Carbon Skeletons and Their.- Organism Sources.- 2. Biogenesis.- 3. Biomimetic Synthesis.- 4. Comparative Biochemistry.- IV. Synthesis and Biological Activity.- 1. Synthesis.- 2. Biological Activity.- Table 4. Summary of Sesterterpenes with Biological Activity.- V. Spectroscopic Analysis.- 1. Introduction.- 2. Acyclic Sesterterpenes.- Table 5. Methyl Chemical Shifts for Tri-Substituted Double Bond Isomers.- 3. Monocarbocyclic Sesterterpenes.- 4. Tri- and Tetracarbocyclic Sesterterpenes.- 5. Pentacarbocyclic Sesterterpenes.- 6. Absolute Stereochemistry.- VI. Physical and Spectroscopic Tables.- 1. Table 6. Summary of Structures and Carbon-13 NMR Chemical Shifts.- 2. Table 7. Physical Properties.- Acknowledgement.- References.- Author Index.

Volume

49 ISBN 9783211819104

Description

Isocoumarins have been isolated from a wide variety of microbial, plant and insect sources and have been shown to possess an impressive array of biological activities. Since the review by BARRY in 1963 (24), the number of known naturally occurring isocoumarins has increased dramatically. This increase is largely due to improvements in isolation procedures and structural analysis. Previous reviews have concentrated on fungal isocoumarins (293,294) and mycotoxic isocoumarins (301). This review lists over 160 naturally occurring isocoumarins. Leading references on isolation, structure elucidation, biosynthesis and synthesis are given in the accompanying Tables. The known natural isocoumarins are listed in the Tables according to the number and orientation of oxygen atoms on the benzenoid ring and by carbon substituents. For completeness, those isocoumarins bearing additional fused carbocyclic rings and those containing nitro- gen substituents are included in separate Tables. It is hoped that by using these Tables in conjunction with the Formula Index, the Trivial Name Index and the Source Index the reader will be able to locate key references in the literature and gain an understanding of the fascin- ating chemistry and action of naturally occurring isocoumarins.

Table of Contents

Naturally Occurring Isocoumarins.- I. Introduction.- II. Nomenclature and Structural Types.- III. Structure Determination.- IV. Synthesis.- V. Biosynthesis.- VI. Biological Activity.- VII. Introduction to the Tables.- Table 1. Isocoumarins with no 8-Oxygenation.- Table 2. Isocoumarins with 8-Oxygenation.- (a) With no Carbon Substituent at C-3.- (b) With a One-Carbon Substituent at C-3.- (c) With a Substituent at C-3 Containing More than One Carbon..- Table 3. Isocoumarins with 6,8-Dioxygenation.- (a) With no Carbon Substituent at C-3.- (b) With a One-Carbon Substituent at C-3.- (c) With a Substituent at C-3 Containing More than One Carbon. 32.- Table 4. Isocoumarins with 6,7,8-Trioxygenation.- (a) With a One-Carbon Substituent at C-3.- (b) With a Substituent at C-3 Containing More than One Carbon. 39.- Table 5. Isocoumarins with Fused Carbocyclic Rings.- (a) 3,4-Fused.- (b) 4,5-Fused.- (c) 6,7-Fused.- Table 6. Isocoumarins with Nitrogen-Containing Substituents.- Formula Index.- Trivial Name Index.- Source Index.- References.- Anthraquinones in the Rubiaceae.- I. Introduction.- II. Biological Activity.- III. Biosynthesis.- IV. Spectroscopy.- 1. UV Spectroscopy.- 2. IR Spectroscopy.- 3. Mass Spectrometry.- 4. 1H-NMR Spectroscopy.- 5. 13C-NMR Spectroscopy.- V. Artifacts.- VI. Separation Methods.- VII. Physical and Spectroscopic Properties of Anthraquinones (Table 7).- VIII. Rubiaceae Species Containing Anthraquinones (Table 8).- References.- Recent Developments in the Field of Marine Natural Products with Emphasis on Biologically Active Compounds.- I. Introduction.- II. Porifera.- 11.1. Steroids from Porifera.- 11.2. Terpenoid Constituents from Porifera.- 11.3. Amino Acid Derived Metabolites from Porifera.- 11.4. Peptide Alkaloids, Peptides, and Proteins from Porifera.- 11.5. Nucleosides from Porifera.- 11.6. Alkaloids and Other Heterocyclic Compounds from Porifera.- 11.7. Macrolides from Porifera.- 11.8. Phenols and Aromatic Ethers from Porifera.- 11.9. Carboxylic Acids from Porifera.- 11.10. Miscellaneous Other Compounds from Porifera.- III. Coelenterata (Cnidaria).- 111.1. Hydrozoa, Cubozoa, and Scyphozoa.- 111.2. Hexacorallia: Sea Anemones.- 111.3. Hexacorallia: Other Organisms.- 111.4. Octocorallia.- 111.4.1. Steroids from Octocorallia.- 111.4.2. Terpenes from Octocorallia.- 111.4.3. Miscellaneous Compounds from Octocorallia.- IV. Bryozoa.- V. Mollusca.- V.1. Gastropoda.- V.1.1. Nudibranchia.- V.1.1.1. Steroids from Nudibranchia.- V.1.1.2. Terpenes from Nudibranchia.- V.1.1.3. Miscellaneous Compounds from Nudibranchia.- V.1.2. Aplysiidae.- V.1.2.1. Terpenes from Aplysiidae.- V.1.2.2. Miscellaneous Compounds from Aplysiidae.- V.1.3. Conidae.- V.1.4. Miscellaneous Compounds from Other Marine Snails.- V.2. Bivalvia.- V.3. Cephalopoda.- VI. Echinodermata.- VI.1. Saponins from Starfish.- VI.2. Steroids from Starfish.- VI.3. Miscellaneous Compounds from Starfish.- VI.4. Saponins from Sea Cucumbers.- VI.5. Steroids from Sea Cucumbers.- VI.6. Crinoids and Ophiuroids.- VI.7. Sea Urchins.- VII. Tunicata.- VIII. Miscellaneous Other Sources.- References.- Author Index.

Volume

50 ISBN 9783211819692

Description

This volume is part of a series, inaugurated in 1938, now referred to simply as "Zechmeister" after its founder, L. Zechmeister. It contains contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a reconized authority in his field, and provides a comprehensive and up-to-date review of the topic in question. This title looks at the chemistry of organic natural products. It is addressed to biologists, technologists and chemists alike. The series can be used by the expert as a source of information and literature citations, and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

The Irones and Their Precursors.- I. Introduction.- II. Isolation and Structure Determination.- III. Structure of the Irone Precursors.- IV. Stereochemistry of the Iridals and the Irones Derived from Them.- V. Minor Triterpenoids in Iris Extracts.- VI. Biogenesis of the Iridals.- VII. Mechanism of Irone Ring Formation.- VIII. Biological Significance of the Compounds.- References.- The Condylocarpine Group of Indole Alkaloids.- 1. Introduction.- 2. Structures.- 2.1. Precondylocarpine.- 2.2. Condylocarpines.- 2.3. Dihydrocondylocarpines.- 2.4. Tubotaiwinal.- 2.5. Aspidospermatidines.- 2.6. 19,20-Dihydroaspidospermatine.- 2.7. Geissovelline.- 2.8. Dichotines.- 3. Isolation and Occurrence.- 3.1. Isolation.- 3.2. Occurrence.- 4. Biogenesis.- 5. Chemistry.- 5.1. Correlation of Alkaloid Structures.- 5.1.1. Precondylocarpine and Condylocarpine.- 5.1.2. Tubotaiwine.- 5.1.3. N-oxides.- 5.1.4. Aspidospermatidines.- 5.1.5. Geissovelline and Dichotine.- 5.1.6. Further Alkaloids from Precondylocarpine.- 5.2. Total Syntheses.- 5.2.1. Condyfoline.- 5.2.2. Tubotaiwine.- 5.2.3. Condylocarpine.- 6. Physical Properties.- 6.1. X-ray Crystallography.- 6.2. 13C NMR Spectroscopy.- 6.3. 1H NMR Spectroscopy.- 6.4. Mass Spectrometry.- 6.5. Other Spectra.- 7. Pharmacology.- References.- The Antibiotics of the Pluramycin Group (4H-Anthra[1,2-b]pyran Antibiotics).- 1. Introduction.- 2. General Structural Characteristics and Nomenclature.- 3. The Families of Pluramycin Antibiotics.- 3.1. Pluramycin A and Neopluramycin.- 3.2. Kidamycin and Isokidamycin.- 3.3. Hedamycin.- 3.4. The Rubiflavins and Rubiflavinones.- 3.5. Largomycin FII Chromophore Constituents.- 3.6. PD 121,222.- 3.7. Chromoxymycin.- 3.8. The Griseorubins.- 3.9. The Indomycins and Indomycinones.- 4. Chemical Properties.- 4.1. Separation Techniques.- 4.1.1. Preparative Separations.- 4.1.2. Analytical Separations.- 4.2. Spectroscopy.- 4.2.1. UV/VIS Spectra.- 4.2.2. IR Spectra.- 4.2.3. 1H-NMR Spectra.- 4.2.4. 13C-NMR Spectra.- 4.2.5. Mass Spectra.- 4.3. Chemical Reactivity.- 4.3.1. General Chemical Characterization.- 4.3.2. Degradation, Decomposition.- 4.3.3. Derivatization.- 4.4. Stereochemistry.- 4.4.1. Configuration.- 4.4.2. Conformations.- 5. Total Synthesis.- 5.1. Pluramycinones.- 5.2. Sugar Moieties.- 5.3. Pluramycin Antibiotics.- 6. Biosynthesis.- 7. Biological and Biochemical Behaviour.- 7.1. General Remarks.- 7.2. Toxicity.- 7.3. Activity Against Bacteria, Yeasts and Other Microorganisms.- 7.4. Interaction with Phages and Lysogenic Bacteria.- 7.5. Cytotoxicity.- 7.6. Interaction with Nucleic Acids and Mode of Action.- Acknowledgement.- Note added in proof.- References.- Cyclosporine and Analogues - Isolation and Synthesis - Mechanism of Action and Structural Requirements for Pharmacological Activity.- 1. Introduction.- 1.1. History and Summary.- 1.2. Nomenclature.- 1.3. Production of Cyclosporine.- 1.4. Elucidation of the Structure of Cyclosporine - Conformation of Cyclosporine in the Crystal.- 1.5. Some Chemical Modifications of Cyclosporine.- 1.6. Natural Cyclosporine Analogues.- 1.7. Pharmacokinetics and Metabolism of Cyclosporine (1).- 1.8. Elucidation of the Conformation of Cyclosporine (1) in Aprotic Solvents.- 1.8.1. Backbone Conformation.- 1.8.2. Carbon Chains Conformations of Amino Acid Residues of Cyclosporine (1).- 1.8.3. Cyclosporine Conformation in Biological Fluids.- 2. Monoclonal Antibodies to Cyclosporine (1).- 2.1. The Antibody Response Induced by Cyclosporine.- 2.2. Fine Specificity of Monoclonal Antibodies.- 2.3. The Conformation of Cyclosporine Seen by Antibodies in Biological Fluids Seems to Be Similar to that Observed in Crystal.- 3. The Biosynthesis of Cyclosporine.- 4. Synthesis of Cyclosporine.- 4.1. Introduction.- 4.2. Synthesis of the Enantiomerically Pure Amino Acid MeBmt (83).- 4.2.1. Synthesis of (2R,3R)-3-methyl-1,2,4-butanetriol (65).- 4.2.2. Synthesis of (2R,3R,5E)-3-methyl-5-heptene-1,2-diol (71).- 4.2.3. Synthesis of (2R,3R,5E)-2-hydroxy-3-methyl-5-heptenal (76).- 4.2.4. Synthesis of (2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoic acid (MeBmt) (83).- 4.3. Strategy Used for the Synthesis of Cyclosporine (1).- 4.4. Cyclosporine Analogues.- 4.4.1. Synthetic Analogues.- 4.4.2. Semi-synthetic Analogues.- 4.4.3. Conformation of Cyclosporine Analogues.- 5. Biological Activity and Structure-activity Relationships of Cyclosporine Analogues.- 5.1. Conclusions.- 6. Mechanism of Action of Cyclosporin A.- 6.1. Introduction.- 6.2. Lymphokines and the Immune System.- 6.3. Importance of Interleukin-2 for Lymphocytes.- 6.4. Cyclosporine and Transcriptional Control.- 6.5. Membrane and Cellular Receptors.- 6.6. Conclusions.- References.- Biosynthesis of Iridoids and Secoiridoids.- I. Introduction.- II. Classification of Iridoids and Secoiridoids.- III. Mevalonoid Origin of Iridoids and Secoiridoids and Mechanism of Formation of Iridane Skeleton from Acyclic Monoterpenes.- 1. Mevalonoid Origin of Iridoids and Secoiridoids.- 2. Mechanism of Formation of Iridane Skeleton from Acyclic Monoterpenes.- IV. Biosynthetic Processes After Cyclopentane Ring Formation.- 1. Intermediacy of Deoxyloganic Acid, 8-Epideoxyloganic Acid and Loganic Acid in Biosynthesis of Iridoids.- 2. Approach to Elucidation of the Mechanism of Cyclopentane Ring Cleavage of Loganin to Secologanin.- V. Biosynthetic Relationships Between Groups of Secoiridoid Glycosides.- 1. Sweroside-Morroniside Type Glycosides.- 2. Oeloside-10-Hydroxyoleoside Type Glycosides.- VI. Biosynthetic Pathways of Alkaloidal Glycosides and Hydrangenosides.- 1. Biosynthesis of Alkaloidal Glycosides and the Role of Strictosidine and Deacetylisoipecoside in the Biosynthesis of Alkaloids.- 2. Biogenesis of Hydrangenosides.- VII. Epilogue.- List of Compounds.- References.- Author Index.

Volume

51 ISBN 9783211819722

Description

The volumes of this classic series, now referred to simply as "Zechmeister" after its founder, L. Zechmeister, have appeared under the Springer imprint ever since the series was founded in 1938. The volumes contain contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a recognized authority in his field and provides a comprehensive and up-to-date review of the topic in question. Addressed to biologists, technologists and chemists alike, the series can be used by the expert as a source of information and literature citations and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

Pigments of Fungi (Macromycetes).- 1. Introduction.- 2. Pigments from the Shikimate-Chorismate Pathway.- 2.1. Compounds Derived from Arylpyruvic Acids.- 2.1.1. Grevillins.- 2.1.2. Terphenylquinones.- 2.1.2.A. Simple Terphenylquinones.- 2.1.2.B. Polyporic Acid and Derivatives.- 2.1.2.C. Ascocorynin.- 2.1.2.D. Atromentin and Derivatives.- 2.1.2.E. Cycloleucomelone and Derivatives.- 2.1.2.F. Cyclovariegatin and Derivatives.- 2.1.2.G. Thelephoric Acid and Derivatives.- 2.1.3. Pulvinic Acid Derivatives.- 2.1.3.A. Common Pulvinic Acid Derivatives.- 2.1.3.B. Less Common Pulvinic Acid Derivatives.- 2.1.3.C. Synthesis and Biosynthesis of Pulvinic Acid Derivatives.- 2.1.3.D. Pulvinones.- 2.1.4. Badione Group.- 2.1.5. Cyclopentanoids.- 2.1.6. Xylerythrin Group.- 2.1.7. Summary.- 2.2. Compounds Derived from Phenylalanine and Tyrosine: L-DOPA, Betalaines, and Muscaflavin.- 2.3. Compounds Derived from Cinnamic Acids.- 2.3.1. Purpurogallin Derivatives.- 2.3.2. Styrylpyrones.- 2.4. Compounds Derived from p-Hydroxybenzoic Acid: Boviquinone Group.- 2.5. Miscellaneous Compounds Which May be Derived from the Shikimate-Chorismate Pathway.- 3. Pigments from the Acetate-Malonate Pathway.- 3.1. Tetraketides.- 3.2. Pentaketides.- 3.3. Hexaketides.- 3.4. Heptaketides.- 3.5. Octaketides.- 3.5.1. Neutral Anthraquinones and Anthraquinone Carboxylic Acids.- 3.5.2. Monomeric Pre-anthraquinones.- 3.5.3. Dimeric Pre-anthraquinones.- 3.5.3.A. Atrovirin Group.- 3.5.3.B. Flavomannin Group.- 3.5.3.C. Pseudophlegmacin Group.- 3.5.3.D. Phlegmacin Group.- 3.5.3.E. Tricolorin Group.- 3.5.3.F. Cortinarin Group.- 3.5.3.G. Rufoolivacin Group.- 3.5.4. Further Octaketides.- 3.6. Nonaketides.- 3.7. Compounds of Fatty Acid or Higher Polyketide Origin.- 3.7.1. Nonisoprenoid Polyene Pigments.- 3.7.2. Quinones with Extended Unbranched Side Chains.- 4. Pigments from the Mevalonate Pathway.- 4.1. Sesquiterpenoids.- 4.2. Carotenoids.- 5. Nitrogen Heterocycles.- 5.1. Phenoxazin-3-ones.- 5.2. Riboflavin and Russupteridines.- 5.3. Indole Pigments.- 5.3.1. Simple Indoles.- 5.3.2. Bisindolylmaleimides.- 5.4. Necatorone.- 5.5. Miscellaneous N-Heterocyclic Pigments.- 6. Further Pigments Containing Nitrogen.- 7. Compounds Responsible for Colour Reactions.- Acknowledgment.- References.- Pigments of Fungi (Macromycetes).- Index of Species (Macromycetes).- Author Index.

Volume

52 : Wien ISBN 9783211819890

Description

The volumes of this classic series, now referred to simply as "Zechmeister" after its founder, L. Zechmeister, have appeared under the Springer imprint ever since the series' inauguration in 1938. The volumes contain contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a recognized authority in his field and provides a comprehensive and up-to-date review of the topic in question. Addressed to biologists, technologists and chemists alike, the series can be used by the expert as a source of information and literature citations and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

• Naturally Occurring Perylenequinones.- 1. Introduction.- 2. Natural Perylenequinones in General.- 2.1. Perylene and Its Derivatives.- 2.2. Types of Perylenequinones Obtainable from Natural Sources. Occurrence.- 2.3. General Properties and Reactions of Natural Perylenequinones.- 2.4. Spectroscopic Properties.- 2.5. Chemical Reactions.- 2.6. Synthesis.- 3. Individual Natural Perylenequinones.- 3.1. 4,9-Dihydroxyperylene-3,10-quinone.- 3.2. Aspergillin.- 3.3. Elsinochromes.- 3.3.1. Occurrence and Formation.- 3.3.2. Isolation and Purification.- 3.3.3. Structure of Elsinochromes.- 3.4. Cercosporin.- 3.5. Phleichromes.- 3.6. Cladochromes.- 3.7. Pigments from Mutants of Cercospora kikuchii.- 3.8. Hypocrellin.- 3.9. The Aphins.- 3.9.1. The Protoaphins.- 3.9.2. The Xanthoaphins and the Chrysoaphins.- 3.9.3. The Erythroaphins
• Rhodoaphin.- 4. Stereochemistry.- 5. Tautomerism.- 6. Biosynthesis.- 7. Biological Activity.- 8. Partially Reduced Perylenequinones.- 8.1. Altertoxin I and Dihydroalterperylenol.- 8.2. Alterperylenol, Alteichin, and Altertoxin II.- 8.3. Stemphyltoxins I-IV.- 8.4. Stemphyperylenol and Altertoxin III.- Addendum.- References.- The Pigments of the Flexirubin-Type. A Novel Class of Natural Products.- I. Introduction.- II. Structure Elucidation of Flexirubin.- III. Isolation and Separation of Flexirubin-Type Pigments.- IV. General Comments on Structure Elucidation of Flexirubin-Type Pigments.- V. Spectroscopic Properties of Flexirubin-Type Pigments.- 1. Mass Spectra.- 2. Proton-NMR-Spectra.- 3. 13C-NMR-Spectra.- 4. Electronic Spectra.- VI. Synthetic Approaches to Flexirubin-Type Pigments.- VII. Biosynthesis of Flexirubin-Type Pigments.- VIII. Closing Remarks.- References.- Structure, Stability and Color Variation of Natural Anthocyanins.- 1. Introduction.- 2. Structure Determination.- 2.1 Mass Spectra of Anthocyanins.- 2.2 1-NMR Spectra.- 2.3 Structure Determination of Heavenly Blue Anthocyanin.- 2.4 Other Anthocyanins Acylated with Two or More Aromatic Acids.- 2.5 Anthocyanins Acylated with Aliphatic Dicarboxylic Acids.- 3. Stabilization Effect of Inorganic Salts.- 4. Self-Association.- 5. Co-Pigmentation.- 6. Intramolecular Sandwich Type Stacking.- 7. Metalloanthocyanins.- 7.1 Commelinin.- 7.2 Protocyanin.- References.- Carbazole Alkaloids.- I. Introduction.- A. Occurrence.- B. Detection of Carbazoles by Chromatographic Methods.- II. Methods of Structure Elucidation.- A. Physical Methods.- 1. 13C NMR Spectra.- B. Synthesis of Carbazoles.- 1. Palladium Promoted Cyclisation of Diphenylamine.- 2. Acid Catalysed Cyclisation of ?-Ketosulphoxide.- 3. In situ Vinyl Indole Synthesis of Carbazoles.- 4. Preparation by Application of the Nenitzescu Synthesis.- 5. Thermal Cyclisation.- 6. Free Radical Cyclisation of Diphenylamine to Carbazole.- 7. Intramolecular Diels-Aider Cycloaddition of Vinylketenimines.- 8. Diels-Alder Reaction of Indole-2,3-quinodimethane.- 9. Synthesis of Carbazoles via 2-Vinylindoles.- 10. Synthesis of Pyranocarbazole Alkaloids of the C18-Carbon Skeleton Group.- III. Biogenesis of Carbazole Alkaloids.- IV. Biological Properties of Carbazole Alkaloids and Related Compounds.- V. Chemistry of Carbazole Alkaloids.- A. Members of the C13-Skeleton Group.- 1. Mukonal.- 2. 2-Methoxy-3-methylcarbazole.- 3. Mukoline and Mukolidine.- 4. 2-Hydroxy-3-methylcarbazole.- 5. Glycozolinol.- 6. Glycozolidol.- 7. Glycozolidal.- 8. Lansine.- 9. Koenoline.- 10. Murrayafoline-A.- B. Members of the C18-Skeleton Group.- 1. Mukonicine.- 2. Heptazolicine.- 3. Clausenapin.- 4. Clausenatin.- 5. Mupamine.- 6. Murrayafoline-B.- 7. Ekeberginine.- C. Members of the C23-Skeleton Group.- 1. Exozoline.- 2. Mahanimbinol.- 3. Mahanimboline.- 4. Isomurrayazoline.- 5. (+) Murrayazoline.- D. Dimeric Carbazoles.- 1. Bismurrayafoline-A.- 2. Bismurrayafoline-B.- 3. (+-) Murrafoline.- E. Carbazolequinones.- 1. Murrayaquinone-A.- 2. Murrayaquinone-B.- 3. Murrayaquinone-C and Murrayaquinone-D.- F. Carbazoles from Other Sources.- 1. Hyellazole.- 2. 6-Chlorohyellazole.- 3. Carbazomycin B.- 4. Carbazomycin A.- References.- Author Index.

Volume

53 ISBN 9783211820742

Description

The volumes in this classic series, now referred to simply as "Zechmeister" after its founder, L. Zechmeister, have appeared under the Springer Imprint ever since the series' inauguration in 1938. The volumes contain contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occuring substances ranging from small molecules to biopolymers. Each contribution is written by a recognized authority in this field and provides a comprehensive and up-to-date review of the topic in question. Addressed to biologists, technologists and chemists alike, the series can be used by the expert as a source of information and literature citations and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

Chemical Ecology and the Social Behavior of Animals.- 1. Introduction.- 2. Terminology.- 3. Origin.- 4. Pheromones as a Multicomponent System.- 5. Perception of Pheromones by Insects and Vertebrates.- 6. Chemical Communication in Vertebrates.- 7. Endocrine Hormone-Pheromone Interaction.- 7.1 Bruce Effect.- 7.2 Whitten Effect.- 7.3 Lee-Boot Effect.- 7.4 Ropartz-Effect.- 8. Maternal Pheromones.- 9. Chemical Communication in Marine Organisms.- 10. The Effect of Anosmia.- 11. Chemical Communication in Invertebrates.- 12. Caste and Kin Recognition in Social Insects.- 13. Insect Sex Pheromones.- 14. Role of Pheromones in Reproductive Isolation of Insects.- 15. Arthropod Defensive Secretions.- 16. Defense in Termites.- 17. Predator-Prey Interactions.- 18. Human Pheromones.- 19. Conclusion.- Acknowledgements.- References.- Phenolic Compounds of the Mulberry Tree and Related Plants.- I. Introduction.- II. Flavonoids Carrying Isoprenoid Substituents Isolated from the Japanese Cultivated Mulberry Tree.- 1. Isolation of Flavonoids Carrying Isoprenoid Substituents.- 2. Structures of Flavonoids Carrying Isoprenoid Substituents.- 3. Synthesis of Tetrahydrokuwanon C Tetramethyl Ether.- III. Photo-Oxidative Cyclization of Prenylflavones.- 1. Photo-Oxidative Cyclization of Morusin.- 2. Mechanism of the Photo-Oxidative Cyclization of Morusin.- 3. Oxidative Cyclization of Morusin.- IV. Phytoalexins and Antifungal Substances in the Mulberry Tree.- V. Diels-Alder Type Adducts of the Cultivated Mulberry Tree.- 1. Hypotensive Constituents, Kuwanons G and H.- 2. Five Novel 2-Arylbenzofuran Derivatives, Chalcomoracin, Mulberrofurans C, F, G, and H.- 3. Coloring Matter of Morus Root Bark, Mulberrofuran I.- 4. Other Phenolic Compounds Related to Mulberrofuran I.- 5. Diels-Alder Type Adducts of Morus Cell Cultures.- 6. Other Diels-Alder Type Adducts of Cultivated Mulberry Tree.- VI. Phenolic Constituents of the Crude Drug "Sang-Bai-Pi".- 1. Structures of the Flavonoids Carrying Isoprenoid Substituents Isolated from "Sang-Bai-Pi".- 2. Structures of Diels-Alder Type Adducts of "Sang-Bai-Pi".- VII. Absolute Configuration of Diels-Alder Type Adducts from Morus Sp..- 1. Classification of Diels-Alder Type Adducts.- 2. Stereochemistry of Diels-Alder Type Adducts.- 3. Absolute Configuration of Mulberrofurans C and J by CD Spectra.- 4. Absolute Configuration of Other Diels-Alder Type Adducts.- 5. Absolute Configuration of the Chiral Centers on the Cyclohexene Ring of Kuwanon L.- 6. Absolute Configuration of the Ketal Compounds, Mulberrofurans F, G, and K.- VIII. Phenolic Constituents of Cudrania tricuspidata (Carr.) Bur. and Broussonetia Sp..- 1. Structures of Xanthone and Flavonoid Derivatives from Cudrania tricuspidata (Carr.) Bur..- 2. Structures of 1,3-Diphenylpropane and Flavonoid Derivatives from Broussonetia Sp.- IX. Biological Activities of Phenolic Constituents of Mulberry Tree and Related Plants.- Acknowledgements.- References.- N-Hydroxyamino Acids and Their Derivatives.- I. Introduction, Scope and Nomenclature.- II. N-Hydroxyamino Acid Residues as Fragments of Natural Products.- III. Physical and Chemical Properties.- IV. Analysis.- V. Naturally-Occurring N-Hydroxypeptides.- VI. Biological Action of N-Hydroxyamino Acids and N-Hydroxypeptides.- VII. Biogenesis of the N-Hydroxyamide Bond.- VIII. Synthesis of N-Hydroxyamino Acids and Their Derivatives.- 1. Reaction of Nitric Oxide with 1,3-Diketo Derivatives.- 2. Strecker Synthesis.- 3. Reduction of Nitro Acids and Nitro Esters.- 4. Reduction of Oximes of ?-Keto Acids and Substituted Aldoximes.- 5. Addition of Hydroxylamine to ?,?-Unsaturated Acids.- 6. Reaction of ?-Halo Acids with Hydroxylamine.- 7. Reaction of ?-Halo Acids with Benzyloxyamine.- 8. From N-Tosyl-O-Benzylhydroxylamine.- 9. From Nitrones.- 9.1. Substitution.- 9.2. Addition.- 10. From Oxaziridines.- 11. Alkylation of Hydroxamic Acids.- 12. Synthesis of N-Hydroxy-sec-amino Acids.- 13. Esterification of N-Hydroxyamino Acids and N-Alkoxyamino Acids.- IX. Synthesis of N-Hydroxypeptides.- 1. N-Hydroxydiketopiperazines.- 2. Linear N-Hydroxypeptides.- X. Reactions of N-Hydroxypeptides.- XI. Final Remarks.- Addendum.- Acknowledgements.- References.- Author Index.

Volume

54 ISBN 9783211820865

Description

The volumes of this classic series have appeared under the Springer imprint ever since L. Zechmeister founded the series in 1938. The volumes contain contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a recognized authority in his field and provides a comprehensive and up-to-date review of the topic in question. Addressed to biologists, technologists and chemists alike, the series can be used by the expert as a source of information and literature citations and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

Occurrence, Structure and Taxonomic Implications of Fern Constituents.- I. Introduction.- II. Occurrence, Structures and Chemotaxonomic Implications.- 1. Aromatic Compounds.- 1.1. Acylphloroglucinols.- 1.2. Hydroxyaromatic Acids.- 1.3. Styrol Glycosides, Dihydrostilbenes, Lignans, Quinones and Naphthalenes.- 1.3.1. Styrol Glycosides.- 1.3.2. Dihydrostilbenes.- 1.3.3. Lignans.- 1.3.4. Quinones.- 1.3.5. Naphthalenes.- 1.4. Chromenes, Coumarins, Chromones, and Chromanones.- 1.4.1. Chromenes.- 1.4.2. Coumarins.- 1.4.3. Chromones.- 1.4.4. Chromanones.- 1.5. Xanthones.- 1.6. Flavonoids.- 1.6.1. Flavones and Flavonols.- 1.6.2. Flavanones and Flavanon-3-ols.- 1.6.3. Biflavonoids.- 1.6.4. Chalcones and Dihydrochalcones.- 1.6.5. Flavan-3-ols and Proanthocyanidins.- 1.6.6. Flavonoids Having the Modified B-Ring.- 1.6.7. Neoflavonoids and Related Compounds.- 2. Terpenoids and Steroids.- 2.1. Monoterpenoids.- 2.2. Sesquiterpenoids.- 2.3. Diterpenoids.- 2.4. Sesterterpenoids.- 2.5. Triterpenoids.- 2.6. Carotenoids.- 2.7. Steroids.- 3. Miscellaneous Compounds.- 3.1. ?-Pyrones and ?-Pyrones.- 3.2. Alicyclic Acids.- 3.3. Carbohydrates.- 3.4. Lipids.- 3.5. Nitrogen-containing Compounds.- 4. Chemotaxonomy of the Filicopsida.- Tables (2-13) Chemical Constituents Found in the Filicopsida.- Table 14. Groups of Pteris Ferns Based on Frond Shapes and Chemical Constituents.- Tables (15-19) Distribution of Flavonoids, Terpenoids and Steroids in the Filicopsida.- References.- Author Index.

Volume

55 ISBN 9783211820872

Description

An up-to-date review of the the chemistry of organic natural products. Addressed to biologists, technologists and chemists, the series can be used by the professional as a source of information and literature citations, and by the non-expert as a means of orientation in a rapidly developing field.

Table of Contents

Naturally Occurring 6-substituted 5,6-dihydro-?-pyrones.- 1. Introduction.- 2. Nomenclature and Classification.- 3. Distribution and Structure Determination.- 3.1. 6-Alkyl-5,6-dihydro-?-pyrones.- 3.2. 6-Alkenyl-5,6-dihydro-?-pyrones.- 3.3. 6-Aryl-5,6-dihydro-?-pyrones.- 4. Physical Methods of Structure Determination.- 4.1. 1H- and 13C-NMR Spectroscopy.- 4.2. Mass Spectrometry.- 4.3. Infrared and Ultraviolet Spectroscopy.- 4.4. Circular Dichroism.- 5. Biosynthesis.- 6. Biological Activity.- References.- Addendum.- Building Blocks for the Total Synthesis of Anthracyclinones.- I. Introduction.- II. General Synthetic Methods.- 1. Friedel-Crafts Reactions.- 2. Diels-Alder Reactions.- 3. Anionic Reactions.- 4. Transition Metal Mediated Reactions.- III. Synthesis of Building Blocks for Rings A and B.- IV. Construction of Ring A.- 1. Diels-Alder Reactions.- 2. Electrophilic Additions.- 3. Nucleophilic Additions.- V. Building Blocks for Rings C and D.- VI. Concluding Remarks.- References.- Indole Alkaloid Production in Catharanthus roseus Cell Suspension Cultures.- 1. Introduction.- 2. Discussion.- 2.1. Indole Alkaloids and Their Formation in the Plant and in Cell Cultures.- 2.2. General Methods of Catharanthus roseus Cell Suspension Culture Work.- 2.2.1. Analytical Methods.- 2.2.2. Development of High Yielding Cell Lines.- 2.2.3. Growth and Alkaloid Production in Catharanthus roseus Cell Suspension Cultures.- 2.2.4. Effects of Culture Conditions on Growth and Alkaloid Production..- 2.2.4.1. Medium Composition.- 2.2.4.2. Addition of Precursors.- 2.2.4.3. Light.- 2.2.4.4. Temperature.- 2.2.4.5. Gaseous Environment.- 2.2.5. One-stage Systems.- 2.2.6. Large-scale Fermentation.- 2.2.7. Immobilized Cell Systems.- 2.2.8. Cell Free Systems.- 3. Conclusions.- References.- Sucrose and Its Derivatives.- 1. Introduction.- 1.1. History.- 1.2. Structure.- 1.3. Nomenclature.- 1.4. Synthesis.- 1.5. Biosynthesis.- 1.6. Conformation.- 2. Protective and Functional Groups.- 2.1. Ethers.- 2.1.1. Tritylation.- 2.1.2. Methylation.- 2.1.3. Silylation.- 2.2. Cyclic Acetals.- 2.3. Esters.- 2.3.1. Carboxylates.- 2.3.1.1. Acetates.- 2.3.1.2. Benzoates.- 2.3.1.3. Benzoylpropionates.- 2.3.1.4. Pivalates.- 2.3.2. Sulphonates.- 2.3.3. Chlorosulphates.- 2.3.4. Other Esters.- 3. Derivatives.- 3.1. Anhydrides (Oxetanes) and Epoxides (Oxiranes).- 3.2. Halides.- 3.3. Unsaturated, Deoxy and Branched-Chain Compounds.- 3.4. Nitrogen-containing Compounds: Azides, Amines and Morpholines.- 3.5. Sulphur Derivatives.- 4. Enhancement of Sweetness: Structure Activity Relationships.- 5. Natural Products Containing Sucrose.- 5.1. ?-D-Fructofuranosyl Derivatives.- 5.2. ?-D-Glucopyranosyl Derivatives.- 5.3. ?-and ?-D-Galactopyranosyl Derivatives.- 5.4. Galloyl Derivatives.- 5.5 Agricinopine A.- 5.6. Sucrose Esters from Potato.- 5.7. Sucrose Esters from Tobacco.- Acknowledgment.- References.- Author Index.

Volume

56 ISBN 9783211821886

Description

The volumes of this classic series, now referred to simply as "Zechmeister" after its founder, L. Zechmeister, have appeared under the Springer Imprint ever since the series' inauguration in 1938. The volumes contain contributions in various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a recognized authority in his field and provides a comprehensive and up-to-date review of the topic in question. Addressed to biologists, technologists, and chemists alike, the series can be used by the expert as a source of information and literature citations and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

Bacterial Lipids Containing Amino Acids or Peptides Linked by Amide Bonds.- I. Introduction.- II. N-Acylamino Acids.- 1. N-Acyl-l-serine.- 1.1. Serratamolide.- 1.2. Flavolipin.- 2. N-Acyl-l-ornithine.- 2.1. Ornithine-containing Lipid.- 2.2. Cerilipin.- 3. Mass Spectrometry.- 4. Biological Properties.- III. N-Acylpeptides.- 1. N-Acylpeptides with a Linear Peptide Moiety.- 1.1. N-Acyldipeptides: Majusculamides A and B.- 1.2. N-Acyltetrapeptides from Rhodococcus erythropolis.- 1.3. N-Acylpentapeptides from. Mycobacterium paratuberculosis.- 1.4. N-Acyloctapeptide: Stenothricin.- 1.5. N-Acylnonapeptide: Fortuitin.- 1.6. N-Acyldecapeptides: Cerexins.- 1.7. N-Acyltridecapeptides: Tridecapeptins.- 1.8. N-Acylundecapeptide: Amphomycin.- 2. N-Acylpeptides Containing a Hydroxy Fatty Acid Involved in a Lactone Ring.- 2.1. N-Acylpentapeptide: Globomycin.- 2.2. N-Acylheptapeptides: Surfactin, Esperin and Related Compounds.- 2.3. N-Acylheptapeptides: Peptidolipin NA.- 3. N-Acylpeptides with a Lactone Ring not Involving the Hydroxyl Group of a Hydroxy Fatty Acid.- 3.1. N-Acyloctapeptides.- 3.1.1. Lipopeptins.- 3.1.2. Neopeptins.- 3.2. N-Acylnonapeptide: Viscosin.- 3.3. N-Acyldecapeptides: Imacidines.- 3.4. N-Acyltridecapeptides: Antibiotic A21978 C.- 3.5. N-Acyltetradecapeptide: Stendomycin.- 4. Peptidolipids with a Lactam Ring.- 4.1. Iturins.- 4.2. Bacillomycins.- 4.3. Mycosubtilin.- 4.4. General Comments on the Peptidolipids of the Iturin Group.- 4.5. Cyclic Peptides: Octapeptins.- 4.6. Cyclic Peptides: Antibiotic EM 49.- 5. Mass Spectrometry of N-Acylpeptides.- 6. Biological Properties of Peptidolipids.- IV. Glycosides of Peptidolipids.- 1. Glycosides of Peptidolipids Isolated from Rhodococcus erythropolis.- 2. Glycoside of N-Acylnonapeptide: Herbicolin A.- 3. Mycosides C and Related Antigenic Compounds.- 3.1. Apolar Mycosides C.- 3.2. Polar Mycosides C: Antigenic Glycopeptidolipids.- 3.3. Mycosides C as Receptors for Mycobacteriophages.- V. Conclusion.- Acknowledgements.- Addendum.- References.- Naturally Occurring Di- and Trithiophenes.- I. Introduction.- II. Nomenclature.- III. Naturally Occurring Dithiophenes: Structures.- IV. Distribution of Dithiophenes.- V. Naturally Occurring Trithiophenes: Structures.- VI. Distribution of Trithiophenes.- VII. Biosynthesis of Di- and Trithiophenes.- VIII. Synthesis of Di- and Trithiophenes.- IX. Photophysical Studies.- X. Photochemical Reactions.- XI. Biological Reactions.- 1. Effect on DNA.- 2. Antiviral Properties.- 3. Effect on Skin.- 4. Effect on Erythrocytes.- 5. Phototoxicity Toward Bacteria and Fungi.- 6. Nematocidal Activity.- 7. Trithiophenes as Insecticides.- 8. Toxicity Toward Fish and Other Aquatic Organisms.- 9. Toxicity of ?-Terthienyl Toward Plants.- XII. Conclusion.- Acknowledgement.- References.- Author Index.

Volume

57 : Wien ISBN 9783211822456

Description

The volumes of this classic series, now referred to simply as Zechmeister after its founder, L. Zechmeister, have appeared under the Springer Imprint ever since the series' inauguration in 1938. The volumes contain contributions in various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a recognized authority in his field and provides a comprehensive and up-to-date review of the topic in question. Addressed to biologists, technologists, and chemists alike, the series can be used by the expert as a source of information and literature citations and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

Lipids and Macromolecular Lipids of the Hydrocarbon-rich Microalga Botryococcus braunii. Chemical Structure and Biosynthesis. Geochemical and Biotechnological Importance.- I. Introduction.- II. Structure, Abundance and Biosynthesis of Lipids and Macromolecular Lipids in B. braunii.- 1. Hydrocarbons.- 1.1 Straight Chain Hydrocarbons (A Race).- 1.2 Botryococcenes (B Race).- 1.3 Lycopadiene (L Race).- 2. Classical Lipids.- 2.1 n-Fatty Acids.- 2.2 Triacylglycerols.- 2.3 Sterols.- 2.4 Carotenoids.- 3. Non-classical Lipids of the A Race.- 3.1 Botryals.- 3.2 n-Alkenylphenols.- 3.3 Epoxides.- 3.4 Ether Lipids.- 3.5 Methyl-branched Fatty Aldehydes and Fatty Acids.- 4. Macromolecular Lipids.- 4.1 B. braunii Rubber.- 4.2 Resistant Biopolymers from Outer Walls (PRB).- III. Geochemical Implications of B. braunii Composition.- 1. Role of PRB in Fossilization.- 2. Role of B. braunii Hydrocarbons as Biomarkers.- IV. B. braunii Biotechnology.- 1. Relationship Between Hydrocarbon Production and Physiological State.- 2. Influence of Various Culture Parameters on Hydrocarbon Production.- 2.1 Medium Composition.- 2.2 Light.- 2.3 B. braunii Strain.- 2.4 Associated Bacteria.- 3. Immobilized Cultures.- 4. Hydrocarbon Recovery.- V. Conclusion.- References.- Carbazole Alkaloids III.- I. Introduction.- A. Nomenclature.- B. Occurrence.- C. Detection of Carbazoles.- II. Methods of Structure Elucidation.- A. Physical Methods.- 1. Ultraviolet Absorption Spectra.- 2. IR Spectra.- 3. NMR Spectra.- (a) 1H-NMR Spectra.- (b) Application of the Nuclear Overhauser Effect.- (c) 13C-NMR Spectra.- 4. Mass Spectra.- 5. X-ray Crystallographic Methods.- B. Degradative Reactions.- C. Synthesis of Carbazoles.- 1. Synthesis of Tricyclic Alkaloids.- (a) From Arylamines.- (i) Electrophilic Aromatic Substitution.- (ii) Lewis-acid Catalysed Aliphatic Diazocoupling.- (b) From Diphenylamines.- (c) From Indoles.- (x) From Indole-2-Carboxylates.- (y) From 2-Alkylated Indoles.- (z) Cycloaddition Reactions.- (i) From 3-Vinylindoles.- (ii) From 2-Vinylindoles.- (iii) From Indole-2,3-quinodimethane and Analogues.- (iv) Benzannelation of Indoles.- (d) Biomimetic hydroxylation of 3-methylcarbazole.- 2. Synthesis of Tetracyclic Alkaloids.- (a) Alkaloids with a C18-Skeleton.- (i) Diphenylamine Route.- (ii) Introduction of a C5-unit with 3,3-Dimethylacrylic acid.- (b) Benzo-b-Carbazoles and Carbazoloquinones.- (c) Tetracyclic Alkaloids with a C23-Skeleton and Their Pentacyclic and Hexacyclic Cyclomers.- 3. Synthesis of Biscarbazoles.- (a) Synthesis of Alkaloids with a C26-Skeleton.- (i) Synthesis of Bismurrayafolinol Acetate.- (ii) Biomimetic Dimerisation.- (b) Formation of Alkaloids with C31- and C36-Skeletons.- (i) Nafion 117 Catalysed Dimerisation.- (ii) BF3-Etherate Catalysed Dimerisation.- 4. Transformations and Photochemical Reactions.- (a) Transformations.- (i) Thermal Transformation of Mahanimbine.- (ii) Racemisation and Inversion of Mahanimbine.- (b) Photochemical Reactions.- (i) Dimerisation of Vinylcarbazole.- (ii) Photo-Fries Rearrangement of N-Substituted Carbazoles.- (iii) Ring Expansion of Pyranocarbazoles.- (c) Formation of Bicyclodihydrooxepinocarbazole from Dihydrooxepinocarbazoles.- (d) Photochemical Synthesis of Benzocarbazoles.- III. Biogenesis of Carbazole Alkaloids.- IV. Biological and Therapeutic Properties of Carbazoles Alkaloids and Congeners.- V. Chemistry of Carbazole Alkaloids.- A. Alkaloids from Higher Plants.- (i) C13-Alkaloids.- 1. Murrayastine.- 2. Murrayaline.- 3. 0-Demethylmurrayanine.- 4. 3-Formylcarbazole.- 5. N-Methoxy-3-formylcarbazole.- 6. Carbazole.- (ii) C18-Alkaloids.- 1. Dihydroxygirinimbine.- 2. Pyrayafoline.- 3. Isomurrayafoline B.- 4. Atanisatin.- (iii) C23-Alkaloids.- 1. Murrayazolinol.- (iv) Carbazoloquinones.- 1. Pyrayaquinone A.- 2. Pyrayaquinone B.- 3. Pyrayaquinone C.- (v) Dimeric Carbazole Alkaloids.- (a) C26-Alkaloids.- 1. Bismurrayafolinol.- 2. Oxydimurrayafoline.- 3. Murrafoline F.- (b) C31-Alkaloids.- 1. Murrafoline B.- 2. Murrafoline D.- 3. Murrafoline E.- (c) C36-Alkaloids.- 1. Murrafoline C.- B. Alkaloids from Lower Plants.- (i) Carbazomycins.- 1. Carbazomycin C.- 2. Carbazomycin D.- 3. Carbazomycinal.- 4. 6-Methoxycarbazomycinal.- 5. Carbazomycin G.- 6. Carbazomycin H.- (ii) Kinamycins.- 1. Kinamycin C.- 2. Kinamycins A, B, and D.- 3. Prekinamycin.- 4. Ketoanhydrokinamycin.- 5. Kinamycin E.- 6. Deacetylkinamycin.- (iii) Tubingensins.- 1. Tubingensin A.- 2. Tubingensin B.- C. Alkaloids from Mammals.- References.- The Bryostatins.- 1. Introduction.- 2. Bryozoans and Bugula neritina Linnaeus.- 3. Isolation and Structure Elucidation of the Bryostatins.- 3.1. Bryostatins 1-3.- 3.2. Bryostatin 4.- 3.3. Bryostatins 5-7.- 3.4. Bryostatin 8.- 3.5. Bryostatin 9.- 3.6. Bryostatins 10 and 11.- 3.7. Bryostatins 12 and 13.- 3.8. Bryostatins A and B.- 4. Bioassay Guided Isolation.- 5. Chemical Transformations.- 6. Absolute Configuration.- 7. Spectral and Analytical Characterization.- 8. Antineoplastic and Cytostatic Activities.- 9. Inhibition of Tumor Promotion.- 10. General Biological Properties.- 10.1. Immunological.- 10.2. Hematopoietic.- 10.3. Microbiological.- 11. Mechanism of Action.- 12. Implications for Cancer Treatment.- 13. Conclusions.- Acknowledgement.- References.- Author Index.

Volume

58 : Wien ISBN 9783211822654

Description

0 e The volumes of this classic series, now referred to simply as "Zechmeister" after its founder, L. Zechmeister, have appeared under the Springer Imprint ever since the series' inauguration in 1938. The volumes contain contributions related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a recognized authority in his field and provides a comprehensive and up-to-date review of the topic in question. Addressed to biologists, technologists, and chemists alike, the series can be used by the expert as a source of information and literature citations and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

• Chemical and Biochemical Aspects of Polyether-Ionophore Antibiotic Biosynthesis.- 1. Introduction
• What is a Polyether Antibiotic?.- 2. A Polyketide Origin for the Polyether Antibiotics.- 3. The Mechanisms of Heterocyclic Ring Formation.- 4. Model Studies Related to the Late Stages of Polyether Biosynthesis.- 5. Evidence for the Processive Strategy of Polyketide Chain Assembly.- 6. A Unified Model of Polyether Antibiotic Structure and Biogenesis.- 7. Biochemistry of Polyketide Biosynthesis and Fatty Acid Biosynthesis.- 7.1. Programming Polyketide Assembly.- 7.2. Stereochemical Aspects of Polyketide Synthase Action.- 7.3. The Structure and Function of Fatty Acid Synthases.- 7.4. The Structure and Function of Bacterial Polyketide Synthases.- References.- Naturally Occurring Plant Coumarins..- I. Scope of the Review.- II. Progress in the Past Decade.- III. Introduction to Tables.- Table 1. 7-Oxygenated Coumarins.- 1.1. 6-Substituted-7-Oxygenated Coumarins.- 1.2. 8-Substituted-7-Oxygenated Coumarins.- 1.3. 5,6-Disubstituted-7-Oxygenated Coumarins.- 1.4. 6,8-Disubstituted-7-Oxygenated Coumarins.- Table 2. 5,7-Dioxygenated Coumarins.- Table 3. 6,7-Dioxygenated Coumarins.- Table 4. 7,8-Dioxygenated Coumarins.- Table 5. 5,6,7-Trioxygenated Coumarins.- Table 6. 5,7,8-Trioxygenated Coumarins.- Table 7. 6,7,8-Trioxygenated Coumarins.- Table 8. 5,6,7,8-Tetraoxygenated Coumarins.- Table 9. 3-Substituted Coumarins.- 9.1. 3-Aryl-Substituted Coumarins.- Table 10. 4-Substituted Coumarins.- 10.1. 4-Aryl-Substituted Coumarins.- Table 11. Miscellaneous Coumarins.- 11.1. 3-Aryl Oxygenated Coumarins.- 11.2. Coumestans.- Table 12. Biscoumarins.- Table 13. Triscoumarins.- Amendments/Additions to Entries in Reference 448.- Table 1. 7-Oxygenated Coumarins.- 1.1. 6-Substituted-7-Oxygenated Coumarins.- 1.2. 8-Substituted-7-Oxygenated Coumarins.- Table 2. 5,7-Disubstituted Coumarins.- Table 3. 6,7-Disubstituted Coumarins.- Table 4. 7,8-Disubstituted Coumarins.- Table 5. 5,6,7-Trisubstituted Coumarins.- Table 6. 5,7,8-Trisubstituted Coumarins.- Table 7. 6,7,8-Trisubstituted Coumarins.- Table 8. 5,6,7,8-Tetrasubstituted Coumarins.- Table 9. 3-Substituted Coumarins.- Table 10. 4-Substituted Coumarins.- Table 11. Miscellaneous Coumarins.- Formula Index.- Trivial Name Index.- References.

Volume

59 : Wien ISBN 9783211822784

Description

The volumes of this classic series, now referred to simply as Zechmeister after its founder, L. Zechmeister, have appeared under the Springer Imprint ever since the series' inauguration in 1938. The volumes contain contributions in various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a recognized authority in his field and provides a comprehensive and up-to-date review of the topic in question. Addressed to biologists, technologists, and chemists alike, the series can be used by the expert as a source of information and literature citations and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

Amino Acids from Mushrooms..- I. Introduction.- II. General Methods.- III. Structure, Occurrence and Biochemistry.- 1. Neutral Aliphatic Amino Acids.- 1.1. Hydroxyvaline, Hydroxyleucines, and Hydroxyisoleucines.- 1.1.1. 3-Hydroxyvaline.- 1.1.2. 4-Hydroxyleucine.- 1.1.3. 4,5-Dihydroxyleucine.- 1.1.4. 4,5,5?-Trihydroxyleucine.- 1.1.5. 4-Hydroxyisoleucine.- 1.1.6. 4,5-Dihydroxyisoleucine.- 1.2. Other Hydroxyamino Acids.- 1.2.1. 2-Amino-3,4-dihydroxybutanoic Acid.- 1.2.2. 2-Amino-4-ethoxy-3-hydroxybutanoic Acid.- 1.2.3. 4-Hydroxynorvaline.- 1.2.4. 2-Amino-7-hydroxyoctanoic Acid.- 1.3. Unsaturated Leucine and Isoleucine Homologues.- 1.3.1. 2-Amino-5-methyl-4-hexenoic Acid.- 1.3.2. 2-Amino-4-methyl-5-hexenoic Acid.- 1.3.3. 3-Methylenenorvaline.- 1.3.4. 2-Amino-3-hydroxymethyl-3-pentenoic Acid and 2-Amino-3-formyl-3-pentenoic Acid.- 1.3.5. 2-Amino-3-methylenehexanoic Acid.- 1.4. Unsaturated Norvalines and Norleucines, and Related Amino Acids.- 1.4.1. 2-Amino-3-butenoic Acid.- 1.4.2. Allylglycine and Propargylglycine.- 1.4.3. 2-Amino-3-hydroxy-4-pentynoic Acid.- 1.4.4. 2-Amino-5-hexenoic Acid.- 1.4.5. 2-Amino-4-hexynoic Acid.- 1.4.6. 2-Amino-5-hexynoic Acid.- 1.4.7. 2-Amino-3-hydroxy-4-hexynoic Acid.- 1.4.8. 2-Amino-6-hydroxy-4-hexynoic Acid.- 1.4.9. 2-Amino-4,5-hexadienoic Acid.- 1.4.10. 2-Aminohept-4-en-6-ynoic Acid.- 1.4.11. Cyclopropylalanine.- 1.5. Unsaturated Chloroamino Acids.- 1.5.1. 2-Amino-4-chloro-4-pentenoic Acid.- 1.5.2. Chlorocrotylglycine.- 1.5.3. 2-Amino-5-chloro-6-hydroxy-4-hexenoic Acid.- 1.5.4. 2-Amino-5-chloro-5-hexenoic Acid.- 1.5.5. 2-Amino-5-chloro-4-hydroxy-5-hexenoic Acid.- 2. Acidic Amino Acids.- 2.1. Hydroxyaspartic Acid.- 2.2. 4-Substituted Glutamic Acids.- 2.2.1. 4-Methylene-, 4-Ethylidene-, and 4-Propylideneglutamic Acid.- 2.2.2. 4-Methylglutamic Acid.- 2.3. 2-Amino-4-methylpimelic Acid.- 2.4. 3-Nitraminoalanine and 2-Amino-4-nitraminobutanoic Acid.- 3. Heterocyclic Amino Acids.- 3.1. Azetidine-2-carboxylic Acid and Derivatives.- 3.1.1. Azetidine-2-carboxylic Acid.- 3.2. Derivatives of Proline.- 3.2.1. 3-Aminoproline.- 3.3. Pipecolic Acid and Derivatives.- 3.3.1. 5-Hydroxypipecolic Acid.- 3.3.2. 3-Hydroxybaikiain.- 4. Amino Acids Containing Heterocycles.- 4.1. Pyrrolidine Amino Acids.- 4.1.1. 1-(3-Amino-3-carboxypropyl)-5-oxo-2-pyrrolidinecarboxylic Acid.- 4.2. Isoxazoline Amino Acids.- 4.2.1. Tricholomic Acid.- 4.2.2. Ibotenic Acid and Muscimol.- 4.2.3. Muscazone.- 4.3. Amino Acids Derived from Phenylalanine.- 4.3.1. Stizolobic Acid and Stizolobinic Acid.- 4.3.2. Muscaflavin.- 4.3.3. Betalains.- 4.3.4. Acromelic Acid A and Acromelic Acid B.- 4.4. Oxygen Heterocyclic Amino Acids.- 4.4.1. 3-(3-Carboxyfuran-4-yl)alanine.- 4.4.2. Lycoperdic Acid.- 5. Aromatic Amino Acids.- 5.1. Derivatives of Phenylalanine.- 5.1.1. 3,4-Dihydroxyphenylalanine.- 5.1.2. 4-Hydroxy-3-methoxyphenylalanine.- 5.2. Derivatives of Tryptophan.- 6. Miscellaneous Amino Acids.- 7. ?-Glutamyl Compounds.- 7.1. ?-Glutamyl Compounds of Protein Amino Acids.- 7.1.1. ?-Glutamylglycine.- 7.1.2. ?-Glutamylmethionine.- 7.1.3. ?-Glutamylcystine and Related Compounds.- 7.1.4. ?-Glutamylglutamic Acid.- 7.1.5. ?-Glutamylhistidine and ?-Glutamyllysine.- 7.2. ?-Glutamyl Compounds of Non-Protein Amino Acids.- 7.2.1. ?-Glutamyl-?-alanine.- 7.2.2. ?-Glutamyl-2-amino-4-hexynoic Acid and ?-Glutamyl-2-amino-3-hydroxy-4-hexynoic Acid.- 7.2.3. ?-Glutamyl-?-ornithine.- 7.2.4. ?-Glutamyl-3-aminoproline.- 7.2.5. ?-Glutamylnicotianine.- 7.3. ?-Glutamylpeptides of Amines.- 7.3.1. N-(?-Glutamyl)ethanolamine.- 7.3.2. Theanine.- 7.3.3. ?-Glutamyl-2-amino-3-hexanone.- 7.3.4. ?-Glutamyl-N-nitroethylenediamine.- 7.3.5. Coprine.- 7.4. Agaritine and Related Compounds.- 7.4.1. ?-Glutaminyl-4-hydroxybenzene.- 7.4.2. Agaritine.- 7.4.3. Xanthodermine.- 7.4.4. Agaridoxin.- 7.5. ?-Glutamyl Compounds Producing Odoriferous Substances.- 7.5.1. Lentinic Acid.- 7.5.2. ?-Glutamylmarasmine.- IV. Conclusions.- Acknowledgments.- Mushroom Index.- References.- Cembranoids, Pseudopteranoids, and Cubitanoids of Natural Occurrence..- I. Introduction.- A. Structural Representation and Nomenclature.- II. Cembranoids from Plants.- A. Plants Other than Tobacco.- B. Tobacco.- 1. Oxidation of the 11,12 Double Bond.- 2. Oxidation of the 7,8 Double Bond.- 3. Oxidation at Positions Allylic to the 11,12 Double Bond.- 4. Oxidation of the Hydroxy Group at C-6.- 5. Acid-Induced Reactions.- III. Cembrenes from Insects.- IV. Cembranoids from Marine Invertebrates.- A. Gorgonacea.- 1. Eunicea Species.- 2. Lophogorgia and Leptogorgia Species.- 3. Plexaura Species.- 4. Pseudopterogorgia Species.- B. Alcyonacea.- 1. Alcyonium Species.- 2. Gersemia Species.- 3. Lobophytum Species.- 4. Sarcophyton Species.- 5. Sinularia Species.- C. Stolonifera.- V. Pseudopteranoids from Marine Invertebrates.- Addendum-Cubitanoids.- Acknowledgements.- References.- Author Index.

Volume

60 : Wien ISBN 9783211823743

Description

The volumes of this classic series, now referred to simply as "Zechmeister" after its founder, L. Zechmeister, have appeared under the Springer Imprint ever since the series' inauguration in 1938. The volumes contain contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers.

Table of Contents

Cyclized Cembranoids of Natural Occurrence.- I. Introduction.- A. Nomenclature and Structural Representation.- II. Cyclized Cembranoids from Tobacco.- III. Cyclized Cembranoids from Insects.- A. Nasutitermitinae.- 1. Bulbitermes Species.- 2. Cortaritermes Species.- 3. Grallatotermes Species.- 4. Hospitalitermes Species.- 5. Longipeditermes Species.- 6. Nasutitermes Species.- 7. Subilitermes Species.- 8. Trinervitermes Species.- 9. Velocitermes Species.- IV. Cyclized Cembranoids from Marine Invertebrates.- A. Gorgonacea.- 1. Astrogorgia, Calicogorgia, Euniceila and Muricella Species.- 2. Briareum Species.- 3. Erythropodium Species.- 4. Junceella and Plexaureides Species.- B. Alcyonacea.- 1. Alcyonium Species.- 2. Cespitularia Species.- 3. Cladiella, Litophyton, Sclerophytum and Sinularia Species.- 4. Gersemia Species.- 5. Minabea Species.- 6. Sarcophyton Species.- C. Stolonifera.- D. Pennatulacea.- 1. Cavernulina, Pteroides, Ptilosarcus, Renilla, Scytalium and Stylatula Species.- 2. Veretillum Species.- Addendum.- Acknowledgements.- References.- Chemical Synthesis of Heparin Fragments and Analogues..- 1. Introduction.- 1.1 Heparin.- 1.2 Heparin Fragments.- 2. Synthesis of the Antithrombin Binding Site.- 2.1 Strategy.- 2.2 Preparation of D-Glucuronic Acid Derivatives.- 2.3 Preparation of L-Iduronic Acid Derivatives.- 2.4 Synthesis of the Fully Protected Pentasaccharides.- 2.5 Synthesis of Building Blocks from Natural Disaccharides.- 2.5.1 Synthesis from Cellobiose.- 2.5.2 Synthesis from Maltose.- 2.6 Deprotection and Functionalisation.- 2.7 Recent Results in the Synthesis of the Antithrombin Binding Site.- 2.7.1 Synthesis of the ?-Methyl Glycoside of the Antithrombin Binding Site.- 2.7.2 Synthesis of the N-Acetylated Antithrombin Binding Sequence.- 3. Synthesis and Biological Properties of Analogues of the Antithrombin Binding Site.- 3.1 Analogues lacking N, O-Sulphate Groups at Defined Positions.- 3.2 Analogues with Modifications of the Carboxylate Groups at Defined Positions.- 3.3 A Potent Analogue with Extra 3-O-Sulphate Group at Unit H.- 3.4 Analogues of the Extra Sulphated, Potent Analogue (81).- 3.5 Analogues Containing "Opened" Uronic Acid Moieties.- 3.6 Analogues with Various Modifications.- 3.7 Alkylated Analogues of Heparin Pentasaccharides.- 4. Conformational Properties.- 5. Interaction of Heparin Pentasaccharide Fragments with Antithrombin III.- Acknowledgements.- References.- Author Index.- General Index Vol. 21-60.

Volume

61 : Wien ISBN 9783211823880

Description

Contents: D. G. I. Kingston, A. A. Molinero, and J. M. Rimoldi: The Taxane Diterpenoids. - Author Index. - Subject Index. The volumes of this classic series, now referred to simply as "Zechmeister" after its founder, L. Zechmeister, have appeared under the Springer Imprint ever since the series' inauguration in 1938. The volumes contain contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a recognized authority in his field and provides a comprehensive and up-to-date review of the topic in question. Addressed to biologists, technologists, and chemists alike, the series can be used by the expert as a source of information and literature citations and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

The Taxane Diterpenoids.- 1. Introduction.- 2. General Structural Characteristic and Nomenclature.- 3. The Families of Taxane Diterpenoids.- 3.1. Taxoids with a C-4(20) Exocyclic Double Bond.- 3.2. Taxoids with a C-4(20) Epoxide.- 3.3. Taxoids with an Oxetane Ring.- 3.4. Miscellaneous Taxoids.- 4. The Chemistry of the Taxoids.- 4.1. Isolation Techniques.- 4.1.1. Extraction.- 4.1.2. Purification and Analysis.- 4.2. Spectroscopy.- 4.2.1. UV and ORD/CD Spectroscopy.- 4.2.2. Infrared Spectroscopy.- 4.2.3. 1H-NMR Spectroscopy.- 4.2.4. 13C-NMR Spectroscopy.- 4.2.5. Mass Spectrometry.- 4.2.6. X-ray Crystallography.- 4.3. Chemical Reactivity.- 4.3.1. Acylation and Other Protective Group Chemistry.- 4.3.2. Hydrolysis.- 4.3.3. Epimerization at C-7.- 4.3.4. Oxidation.- 4.3.5. Reduction.- 4.3.6. Rearrangements and Related Reactions.- 4.3.7. Photochemistry.- 5. Approaches to the Synthesis of Taxane Diterpenoids.- 5.1. Linear Strategies.- 5.1.1. Biomimetic Approaches.- 5.1.1.1. Kato's Approach.- 5.1.1.2. Frejd's Approach.- 5.1.1.3. Pattenden's Approach.- 5.1.2. Intramolecular Diels-Alder Approaches.- 5.1.2.1. Shea's Approach..- 5.1.2.2. Jenkin's Approach.- 5.1.2.3. Sakan's Approach.- 5.1.2.4. Yadav's Approach.- 5.1.3. AB?ABC Approaches.- 5.1.3.1. Martin's Approach.- 5.1.3.2. Holton's Approaches: The Synthesis of Taxusin.- 5.1.3.3. Oishi's Approach.- 5.1.3:4. Fetizon's Second Approach.- 5.1.3.5. Blechert's Second Approach.- 5.1.3.6. Wender's C-Ring Annulation Approach.- 5.1.3.7. Kraus' Approach.- 5.1.3.8. Yamada's Approach.- 5.1.3.9. Fetizon's Third Approach.- 5.1.3.10. Gadwood's Approach.- 5.1.4. BC?ABC Approaches.- 5.1.4.1. Swindell's Approach.- 5.1.4.2. Wender's A-Ring Annulation Approach.- 5.1.4.3. Sieburth's Approach.- 5.1.4.4. Kanematsu's Approach.- 5.2. Convergent Strategies.- 5.2.1. AC?ABC Approaches.- 5.2.1.1. Kitagawa's Approach.- 5.2.1.2. Fetizon's First Approach.- 5.2.1.3. Kende's Approach.- 5.2.1.4. Funk's Approach.- 5.2.1.5. Kuwajima's Approach.- 5.2.2. A[B]C?ABC Approaches.- 5.2.2.1. Trost's Approach.- 5.2.2.2. Inouye's First Approach.- 5.2.2.3. Blechert's First Approach.- 5.2.2.4. Clark's Approach.- 5.2.2.5. Berkowitz's Approach.- 5.2.2.6. Inouye's Second Approach.- 5.2.2.7. Winkler's Approach.- 5.2.2.8. A Variation on Fetizon's Second Approach.- 5.2.2.9. Ghosh's Approach.- 5.2.2.10. Paquette's Approach.- 5.2.2.11. Snider's Approach.- 5.2.2.12. Zucker's Approach.- 5.2.2.13. Frejd's Synthesis of a Secotaxoid.- 5.3. Partial Synthesis of Taxol and Related Compounds.- 5.3.1. Synthesis of Taxol and Taxol Analogues from 13-innamoylbaccatin III.- 5.3.2. Synthesis of Taxol by Acylation of Baccatin III with a Pre-formed Side Chain.- 5.3.3. Acylation of Baccatin III with (3-Lactams or Oxazinones.- 5.3.4. Synthesis of Taxol Analogues.- 5.3.5. Synthesis of Oxetane Models.- 6. Biosynthesis and Biotransformation of Taxoids.- 6.1. Biosynthesis of Taxoids.- 6.2. Biotransformation of Taxoids.- 7. Bioactivity of Taxol and Other Taxoids.- 7.1. Toxicity of Taxus Alkaloids.- 7.2. Biological Activity of Taxol and Related Compounds.- 7.2.1. Antitumor Activity of Taxol.- 7.2.2. Microtubule Assembly Activity of Taxol.- 7.2.3. Structure-activity Relationships of Taxol Analogs.- Addendum.- Acknowledgements.- References.- Author Index.

Volume

62 : Wien ISBN 9783211824023

Description

This volume is part of a series, inaugurated in 1938, now referred to simply as "Zechmeister" after its founder, L. Zechmeister. It contains contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a reconized authority in his field, and provides a comprehensive and up-to-date review of the topic in question. This title looks at the chemistry of organic natural products. It is addressed to biologists, technologists and chemists alike. The series can be used by the expert as a source of information and literature citations, and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

• Forskolin and congeners, S.V. Bhat
• steroidal oligoglycosides and polyhydroxysteroids from echinoderms, L. Minale et al.

Volume

63 : Wien ISBN 9783211824436

Description

Contents: A.B. Ray and M. Gupta: Withasteroids, a Growing Group of Naturally Occurring Steroidal Lactones. * L. Rodriguez-Hahn, B. Esquivel, and J. Cardenas: Clerodane Diterpenes in Labiatae. * Author Index. * Subject Index. The volumes of this classic series, now referred to simply as "Zechmeister" after its founder, L. Zechmeister, have appeared under the Springer Imprint ever since the series' inauguration in 1938. The volumes contain contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a recognized authority in his field and provides a comprehensive and up-to-date review of the topic in question. Addressed to biologists, technologists, and chemists alike, the series can be used by the expert as a source of information and literature citations and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

Withasteroids, a Growing Group of Naturally Occurring Steroidal Lactones.- I. Introduction.- A. Features of Withasteroids and Their Classification.- B. Distribution of Withasteroids.- II. Structure Elucidation Methods.- A. Physical Methods.- 1. Ultraviolet Absorption Spectra.- 2. Infrared Spectra.- 3. Nuclear Magnetic Resonance Spectra.- (a) 1H-NMR Spectra.- (b) 13C-NMR Spectra.- 4. Mass Spectra.- 5. Circular Dichroism Spectra.- 6. X-Ray Crystallographic Methods.- B. Degradative Reactions.- C. Chemical Transformations.- D. Synthesis of Withanolides.- III. Biogenesis and Biosynthesis of Withasteroids.- IV. Chemotypes and Chemogenetics.- V. Biological Activity of Withasteroids.- VI. Chemistry of Withasteroids.- A. Withanolides.- 1. Minabeolides.- 2. Withametelin, Isowithametelin, Secowithametelin and Withametelin B.- 3. Daturataturins A and B.- 4. Withasomniferin A and 5-Dehydroxywithanolide R.- 5. Daturametelins D, E, F and G.- 6. Withacoagin.- 7. Sominone and Sominolide.- 8. Withanolide Y.- 9. Withaperuvin H.- 10. Physagulin C.- 11. Jaborosalactol M and Jaborosalactone M.- 12. Jaboromagellone.- B. Ring A Aromatic Withanolides.- 1. Jaborol.- 2. Jaborosalactone Q.- C. Ring D Aromatic Withanolide.- 1. Salpichrolide A.- D. Ixocarpalactones.- 1. Trechonolide A.- 2. Jaborosalactone P.- 3. Taccalonolides A and B.- E. Physalins.- 1. Physalins L and M.- F. Acnistins.- 1. Tubocaposides A and B.- Addendum.- Structure Formulas.- References.- Clerodane Diterpenes in Labiatae.- I. Introduction.- II. Clerodane Diterpenes.- 1. Ajuga Species.- 2. Scutellaria Species.- 3. Teucrium Species.- Absolute Stereochemistry of Clerodane Diterpenoids from Teucrium Species.- 4. Salvia Species.- 5. Leonurus and Stachys Species.- III. Biological Activity.- Acknowledgement.- Table I. Distribution of Clerodane Diterpenoids in Teucrium sp.- Addendum.- References.- Author Index.

Volume

64 : Wien ISBN 9783211825334

Description

The volumes of this classic series, now referred to simply as "Zechmeister" after its founder, L. Zechmeister, have appeared under the Springer Imprint ever since the series' inauguration in 1938. The volumes contain contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a recognized authority in his field and provides a comprehensive and up-to-date review of the topic in question. Addressed to biologists, technologists, and chemists alike, the series can be used by the expert as a source of information and literature citations and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

Chemistry and Sources of Mono- and Bicyclic Sesquiterpenes from Ferula Species.- I. Introduction.- II. Biosynthetic Relationships.- III. Extraction and Isolation.- IV. Determination and Structural Types.- V. Monocyclic Sesquiterpenes.- VI. Bicyclic Sesquiterpenes.- 1. Bicyclic Alcohol Esters with a Hydroxy Group at C-10.- 2. Bicyclic Alcohol Esters with a Hydroxy Group at C-6.- VII. Other Sesquiterpenoids from Ferula Species.- VIII. Common Ester Side Chains in Sesquiterpenes from Ferula Species.- References.- The Chemistry of Melanins and Melanogenesis.- I. Introduction.- II. The Tangled Yarn of Melanin Research.- A. The Early Studies.- B. Melanogenesis in Vitro.- C. Melanogenesis in Vivo.- III. Note on Terminology.- IV. Eumelanins.- A. Protein Content.- B. Isolation and Analysis.- C. Synthetic Melanins.- D. Free Radicals and Redox Properties.- E. Carboxylic and Phenolic Groups.- F. Chemical Degradation.- G. Biomimetic and Biosynthetic Studies.- 1. Rearrangement of Dopachrome.- a. Mechanism of Reaction.- b. Regulatory Factors.- 2. Polymerization of Eumelanin Precursors.- a. 5,6-Dihydroxyindole.- b. 5,6-Dihydroxyindole-2-Carboxylic Acid.- V. Pheomelanins and Related Pigments.- A. Trichochromes.- B. Gallopheomelanins.- 1. Isolation and General Properties.- 2. Gallopheomelanin-1.- C. Biosynthetic Studies.- 1. The Pigment Precursors.- 2. Occurrence and Origin of Cysdopas.- 3. 1,4-Benzothiazinylalanines.- VI. Overview of Reaction Pathways.- Abbreviations.- References.- Structure, Occurrence, Biosynthesis, Biological Activity, Synthesis, and Chemistry of Aromadendrane Sesquiterpenoids.- 1. Structure and Occurrence.- 2. Biosynthesis.- 3. Biological Activity.- 4. Total Syntheses of Aromadendranes.- 5. Aromadendranes as Starting Materials in the Synthesis of Sesquiterpenes.- References.- Author Index.

Volume

65 : Wien ISBN 9783211825761

Description

Contents: Y. Asakawa: Chemical Constituents of the Bryophytes. The volumes of this classic series, now referred to simply as "Zechmeister" after its founder, L. Zechmeister, have appeared under the Springer Imprint ever since the series' inauguration in 1938. The volumes contain contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a recognized authority in his field and provides a comprehensive and up-to-date review of the topic in question. Addressed to biologists, technologists, and chemists alike, the series can be used by the expert as a source of information and literature citations and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

Chemical Constituents of the Bryophytes.- I. Introduction.- II. Chemical Constituents of Hepaticae (Liverworts).- 1. Monoterpenoids.- 2. Tris-normonoterpenoids.- 3. Homomonoterpenoids.- 4. Tris-norsesquiterpenoids.- 5. Sesquiterpenoids.- 5.1 Acoranes and Noracoranes.- 5.2 Africanes, Norafricanes and Secoafricanes.- 5.3 Aristolanes.- 5.4 Aromadendranes, Secoaromadendranes and Norsecoaromadendranes.- 5.5 Azulenes and Indenes.- 5.6 Barbatanes (Gymnomitranes).- 5.7 Bazzananes.- 5.8. Bergamotanes, Bicycloelemanes and Elemanes.- 5.9 Bicyclogermacranes, Isobicyclogermacranes and Lepidozanes.- 5.10 Bisabolanes, Bourbonanes and Brasilanes.- 5.11 Cadinanes, Amorphanes and Muurolanes.- 5.12 Calamenanes, Calacoranes and Cadalenes.- 5.13 Caryophyllanes, Cedranes and Chamigranes.- 5.14 Chiloscyphanes, Oppositanes, Copaanes and Cubebanes.- 5.15 Cuparanes and Herbertanes (Isocuparanes).- 5.16 Daucanes (Carotanes) and Drimanes.- 5.17 Eremophilanes and Eudesmanes.- 5.18 Farnesanes and Germacranes.- 5.19 Gorgonanes and Guaianes.- 5.20 Himachalanes and Humulanes.- 5.21 Longifolanes, Longibornanes, Longipinanes and Longicyclanes.- 5.22 Maalianes and Monocyclofarnesanes.- 5.23 Myltaylanes and Cyclomyltaylanes.- 5.24 Pacifigorgianes and Patchoulanes.- 5.25 Pinguisanes and Norpinguisanes.- 5.26 Santalanes, Spirovetivanes, Thujopsanes and Valencanes.- 5.27 Vitranes, Widdranes and Zieranes.- 5.28 Miscellaneous Sesquiterpenoids.- 6. Diterpenoids.- 6.1 Abietanes and Cembranes.- 6.2 Clerodanes, Secoclerodanes and Spiroclerodanes.- 6.3 Dolabellanes.- 6.4 Fusicoccanes.- 6.5 Kauranes.- 6.6 Labdanes and Chettaphanins.- 6.7 Phytanes, Pimaranes and Rearranged Pimaranes.- 6.8 Sacculatanes.- 6.9 Sphenolobanes.- 6.10 Trachylobanes and Verrucosanes.- 6.11 Verticillanes.- 7. Steroids and Triterpenoids.- 8. Aromatic Compounds.- 8.1 Benzoic Acid and Cinnamic Acid Derivatives.- 8.2 Bibenzyls.- 8.3 Bis-Bibenzyls.- 8.4 Long Chain Alkyl Phenols.- 8.5 Naphthalenes and Isocoumarins.- 8.6 Neolignan, Phenanthrenes and Phthalides.- 8.7 Miscellaneous Aromatic Compounds.- 8.8 Flavonoids.- 9. Lipids.- 9.1 n-Alkanes and Related Compounds.- 9.2 Fatty Acids.- 10. Sulfur-Containing Compounds.- 11. Carbohydrates.- III. Chemical Constituents of Musci (Mosses).- 1. Mono- and Diterpenoids.- 2. Steroids, Triterpenoids and Carotenoids.- 3. Aromatic Compounds.- 3.1 Benzoic and Cinnamic Acid Derivatives.- 3.2 Flavonoids.- 3.2.1 Flavones.- 3.2.2 Isoflavones.- 3.2.3 Biflavones.- 3.2.4 Aurones and Anthocyanins.- 3.3 Benzonaphthoxanthenones.- 4. Lipids.- 4.1 n-Alkanes and Related Compounds.- 4.2 Fatty Acids.- 5. Miscellaneous.- IV. Chemical Constituents of Anthocerotae (Hornworts).- 1. Sesquiterpenoids.- 2. Aromatic Compounds.- 2.1 Cinnamic Acid Derivatives.- 2.2 Lignans.- V. Biologically Active Substances of Bryophytes.- 1. Characteristic Scents.- 2. Pungency, Bitterness and Sweetness.- 3. Allergenic Contact Dermatitis.- 4. Antitumor Activity.- 5. Antimicrobial and Antifungal Activity.- 6. Insect Antifeedant and Molluscicidal Activity.- 7. Plant Growth Regulatory Activity.- 8. Superoxide Release Inhibitory Activity.- 9. 5-Lipoxygenase, Calmodulin and Thromboxane Synthetase Inhibitory Activity.- 10. Vasopressin (VP) Antagonist and Cardiotonic Activity.- 11. Piscicidal Activity.- 12. Neuritic Sprouting Activity.- 13. Muscle Relaxing Activity.- 14. Miscellaneous.- VI. Chemosystematics of Hepaticae.- 1. Jungermanniidae.- 1.1 Metzgeriales.- 1.1.1 Metzgeriaceae.- 1.1.2 Aneuraceae (Riccardiaceae).- 1.1.3 Pallaviciniaceae.- 1.1.4 Blasiaceae.- 1.2 Calobryales.- 1.2.1 Haplomitriaceae.- 1.3 Jungermanniales.- 1.3.1 Jungermanniaceae.- 1.3.2 Lophoziaceae.- 1.3.3 Gymnomitriaceae (Marsupellaceae).- 1.3.4 Arnelliaceae.- 1.3.5 Plagiochilaceae.- 1.3.6 Lophocoleaceae.- 1.3.7 Scapaniaceae.- 1.3.8 Balantiopsidaceae.- 1.3.9 Adelanthaceae.- 1.3.10 Schistochilaceae.- 1.3.11 Antheliaceae.- 1.3.12 Lepidoziaceae.- 1.3.13 Calypogeiaceae.- 1.3.14 Isotachidaceae.- 1.3.15 Trichocoleaceae.- 1.3.16 Ptilidiaceae.- 1.3.17 Herbertaceae.- 1.3.18 Radulaceae.- 1.3.19 Pleuroziaceae.- 1.3.20 Porellaceae.- 1.3.21 Frullaniaceae.- 1.3.22 Lejeuneaceae.- 2. Marchantiidae.- 2.1 Sphaerocarpales.- 2.2 Monocleales.- 2.3 Marchantiales.- 2.3.1 Targioniaceae.- 2.3.2 Aytoniaceae (Grimaldiaceae).- 2.3.3 Conocephalaceae.- 2.3.4 Lunulariaceae.- 2.3.5 Marchantiaceae.- 2.3.6 Ricciaceae.- VII. Chemosystematics of Musci and Anthocerotae.- VIII. Chemical Relationships Between Algae, Bryophytes and Pteridophytes-Evolution of Bryophytes.- 1. Similarities and Differences in Terpenoid and Steriod Content.- 2. Similarities and Differences in Content of Aromatic Compounds.- 3. Similarities and Differences in Alkane and Fatty Acid Content.- Acknowledgements.- References.- Author Index.

Volume

66 : Wien ISBN 9783211825976

Description

The volumes of this classic series, now referred to simply as "Zechmeister" after its founder, L. Zechmeister, have appeared under the Springer Imprint ever since the series' inauguration in 1938. The volumes contain contributions on various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a recognized authority in his field and provides a comprehensive and up-to-date review of the topic in question. Addressed to biologists, technologists, and chemists alike, the series can be used by the expert as a source of information and literature citations and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

Hydrolyzable Tannins and Related Polyphenols.- 1. Introduction.- 2. Monomeric Hydrolyzable Tannins.- 2.1. Galloyl Esters.- 2.2. Ellagitannins, Dehydroellagitannins and Naturally Occurring Oxidation Products.- 2.3. Condensates of Geraniin with Ascorbic Acid and Other Compounds.- 2.4. C-Glucosidic Tannins and Complextannins.- 3. Oligomeric Hydrolyzable Tannins.- 3.1. Classification of Oligomeric Hydrolyzable Tannins According to the O-Donating Monomer.- 3.2. Subsidiary Classification of Oligomers Based on the Type of Linkage.- 3.3. Detection and Isolation of Oligomers from Plants.- 3.4. Spectroscopic Analysis of Oligomeric Hydrolyzable Tannins.- 3.5. Significance of Oligomers as Taxonomic Markers.- 4. Chemical Transformations of Ellagitannins.- 4.1. Isomerization by the Smiles Rearrangement.- 4.2. Chemical Transformation of Ellagitannins to C-Glucosidic and Complextannins.- 4.3. Hydrolysis of Ellagitannins.- 5. Caffeic Acid Esters and Derivatives.- 6. Seasonal Change of Tannin Structures and Their Biogenesis.- 7. Distribution of Hydrolyzable Tannins in Plants.- 8. Production of Hydrolyzable Tannins in Tissue Cultures.- 9. Biosynthesis of Hydrolyzable Tannins.- 10. Biological and Pharmacological Activities of Hydrolyzable Tannins.- 10.1. Antioxidant Activities.- 10.2. Antitumor Activities.- 10.3. Antiviral Activities.- 10.4. Mutually Reverse Effects on Enzyme.- 10.5. Other Activities.- 10.6. Absorption and Metabolism of Tannins in Animals.- Addendum.- List of Compounds.- References.- Some Aspects of Guanidine Secondary Metabolites.- 1. Introduction.- 2. Physico-Chemical Properties of Guanidine.- 3. Guanidine Secondary Metabolites from Microorganisms.- 3.1. Streptothricins and Related Antibiotics.- 3.2. Streptomycin and Related Antibiotics.- 3.3. Viomycin and Related Tuberculostatic Compounds.- 3.4. Blasticidin S and Related Compounds.- 3.5. Netropsin (Congocidine).- 3.6. Macrocyclic Lactone Antibiotics.- 3.7. Peptide Guanidines.- 3.8. Other Guanidine Derivatives Originating from Microorganisms.- 4. Guanidine Secondary Metabolites from Marine and Freshwater Organisms.- 4.1. Marine and Freshwater Microorganisms.- 4.2. Marine Algae.- 4.3. Marine Sponges.- 4.4. Other Marine Invertebrates.- 5. Guanidine Secondary Metabolites from Higher Plants.- 6. Guanidine Secondary Metabolites from Terrestrial Invertebrates and Vertebrates.- 6.1. Spiders.- 6.2. Toads.- 7. 13C-NMR of Guanidine Natural Products.- 8. Conclusion.- References.- Author Index.

Volume

67 : Wien ISBN 9783211826959

Description

Contents: A.A. Leslie Gunatilaka: Triterpenoid Quinonemethides and Related Compounds (Celastroloids). - P. Walser-Volken and Ch. Tamm: The Spirostaphylotrichins and Related Microbial Metabolites. The volumes of this classic series, now referred to simply as "Zechmeister" after its founder, L. Zechmeister, have appeared under the Springer Imprint ever since the series' inauguration in 1938. The volumes contain contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a recognized authority in his field and provides a comprehensive and up-to-date review of the topic in question. Addressed to biologists, technologists, and chemists alike, the series can be used by the expert as a source of information and literature citations and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

Triterpenoid Quinonemethides and Related Compounds (Celastroloids).- 1. Introduction.- 2. General Structural Features and Nomenclature.- 3. The Families of Celastroloids.- 3.1. Quinonemethide Triterpenoids.- 3.2. 14(15)-Enequinonemethide Triterpenoids.- 3.3. 9(1 l)-Enequinonemethide Triterpenoids.- 3.4. Phenolic and 6-Oxophenolic Triterpenoids.- 3.5. 7-Oxoquinonemethide Triterpenoids.- 3.6. Dimeric Celastroloids.- 3.7. Miscellaneous Celastroloids.- 4. Natural Occurrence.- 4.1. Taxonomic Considerations.- 4.2. Plant Sources of Celastroloids.- 4.3. Distribution of Natural Celastroloids.- 4.4. Celastroloids from Tissue Cultures.- 5. Derivatives of Celastroloids.- 6. The Chemistry of Celastroloids.- 6.1. Isolation Techniques.- 6.2. Structure Elucidation.- 6.2.1. Early Structural Studies of Celastrol and Pristimerin.- 6.2.2. Application of Spectroscopic Techniques.- 6.2.2.1. UV/VIS and ORD/CD Spectroscopy.- 6.2.2.2. Infrared Spectroscopy.- 6.2.2.3. NMR Spectroscopy.- 6.2.2.3.1. 1H-NMR Spectroscopy.- 6.2.2.3.2. 13C-NMR Spectroscopy.- 6.2.2.4. Mass Spectrometry.- 6.2.2.5. X-Ray Crystallography.- 6.3. Chemical Reactions.- 6.3.1. General Chemical Characterization.- 6.3.2. Degradation and Oxidation.- 6.3.3. Reduction and Derivatization.- 6.3.4. Addition Reactions.- 6.3.5. Rearrangements.- 6.3.6. Photochemistry.- 7. Partial Synthesis.- 8. Biosynthetic Aspects.- 9. Biological Activity.- 9.1. Antimicrobial Activity.- 9.2. Antitumor Activity.- 9.3. Other Biological Activities.- 10. Conclusions.- Addendum.- Acknowledgements.- References.- The Spirostaphylotrichins and Related Microbial Metabolites.- 1. Introduction.- 2. Isolation of Spirostaphylotrichin A (1), B (2), C and D (3/4), Q (5), R (6) and F (7) from Cultures of Staphylotrichum coccosporum.- 3. Biosynthetic Studies.- 3.1. Feeding Experiments with 14C-, 13C, and 2H-Labelled Precursors.- 3.1.1. Experiments with 14C-Labelled Precursors.- 3.1.2. Experiments with 13C- and 2H-Labelled Precursors.- 3.2. Investigation of Mutant Strains and Isolation of Further Spirostaphylotrichins.- 3.2.1. Mutagen Treatment and Selection of Mutants.- 3.2.2. The Mutant Strain P 84.- 3.2.3. The Mutant Strain P 649.- 4. Investigation of the Epimerization of Spirostaphylotrichins.- 5. Discussion of the Results Regarding the Biosynthesis of the Spirostaphylotrichins.- 6. Synthetic Approaches Towards the Spirostaphylotrichins.- 7. Related Fungal Metabolites: Triticones, Arthropsolides, and Other Compounds.- 7.1. Triticones.- 7.2. Arthropsolides and Related Compounds.- References.- Author Index.

Volume

68 : Wien ISBN 9783211827024

Description

The objective of this ASI was to bring together specialists in several complex variables (many of whom have contributed to complex potential theory) and specialists in potential theory (all of whom have contributed to several complex variables) together with young researchers and graduate students for an interchange of ideas and techniques. Not only was the status of current research presented, but also the relevant background, much of which is not yet available in books. The following topics and interconnections among them were discussed: 1. Real and Complex Potential Theory. Capacity and approximation, basic prop- erties of plurisubharmonic functions and methods to manipulate their singularities and study their growth, Green functions, Chebyshev-type quadratures, electrostatic fields and potentials, propagation of smallness. 2. Complex Dynamics. Review of complex dynamics in one variable, Julia sets, Fatou sets, background in several variables, Henon maps, ergodicity, use of potential theory and multifunctions. 3. Banach Algebras and Infinite Dimensional Holomorphy. Analytic multi- functions, spectral theory, analytic functions on a Banach space, semigroups of holomor- phic isometries, Pick interpolation on uniform algebras and Von Neumann inequalities for operators on a Hilbert space. The basic notion of complex potential theory is that of a plurisubharmonic function.

Table of Contents

Naturally Occurring Organohalogen Compounds-A Comprehensive Survey.- 1. Introduction.- 2. Origins.- 3. Occurrence.- 3.1. Simple Alkanes.- 3.1.1. Chloromethane.- 3.1.2. Dichloromethane.- 3.1.3. Chloroform.- 3.1.4. Carbon Tetrachloride.- 3.1.5. Other Simple Haloalkanes.- 3.2. Simple Functionalized Acyclic Organohalogens.- 3.3. Simple Functionalized Cyclic Organohalogens.- 3.3.1. Cyclopentanes.- 3.3.2. Cyclitols and Benzoquinones.- 3.4. Terpenes.- 3.4.1. Monoterpenes.- 3.4.1.1. Acyclic Monoterpenes.- 3.4.1.2. Alicyclic Monoterpenes.- 3.4.2. Sesquiterpenes.- 3.4.2.1. Terrestrial Sesquiterpene Lactones.- 3.4.2.2. Indanone Sesquiterpenes.- 3.4.2.3. Other Terrestrial Sesquiterpenes.- 3.4.2.4. Marine Sesquiterpenes.- 3.4.2.4.1. Monocyclic and Other Simple Sesquiterpenes.- 3.4.2.4.2. Chamigrene and Related Types.- 3.4.2.4.3. Eudesmane and Other Types.- 3.4.2.4.4. Cuparene, Laurene, and Other Aromatic Types.- 3.4.3 Diterpenes.- 3.4.3.1 Terrestrial Diterpenes.- 3.4.3.2. Marine Diterpenes.- 3.4.3.2.1. Diterpenes of Aplysia.- 3.4.3.2.2. Diterpenes of Laurencia.- 3.4.3.2.3. Sphaerococcus and Other Red Algae Diterpenes.- 3.4.3.2.4. Sponge Diterpenes.- 3.4.3.2.5. Gorgonian Diterpenes.- 3.4.4. Higher Terpenes.- 3.5. Steroids.- 3.6. Marine Nonterpenes-C15 Acetogenins.- 3.7. Iridoids.- 3.8. Lipids and Fatty Acids.- 3.9. Fluorine-Containing Carboxylic Acids.- 3.10. Prostaglandins.- 3.11. Furanones.- 3.12. Amino Acids and Peptides.- 3.13. Alkaloids.- 3.14. Heterocycles.- 3.14.1. Pyrroles.- 3.14.2. Indoles.- 3.14.3. Carbazoles.- 3.14.4. Indolocarbazoles.- 3.14.5. Carbolines.- 3.14.6. Quinolines and Other Nitrogen Heterocycles.- 3.14.7. Benzofurans and Related Compounds.- 3.14.8. Pyrones.- 3.14.9. Coumarins and Isocoumarins.- 3.14.10. Flavones and Isoflavones.- 3.15. Polyacetylenes.- 3.15.1. Terrestrial Polyacetylenes and Derived Thiophenes.- 3.15.2. Marine Polyacetylenes.- 3.16. Enediynes.- 3.17. Macrolides.- 3.18. Naphthoquinones and Higher Quinones.- 3.19. Tetracyclines.- 3.20. Aromatics.- 3.21. Simple Phenols.- 3.21.1. Terrestrial.- 3.21.2. Marine.- 3.22. Complex Phenols.- 3.22.1. Diphenylmethanes and Related Compounds.- 3.22.2. Diphenyl Ethers and Related Compounds.- 3.22.3. Tyrosines.- 3.22.3.1. Simple Tyrosines, Thyroxine, and Related Compounds.- 3.22.3.2. Transformed Single Tyrosines.- 3.22.3.3. Transformed Multiple Tyrosines.- 3.22.3.4. Bastadins.- 3.22.4. Depsides.- 3.22.5. Depsidones.- 3.22.6. Xanthones.- 3.22.7. Anthraquinones and Related Compounds.- 3.22.8. Griseofulvin and Related Compounds.- 3.22.9. Miscellaneous Fungal Metabolites and Other Complex Phenols.- 3.23. Glycopeptides.- 3.24. Orthosomycins.- 3.25. Dioxins.- 3.26. Humic Acids.- 4. Biohalogenation.- 4.1. Introduction and Early Examples.- 4.2. Chloroperoxidase.- 4.3. Bromoperoxidase.- 4.4. Other Peroxidases.- 5. Biodegradation.- 6. Natural Function.- 7. Significance.- 8. Future Outlook.- Addendum.- Acknowledgements.- References.- Author Index.

Volume

69 : Wien ISBN 9783211828243

Description

The volumes of this classic series, now referred to simply as "Zechmeister" after its founder, L. Zechmeister, have appeared under the Springer Imprint ever since the series' inauguration in 1938. The volumes contain contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a recognized authority in his field and provides a comprehensive and up-to-date review of the topic in question. Addressed to biologists, technologists, and chemists alike, the series can be used by the expert as a source of information and literature citations and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

Non-Macrocyclic Trichothecenes, Part 2.- 1. Introduction and Nomenclature.- 2. Naturally Occurring Compounds.- 3. Unnatural Trichothecenes.- 4. Chemistry.- 4.1. Ethylenic Double Bonds.- 4.1.1. Isomerization.- 4.1.2. Catalytic Reduction.- 4.1.3. Electrophilic Addition Reactions.- 4.1.3.1. Epoxidation of 9-Enes.- 4.1.3.2. Epoxidation of 12-Enes.- 4.1.3.3. Epoxidation of 7-Enes.- 4.1.3.4. Hydroxylation.- 4.1.3.5. Bromination.- 4.1.3.6. Carbene Addition.- 4.1.4. Reactions at the ?-Carbon Atom.- 4.1.5. Ozonolysis.- 4.2. Hydroxyl Groups.- 4.2.1. Regioselective Esterification and Etherification, and Regeneration of the Hydroxyl Function.- 4.2.1.1. Verrucarol.- 4.2.1.2. Scirpenetriol.- 4.2.1.3. T-2 Tetraol.- 4.2.1.4. Vomitoxin and Nivalenol.- 4.2.1.5. 12-Ols.- 4.2.2. Regioselective Oxidation.- 4.2.2.1. 8-Ols.- 4.2.2.2. 15-Ols.- 4.2.2.3. 3-Ols.- 4.2.2.4. 4-Ols.- 4.2.2.5. 12-Ols.- 4.2.3. Deoxygenation.- 4.2.4. Nucleophilic Substitution.- 4.3. Keto Groups.- 4.3.1. Derivative Formation.- 4.3.2. Regio- and Stereo-Selective Reduction.- 4.3.3. Nucleophilic Addition Reactions.- 4.3.3.1. Phosphorus Ylides.- 4.3.3.2. Sulphur Ylides.- 4.3.4. Enolization, and Reactions at the ?-Carbon Atom.- 4.3.5. Isomerization.- 4.4. Epoxide Function.- 4.4.1. 12,13-Epoxide.- 4.4.1.1. The Trichothecene ? 10,13-Cyclotrichothecane Rearrangement.- 4.4.1.2. The Trichothecene ? Apotrichothecene Rearrangement.- 4.4.1.3. Deoxygenation.- 4.4.2. 7,8-Epoxide.- 4.4.3. 9,10-Epoxide.- 5. Biosynthesis.- 5.1. Mevalonate to Trichodiene.- 5.2. Trichodiene (and Its Relatives) to 12,13-Epoxytrichothecene and Isotrichodermin.- 5.3. Further Oxygenation and Esterification of the Trichothecene Nucleus.- 5.4. Inhibitors of Trichothecene Biosynthesis.- 6. Metabolism.- 6.1. Cleavage of Ester Groups.- 6.2. Hydroxylation.- 6.3. 12,13-Deoxygenation.- 6.4. Glucuronide Formation.- 7. Spectroscopy.- 7.1. Nuclear Magnetic Resonance Spectra.- 7.1.1. 1H-Spectra.- 7.1.2. 13C-Spectra.- 7.2. Mass Spectra.- References.- Cardiac Glycosides.- 1. Introduction.- 2. Isolation and Identification.- 2.1. Structural Features of Cardiac Genins.- 2.2. Sugars of Cardiac Glycosides.- 2.3. Sequence, Number and Identification of Monosaccharides.- 2.4. I.R. Spectroscopy of Cardiac Glycosides.- 2.5. Mass Spectrometry of Cardiac Glycosides.- 2.6. NMR Spectrometry of Cardiac Glycosides.- 3. Biological Activity.- Acknowledgements.- Table 1. Cardenolide Glycosides Isolated from Plants.- Table 2. Bufadienolide Glycosides Isolated from Plants.- Table 3. Formulas of Cardiac Glycosides.- References.- Aspects of the Enzymology of the Shikim Pathway.- 1. Introduction.- 2. The Shikimate Metabolic Pathway.- 2.1. Common Pathway - Enzymes and Intermediates.- 2.2. Common Pathway - Enzymology.- 2.2.1. 3-Deoxy-D-arabino-heptulosonate 7-phosphate (DAHP) Synthase.- 2.2.2. 3-Dehydroquinate Synthase.- 2.2.3. 3-Dehydroquinate Dehydratase (3-Dehydroquinase).- 2.2.4. Shikimate Dehydrogenase (Shikimate Oxido-Reductase).- 2.2.5. Shikimate Kinase.- 2.2.6. 5-Enolpyruvylshikimate-3-phosphate Synthase (5-EPSP Synthase).- 2.2.7. Chorismate Synthase.- 2.3. Pathways Beyond Chorismate - Enzymes and Intermediates.- 2.3.1. Pathways to L-Phenylalanine and L-Tyrosine.- 2.3.1.1. Chorismate Mutase - Monofunctional.- 2.3.1.2. Chorismate Mutase - Bifunctional.- 2.3.1.3. Monofunctional Prephenate Dehydratase and Prephenate Dehydrogenase.- 2.3.1.4. Aminotransferases.- 2.3.1.5. L-Arogenate ( "Pretyrosine") Metabolism.- 2.3.2. Pathway to L-Tryptophan.- 2.3.2.1. Anthranilate Synthase.- 2.3.2.2. Anthranilate-5?-phosphoribose-l-pyrophosphate Phosphoribosyl Transferase, iV-(5?-Phosphoribosyl)-anthranilate Isomerase and Indole-3-glycerolphosphate Synthase.- 2.3.2.3. Tryptophan Synthase.- 2.3.3. Folate Coenzymes, Isoprenoid Quinones and Enterochelin.- 2.3.3.1. p-Aminobenzoate Synthase.- 2.3.3.2. Isochorismate Synthase and Enterochelin (Enterobactin).- 2.3.4. Phenylpropanoid Metabolism in Plants.- 2.3.4.1. L-Phenylalanine Ammonia Lyase (PAL).- 2.4. Metabolic "Costs" of Aromatic Amino Acid Biosynthesis.- 3. Enzyme Mechanisms.- 3.1. 3-Deoxy-D-arabino-heptulosonate-7-phosphate (DAHP) Synthase.- 3.2. 3-Dehydroquinate Synthase (7-Phospho-3-deoxy-D-arabimo-heptulosonate Phosphate Lyase).- 3.3. 5-Enolpyruvylshikimate-3-phosphate (5-EPS-3-P) Synthase.- 3.3.1. Glyphosate.- 3.4. Chorismate Synthase.- 3.5. Chorismate Mutase.- 4. Multifunctional Enzymes.- 5. Genetic Engineering.- 5.1. Biocatalytic Syntheses of Aromatics from D-Glucose.- 5.2. Anthocyanin Biosynthesis - Genetic Manipulation of Flower Colour.- Notes Added in Proof.- References.- Author Index.

Volume

70 : Wien ISBN 9783211828250

Description

The volumes of this classic series, now referred to simply as "Zechmeister" after its founder, L. Zechmeister, have appeared under the Springer Imprint ever since the series' inauguration in 1938. The volumes contain contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a recognized authority in his field and provides a comprehensive and up-to-date review of the topic in question. Addressed to biologists, technologists, and chemists alike, the series can be used by the expert as a source of information and literature citations and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

The Dolastatins.- 1. Introduction.- 2. Dolabella auricularia.- 3. Isolation and Structure Determination of the Dolastatins.- 4. Synthesis of the Dolastatins.- 4.1 Dolastatin 3.- 4.2 Dolastatin 10.- 4.2.1 Dolaphenine (Doe).- 4.2.2 Dolaproine (Dap).- 4.2.3 Dolaisoleuine (Dil).- 4.2.4 Dolaproinyl-Dolaphenine (Dap-Doe).- 4.2.5 Conversion of Dap-Doe to Dolastatin 10.- 4.2.6 Chromatography of Dolastatin 10.- 4.2.7 High-Field NMR Analysis of Dolastatin 10.- 4.3 Syntheses of (6R)-Isodolastatin 10 and Other Chiral modifications of Dolastatin 10.- 4.3.1 Crystal Structure of (6R)-Isodolastatin 10.- 4.3.2 Molecular Modeling of (6R)-Isodolastatin 10.- 4.4 Structural Modifications of Dolastatin 10.- 4.5 Synthesis of Dolastatin 15.- 4.6 Synthesis of Dolastatin C.- 5. Spectral and Analytical Characterization.- 5.1 Dolastatin 10.- 5.2 Dolastatins 11 and 12.- 5.3 Dolastatin 13.- 5.4 Dolastatin 14.- 5.5 Dolastatin 15.- 6. Cytostatic and Antineoplastic Activities.- 6.1 Dolastatins 10-15.- 6.2 Dolastatin 10 Structural Modifications.- 6.2.1 Chiral Isomers.- 6.2.2 Structural Substitutions.- 7. Biochemical Mechanisms of Action.- 7.1 Inhibition of Tubulin Assembly and Mitosis.- 7.2 Effects on Actin.- 8. Pharmacology and Toxicology.- 9. Conclusion.- Acknowledgements.- References.- Acetogenins from Annonaceae.- I. Introduction.- II. Classification.- Synonyms of Acetogenins.- Listing (Structures and Physical Data).- Distribution.- III. Extraction and Isolation.- IV. Structure Elucidation.- V. Biogenetic Hypotheses.- VI. Syntheses.- VII. Biological Activities.- Acknowledgements.- References.- Author Index.

Volume

71 : Wien ISBN 9783211828502

Description

The volumes of this classic series, now referred to simply as 'Zechmeister' after its founder, L. Zechmeister, have appeared under the Springer Imprint ever since the series' inauguration in 1938. The volumes contain contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances, ranging from small molecules to biopolymers. Each contribution is written by a recognized authority in his field and provides a comprehensive and up-to-date review of the topic in question. Addressed to biologists, technologists, and chemists alike, the series can be used by the expert as a source of information and literature citations and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

The Explosion of Structural Information on Insect Neuropeptides.- 1. Introduction.- 2. General Methods Used for Isolation, Identification and Characterization of Insect Neuropeptides.- 2.1. Biological Assays.- 2.1.1. Adipokinetic Bioassay.- 2.1.2. Myotropic Bioassay.- 2.2. Liquid Chromatography.- 2.3. Edman Degradation Sequencing, Mass Spectrometry and Peptide Synthesis.- 2.4. Immunological Techniques (RIA, ELISA, Immunocytochemistry).- 2.5. Molecular Biological Techniques.- 3. The Insect Neuropeptides.- 3.1. Peptides Involved in Homeostasis and Metabolism.- 3.1.1. Adipokinetic and Hypertrehalosaemic Peptides.- 3.1.2. Diuretic and Antidiuretic Peptides.- 3.2. Peptides Regulating Reproduction, Growth and Development.- 3.2.1. Pheromone Biosynthesis Activating Neuropeptides.- 3.2.2. Allatotropins and Allatostatins.- 3.2.2.1. Allatotropins.- 3.2.2.2. Allatostatins.- 3.2.3. Prothoracicotropic Hormone, Bombyxin and Other Insulin-Related Neuropeptides.- 3.2.3.1. Prothoracicotropic Hormone.- 3.2.3.2. Bombyxin.- 3.2.3.3. Locusta Insulin-Related Peptide.- 3.2.4. Eclosion Hormones.- 3.2.5. Peptides Affecting Gonad Activity.- 3.2.5.1. Ovary Maturating Peptide and Neuroparsin of Locusta migratoria.- 3.2.5.2. Oostatic Hormones of Diptera.- 3.2.6. Diapause Hormones.- 3.3. Peptides Modifying Spontaneous Muscle Contractions:Mytropic Peptides.- 3.3.1. Proctolin and Cardiostimulatory Peptides.- 3.3.2. Myokinins.- 3.3.3. Sulfakinins.- 3.3.4. Pyrokinins/Myotropins.- 3.3.5. Tachykinins.- 3.3.6. Periviscerokinin.- 3.3.7. Accessory Glands- and Midgut Myotropins and Others.- 3.3.8. Myoinhibitory Peptides and Other FMRF amide Related Peptides (FaRPs).- 3.4. Chromatotropic Factors in Insects.- 4. Conclusions.- Acknowledgments.- References.- Sesquiterpenoids from Thapsia Species and Medicinal Chemistry of the Thapsigargins.- 1. Introduction.- 2. Taxonomy of Thapsia.- 2.1. Thapsia garganica and Thapsia transtagana.- 2.2. Thapsia maxima.- 2.3. Thapsia villosa.- 2.4. Thapsia gymnesica.- 3. Elucidation of the Structure of Thapsigargin.- 4. Proazulenic Slovanolides.- 5. Non-lactonic Sesquiterpenoids from Thapsia.- 6. Pharmacological Activity of the Thapsigargins.- 7. Molecular Pharmacology.- 8. Chemistry of Thapsigargin.- 8.1. Changes at C(8).- 8.2. Changes at C(3).- 8.3. Changes of the Vicinal Diol.- 8.4. Changes of Lactone Carbonyl Group.- 8.5. Changes at O(10).- 9. Structure Activity Relationships.- 10. Metabolic Catabolism of Thapsigargin.- References.- Pregnane Glycosides.- 1. Introduction.- 2. Isolation and Identification.- 2.1. Thin Layer and Column Chromatography.- 2.2. Sephadex LH-20 Chromatography.- 2.3. Flash Chromatography.- 2.4. Low Pressure Liquid Chromatography (LPLC).- 2.5. High Performance Liquid Chromatography (HPLC).- 3. Structure Elucidation.- 3.1. One-Dimensional NMR Spectroscopy.- 3.2. Two-Dimensional NMR Spectroscopy.- 3.3. Mass Spectrometry.- 3.4. I.R. Spectroscopy.- 3.5. U.V. Spectroscopy.- 3.6. Optical Rotatory Dispersion.- 3.7. Hydrolysis of Pregnane Glycosides.- 4. Pregnane Aglycons.- 5. Sugars of Pregnane Glycosides.- 5.1. General and Monosaccharides.- 5.2. Disaccharides from Pregnane Glycosides.- 5.3. Trisaccharides from Pregnane Glycosides.- 6. Biosynthesis of Pregnane Glycosides.- 7. Biological Activity.- Acknowledgement.- References.- Author Index.

Volume

72 : Wien ISBN 9783211828793

Description

The volumes of this classic series, now referred to simply as "Zechmeister" after its founder, L. Zechmeister, have appeared under the Springer Imprint ever since the series' inauguration in 1938. The volumes contain contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a recognized authority in his field and provides a comprehensive and up-to-date review of the topic in question. Addressed to biologists, technologists, and chemists alike, the series can be used by the expert as a source of information and literature citations and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

Naturally Occurring Plant Coumarins.- I. Scope of the Review.- II. Progress in the Past Six Years.- III. Introduction to Tables.- Table 1. 7-Oxygenated Coumarins.- 1.1 6-Substituted-7-Oxygenated Coumarins.- 1.2 8-Substituted-7-Oxygenated Coumarins.- 1.3 5,6-Disubstituted-7-Oxygenated Coumarins.- 1.4 6,8-Disubstituted-7-Oxygenated Coumarins.- Table 2. 5,7-Dioxygenated Coumarins.- Table 3. 6,7-Dioxygenated Coumarins.- Table 4. 7,8-Dioxygenated Coumarins.- Table 5. 5,6,7-Trioxygenated Coumarins.- Table 6. 5,7,8-Trioxygenated Coumarins.- Table 7. 6,7,8-Trioxygenated Coumarins.- Table 8. 5,6,7,8-Tetraoxygenated Coumarins.- Table 9. 3-Substituted Coumarins.- 9.1 3-Aryl-Substituted Coumarins.- Table 10. 4-Substituted Coumarins.- 10.1 4-Aryl-Substituted Coumarins.- Table 11. Miscellaneous Coumarins.- 11.1 3-Aryl-Oxygenated Coumarins.- 11.2 Coumestans.- Table 12. Biscoumarins.- Table 13. Triscoumarins.- Amendments/Additions to Entries in Reference (171) and/or Reference [172]..- Table 1. Coumarin and 7-Oxygenated Coumarins.- 1.1 6-Substituted-7-Oxygenated Coumarins.- 1.2 8-Substituted-7-Oxygenated Coumarins.- Table 2. 5,7-Dioxygenated Coumarins.- Table 3. 6,7-Dioxygenated Coumarins.- Table 4. 7,8-Dioxygenated Coumarins.- Table 5. 5,6,7-Trioxygenated Coumarins.- Table 6. 5,7,8-Trioxygenated Coumarins.- Table 7. 6,7,8-Trioxygenated Coumarins.- Table 8. 5,6,7,8-Tetraoxygenated Coumarins.- Table 9. 3-Substituted Coumarins.- 9.1 3-Aryl-Substituted Coumarins.- Table 10. 4-Substituted Coumarins.- 10.1 4-Aryl-Substituted Coumarins.- Table 11. Miscellaneous Coumarins.- 11.1 3-Aryl-Oxygenated Coumarins.- 11.2 Coumestans.- Table 12. Biscoumarins.- Formula Index.- Trivial Name Index.- References.- Artemisinin: An Endoperoxidic Antimalarial from Artemisia annua L..- 1. Introduction.- 1.1. Historical.- 1.2. History of the Qinghao Plant.- 1.3. Modern History of Artemisia annua L. in Chinese Medicine.- 2. Artemisia annua L. and its Constituents.- 2.1. Taxonomy.- 2.2. Geographic Distribution.- 2.3. Cultivation.- 2.4. Cell Culture.- 2.5. Isolation of Artemisinin from A. annua.- 2.6. Other Constituents of A. annua.- 3. Artemisinin Structure Determination.- 4. Artemisinin Syntheses.- 4.1. From ( - )-Isopulegol.- 4.2. From (R)-(+)-Hydroxymenthol.- 4.3. From 3(R)-Methyl-6-phenylsulfmyl-cyclohexanone.- 4.4. From ( + )-Isolimonene.- 4.5. From Artemisinic Acid.- 4.6. From Arteannunin B.- 5. Physical Measurements and Analyses.- 5.1. NMR.- 5.1.1. 1H.- 5.1.2. 13C.- 5.2. Circular Dichroism.- 5.3. Infrared.- 5.4. Mass Spectroscopy.- 5.5. X-Ray Crystallography.- 5.6. Quantitative TLC.- 5.7. Titrimetric.- 5.8. HPLC.- 5.8.1. Electrochemical Detection.- 5.8.2. UV Detection Methods.- 5.8.3. Capillary Gas Chromatography.- 5.8.4. Diverse Analytical Methods.- 5.8.5. Radiolabelling.- 5.8.6. Radioimmuno Assay.- 6. Reactions of Artemisinin and its Derivatives.- 6.1. Thermolysis.- 6.2. Chemical.- 6.2.1. Reactions with Alkali.- 6.2.2. Reactions with Ammonia and Amines.- 6.2.3. Reactions with Acid.- 6.2.3.1. Arteether.- 6.2.3.2. Dihydroartemisinin.- 6.2.3.3. Acid-Catalyzed Additions to Anhydrodihydroartemisinin.- 6.2.3.3.1. Triphenylphosphine Hydrobromide.- 6.2.3.3.2. p-Toluenesulfonic Acid.- 6.2.3.4. Acid-Catalyzed Rearrangements of Artemisinin Derivatives.- 6.2.3.4.1. Lewis Acids.- 6.2.3.4.2. Silica Gel-Catalyzed Rearrangements.- 6.2.4. Reaction of Artemisinin with Reducing Agents.- 6.2.4.1.Lithium Aluminum Hydride.- 6.2.4.2. Sodium Borohydride.- 6.2.4.3. A Mixture of Sodium Borohydride and Boron Trifluoride.- 6.2.4.4. Hydrogenation.- 6.2.5. Bromination.- 6.2.6. Fluorinated Artemisinin Derivatives.- 6.2.7. Epoxidation of Anhydrodihydroartemisinin.- 6.2.8. Osmium Tetroxide Oxidation.- 7. Dihydroartemisinin Derivatives.- 7.1. Derivatives with Enhanced Oil Solubility.- 7.1.1. Ethers.- 7.1.2. Esters.- 7.1.3. Carbonates.- 7.2. Derivatives with Enhanced Water Solubility.- 7.2.1. Sodium Artesunate.- 7.2.2. Sodium Artelinate and Related Derivatives.- 7.3. Artemisinin Derivatives.- 7.3.1. (+)-Deoxoartemisinin.- 7.3.2. (+)-Homodeoxoartemisinin.- 7.3.3. (+)-10-Alkyldeoxoartemisinin.- 7.3.4. (+)-10?-Allyldeoxoartemisinin.- 7.3.5. C-3 and C-9 Substituted 10-Deoxoartemisinins.- 7.3.6. C-14 Modified Deoxoartemisinins.- 8. Simplified Artemisinin Derivatives.- 8.1. 9-Desmethylartemisinin.- 8.2. 6,9-Bisnorartemisinin.- 8.3. (+)-8a,9-Secoartemisinin.- 8.4. (+)-4,5-Secoartemisinin.- 8.5. (+)-Hexahydroisochroman-3-one.- 8.6. 4,5-Desethanoartemisinin.- 8.7. 9-Alkyl-9-desmethylartemisinin.- 8.8. C-3 and C-9 Modified Artemisinin Derivatives.- 8.9. Carba-Analogs of Artemisinin.- 9. Quantitative Structure-Activity Analyses.- 10. Tricyclic 1,2,4-Trioxane Analogs.- 11. Metabolism.- 11.1. Microbial Metabolites of Artemisinin and its Derivatives.- 11.2. Mammalian Metabolites.- 12. Test Data of Artemisinin Derivatives.- 12.1. In Vitro.- 12.2. In Vivo.- 13. Toxicity.- 14. Pharmacology and Pharmacokinetics.- 15. Clinical Evaluation of Artemisinin and Derivatives.- 15.1. Dihydroartemisinin.- 16. Mechanisms of Action.- 17. Other Peroxides.- 17.1. Naturally Occurring Peroxides.- 17.2. Synthetic Peroxides.- 18. Conclusion.- References.- Marine Glycolipids.- 1. Introduction.- 2. Isolation Procedures.- 3. Determination of the Structure of Glycolipids.- 3.1. Determination of the Structure of the Sugar Portion.- 3.2. Determination of the Structure of the Lipid Portion.- 4. Glycoglycerolipids.- 5. Glycosphingolipids.- 5.1. Neutral Glycosphingolipids.- 5.2. Phosphorus-Containing Glycosphingolipids.- 5.3. Gangliosides.- 6. Other Glycolipids.- 7. Biological Activities.- 7.1. Immunological Activity.- 7.2. Pharmacological Activity.- References.- Author Index.

Volume

73 : Wien ISBN 9783211830192

Description

The Leguminosae is an economically important family in the Dicotyledonae with many cultivated species, e. g. , beans and peas. The family also contains many well-known medicinal plants. It is composed of 17,000 or more species that constitute nearly one twelfth of the world's flowering plants (1). Traditionally the family has been divided into three subfamilies, Caesalpinioideae, Mimosoideae and Papilionoi- deae, which are sometimes recognized as separate families Caesalpinia- ceae, Mimosaceae and Papilionaceae. The International Code of Botanical Nomenclature permits alternative nomenclatures, the family names being replaced by Fabaceae, Fabales and Faboideae, and this usage will be common (2). Licorice (liquorice, kanzoh in Japanese, gancao in Chinese) is the name applied to the roots and stolons of some Glycyrrhiza species (Fabaceae) and has been used by human beings for at least 4000 years. The earliest written reference to the use of licorice is contained in the Codex Hammurabi dating from 2100 B. C. , and the subsequent history in the West has been described in the earlier reviews (3-6). In the Far East, references to the effectiveness of licorice are contained in the "Shen Nong Ben Cao Jing", the first Chinese dispensatory whose original anonymous volumes probably appeared by the end of the third century (7, 8).

Table of Contents

Phenolic Constituents of Licorice (Glycyrrhiza Species).- 1. Introduction.- 2. Triterpenoid Saponins.- 2.1. Glycyrrhizic Acid.- 2.2. Structures of Minor Sapogenins.- 2.3. Structures of Minor Saponins.- 3. Phenolic Compounds.- 3.1. Flavonoids and Coumarins from Underground Parts.- 3.2. Phenolic Compounds from Aerial Parts.- 3.3. Phenolic Compounds from Whole Plants.- 3.4. Phenolic Compounds from Cell Cultures.- 4. Recent Methods of Structure Determination of Prenylated Phenols.- 4.1. Variations in the Chemical Shift of the Methylene Carbon of a Prenyl Group.- 4.2. Variations in the Chemical Shift of the 5-Hydroxyl Proton of 6- or 8-Prenylated Flavonoids.- 4.3. Variations in the Chemical Shift of the 5-Hydroxyl Proton of Pyranoflavonoids.- 4.4. CD Spectra of Licorice Isoflavans.- 5. Biological Activities of Phenolic Constituents of Glycyrrhiza Species.- Acknowledgments.- References.- Author Index.

Volume

74 : Wien ISBN 9783211830338

Description

Saponins are complex molecules made up of sugars linked to a triterpenoid or a steroid or a steroidal alkaloid. These natural products are attracting much attention in recent years because of the host of biological activities they exhibit. The diversity of structural features, the challenges of isolation because of their occurrence as complex mixtures, the pharmacological and biological activities still to be discovered, and the prospect of commercialization - these all are driving the study of saponins. Triterpenoid saponins are dominating constituents of this class and occur widely throughout the plant kingdom including some human foods e. g. beans, spinach, tomatoes, and potatoes, and animal feed e. g. alfalfa and clover. Saponins were initially a rather neglected* area of research primarily because of great difficulties in their isolation and characterization. With the advent of more sophisticated methods of isolation and structure elucidation through the last two decades, there has been increased interest in these natural products. Besides structure determination, research activities are now moving forward to clarify structure-activity relationships. Our previous reviews on triterpenoid saponins (l, 2) covered literature from 1979 to mid-1989. The literature on triterpenoid saponins up to 1988 has also been covered by two reviews by HILLER et at. (3, 4). This review incorporates newer trends in isolation and structure determination of triterpenoid saponins, new triterpenoid saponins isolated and biological properties of these products reported during the period late 1989-mid 1996. 2.

Table of Contents

Triterpenoid Saponins.- 1. Introduction.- 2. Isolation.- 3. Structure Elucidation.- 3.1. Mass Spectroscopy.- 3.2. NMR Spectroscopy.- 4. Biological Activity.- 4.1. Antifungal Activity.- 4.2. Immunomodulatory Activity.- 4.3. Molluscicidal Activity.- 4.4. Spermicidal Activity.- 4.5. Hypoglycemic Activity.- 4.6. Antitumor Activity.- 4.7. Hypocholesterolemic Effect.- 4.8. Antiaging Effect.- 4.9. Cardiovascular Activity.- 4.10. Antiviral Activity.- 4.11. Antisweet Activity.- 4.12. Analgesic Activity.- 4.13. Antileishmanial Activity.- 4.14. Miscellaneous Effects.- 5. Production of Saponins by Tissue Culture.- 6. Future Possibilities.- 7. Reports of New Triterpenoid Saponins.- Acknowledgements.- References.- Synthesis of 6-Deoxyamino Sugars.- 1. Introduction.- 1.1. General.- 1.2. Antibiotics.- 2. Known 6-Deoxyaminohexoses.- 3. Synthetic Aspects.- 3.1. Carbohydrates as Starting Materials.- 3.1.1. Monoamino Dideoxyhexoses.- 3.1.2. Monoamino Trideoxyhexoses.- 3.1.3. Monoamino Tetradeoxyhexoses.- 3.2. Non-Carbohydrates as Starting Materials.- 3.2.1. Monoamino Dideoxyhexoses.- 3.2.2. Monoamino Trideoxyhexoses.- 3.2.3. Monoamino Tetradeoxyhexoses.- References.- Author Index.

Volume

75 : Wien ISBN 9783211830536

Description

The volumes of this classic series, now referred to simply as "Zechmeister" after its founder, L. Zechmeister, have appeared under the Springer Imprint ever since the series' inauguration in 1938. The volumes contain contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a recognized authority in his field and provides a comprehensive and up-to-date review of the topic in question. Addressed to biologists, technologists, and chemists alike, the series can be used by the expert as a source of information and literature citations and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

Cyclopeptide Alkaloids.- 1. Introduction.- 2. Classification.- 3. Structure Elucidation - Stereochemistry.- 3.1. NMR Spectroscopy.- 3.2. UV, IR, CD Spectroscopy.- 3.3. MS.- 4. MS Fragmentation of Cyclopeptide Alkaloids and Related Compounds.- 4.1. Fragmentation of 4(14)-Frangulanine- and -Integerrine-Type Cyclopeptide Alkaloids.- 4.2. Fragmentation of 4(14)-Pandamine-Type Cyclopeptide Alkaloids.- 4.3. Fragmentation of 5(13)-Zizyphine-A- and 5(14)-Amphibine-B-Type Cyclopeptide Alkaloids.- 4.4. Fragmentation of 5(14)-Scutianine-A-Type Cyclopeptide Alkaloids (Hymenocardine included).- 4.5. Fragmentation of 4(14)-Amphibine-F-Type Cyclopeptide Alkaloids.- 4.6. Fragmentation of 4(13)-Nummularine-C-Type Cyclopeptide Alkaloids.- 4.7. Fragmentation of 4(15)-Mucronine-A-Type Cyclopeptide Alkaloids.- 4.8. Fragmentation of Linear Peptide Alkaloids.- 4.9. Fragmentation of Neutral Compounds Related to Cyclopeptide Alkaloids.- 4.10. Miscellaneous.- 4.11. Common Fragments.- 5. Identification Strategy.- 6. Physical and Spectral Data of Cyclopeptide Alkaloids and Related Compounds.- 7. Synthesis.- 8. Biological Activity.- 8.1. Sedative Activity.- 8.2. Antibacterial Activity.- 8.3. Antifungal Activity.- 9. Biosynthesis - Tissue Culture.- 10. Conclusions.- 11. General Tables.- Table 7. Cyclopeptide Alkaloids and Related Compounds in Order of Increasing Molecular Weight.- Table 8. Alphabetical List of Cyclopeptide Alkaloids and Related Compounds.- Table 9. Plant Index.- Addendum.- References.- Naturally Occurring 6-Substituted 5,6-Dihydro-?-Pyrones.- 1. Introduction.- 2. 6-Alkyl-5,6-dihydro-?-pyrones.- 3. 6-Alkenyl-5,6-dihydro-?-pyrones.- 4. 6-Aryl-5,6-dihydro-?-pyrones.- 5. Physical Methods of Structure Determination.- References.- Author Index.

Volume

76 : Wien ISBN 9783211831656

Description

In order to make further progress in elucidating the mechanism of NOS catalysis it will be essential to throw light on the interaction between the enzyme and its substrate. An understanding of the catalytic site will also assist the development of therapeutically important NOS inhibitors. In particular. it will be useful to uncover any differences that exist between the substrate binding sites of the three NOS isozymes which might be exploited for the development of isoform selective NOS inhibitors. A comparison of NOS to other Arg-binding proteins has shown no significant sequence homology (159). Moreover, the lack of a 3D structure and absence of significant sequence homology between the NOS oxygenase domain and known cytochromes P450 has made it difficult to identify residues and construct a model of the distal heme pocket responsible for substrate binding. However, a number of groups are currently working towards crystallisation of the separate NOS reductase and oxygenase domains of the three isoforms for X-ray diffraction studies; the first X-ray structure is likely to be forthcoming within a matter of months. * The results of these studies are expected to resolve many of the uncertainties surrounding the structure of the NOS catalytic site. Preliminary X-ray diffraction analysis of CPR from rat liver has already been reported by MASTERS et al. (524) and the future emergence of a detailed structure for this protein should throw light on the structure and function of the NOS reductase domain.

Table of Contents

Nitric Oxide: Physiological Roles, Biosynthesis and Medical Uses.- List of Abbreviations and Acronyms.- 1. Introduction.- 2. Discovery in the Vasculature.- 3. Platelet Aggregation.- 4. NO and the Immune System.- 5. NO and the Nervous System.- 6. S-Nitrosothiols.- 6.1. NO-Release.- 6.2. Endogenous S-Nitrosothiols.- 6.3. S-Nitrosothiols as NO-Donor Drugs.- 7. NO Activity in the Mammalian Eye.- 8. The NO Biosynthetic Pathway.- 8.1. Introduction.- 8.2. Relation of Nitric Oxide Synthase to Cytochrome P 450.- 8.3. NO Synthase Isoforms.- 9. Mechanism of the Nitric Oxide Synthase-Catalysed Reaction.- 9.1. Mechanism of Cytochrome P450-Mediated Oxidations.- 9.1.1. P450-Mediated Hydroxylation.- 9.1.2. P450-Mediated N-Oxidation and N-Dealkylation.- 9.1.3. P450-Mediated Epoxidation.- 9.1.4. Aromatase Chemistry.- 9.2. Mechanism of NOS Monooxygenation I.- 9.3. Mechanism of NOS Monooxygenation II.- 9.4. Mechanism-Based Inhibitors of NOS.- 9.5. Summary.- 10. Nitric Oxide Synthase Structure.- 10.1. Primary Structure and Domain Organisation of NOS.- 10.1.1. Primary Structure.- 10.1.2. Domain Organisation.- 10.2. Function of the NOS Reductase Domain.- 10.3. The Calmodulin Binding Site.- 10.4. Membrane Association of NOS.- 10.5. Structure and Topology of the NOS Catalytic Site.- 10.5.1. Identification of Heme Thiolate Ligand.- 10.5.2. Characterisation of the NOS Heme Spin State.- 10.5.3. Structure of the NOS Catalytic Site.- 10.5.4. Identification of Residues that contribute to the Catalytic Site.- 10.5.5. Complementation Analysis with NOS Heterodimers.- 10.5.6. Summary.- 10.6 Role of the Biopterin Cofactor in NOS Catalysis.- 10.6.1. NOS and Pteridine-Dependent Hydroxylases: Dissimilarity in the Catalytic Role of H4B.- 10.6.2. An Allosteric Role for H4B in NOS Catalysis.- 10.6.3. A Redox Role for H4B in NOS Catalysis.- 10.6.4. The H4B Binding Site.- 10.7. NOS Dimer Assembly.- 10.8. Autoinactivation/NO Feedback Inhibition of NOS.- 10.9. Distinctive Features of NOS Isoforms.- 11. Clinical Uses of NO and Its Inhibitors.- 11.1. Respiratory Systems.- 11.2. Airway Modulation and Asthma.- 11.3. Toxicology.- 11.4. Adult Respiratory Distress Syndrome.- 11.5. Sepsis.- 11.6. NO, Inflammation, and the Immune System.- 11.7. NOS Inhibition in Sepsis.- 11.8. NO and Cardiovascular Disease.- 11.9. NO and Interventional Cardiology.- 11.10. Pregnancy.- 11.11. Pre-Eclampsia.- 11.12. Nervous System.- 11.13. Bone.- 11.14. Conclusion.- 12. Addendum.- Acknowledgements.- References.- Author Index.

Volume

77 : Wien ISBN 9783211832646

Description

The condensed tannins (syn. polymeric proanthocyanidins) represent a major group of phenolic compounds in woody and some herbaceous plants (1-3). Their exceptional concentrations in the barks and heartwoods of a variety of tree species have resulted in their commercial extraction with the initial objective of applying the extracts in leather manufacture (4). Essentially all of their biological significance, e. g. the protection of plants from insects, diseases and herbivores, and most of the current, e. g. leather manufacture, and also most promising new uses, e. g. pharmaceuticals or wood preservatives, rest on their com plexation with other biopolymers like proteins and carbohydrates, or metal ions (5, 6). Increasing attention has thus been directed to understanding their conformation and conformational flexibility (7-20) in order to explain their biological activity and to provide a basis for further development of uses for these renewable phenolic compounds. Recent developments have also been initiated by the growing realization that the condensed tannins may additionally be credited for the profound health-beneficial properties of tea, fruit juices and red wine. This is mainly due to their in vitro radical scavenging (21) or antioxidant (22) biological properties, while the polymeric proanthocyanidins in red wine have been implicated in protection against cardiovascular disorders (23), e. g. the "French paradox" (24-26). Collectively these 'positive' characteristics of the polymeric proanthocyanidins have transformed "a relatively unattractive and therefore neglected area of study" (27) into, yet again, a fashionable research field.

Table of Contents

Secondary Metabolites and the Control of Some Blue Stain and Decay Fungi.- Condensed Tannins.- Constituents of Lactarius (Mushrooms).- Author Index.

Volume

78 ISBN 9783211833117

Description

It was in 1979 when GROVE et al. isolated from pollen of rape (Brassica nap us) a highly active plant growth promoter, named it brassinolide and elucidated its structure as (22R,23R,24S)-2

Table of Contents

Brassinosteroids.- 1. Introduction.- 2. Natural Occurrence and Distribution.- 3. Structures.- 4. Isolation and Purification.- 5. Analysis of Brassinosteroids.- 5.1. GC-MS Analysis.- 5.2. HPLC Analysis.- 5.3. NMR Spectroscopy.- 6. Synthesis.- 7. Biosynthesis.- 7.1. Biosynthesis in Catharanthus roseus.- 7.2. Biosynthesis in Other Species.- 8. Metabolism of Brassinosteroids.- 8.1. Metabolism in Plants.- 8.2. Metabolism in Cell Cultures of Lycopersicon esculentum.- 8.3. Metabolism in Cell Cultures of Ornithopus sativus.- 9. Physiological Action.- 10. Molecular Mode of Action.- 11. Conclusions.- References.- Chemistry of the Neem Tree (Azadirachta indica A. Juss.).- 1. Introduction.- 2. Chemistry of Limonoids.- 2.1. Protolimonoids.- 2.2. Apo-Protolimonoids.- 2.3. Apo-Protolimonoids Derived from Loss of 4C-Atoms from the Side Chain which Possess a Hemiacetal Group.- 2.4. Limonoids with Intact Four Rings and a ?-Hydroxybutenolide Side Chain.- 2.5. Azadirone and its Natural Analogues.- 2.6. Homoazadirone Group.- 2.7. Gedunin Group.- 2.8. Vilasinin Group.- 2.9. Nimbin Group.- 2.10. Nimbolide Group.- 2.11. Nimbinene Group.- 2.12. Nimbolinin Group.- 2.13. Salannin Group.- 2.14. Azadirachtol Group.- 2.15. Meliacarpin Group.- 2.16. Meliacarpinin and Azadirachtinin Group.- 2.17. Azadirachtin Group.- 2.18. Azadirachtin.- 2.18.1. Biological Activity.- 2.18.2. Structure-Activity Relationships.- 2.18.3. Structure Determination.- 2.18.4. Chemical Reactions.- 2.18.4.1. Reaction of -OH Group.- 2.18.4.1.1. Acetylation.- 2.18.4.1.2. Silylation.- 2.18.4.1.3. Methylation.- 2.18.4.2. Hydrogenation.- 2.18.4.3. Reactions of the Enol Ether Functions.- 2.18.4.4. Saponification Reactions.- 2.18.4.5. Functional Group Chemistry of Azadirachtol.- 2.18.4.6. Oxidation Reactions.- 2.18.4.7. Functional Group Chemistry of 7-Keto Azadirachtins.- 2.18.4.8. Retro-Aldo1 Reaction.- 2.18.4.9. Skeletal Rearrangements.- 2.18.5. Synthesis.- 2.18.5.1. Synthesis of Dihydrofuranacetal Fragment 'A'.- 2.18.5.1.1. Preparation of Prototype Coupling Fragment.- 2.18.5.2. Decalin 'B' Synthesis.- 2.18.5.3. Coupling of 'A' and 'B' Fragments.- 3. Other Compounds.- 3.1. Diterpenoids.- 3.2. Steroids and Other Triterpenoids.- 3.3. Phenolic Compounds.- 3.3.1. Flavonoids.- 3.3.2. Flavonoglycosides.- 3.3.3. Coumarins.- 3.3.4. Dihydrochalcone.- 3.3.5. Tannins.- 3.4. Carbohydrates and Proteins.- 3.5. Sulphur Compounds.- 3.6. Hydrocarbons, Acids and Esters.- References.- Author Index.

Volume

79 ISBN 9783211833612

Table of Contents

List of Contributors.- Synthetic Aspects of Iridoid Chemistry.- 1. Introduction.- 2. Classification of Iridoids.- 2.1. Iridoid Glycosides.- 2.2. Non-Glycosidic Iridoids.- 2.3. Nitrogen-Containing Compounds.- 3. Availability and Production of Iridoids.- 3.1. Plant Sources.- 3.2. Cell-Cultures.- 3.3. Isolation and Purification Methods.- 4. Semi-Synthetic Conversions Between Iridoids.- 4.1. Hydrolysis and Lactonization.- 4.2. Decarboxylation of Iridoid Glucosides.- 4.3. Reduction and Oxidation of Iridoid Glucosides.- 4.4. Miscellaneous Transformations Used in Structure Elucidation.- 4.5. Non-Glucosidic Iridoids.- 4.6. Ring-Cleavage Sequences and Secoiridoid Chemistry.- 5. Monoterpene Alkaloids Structurally Related to lridoids.- 5.1. PMTAs - Natural Compounds or Artifacts?.- 5.2. Semi-Synthesis of Pyridine Monoterpene Alkaloids.- 5.3. Bacterial Metabolism of Iridoid Glucosides.- 5.4. Total Synthesis of Pyridine Monoterpene Alkaloids.- 5.5. Diversity of Bicyclic Cyclopentanoid Piperidines.- 5.6. Synthesis of Bicyclic Cyclopentanoid Piperidines.- 5.7. Semi-Synthesis of Glucosidic Secoiridoid Alkaloids.- 6. Syntheses from Iridoids.- 6.1. Formation of Colored Compounds.- 6.2. Reactions of Secoiridoids.- 6.3. Preparation of Marine Diterpenoids.- 6.4. Building Blocks for Other Types of Cyclopentanoids.- 6.5. Modifications of the Sugar Moiety in Iridoid Glucosides.- References.- The Defensive Chemistry of Ants.- 1. Introduction.- 2. Alkaloids.- 2.1. Structures, Occurrence, and Function.- 2.1.1. Piperidines and Pyridines.- 2.1.2. Pyrrolidines and Pyrrolines.- 2.1.3. Pyrrolizidines.- 2.1.4. Indolizidines.- 2.1.5. Tetraponerines.- 2.1.6. Other Alkaloids.- 2.2. Synthesis.- 2.2.1. Piperidines.- 2.2.2. Pyrrolidines.- A. Synthesis of Racemic Pyrrolidines 13.- B. Syntheses of Nonracemic Pyrrolidines 13.- 2.2.3. Pyrrolines.- 2.2.4. Pyrrolizidines.- 2.2.4.1. 3,5-Dialkylpyrrolizidines 15.- A. Xenovenine.- B. (5E,8E)-3-Butyl-5-hexylpyrrolizidine.- 2.2.4.2. 3-Methyl-5-alkenylpyrrolizidines and 3,5-Dialkenylpyrrolizidines 16.- 2.2.5. Indolizidines.- 2.2.5.1. Monomorine I 16.- A. Syntheses of Racemic Monomorine I.- B. Syntheses of Nonracemic Monomorine I.- 2.2.5.2. 3,5-Dialkylindolizidines 19.- A. 3-Butyl-5(4-penten-l-yl)indolizidine.- B. 3-Ethyl- and 3-Hexyl-5-methylindolizidines.- C. Myrmicarin 237A and 237B.- D. Myrmicarin 217.- 2.2.6. Tetraponerines.- A. Syntheses of Racemic Tetraponerines 20.- B. Syntheses of Nonracemic Tetraponerines 20.- 3. Nonalkaloidal Compounds.- 4. Biosynthesis.- References.

Volume

80 ISBN 9783211834282

Description

Glycosmis is a clearly defined genus within the tribe Clauseneae of the Aurantioideae subfamily of the family Rutaceae comprising about 40 species (1). Its range of distribution is centered in south and southeast Asia (India, Sri Lanka, Myanmar, Thailand, Malaysia, Indonesia) and extends to south China and Taiwan as well as to New Guinea and north Australia. Exceptions are only cultivated species like the Chinese G. parvijiora (Sims) Little, formerly called G. citrifolia (Willd. ) Lindley, which became naturalized in tropical America and Africa (Angola) (1). The shrubs or small trees are unarmed and possess pinnate or simple leaves with translucent punctate glands emitting an aromatic odor when crushed. The axillary inflorescences are usually dispersed closed panicles with small white flowers. The fruits are mostly pink, reddish or white berries of about I cm in diameter with only one or two seeds. The genus name Glycosmis originates from the sweet smell of the flowers and the sweet taste of the fleshy pericarp of the fruits. A good field and herbarium character of the genus is that the buds of new leaves are usually covered with short rusty-red hairs. In spite of the good delimitation of Glycosmis from the other closely related Clauseneae genera Clausena, Micromelum, Murraya, and Merrillia and the already existing subrevisionary treatment by Stone (1), there are still many unresolved taxonomic problems at the species level.

Table of Contents

Naturally Occurring Isocyano/Isothiocyanato and Related Compounds.- 1. Introduction.- 1.1. Occurrence and Distribution.- 1.2. Nomenclature and Structural Representation.- 1.3. Isolation and Identification.- 1.3.1. Physical and Chemical Properties.- 1.3.2. Spectral Characterization.- 2. Monoterpene Indole Alkaloids from Blue-Green Algae.- 2.1. C21-Compounds.- 2.1.1. Hapalindolcs.- 2.1. 1. 1. Tetracyclic Hapalindoles 1.- 2.1.1.2. Tricyclic Hapalindoles 1.- 2.1.2. Fischerindoles.- 2.2. Oxindoles and Modified Oxygenated C'21-Indoles.- 2.2.1. Hapaloxindoles.- 2.2.2. Hapalonamides.- 2.2.3. Hapalindolinones.- 2.2.4. Welwitindolinoncs.- 2.3. C26-Indole Alkaloids.- 2.3.1. Ambiguine Isonitriles.- 2.4. Reactions of Hapalindoles.- 2.5. Syntheses of Hapalindolcs.- 3. Marine Diterpenes from Sponges.- 3.1. Acyclics.- 3.2. Kalihinanes.- 3.2.1. Kalihinols from Actin/he/hi Sponges.- 3.2.2. Tetrahydropyrans.- 3.2.3. Tetrahydrofurans.- 3.2.4. Dihydropyrans.- 3.3. Amphilectanes.- 3.3.1. Isocyanoditcrpencs from Crnihastela hooperi.- 3.3.2. Amphilectanes.- 3.3.3. Cycloamphilectanes.- 3.3.4. Isocycloamphilectanes.- 3.3.5. Veo-and "Prc"-amphilcctadicncs.- 3.4. Diterpene Syntheses.- 4. Marine Sesquiterpenes from Sponges.- 4.1. Skeletal Types.- 4.2. The Triads from Axinella cannabina.- 4.3. Sesquiterpenoid Compounds.- 4.3.1. Axanes.- 4.3.2. Aromadendranes.- 4.3.3. Eudesmanes.- 4.3.4. Cadinanes.- 4.3.5. Epimaalianes.- 4.3.6. Spiroaxanes.- 4.3.7. Bisbolanes.- 4.3.8. Guaiane-Types.- 4.3.9. Pupukeanane-Types.- 4.4. Sesquiterpene Syntheses.- 5. Uncommon Marine Analogs.- 5.1. Carbonimidic Dichloride Terpenes.- 5.2. Isothiocyanato and Thiocyanato Nonterpenoids.- 5.2.1. Ascidians.- 5.2.2. Sponges.- 5.3. Marine Cyanides.- 6. Other Terrestrial Compounds.- 6.1. Isocyanides from Lower Organisms.- 6.1.1. Xanthocillins.- 6.1.2. Cyclopentanes.- 6.1.2.1. Dermadin-Types 12.- 6.1.2.2. Trichoviridin-Types 12.- 6.2. Other Terrestrial Isocyanides.- 6.3. Other Terrestrial Analogs.- 6.4. Syntheses of Terrestrial Isocyanides.- 7. Biogenesis and Biosynthesis.- 7.1. Monoterpene Indole Alkaloids.- 7.2. Diterpenes.- 7.3. Sesquiterpenes.- 7.4. Other Terrestrial Isocyanides and Isothiocyanates.- 8. Discussion and Summary.- Addendum.- Acknowledgment.- References.- Sulfur-Containing Amides from Glycosmis Species (Rutaceae).- I. Introduction.- 2. Isolation and Structure Elucidation.- 2.1. Analytical HPLC and Preparative MPLC.- 2.2. Structure Elucidation and Stereochemistry.- 3. Methylthiopropenoic Acid Amides.- 4. Methylsulfinylpropenoic Acid Amides.- 5. Methylsulfonylpropenoic Acid Amides.- 5.1. p-Prenyloxyphenethylamides.- 5.2. O-Geranyltyramides.- 5.3. p-O-Geranyldopamides.- 5.4. 13-Hydroxy-O-geranyltyramides.- 6. Methylthiocarbonic Acid Amides.- 7. Synthesis of Biogenic Sulfur-Containing Amides.- 8. Biological Activity.- 9. Biosynthesis.- 10. Chemotaxonomy.- Appendix: Sulfur-Containing Bisamides from Aglaia Species (Meliaceae).- References.- Author Index.

Volume

81 ISBN 9783211835180

Description

The volumes of this classic series, now referred to simply as "Zechmeister" after its founder, L. Zechmeister, have appeared under the Springer Imprint ever since the series' inauguration in 1938. The volumes contain contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a recognized authority in his field and provides a comprehensive and up-to-date review of the topic in question. Addressed to biologists, technologists, and chemists alike, the series can be used by the expert as a source of information and literature citations and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

New Results on the Chemistry of Lichen Substances.- Abbreviations.- 1. Introduction.- 2. Methods for Identification and Structure Elucidation of Lichen Substances.- 2.1. Spot Tests.- 2.2. Thin Layer Chromatography (TLC).- 2.3. High Performance Liquid Chromatography (HPLC).- 2.4. Droplet Counter-Current Chromatography.- 2.5. NMR Spectroscopy.- 2.6. Mass Spectrometry.- 2.7. X-ray Analysis.- 2.8. Cathodoluminescence and X-ray Microanalysis.- 2.9. Laser Microprobe Mass Spectrometry (LAMMA).- 2.10. Fluorescence Microscopy.- 2.11. Computer Program for Identification of Lichen Substances(WINTABOLITES).- 3. General Methods for Derivatization and Regeneration of Lichen Substances.- 3.1. Carboxyl Groups.- 3.1.1. Methylation.- 3.1.2. Benzylation and Debenzylation.- 3.1.3. Carboxylation and Decarboxylation.- 3.2. Alcoholic and Phenolic Groups.- 3.2.1. Acetylation.- 3.2.2. Methylation and Demethylation.- 3.2.3. Isopropylation and Deisopropylation.- 3.2.4. Benzylation and Debenzylation.- 3.2.5. Oxidation of Alcohols.- 3.3. Substitution at Aromatic Rings.- 3.3.1. Halogenation and Dehalogenation.- 3.3.2. Hydroxylation.- 3.4. Synthesis of Aldehydes.- 3.4.1. Reduction of Aldehydes.- 3.4.2. Oxidation of Aldehydes.- 3.5. Cleavage and Formation of the Depside Ester Bond.- 4. Structure Elucidation and Synthesis of Lichen Substances.- 4.1. Nitrogen Containing Compounds.- 4.2. Phosphorus Containing Compounds.- 4.3. Polyols, Mono- and Polysaccharides and Carbohydrates.- 4.4. Aliphatic and Cycloaliphatic Compounds.- 4.4.1. Hydrocarbons.- 4.4.2. Aliphatic Alcohols.- 4.4.3. Aliphatic Acids and Esters.- 4.4.4. Aliphatic Tricarboxylic Acids.- 4.4.5. ?-Lactonic Acids.- 4.4.6. Macrocyclic Lactones and Bis-Lactones.- 4.4.6.1. Aspicilin.- 4.4.6.2. Lepranthin.- 4.4.7. Anhydrides.- 4.5. Aromatic Compounds.- 4.5.1. Aromatic Units.- 4.5.2. Biphenyls.- 4.5.3. Terphenyls.- 4.5.4. Diphenylmethanes.- 4.5.5. Diphenyl Ethers (Pseudodepsidones).- 4.5.6. Depsides.- 4.5.7. Depsidones.- 4.5.8. Depsones.- 4.5.9. Chromanes and Chromones.- 4.5.10. Xanthones.- 4.5.11. Benzofurans.- 4.5.12. Dibenzofurans.- 4.5.13. Usnic Acid and Related Compounds.- 4.5.14. Naphthopyrans.- 4.5.15. Quinones.- 4.5.15.1. Benzofuranoquinones and Benzoquinones.- 4.5.15.2. Naphthaquinones and bis-Naphthaquinones.- 4.5.15.3. Anthraquinones.- 4.5.15.4. Phenanthroquinones.- 4.5.15.5. Phenanthroperylenequinones.- 4.5.15.6. Perylenequinones.- 4.5.16. Pulvinic Acid Derivatives.- 4.6. Terpenoids.- 4.6.1. Monoterpenoids.- 4.6.2. Sesquiterpenoids.- 4.6.3. Diterpenoids.- 4.6.4. Sesterterpenoids.- 4.6.5. Triterpenoids.- 4.6.6. Steroids.- 4.6.7. Carotenoids.- 5. Culture and Chemistry of Lichen Symbionts and Cell Culture of Lichens.- 5.1. Culture of Mycobionts.- 5.2. Lichen Tissue Cultures and their Metabolites.- 5.3. Culture of Lichen Phycobionts.- 5.4. Metabolites from Lichen Phycobionts.- 6. Biosynthesis of Lichen Substances.- 7. Chemotaxonomy of Lichens.- 8. Biological Activities of Lichen Substances and Lichens.- 8.1. Activity against Microorganisms.- 8.1.1. Antiviral Activity.- 8.1.2. Activity Against Bacteria and Fungi.- 8.2. Activity Against Algae.- 8.3. Activity on Bryophytes.- 8.4. Activity on Higher Plants.- 8.5. Activity on Animals.- 8.6. Activity on Man.- 8.7. Tumour and Anti-Tumour Activity.- 8.8. Inhibition of Enzymes.- 8.9. Antioxydant Activity.- 9. Harmful Effects of Lichens.- 10. Commercial Uses of Lichens and Lichen Substances.- 10.1. Uses in Perfume Production and in Cosmetics.- 10.2. Lichens as Biomonitors.- 10.3. Lichens for Dyeing.- Acknowledgement.- Notes Added in Proof.- References.- Author Index.

Volume

83 ISBN 9783211836019

Description

This work on the progress in the chemistry of organic natural products offers examination on topics such as: the naturally occuring coumarins; variations of ring-attached five-carbon units found in coumarins; and variations of five carbon units attached to carbon and oxygen in coumarins.

Table of Contents

The Naturally Occurring Coumarins.- 1. Scope of the Review.- 2. Progress in the Past Three Years.- 3. Introduction to Tables.- 4. Schemes and Tables.- Scheme 1. Variations of Ring-Attached Five-Carbon Units found in Coumarins.- Scheme 2. Variations of Five-Carbon Units Attached to Carbon and Oxygen in Coumarins.- Table 1. Non-Oxygenated Coumarins.- Table 2. 3-Oxygenated Coumarins.- Table 3. 4-Oxygenated Coumarins.- Table 4. 5-Oxygenated Coumarins.- Table 5. 6-Oxygenated Coumarins.- Table 6. 7-Oxygenated Coumarins.- Table 7. 8-Oxygenated Coumarins.- Table 8. 3,4-Dioxygenated Coumarins.- Table 9. 3,7-Dioxygenated Coumarins.- Table 10. 4,6-Dioxygenated Coumarins.- Table 11. 4,7-Dioxygenated Coumarins.- Table 12. 4,8-Dioxygenated Coumarins.- Table 13. 5,7-Dioxygenated Coumarins.- Table 14. 5,8-Dioxygenated Coumarins.- Table 15. 6,7-Dioxygenated Coumarins.- Table 16. 7,8-Dioxygenated Coumarins.- Table 17. 3,4,5-Trioxygenated Coumarins.- Table 18. 3,4,6-Trioxygenated Coumarins.- Table 19. 3,4,7-Trioxygenated Coumarins.- Table 20. 3,4,8-Trioxygenated Coumarins.- Table 21. 3,6,7-Trioxygenated Coumarins.- Table 22. 3,7,8-Trioxygenated Coumarins.- Table 23. 4,5,7-Trioxygenated Coumarins.- Table 24. 4,6,7-Trioxygenated Coumarins.- Table 25. 4,7,8-Trioxygenated Coumarins.- Table 26. 5,6,7-Trioxygenated Coumarins.- Table 27. 5,7,8-Trioxygenated Coumarins.- Table 28. 6,7,8-Trioxygenated Coumarins.- Table 29. 3,4,5,7-Tetraoxygenated Coumarins.- Table 30. 3,4,6,8-Tetraoxygenated Coumarins.- Table 31. 3,4,7,8-Tetraoxygenated Coumarins.- Table 32. 4,5,6,7-Tetraoxygenated Coumarins.- Table 33. 4,5,7,8-Tetraoxygenated Coumarins.- Table 34. 5,6,7,8-Tetraoxygenated Coumarins.- Table 35. Biscoumarins.- Table 36. Triscoumarins.- Table 37. Structure Revision Required.- Formula Index.- Trivial Name Index.- Acknowledgements.- References.- Author Index.

Volume

82 ISBN 9783211836538

Description

1. 1. General 1. 1. 1. Biaryls-Structural and Biosynthetic Variety The biaryl axis is the joint central structural element of a broad variety of structurally (in particular stereochemically) and biosynthetically inter- esting as well as pharmacologically promising natural products. The increasing importance of this challenging class of secondary metabolites, its widespread occurrence, its pharmacological implications, and, in particular, the phenomenon of axial chirality, have so far been largely underestimated, if not neglected. This is reflected by the fact that there is as yet no true comprehensive review on naturally occurring biaryls in the literature. By this article, we do not intend to provide such a fully comprehensive review, but still want to draw the attention of the scientific community on the manifold rewarding facets of this exciting class of natural products, which is rapidly growing now, with more and more sophisticated analytical and synthetic tools becoming available. Natural biaryls occur far more frequently than initially assumed, among them constitutionally symmetric, simple dimeric monoterpenoid biphenyls like I (I) (see Fig. 1), binaphthalenes like (-)-gossypol (2) (2), bianthraquinones like skyrin (3) (3-7), and biaryls with annelated heterocyclic rings like bismurrayafoline-B (4) (8) and desertorin A (Sa) (9, 10), which is-although built up from a single monomeric precursor -constitutionally unsymmetric.

Table of Contents

Contents Biaryls in Nature: A Multi-Facetted Class of Stereochemically, Biosynthetically, and Pharmacologicall Intriguing Secondary Metabolites (G. Bringmann, C. Günther, M. Ochse, O. Schupp, S. Tasler) Introduction * General * The Elucidation and Stereochemical Description of the Absolute Configuration at Biaryl Axes Non-Bridged Biaryls * Bi- and Polyphenyls * Dimeric Naphthalene Systems * Dimeric Anthracenes and Anthraquinones * Monomeric 9,10-Dihydrophenanthrenes, Dimeric Phenanthrenes, and 9,10-Dihydrophenanthrenes * Natural Bicoumarins with Biaryl Axes * Biflavonoids and Related Compounds * Phenylphenalenones * Constitutionally Unsymmetric, Cross-Coupled Biaryls With Various Iso-or Heterocyclic Building Blocks * Arylnaphthalene Lignans * Naphthylisoquinoline Alkaloids * Unbridged Biaryl Alkaloids Bridged Biaryls * Lactone-Bridged Biaryls * The Dibenzocyclooctadiene Lignans * Macrocyclic Biphenyls * Bridged Biaryl Alkaloids * Biaryl Glycopeptides and Other Cyclic Peptides with a Biphenyl Unit

Volume

84 ISBN 9783211837078

Description

Of the porphyrinoid structures occurring in nature the most important and most widespread are the red blood pigment heme (1), the green pigment of plant photosynthesis chlorophyll a (2), the bacterial photo- synthetic pigment bacteriochlorophyll a (3), and the "antipernicious" red pigment vitamin BJ2 (4). The basic function of these cofactors are determined by the incorporation of the different metal ions into the macrotetracycles. The different oxidation levels of the macrocyclic ligand system regulate the fine tuning of these functions. The final adaptation of the cofactors to their special molecular environments in the cell compartments is effected by variation of the substitution patterns of the chromophores. HCO,C 3 CO,Phytyl 2 Heme Chlorophyll a CONH, CONH, ~ H,NOC 1 , CONH, /I(Y N~ 3 4 Bacteriochlorophyll a Vitamin B" HO References, pp. 42-51 Naturally Occurring Cyclic Tetrapyrroles 3 Until the mid-1970s the four classic cyclic tetrapyrrolic structures with their porphyrin, chi orin, bacteriochlorin, and corrin skeletons were almost the only representatives in the class of porphyrinoid natural products (1-10). Although other partially reduced porphyrins were conceivable, none of these partially saturated porphyrinoid structures had hitherto been found in nature.

Table of Contents

Naturally Occurring Cyclic Tetrapyrroles.- 1. Introduction.- 2. Classification.- 3. General Aspects of Cyclic Tetrapyrrole Biosynthesis.- 4. Porphyrins.- 5. Chlorins.- 6. Bacteriochlorins.- 7. Isobacteriochlorins.- 8. Higher Saturated Hydroporphyrins.- 9. Corrins.- Acknowledgments.- References.- The Chemistry of Taxol and Related Taxoids.- 1. Introduction.- 2. A-Ring Chemistry.- 3. B-Ring Chemistry.- 4. C-Ring Chemistry.- 5. D-Ring Chemistry.- 6. Rearrangements and Related Reactions.- 7. The Side Chain.- 8. Synthesis of Taxol and Taxol Side Chain Analogs from Baccatin III.- 9. Taxol Metabolites.- 10. Taxol Analogs and Prodrugs.- 11. Labeled Taxol Analogs.- 12. The Synthesis of Taxol and Taxol Analogs from Precursors other than Baccatin III.- 13. The Synthesis of Simplified and Unusual Taxol Analogs.- 14. The Synthesis of Taxol.- 15. The Interaction of Taxol with Tubulin.- Addendum.- Acknowledgements.- References.- Author Index.

Volume

85 ISBN 9783211837832

Description

The volumes of this classic series, now referred to simply as "Zechmeister" after its founder, L. Zechmeister, have appeared under the Springer Imprint ever since the series' inauguration in 1938. The volumes contain contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a recognized authority in his field and provides a comprehensive and up-to-date review of the topic in question. Addressed to biologists, technologists, and chemists alike, the series can be used by the expert as a source of information and literature citations and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

Natural Products Derived from Naphthalenoid Precursors by Oxidative Dimerization.- 1. Introduction.- 2. Isolation and Structure Elucidation.- 2.1. Spirobisnaphthalenes with Two Oxygen Bridges.- 2.2. Spirobisnaphthalenes with Three Oxygen Bridges (Preussomerins).- 2.3. Spirobisnaphthalenes with Two Oxygen Bridges and One C-C Bridge (Spiroxins).- 2.4. Determination of Relative and Absolute Stereochemistry.- 3. Biological Activity.- 4. Biosynthesis.- 5. Synthesis.- 5.1. Biomimetic Type Approach.- 5.2. Spiroketalization Approach.- Acknowledgements.- References.- Prokaryotic Glycoproteins.- 1. Introduction.- 2. S-Layer Glycoproteins.- 2.1. Uniqueness of S-Layer Glycoproteins.- 2.2. From Chemical Composition to Structural Concept.- 2.3. Biosynthesis.- 2.4. Molecular Biological Insights.- 2.5. Perspectives.- 3. Non-S-Layer Glycoproteins.- 3.1. Intracellular Glycoproteins.- 3.2. Membrane-Associated Glycoproteins.- 3.3. Surface-Associated Glycoproteins.- 3.4. Extracellular Glycoproteins.- 3.5. "Cellular" Glycoproteins.- 3.6. Synthetic Glycopeptides and Glycoproteins.- 4. Conclusions.- Acknowledgements.- References.- Carbazole Alkaloids IV.- I. Introduction.- A. Nomenclature.- B.Occurrence.- II. Methods of Structure Elucidation.- A. Physical Methods.- 1. Ultraviolet Absorption Spectra.- 2. IR Spectra.- 3. NMR Spectra.- 4. Mass Spectra.- 5. X-ray Crystallography.- B. Chemical Methods.- C. Synthesis.- 1. Synthesis from Monocyclic Systems.- 2. Synthesis from Bicyclic Systems.- 3. Synthesis from Tricyclic Systems.- 4. Synthesis of Carbazoles by Electrocyclisation.- 5. Synthesis by Photolytic Methods.- III. Biogenesis of Carbazole Alkaloids.- IV. Biological and Therapeutic Properties of Carbazoles and Carbazole Alkaloids.- V. Chemistry of Carbazole Alkaloids.- A. Alkaloids from Higher Plants.- i) C13-Alkaloids.- 1. 9-Carboethoxy-3-methylcarbazole.- 2. Clausenol.- 3. Clausenine.- 4. 9-Formyl-3-methylcarbazole.- 5. Murrayaline B.- 6. 2-Methyl-7-hydroxycarbazole or 2-Hydroxy-7-methylcarbazole.- 7. N-Methoxy-3-hydroxymethylcarbazole.- 8. 3-Formyl-7-hydroxycarbazole.- 9. 0-Methylmukonal.- 10. 3-Formyl-6-methoxycarbazole.- 11. 7-Methoxymukonal.- 12. Clausenal.- 13. 6-Methoxymurrayanine.- 14. 7-Methoxy-O-methylmukonal.- 15. Murrayaline C.- 16. Carbazole-3-carboxylic Acid.- 17.3-Carbomethoxycarbazole.- 18. Clauszoline C.- 19. 3-Carbomethoxy-6-methoxycarbazole.- 20. Clauszoline I.- 21. Clauszoline J.- 22. Clauszoline K.- 23. Clauszoline L.- 24. Clauszoline M.- ii) C18-Alkaloids.- 1. Clauszoline B.- 2. Clauszoline D.- 3. Euchrestine A.- 4. Eustofoline D.- 5. Furostifoline.- 6. Glycomaurine.- 7. Glycomaurol.- 8. 7-Methoxyheptaphylline.- 9. 7-Methoxymurrayacine.- 10. Murrayamine A.- 11. Pyrayafoline B.- 12. Pyrayafoline C.- 13. Mukoenine A.- 14. Mukoenine C.- 15. Murrayaquinone E.- 16. Clauszoline H.- iii) C23-Alkaloids.- 1. Clauszoline A.- 2. Clauszoline F.- 3. Euchrestine B.- 4. Euchrestine C.- 5. Euchrestine D.- 6. Euchrestine E.- 7. Eustifoline B.- 8. Eustifoline C.- 9. Isomahanine.- 10. (+)-Mahanine.- 11. Murrayaline D.- 12. Murrayamine B.- 13..Murrayamine C.- 14. Murrayanol.- 15. Pyrayafoline D.- 16. Murrayaquinone C.- 17. Murrayaquinone D.- 18. Pyrayafoline E.- 19. Mukoenine B.- iv) Dimeric Carbazole Alkaloids from Higher Plants.- a) C26-Alkaloids.- 1. Indole Dimer.- 2. Bis-2-hydroxy-3-methylcarbazole.- 3. Bismurrayaquinone A.- 4. Chrestifoline A.- 5. Cherestifoline D.- 6. Murrastifoline A.- 7. Murrastifoline B.- 8. Murrastifoline F.- b) C31-Alkaloids.- 1. Chrestifoline B.- 2. Murrafoline G.- 3. Murrastifoline D.- 4. Murrastifoline E.- c) C36-Alkaloids.- 1.Chrestifoline C.- 2. Murrafoline H.- 3. Murrastifoline C.- 4. Bis-7-hydroxygirinimbine A.- 5. Bis-7-hydroxygirinimbine B.- 6. Murranimbine.- d) C46-Alkaloids.- 1. Bismahanine.- 2. Bismurrayafoline C.- 3. Bismurrayafoline D.- B. Alkaloids from Lower Plants.- i) Alkaloids from Microbial Sources.- a) Alkaloids Built on a Carbazole Skeleton.- 1. Aflavazole.- 2. Carazostatin.- 3. Carquinostatin A.- b) Indolocarbazoles.- i) Alkaloids Built on an Indolocarbazole Skeleton (Two Nitrogens).- 1. Antitumor Compound AT 2433 Al.- 2. Antitumor Compound AT 2433 A2.- 3. Antitumor Compound AT 2433 B1.- 4. Antitumor Compound AT 2433 B2.- 5. Arcyriaflavin B.- 6. Arcyriaflavin C.- 7. Protein Kinase C Inhibitor K-252a.- 8. Protein Kinase C Inhibitor K-252b.- 9. Protein Kinase C Inhibitor K-252c.- 10. Protein Kinase C Inhibitor K-252d.- 11. Rebeccamycin.- 12. Staurosporine.- 13. Tan 1030 A.- 14. Tan 999.- 15. UCN-01.- ii) Alkaloids from Marine Sources.- 1. 1-Methylcarbazole.- 2. 1-Acetylcarbazole.- 3. Aldose Reductase Inhibitors.- References.- Author Index.

Volume

86 ISBN 9783211838891

Table of Contents

Monopyrrolic Natural Compounds Including Tetramic Acid Derivatives (Albert Gossauer) Introduction / Pyrroles from Vertebrates / Pyrroles from Invertebrates / Pyrroles from Plants / Pyrroles from Fungi / Pyrroles from Bacteria / References

Volume

92 ISBN 9783211996607

Description

Resin glycosides are part of a very extensive family of secondary metabolites known as glycolipids or lipo-oligosaccharides and are constituents of complex resins (glycoresins) (1) unique to the morning glory family, Convolvulaceae (2). These active principles are responsible for the drastic purgative action of all the important Convolvulaceous species used in traditional medicine throughout the world since ancient times. Several commercial purgative crude drugs can be prepared from the roots of different species of Mexican morning glories. Their incorporation as therapeutic agents in Europe is an outstanding example of the assimilation of botanical drugs from the Americas as substitutes for traditional Old World remedies (3). Even though phytochemical investigations on the constituents of these drugs were initiated during the second half of the nineteenth century, the structure of their active ingredients still remains poorly known for some examples of these purgative roots. During the last two decades, the higher resolution c- abilities of modern analytical isolation techniques used in conjunction with pow- ful spectroscopic methods have facilitated the elucidation of the active principles of these relevant herbal products. This chapter describes the ethnobotanical information associated with the p- gative morning glory species and how traditional usages were instrumental in plant selection for chemical studies. The advantages and limitations of available analy- cal techniques for the isolation, puri?cation, and structure characterization of the individual constituents of these complex glycoconjugates are also discussed.

Table of Contents

Microbial Siderophores.- Resin Glycosides from the Morning Glory Family.

Volume

93 ISBN 9783709101391

Description

Lignans, by convention, are a group of natural products that are formed by linking two phenylpropanoid units (C C units) by oxidative coupling. Most importantly, in 6 3 a lignan, two (C C units) are bound through the central carbon of their side chains, 6 3 0 i. e. the 8 and 8 positions (1, 2). The occurrence of C C -dimers, linked at sites other 6 3 0 than the 8-8 positions, is also known and these compounds have been termed neolignans (3, 4). As these two groups of compounds have close structural as well as biosynthetic relationships, they are often associated together and incorporated under the general term "lignan" (5). The diverse structural categorization of true lignans and of a few neolignans is presented in Fig. 1. Through the years, several review articles or books covering different facets of lignans, including their ch- istry (6, 7), biogenesis (8), synthesis (9), and biological activities (10) have been published. Enduring research for the investigation of secondary metabolites of plants has evidenced some compounds that are biogenetically related to true lignans or neolignans but bear some features not discerned in conventional lignans. These compounds or groups of compounds have been termed as "non-conventional lignans", and include coumarinolignans, ?avonolignans, and stilbenolignans. The non-conventional lignans, like the conventional ones, have two C C units linked 6 3 together but have additional structural features to place them also under the category of coumarins, ?avonoids, or stilbenes.

Table of Contents

List of Contributors Nonconventional Lignans: Coumarinolignans, Flavonolignans, and Stilbenolignans by Sajeli A. Begum, Mahendra Sahai, and Anil B. Ray 1. Introduction 2. Coumarinolignans 3. Flavonolignans 4. Stilbenolignans References Picrotoxanes by Edda Goessinger 1. Introduction 2. Tabular Overview of the Picrotoxanes 3. Occurrence 4. Isolation of Picrotoxanes 5. Structure Determination of Picrotoxanes 6. Total Syntheses of Picrotoxanes 7. Biosynthesis of Picrotoxanes 8. Physiological Activity of Picrotoxanes Abbreviations References Combinatorial and Synthetic Biosynthesis in Actinomycetes by Marta Luzhetska, Johannes Harle, and Andreas Bechthold 1. Introduction 2. Combinatorial Biosynthesis and Synthetic Biosynthesis References Author Index Subject Index

by "Nielsen BookData"

Details

• NCID: BA0096933X
• ISBN:
  • 3211809759
  • 3211810242
  • 3211810625
  • 3211811729
  • 3211812555
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  • 3211836535
  • 3211836012
  • 3211837078
  • 3211837833
  • 3211838899
  • 9783211027806
  • 3211206884
  • 9783211740187
  • 9783211996607
  • 9783709101391
• Country Code: au
• Title Language Code: eng
• Text Language Code: eng
• Place of Publication: Wien
• Pages/Volumes: v.
• Size: 24 cm
• Classification:
  • NDC8 : 439