Recent advances in polyphenol research

著者

• Daayf, Fouad
• Lattanzio, Vincenzo
• Santos-Buelga, Celestino
• Escribano-Bailon, Maria Teresa

書誌事項

Recent advances in polyphenol research

edited by Fouad Daayf, Vincenzo Lattanzio

Blackwell Pub., 2008-

• v. 1
• v. 2
• v. 3
• v. 4
• v. 5
• v. 6

注記

Includes bibliographical references and indexes

Vol. 2: edited by Celestino Santos-Buelga, Maria Teresa Escribano-Bailon, Vincenzo Lattanzio

Imprint varies: Wiley-Blackwell

Vol. 3: edited by Véronique Cheynier, Pascale Sarni-Manchado, Stéphane Quideau

Vol. 4: edited by Annalisa Romani, Vincenzo Lattanzio, Stéphane Quideau

Vol. 5: edited by Kumi Yoshida, Véronique Cheynier, Stéphane Quideau

Vol. 6: edited by Heidi Halbwirth ... [et al.]

内容説明・目次

巻冊次

v. 4 ISBN 9781118329672

内容説明

Plant polyphenols are secondary metabolites that constitute one of the most common and widespread groups of natural products. They express a large and diverse panel of biological activities including beneficial effects on both plants and humans. Many polyphenols, from their structurally simplest representatives to their oligo/polymeric versions (also referred to as vegetable tannins) are notably known as phytoestrogens, plant pigments, potent antioxidants, and protein interacting agents. Sponsored by the scholarly society Groupe Polyphenols, this publication, which is the fourth volume in this highly regarded Recent Advances in Polyphenol Research series, is edited by Annalisa Romani, Vincenzo Lattanzio, and Stephane Quideau. They have once again, like their predecessors, put together an impressive collection of cutting-edge chapters written by expert scientists, internationally respected in their respective field of polyphenol sciences. This Volume 4 highlights some of the latest information and opinion on the following major research topics about polyphenols: Biosynthesis and genetic manipulation Ecological role of polyphenols in plant defense Actions of polyphenols in human health protection Physical organic chemistry and organic synthesis Chemists, biochemists, plant scientists, pharmacognosists and pharmacologists, biologists, ecologists, food scientists and nutritionists will all find this book an invaluable resource. Libraries in all universities and research institutions where these disciplines are studied and taught should have copies on their bookshelves.

目次

Acknowledgments vii Contributors xvii Preface xix 1 Monolignol Biosynthesis and its Genetic Manipulation: The Good, the Bad, and the Ugly 1 Richard A. Dixon, M.S. Srinivasa Reddy, and Lina Gallego-Giraldo 1.1 Introduction 2 1.2 Function and distribution of lignin in plants 2 1.3 Targets for modification of lignin biosynthesis 5 1.3.1 Gene targets 1. Biosynthetic enzymes 5 1.3.1.1 L-phenylalanine ammonia-lyase (PAL) 6 1.3.1.2 Cinnamate 4-hydroxylase (C4H) 6 1.3.1.3 4-coumarate: coenzyme-A ligase (4CL) 6 1.3.1.4 Enzymes of the coumaroyl shikimate shunt 7 1.3.1.5 Caffeoyl-CoA 3-O-methyltransferase (CCoAOMT) 7 1.3.1.6 Ferulate 5-hydroxylase (F5H) 8 1.3.1.7 Caffeic acid 3-O-methyltransferase (COMT) 8 1.3.1.8 Cinnamoyl-CoA reductase 8 1.3.1.9 Cinnamyl alcohol dehydrogenase (CAD) 9 1.3.2 Gene targets 2. Transcription factors 9 1.4 Impacts of lignin modification through targeting of the monolignol biosynthetic pathway 9 1.4.1 L-phenylalanine ammonia-lyase (PAL) 10 1.4.2 Cinnamate 4-hydroxylase (C4H) 10 1.4.3 4-coumarate: coenzyme-A ligase (4CL) 11 1.4.4 Hydroxycinnamoyl-CoA: shikimate hydroxycinnamoyl transferase (HCT) 13 1.4.5 4-coumaroyl shikimate 3'-hydroxylase (C3'H) 14 1.4.6 Caffeoyl CoA 3-O-methyltransferase (CCoAOMT) 15 1.4.7 Ferulate 5-hydroxylase (F5H) 17 1.4.8 Caffeic acid O-methyltransferase (COMT) 18 1.4.9 Cinnamoyl-CoA reductase (CCR) 20 1.4.10 Cinnamyl alcohol dehydrogenase (CAD) 22 1.5 Impacts of lignin modification through targeting of TFs 23 1.5.1 NAC master switches 24 1.5.2 MYB repressors of monolignol biosynthesis 24 1.5.3 WRKY repressors of lignification in pith 24 1.6 Monolignol pathway modification and plant growth 25 1.7 Conclusions: it isn't all that bad! 26 References 27 2 Perturbing Lignin Biosynthesis: Metabolic Changes in Response to Manipulation of the Phenylpropanoid Pathway 39 Nickolas A. Anderson and Clint Chapple 2.1 Introduction 40 2.1.1 Cell wall-bound phenylpropanoids 40 2.1.2 Soluble phenylpropanoids 43 2.2 Changes in metabolism associated with phenylpropanoid-pathway disruptions 44 2.2.1 Phenylalanine ammonia-lyase (PAL) 44 2.2.2 Cinnamate 4-hydroxylase (C4H) 45 2.2.3 4-coumarate: CoA ligase (4CL) 46 2.2.4 Hydroxycinnamoyl-coenzyme A: shikimate/quinate hydroxycinnamoyltransferase (HCT)/p-coumaroyl shikimate 3'-hydroxylase (C3'H) 46 2.2.5 Cinnamoyl CoA reductase (CCR) 47 2.2.6 Ferulate 5-hydroxylase (F5H) 48 2.2.7 Caffeic acid/5-hydroxyferulic acid O-methyltransferase (COMT)/caffeoyl CoA 3-O-methyltransferase (CCoAOMT) 49 2.2.8 Cinnamyl alcohol dehydrogenases (CAD) 50 2.3 Atypical lignins 50 2.4 Dwarfism 51 2.5 Conclusions 52 References 52 3 Function, Structure, and Evolution of Flavonoid Glycosyltransferases in Plants 61 Keiko Yonekura-Sakakibara and Kazuki Saito 3.1 Introduction 61 3.2 UDP-dependent glycosyltransferases 63 3.2.1 Functional identification of flavonoid UGTs 63 3.2.1.1 Flavonoid 3-O-glycosyltransferases 63 3.2.1.2 Flavonoid 7-O-glycosyltransferases 63 3.2.1.3 Flavonoid glycosyltransferases that glycosylate the sugar moiety attached to a flavonoid aglycone 67 3.2.1.4 Flavonoid 3'-O-glycosyltransferase 69 3.2.1.5 Flavonoid C-glycosyltransferase 69 3.2.2 3D structures of flavonoid UGTs 70 3.2.3 Functional evolution in UGTs 72 3.2.3.1 Functional evolution in flavonoid UGTs 74 3.3 Glycoside hydrolase-type glycosyltransferases 75 3.3.1 Functional identification of flavonoid GH1-type glycosyltransferases 75 3.3.1.1 Anthocyanin 5/7-O-glycosyltransferases 75 3.3.1.2 Anthocyanin 3-O-6''-O-coumaroylglucoside: glucosyltransferase 76 3.3.2 The reaction mechanism of GH1-type glycosyltransferases 78 3.4 Conclusions 78 References 78 4 The Chemistry and Chemical Ecology of Ellagitannins in Plant-Insect Interactions: From Underestimated Molecules to Bioactive Plant Constituents 83 Juha-Pekka Salminen 4.1 Introduction 84 4.2 Definitions and chemical structures of hydrolyzable tannins 85 4.3 Biosynthetic pathways of hydrolyzable tannins in plants 87 4.3.1 Tannin biosynthetic pathways have many branching points that affect the flux of biosynthetic energy towards different tannins 90 4.3.2 Biosynthesis of gallic acid, galloylglucoses, and gallotannins 91 4.3.3 Biosynthesis of ellagitannins 92 4.4 Distributions of different types of tannin in plants 94 4.5 Tannins in plant-herbivore interactions 98 4.5.1 General aspects of tannins and plant-herbivore interactions 98 4.5.2 The tannin oxidation hypothesis and its verification in plant-herbivore interactions 102 4.5.3 The ease of oxidation of individual ellagitannins can be predicted by their chemical structures and chromatographic properties 104 4.5.4 Other factors that may affect ellagitannin activities against insect herbivores 107 4.6 Conclusions 108 Acknowledgments 109 References 109 5 Diverse Ecological Roles of Plant Tannins: Plant Defense and Beyond 115 C. Peter Constabel, Kazuko Yoshida, and Vincent Walker 5.1 Introduction 115 5.2 Overview of tannin structure and function in defense 116 5.2.1 Structural diversity and distribution 116 5.2.2 In vitro biochemical activities 119 5.2.3 Old and new views on tannins in defense 120 5.2.4 The antimicrobial nature of tannins 122 5.3 Tissue localization and ecological function 124 5.3.1 Distribution of tannins in vegetative tissues 125 5.3.2 Tannins in seeds and fruit 126 5.3.3 Ecology of fruit tannins 127 5.4 Tannins in plant-soil-environment interactions 129 5.4.1 Tannin distribution and stability in soil 129 5.4.2 Impact of tannins on soil nitrogen cycling and microbial activity 130 5.4.3 Interaction with community and ecosystem processes 131 5.4.4 Tannins and other plant stress adaptations 133 5.5 Conclusions 134 Acknowledgments 134 References 134 6 Epigenetics, Plant (Poly)phenolics, and Cancer Prevention 143 Clarissa Gerhauser 6.1 Introduction 143 6.2 Influence of polyphenols on DNA methylation 145 6.2.1 DNA methylation in normal and tumor cells 145 6.2.2 Inhibition of DNMTs in vitro 145 6.2.3 Inhibition of DNA methylation in cellular systems and in vivo 147 6.2.3.1 Quercetin 147 6.2.3.2 Nordihydroguaiaretic acid (NDGA) 147 6.2.3.3 Resveratrol 158 6.2.3.4 Apple polyphenols 159 6.2.3.5 Black raspberry polyphenols 159 6.3 Influence of polyphenols on histone-modifying enzymes 160 6.3.1 Acetylation of histones and non-histone proteins 161 6.3.1.1 Anacardic acid 161 6.3.1.2 Curcumin 165 6.3.1.3 Garcinol 166 6.3.1.4 Gallic acid 167 6.3.1.5 Delphinidin 167 6.3.2 Deacetylation by HDACs and sirtuins 168 6.3.2.1 Inhibition of HDAC activity 168 6.3.2.2 Modulation of sirtuin activity 168 6.3.3 Histone methylation marks 171 6.3.3.1 Histone lysine methylation 171 6.3.3.2 Histone lysine demethylation 171 6.4 Influence of noncoding miRNAs on gene expression 172 6.5 Chemopreventive polyphenols affecting the epigenome via multiple mechanisms 173 6.5.1 ( )-epigallocatechin 3-gallate (EGCG) and green-tea polyphenols (GTPs) 173 6.5.1.1 DNA methylation 174 6.5.1.2 Histone-modifying enzymes (HATs, HDACs, HMTs) 178 6.5.1.3 miRNAs 181 6.5.2 Genistein and soy isoflavones 183 6.5.2.1 DNA methylation 183 6.5.2.2 Influence on histone acetylation and methylation 189 6.5.2.3 miRNAs affected by isoflavones 192 6.6 Conclusions 195 6.6.1 DNA methylation 195 6.6.2 Histone-modifying enzymes 195 6.6.3 miRNAs 196 6.6.4 Summary 196 References 196 7 Discovery of Polyphenol-Based Drugs for Cancer Prevention and Treatment: The Tumor Proteasome as a Novel Target 209 Fathima R. Kona, Min Shen, Di Chen, Tak Hang Chan, and Q. Ping Dou 7.1 Introduction 209 7.2 Secondary metabolites of plants 210 7.3 Plant polyphenols and their analogs 211 7.3.1 Classification and bioavailability of plant polyphenols 211 7.3.2 Tea and tea polyphenols 212 7.3.3 Targeting of the tumor proteasome by tea polyphenols 216 7.3.4 EGCG analogs as proteasome inhibitors 217 7.3.4.1 Peracetate and other prodrugs of EGCG 219 7.3.4.2 Fluoro-substituted EGCG analogs 222 7.3.4.3 Para-amino substituent on the D ring 222 7.3.4.4 Bis-galloyl derivatives of EGCG 223 7.3.4.5 Methylation-resistant ( )-EGCG analogs 223 7.3.5 Other molecular targets of tea polyphenols 224 7.3.5.1 AMPK activation 224 7.3.6 Proteasome inhibitory action of other plant polyphenols 225 7.4 Natural polyphenols in reversal of drug resistance 226 7.4.1 Mechanisms of tumor drug resistance 226 7.4.2 The ubiquitin-proteasome pathway in drug resistance 226 7.4.3 EGCG and overcoming drug resistance 227 7.4.4 Genistein and overcoming drug resistance 228 7.4.5 Curcumin and overcoming drug resistance 228 7.4.6 Clinical trials using polyphenols and chemotherapy 229 7.5 Conclusions 231 Acknowledgments 231 References 231 8 Flavonoid Occurrence, Bioavailability, Metabolism, and Protective Effects in Humans: Focus on Flavan-3-ols and Flavonols 239 Luca Calani, Margherita Dall'Asta, Renato Bruni, and Daniele Del Rio 8.1 Introduction 240 8.2 Focus on flavan-3-ols and flavonols: chemical structures and dietary sources 240 8.2.1 Flavan-3-ols 240 8.2.2 Flavonols 243 8.3 Metabolism and bioavailability of flavonoids in humans 244 8.3.1 Flavan-3-ols 245 8.3.2 Flavonols 251 8.4 In vitro studies 255 8.4.1 Flavan-3-ols 256 8.4.1.1 Phase II metabolites 256 8.4.1.2 Microbe-derived metabolites 259 8.4.2 Flavonols 260 8.4.2.1 Phase II metabolites 260 8.4.2.2 Microbe-derived metabolites 265 8.5 In vivo studies 266 8.5.1 Cardiovascular and endothelial protection 267 8.5.1.1 Flavan-3-ols 267 8.5.1.2 Flavonols 268 8.5.2 Neuroprotection 269 8.5.2.1 Flavan-3-ols 269 8.5.3 Cancer prevention 269 8.5.3.1 Flavan-3-ols 269 8.5.3.2 Flavonols 270 8.6 Conclusions 271 References 272 9 Inhibition of VEGF Signaling by Polyphenols in Relation to Atherosclerosis and Cardiovascular Disease 281 Rebecca L. Edwards and Paul A. Kroon 9.1 Introduction 282 9.2 VEGF and VEGF signaling 282 9.3 VEGF signaling and angiogenesis 286 9.4 Angiogenesis and atherosclerosis 286 9.5 Polyphenols in foods and diets, and their absorption and metabolism 289 9.6 Effects of polyphenols on VEGF signaling, angiogenesis, and atherosclerosis 290 9.6.1 VEGF signaling 314 9.6.2 Angiogenesis 315 9.6.3 Atherosclerosis 315 9.7 Relationships between polyphenol consumption and CVD risk 316 9.7.1 Epidemiological studies 316 9.7.2 Intervention studies 318 9.8 Conclusions 319 Acknowledgments 320 References 320 10 Phenolic Compounds from a Sex-Gender Perspective 327 Ilaria Campesi, Annalisa Romani, Maria Marino, and Flavia Franconi 10.1 Introduction 328 10.2 Phenolic compound classification and molecular mechanisms 329 10.3 Sex-gender and the xenokinetics of phenolic compounds 330 10.4 Sex-gender differences in xenodynamics 333 10.5 Conclusions 334 References 334 11 Thermodynamic and Kinetic Processes of Anthocyanins and Related Compounds and their Bio-Inspired Applications 341 Fernando Pina 11.1 Introduction 342 11.2 Anthocyanins in aqueous solution 342 11.2.1 Step-by-step procedure for calculating rate and equilibrium constants 349 11.2.1.1 Step 1: determination of the equilibrium constant K'a 349 11.2.1.2 Step 2: determination of the equilibrium constant Ka 349 11.2.1.3 Step 3: determination of the equilibrium constant Kt and the respective rate constants 350 11.2.1.4 Step 4: determination of the hydration rate and equilibrium constants 350 11.2.1.5 Step 5: determination of the isomerization rate and equilibrium constants 350 11.2.1.6 Step 6: verification of the self-consistency of all the data 351 11.3 Influence of anthocyanin self-aggregation on the determination of rate and equilibrium constants 351 11.4 Photochromism: applications bio-inspired in anthocyanins 357 11.4.1 Systems lacking the cis-trans isomerization barrier 357 11.4.2 Systems exhibiting high cis-trans isomerization barriers 361 11.4.2.1 The concept of right-lock-read-unlock-erase optical memories 361 11.4.3 Styryl-1-benzopyrylium (styryl flavylium) and naphthoflavylium 362 11.4.4 Dye-sensitized solar cells based on anthocyanins 362 11.5 How to construct an energy-level diagram 364 11.6 How to calculate the mole-fraction distribution of a network species 367 References 368 12 Synthetic Strategies and Tactics for Catechin and Related Polyphenols 371 Ken Ohmori and Keisuke Suzuki 12.1 Introduction 371 12.2 Early synthetic work 375 12.3 Stereoselective approaches to flavan-3-ols 380 12.3.1 Synthesis of catechin-series (= 2,3-trans) derivatives 380 12.3.2 Synthesis of epi-series (= 2,3-cis) catechins 393 12.4 Conclusions 407 Abbreviations 407 Acknowledgments 408 References 408 Index 411

巻冊次

v. 5 ISBN 9781118883266

内容説明

Plant polyphenols are secondary metabolites that constitute one of the most common and widespread groups of natural products. They express a large and diverse panel of biological activities including beneficial effects on both plants and humans. Many polyphenols, from their structurally simplest representatives to their oligo/polymeric versions (also referred to as vegetable tannins), are notably known as phytoestrogens, plant pigments, potent antioxidants, and protein interacting agents. Sponsored by the scholarly society Groupe Polyphenols, this publication, which is the fifth volume in this highly regarded Recent Advances in Polyphenol Research series, is edited by Kumi Yoshida, Veronique Cheynier and Stephane Quideau. They have once again, like their predecessors, put together an impressive collection of cutting-edge chapters written by expert scientists, internationally respected in their respective field of polyphenol sciences. This Volume 5 highlights some of the latest information and opinion on the following major research topics about polyphenols: * Chemistry, physicochemistry & materials science * Biosynthesis, genetic & metabolic engineering * Plant & ecosystem, lignocellulosic biomass * Food, nutrition & health * Natural medicine & Kampo * Tannins & their functions Chemists, biochemists, plant scientists, pharmacognosists and pharmacologists, biologists, ecologists, food scientists and nutritionists will all find this book an invaluable resource. Libraries in all universities and research institutions where these disciplines are studied and taught should have copies on their bookshelves.

目次

Contributors xv Preface xix 1 The Physical Chemistry of Polyphenols: Insights into the Activity of Polyphenols in Humans at the Molecular Level 1 Olivier Dangles, Claire Dufour, Claire Tonnele and Patrick Trouillas 1.1 Introduction 1 1.2 Molecular complexation of polyphenols 4 1.3 Polyphenols as electron donors 11 1.4 Polyphenols as ligands for metal ions 21 1.5 Conclusions 27 References 28 2 Polyphenols in Bryophytes: Structures, Biological Activities, and Bio- and Total Syntheses 36 Yoshinori Asakawa 2.1 Introduction 36 2.1 Distribution of cyclic and acyclic bis-bibenzyls in Marchantiophyta (liverworts) 37 2.3 Biosynthesis of bis-bibenzyls 39 2.4 The structures of bis-bibenzyls and their total synthesis 50 2.5 Biological activity of bis-bibenzyls 58 2.6 Conclusions 60 Acknowledgments 61 References 61 3 Oxidation Mechanism of Polyphenols and Chemistry of Black Tea 67 Yosuke Matsuo and Takashi Tanaka 3.1 Introduction 67 3.2 Catechin oxidation and production of theaflavins 71 3.3 Theasinensins 73 3.4 Coupled oxidation mechanism 75 3.5 Bicyclo[3.2.1]octane intermediates 77 3.6 Structures of catechin oxidation products 78 3.7 Oligomeric oxidation products 82 3.8 Conclusions 84 Acknowledgments 85 References 85 4 A Proteomic-Based Quantitative Analysis of the Relationship Between Monolignol Biosynthetic Protein Abundance and Lignin Content Using Transgenic Populus trichocarpa 89 Jack P. Wang, Sermsawat Tunlaya-Anukit, Rui Shi, Ting-Feng Yeh, Ling Chuang, Fikret Isik, Chenmin Yang, Jie Liu, Quanzi Li, Philip L. Loziuk, Punith P. Naik, David C. Muddiman, Joel J. Ducoste, Cranos M. Williams, Ronald R. Sederoff and Vincent L. Chiang 4.1 Introduction 90 4.2 Results 94 4.3 Discussion 101 4.4 Materials and methods 102 References 104 5 Monolignol Biosynthesis and Regulation in Grasses 108 Peng Xu and Laigeng Li 5.1 Introduction 108 5.2 Unique cell walls in grasses 109 5.3 Lignin deposition in grasses 110 5.4 Monolignol biosynthesis in grasses 111 5.5 Regulation of monolignol biosynthesis in grasses 114 5.6 Remarks 119 Acknowledgments 119 References 120 6 Creation of Flower Color Mutants Using Ion Beams and a Comprehensive Analysis of Anthocyanin Composition and Genetic Background 127 Yoshihiro Hase 6.1 Introduction 127 6.2 Induction of flower color mutants by ion beams 129 6.3 Mutagenic effects and the molecular nature of the mutations 131 6.4 Comprehensive analyses of flower color, pigments, and associated genes in fragrant cyclamen 131 6.5 Mutagenesis and screening 133 6.6 Genetic background and the obtained mutants 136 6.7 Carnations with peculiar glittering colors 137 6.8 Conclusion 139 Acknowledgments 140 References 140 7 Flavonols Regulate Plant Growth and Development through Regulation of Auxin Transport and Cellular Redox Status 143 Sheena R. Gayomba, Justin M. Watkins and Gloria K. Muday 7.1 Introduction 143 7.2 The flavonoids and their biosynthetic pathway 144 7.3 Flavonoids affect root elongation and gravitropism through alteration of auxin transport 146 7.4 Mechanisms by which flavonols regulate IAA transport 149 7.5 Lateral root formation 151 7.6 Cotyledon, trichome, and root hair development 152 7.7 Inflorescence architecture 154 7.8 Fertility and pollen development 154 7.9 Flavonols modulate ROS signaling in guard cells to regulate stomatal aperture 155 7.10 Transcriptional machinery that controls synthesis of flavonoids 157 7.11 Hormonal controls of flavonoid synthesis 160 7.12 Flavonoid synthesis is regulated by light 161 7.13 Conclusions 162 Acknowledgments 163 References 163 8 Structure of Polyacylated Anthocyanins and Their UV Protective Effect 171 Kumi Yoshida, Kin-ichi Oyama and Tadao Kondo 8.1 Introduction 171 8.2 Occurrence and structure of polyacylated anthocyanins in blue flowers 173 8.3 Molecular associations of polyacylated anthocyanins in blue flower petals 178 8.4 UV protection of polyacylated anthocyanins from solar radiation 183 8.5 Conclusion 187 References 188 9 The Involvement of Anthocyanin-Rich Foods in Retinal Damage 193 Kenjirou Ogawa and Hideaki Hara 9.1 Introduction 193 9.2 Anthocyanin-rich foods for eye health 195 9.3 Experimental models to mimic eye diseases and the effect of anthocyanin-rich foods 196 9.4 Conclusions 201 References 203 10 Prevention and Treatment of Diabetes Using Polyphenols via Activation of AMP-Activated Protein Kinase and Stimulation of Glucagon-like Peptide-1 Secretion 206 Takanori Tsuda 10.1 Introduction 206 10.2 Activation of AMPK and metabolic change 207 10.3 GLP-1 action and diabetes prevention/suppression 212 10.4 Future issues and prospects 220 References 222 11 Beneficial Vascular Responses to Proanthocyanidins: Critical Assessment of Plant-Based Test Materials and Insight into the Signaling Pathways 226 Herbert Kolodziej 11.1 Introduction 227 11.2 Appraisal of test materials 228 11.3 Endothelial dysfunction 233 11.4 In vitro test systems 234 11.5 Vasorelaxant mechanisms 235 11.6 Bioavailability and metabolic transformation: the missing link in the evidence to action in the body 249 11.7 Conclusions 250 References 251 12 Polyphenols for Brain and Cognitive Health 259 Katherine H. M. Cox and Andrew Scholey 12.1 Introduction 259 12.2 Studies of total polyphenols and cognition 260 12.3 Pine bark 272 12.4 Discussion and conclusions 283 References 283 13 Curcumin and Cancer Metastasis 289 Ikuo Saiki 13.1 Introduction 290 13.2 Effects of curcumin on intra-hepatic metastasis of liver cancer 293 13.3 Effects of curcumin on lymp node metastasis of lung cancer 298 13.4 Effects of curcumin on tumor angiogenesis 303 13.5 Conclusions 307 References 307 14 Phytochemical and Pharmacological Overview of Cistanche Species 313 Hai-Ning Lv, Ke-Wu Zeng, Yue-Lin Song, Yong Jiang and Peng-Fei Tu 14.1 Introduction 313 14.2 Chemical constituents of Cistanche species 314 14.3 Bioactivities of the extracts and pure compounds from Cistanche species 322 14.4 Conclusions 334 References 334 Index 342

巻冊次

v. 6 ISBN 9781119427933

内容説明

Plant polyphenols are secondary metabolites that constitute one of the most common and widespread groups of natural products. They are crucial constituents of a large and diverse range of biological functions and processes, and provide many benefits to both plants and humans. Many polyphenols, from their structurally simplest representatives to their oligo/polymeric versions, are notably known as phytoestrogens, plant pigments, potent antioxidants, and protein interacting agents. This sixth volume of the highly regarded Recent Advances in Polyphenol Research series is edited by Heidi Halbwirth, Karl Stich, Veronique Cheynier and Stephane Quideau, and is a continuance of the series' tradition of compiling a cornucopia of cutting-edge chapters, written by some of the leading experts in their respective fields of polyphenol sciences. Highlighted herein are some of the most recent and pertinent developments in polyphenol research, covering such major areas as: Chemistry and physicochemistry Biosynthesis, genetics & metabolic engineering Roles in plants and ecosystems Food, nutrition & health Applied polyphenols This book is a distillation of the most current information, and as such, will surely prove an invaluable source for chemists, biochemists, plant scientists, pharmacognosists and pharmacologists, biologists, ecologists, food scientists and nutritionists.

目次

Contributors xiii Preface xvii Acknowledgements xxi 1 The Lignans: A Family of Biologically Active Polyphenolic Secondary Metabolites 1 Anna K.F. Albertson and Jean-Philip Lumb 1.1 Introduction 1 1.2 Biosynthesis of Lignans 3 1.3 Synthetic Approaches to Lignans and Derivatives 7 1.4 Conclusion 60 References 65 2 Anthocyanin Accumulation is Controlled by Layers of Repression 71 Andrew C. Allan, Kathy E. Schwinn, and Richard V. Espley 2.1 Introduction 71 2.2 MYBs and bHLHs Directly Activate Anthocyanin Production 72 2.3 Exciting Phenotypes in Horticulture are often caused by Variations in the Expression of Key MYBs 73 2.4 Is There a Cost to the Plant of over accumulation of Anthocyanins? 74 2.5 Controlling Anthocyanin Levels 75 2.6 The MYB Activator is Degraded at Night 76 2.7 MYB Activator Competes with MYB Repressors 77 2.8 miRNA- Targeted Degradation of MYB Transcript 78 2.9 Turnover of Anthocyanin Vacuolar Content by Peroxidases 78 2.10 Summary 79 References 79 3 The Subtleties of Subcellular Distribution: Pointing the Way to Underexplored Functions for Flavonoid Enzymes and End Products 89 Brenda S.J. Winkel 3.1 Multienzyme Complexes and Metabolic Networks 89 3.2 New Insights from Global Surveys of Protein Interactions 90 3.3 The Flavonoid Metabolon 91 3.4 Subcellular Distribution of Flavonoid Enzymes and Evidence for Alternative Metabolons 94 3.5 Posttranslational Modifications - An Underexplored Area of Flavonoid Metabolism 98 3.6 Why Do We Need to Know? 99 3.7 Future Prospects 99 References 100 4 Transcriptional and Metabolite Profiling Analyses Uncover Novel Genes Essential for Polyphenol Accumulation 109 Wilfried Schwab, Ludwig Ring, and Chuankui Song 4.1 Introduction 109 4.2 Transcriptional and Metabolite Profiling Analyses in Strawberry Fruit 110 4.3 Characterization of Peroxidase 27 113 4.4 Competition of the Lignin and Flavonoid/Anthocyanin Pathways as Demonstrated by the Activity of Peroxidase 27 115 4.5 Candidate Genes Putatively Correlated with Phenolics Accumulation in Strawberry Fruit 115 4.6 Acylphloroglucinol Biosynthesis in Strawberry Fruit 118 4.7 Glucosylation of Acylphloroglucinols 120 4.8 Conclusion References 124 5 Dietary (Poly)Phenols and Vascular Health 127 Christine Morand, Nicolas Barber-Chamoux, Laurent-Emmanuel Monfoulet, and Dragan Milenkovic 5.1 Introduction 127 5.2 Vascular Health: A Prerequisite to Prevent Cardiometabolic Diseases and Cognitive Decline 128 5.3 Diet and Vascular Health 130 5.4 (Poly)Phenols: A Major Family of Dietary Plant Bioactive Compounds 131 5.5 Fate of (Poly)Phenols in the Body and Biological Activities 133 5.6 Nutritional Effects of Flavonoids in Protecting Cardiovascular Health 135 5.7 Limitation of Knowledge and Strategy for Research 138 5.8 Findings from Translational Research on Citrus Flavanones and Vascular Health 139 5.9 Conclusion 142 References 142 6 Cellular-Specific Detection of Polyphenolic Compounds by NMR-and MS-Based Techniques: Application to the Representative Polycyclic Aromatics of Members of the Hypericaceae, the Musaceae and the Haemodoraceae 149 Dirk Hoelscher, 6.1 Introduction 149 6.2 The Plant Genus Hypericum 150 6.3 Phenylphenalenones: Plant Secondary Metabolites of the Haemodoraceae 151 6.4 Phenalenone- Type Phytoalexins 157 6.5 Laser Microdissection and Cryogenic NMR as a Combined Tool for Cell Type-Specific Metabolite Profiling 160 6.6 Matrix- free UV Laser Desorption/Ionization (LDI) at the Single-Cell Level: Distribution of Secondary Metabolites of Hypericum Species 163 6.7 LDI- MSI-Based Detection of Phenalenone-Type Phytoalexins in a Banana- Nematode Interaction 166 6.8 LDI- FT-ICR-MSI Reveals the Occurrence of Phenylphenalenones in Red Paracytic Stomata 169 6.9 Conclusion 171 6.10 Acknowledgements 171 References 171 7 Metabolomics Strategies for the De replication of Polyphenols and Other Metabolites in Complex Natural Extracts 183 Jean-Luc Wolfender, Pierre-Marie Allard, Miwa Kubo, and Emerson Ferreira Queiroz 7.1 Introduction 183 7.2 Metabolite Profiling and Metabolomics 184 7.3 Metabolite Annotation and Dereplication 188 7.4 Targeted Isolation of Original Polyphenols 198 7.5 Conclusion 201 References 201 8 Polyphenols from Plant Roots: An Expanding Biological Frontier 207 Ryosuke Munakata, Romain Larbat, Leonor Duriot, Alexandre Olry, Carole Gavira, Benoit Mignard, Alain Hehn, and Frederic Bourgaud 8.1 Introduction 207 8.2 Polyphenols in Roots versus Shoots: Not More, Not Less, But Often Different 207 8.3 Allelochemical Functions of Root Polyphenols 213 8.4 Physiological Functions of Root Polyphenols in Plants 217 8.5 Biotechnologies to Produce Root Polyphenols 220 8.6 Conclusion 227 References 227 9 Biosynthesis of Polyphenols in Recombinant Micro-organisms: A Path to Sustainability 237 Kanika Sharma, Jian Zha, Sonam Chouhan, Sanjay Guleria, and Mattheos A.G. Koffas 9.1 Introduction 237 9.2 Flavonoids 239 9.3 Stilbenes 247 9.4 Coumarins 251 9.5 Conclusion 253 References 254 10 Revisiting Wine Polyphenols Chemistry in Relation to Their Sensory Characteristics 263 Victor de Freitas 10.1 Introduction 263 10.2 Astringency of Polyphenols 265 10.3 Bitter Taste of Polyphenols 269 10.4 Red Wine Colour 271 10.5 Conclusion 276 References 278 11 Advances in Bio-based Thermosetting Polymers 285 Helene Fulcrand, Laurent Roumeas, Guillaume Billerach, Chahinez Aouf, and Eric Dubreucq 11.1 Introduction 285 11.2 Industrial Sources of Polyphenols 289 11.3 Principles of Thermoset Production 290 11.4 Relationships between Structure and Reactivity of Polyphenols 292 11.5 Thermosets from Industrial Lignins and Tannins 295 11.6 Depolymerization of Lignins and Tannins to Produce Phenolic Building Blocks and their Glycidylether Derivatives 306 11.7 Development of Dimethyloxirane Monophenols and Bisphenols as Thermosetting Building Blocks 310 11.8 Conclusion 322 References 323 12 Understanding the Misunderstood: Products and Mechanisms of the Degradation of Curcumin 335 Claus Schneider 12.1 Introduction 335 12.2 Degradation of Curcumin - A Historical and Personal Perspective 336 12.3 The Degradation is an Autoxidation 341 12.4 Novel Products of the Degradation/Autoxidation of Curcumin 344 12.5 Transformation of Curcumin to Bicyclopentadione 348 12.6 A Proposed Mechanism for the Autoxidation of Curcumin 350 12.7 Microbial Degradation of Curcumin 354 12.8 Conclusion 357 References 357 13 How to Model a Metabolon: Theoretical Strategies 363 Julien Diharce and Serge Antonczak 13.1 Introduction 363 13.2 Localization 364 13.3 Existing Structures 365 13.4 Three- Dimensional Structures of Enzymes: Homology Modelling 367 13.5 Modes of Access to Active Sites: Randomly Accelerated Molecular Dynamics 370 13.6 Protein- Protein Association: Protein-Protein Docking 372 13.7 Substrate Channelling and Molecular Dynamics 374 13.8 Metabolon 378 13.9 Conclusion 379 References 381 Index 387

巻冊次

v. 1 ISBN 9781405158374

内容説明

Polyphenols are the second most abundant class of substances in nature, and include tannins and flavonoids, many of which have extremely important antioxidant properties which have now been shown to have a key role in the prevention of cancer in humans. This important book covers polyphenol chemistry, biosynthesis and genetic manipulation, ecology and plant physiology, food and nutritional aspects and the effects of polyphenols on health. Included within the contents are cutting edge chapters on biotic and abiotic stress in plants, safety and toxicity in foods, functionality and nutraceutical benefits in nutrition, and aspects of pharmaceutical and cosmetic discovery and development. Sponsored by Groupe Polyphenols, this landmark book has been edited by Professor Fouad Daayf and Professor Vincenzo Lattanzio, who have drawn together an impressive list of internationally respected contributing authors, each providing a comprehensive review of the current situation regarding each important subject covered. Recent Advances in Polyphenol Research is an important publication which will be of great use to chemists, biochemists, plant scientists, pharmacognosists and pharmacologists, food scientists and nutritionists. Libraries in all universities and research establishments where these subjects are studied and taught should have copies of this book on their shelves.

目次

1 Introduction: plant phenolics - secondary metabolites with diverse functions. Vincenzo Lattanzio, Paul A. Kroon, Stephane Quideau and Dieter Treutter. 2 Lignification: are lignins biosynthesized via simple combinatorial chemistry or via proteinaceous control and template replication?. John Ralph, Goesta Brunow, Philip Harris, Richard A. Dixon and Wout Boerjan. 3 Flavonoid-protein binding processes and their potential impact on human health. Olivier Dangles and Claire Dufour. 4 Methods for synthesizing the cocoa-derived oligomeric epi-catechins - observations on the anticancer activity of the cocoa polyphenols. Alan P. Kozikowski and Werner Tuckmantel. 5 Gene discovery and metabolic engineering in the phenylpropanoid pathway. Luzia V. Modolo, Yongzhen Pang, Li Tian and Richard A. Dixon. 6 Recent advances in the molecular biology and metabolic engineering of flavonoid biosynthesis in ornamental plants. Kevin M. Davies, Huaibi Zhang and Kathy E. Schwinn. 7 Recent advances in the field of anthocyanins - main focus on structures. Oyvind M. Andersen. 8 Salicylic acid and induced plant defenses. Jean-Pierre Metraux, Elisabeth Lamodiere, Jeremy Cattinot, Olivier Lamotte and Christophe Garcion. 9 Phenols and the onset and expression of plant disease resistance. Ray Hammerschmidt and Samantha I. Hollosy. 10 Bioactivity, absorption, and metabolism of anthocyanins. Giuseppe (Joe) Mazza and Colin D. Kay. 11 Bioavailability, metabolism, and bioactivity of food ellagic acid and related polyphenols. Francisco A. Tomas-Barberan, Maria Teresa Garcia-Conesa, Mar Larrosa, Begona Cerda, Rocio Gonzalez-Barrio, Maria Jose Bermudez-Soto, Antonio Gonzalez-Sarrias and Juan Carlos Espin. 12 Multiplicity of phenolic oxidation products in apple juices and ciders, from synthetic medium to commercial products. Sylvain Guyot, Stephane Bernillon, Pascal Poupard and Catherine M.G.C. Renard. 13 Phytoestrogens in drug discovery for controlling steroid biosynthesis. Sampo Karkola, Annamaria Lilienkampf and Kristiina Wahala. 14 Recent advances in the chemical synthesis and the biological activity of phenolic metabolites. Denis Barron. 15 Polyphenols and gene expression. Uwe Wenzel and Hannelore Daniel

巻冊次

v. 2 ISBN 9781405193993

内容説明

Recent Advances in Polyphenol Research Volume 2 Edited by Santos-Buelga, Escribano-Bailon and Lattanzio Plant phenolics are secondary metabolites that constitute one of the most common and widespread groups of substances in plants. Polyphenols have a large and diverse array of beneficial effects on both plants and animals. For example they are famous as antioxidants, hormones, constituents of essential oils and natural neurotransmitters. Sponsored by Groupe Polyphenols, this publication, which is the second volume in this ground-breaking series, is edited by Celestino Santos-Buelga, Maria Teresa Escribano-Bailon, and Vincenzo Lattanzio, who have drawn together an impressive list of internationally respected authors, each providing cutting edge chapters covering some of the major topics of recent research and interest. Information included in this important new addition to the series include the following areas: * Flavonoid chemistry of the leguminosae * Chemistry and biological activity of ellagitannins * Chemistry and function of anthocyanins in plants * An update of chemical pathways leading to new phenolic pigments during wine ageing * Metabolic engineering of the flavonoid pathway * The translation of chemical properties of polyphenols into biological activity with impacts in human health * Plant phenolic compounds controlling leaf movement * Biological activity of phenolics in plants Chemists, biochemists, plant scientists, pharmacognosists and pharmacologists, food scientists and nutritionists will all find this book an invaluable resource. Libraries in all universities and research establishments where these subjects are studied and taught should have copies on their shelves.

目次

Contributors xiv Preface xviii 1 The Visible Flavonoids or Anthocyanins: From Research to Applications 1 Raymond Brouillard, Stefan Chassaing, Geraldine Isorez, Marie Kueny-Stotz, and Paulo Figueiredo 1.1 Introduction 1 1.2 Copigmentation of anthocyanins 5 1.3 Formation of inclusion complexes 6 1.4 Ion-pair formation 7 1.5 Metalloanthocyanins 7 1.6 Z-Chalcones: unexpected open cavities for the ferriccation 11 1.7 Anthocyanin biological activity 14 1.8 Some thoughts on applications 15 1.9 References 17 2 Flavonoid Chemistry of the Leguminosae 23 Nigel C. Veitch 2.1 Introduction 23 2.1.1 Classification and nomenclature of the Leguminosae: a brief synopsis 24 2.2 Flavonoid structures in the Leguminosae: trends and distribution 26 2.2.1 Occurrence of 5-deoxyfl avonoids in the Leguminosae 28 2.2.2 Isofl avonoids in subfamily Papilionoideae 30 2.2.2.1 Recent advances in biosynthetic studies 32 2.2.2.2 Isoflavonoid glycosides 35 2.2.2.3 Isoflavone glucosyltransferases 35 2.2.2.4 Acylated isoflavone glycosides 36 2.2.3 Leguminosae anthocyanins: malonyltransferases of Clitoria ternatea 38 2.3 Advances in analytical methodology applied to Leguminosae flavonoids 38 2.3.1 Hyphenated MS techniques 40 2.3.2 Hyphenated NMR techniques and miniaturization 41 2.3.3 Chiroptical methods 43 2.4 Leguminosae flavonoids and chemosystematics 44 2.4.1 The disputed position of the Swartzieae: subfamily Caesalpinioideae or Papilionoideae? 44 2.4.2 Generic delimitation in the aldinoid clade of swartzioid legumes: Cordyla and Dupuya 47 2.4.3 Species-level studies of the isoflavonoid chemistry of Cicer 50 2.5 Concluding remarks 52 2.6 Acknowledgments 52 2.7 References 52 3 Updating Wine Pigments 59 Victor A.P. de Freitas and Nuno Mateus 3.1 General overview 59 3.2 Factors that affect wine color intensity and stability 60 3.3 Chemical transformations of flavonoids 63 3.3.1 Condensation between anthocyanins and flavanols mediated by aldehydes 65 3.3.2 Reaction between flavanols and aldehydes 67 3.3.3 Direct condensation between flavanols and anthocyanins 68 3.3.4 Pyranoanthocyanins 69 3.3.4.1 Reaction between anthocyanins and vinyl compounds 70 3.3.4.2 Yeast metabolites involved in anthocyanin transformations 72 3.3.5 Vinylpyranoanthocyanins (portisins) 74 3.4 Final remarks 75 3.5 Acknowledgments 76 3.6 References 76 4 Ellagitannins - An Underestimated Class of Plant Polyphenols: Chemical Reactivity of C-Glucosidic Ellagitannins in Relation to Wine Chemistry and Biological Activity 81 Stephane Quideau, Michael Jourdes, Dorothee Lefeuvre, Patrick Pardon, Cedric Saucier, Pierre-Louis Teissedre, and Yves Glories 4.1 Ellagitannins: an underestimated class of bioactive plant polyphenols 81 4.2 C-Glucosidic ellagitannins: a special subclass of ellagitannins 95 4.2.1 Major C-glucosidic ellagitannins in oak and chestnut heartwoods 100 4.2.2 Complex C-glucosidic ellagitannins 102 4.2.3 Biosynthesis of C-glucosidic ellagitannins 107 4.2.4 Chemical reactivity of vescalagin and castalagin 110 4.2.5 Diastereofacial differentiation of the vescalagin-derived benzylic cation 113 4.3 Implications of C-glucosidic ellagitannins in wine chemistry 114 4.3.1 Hemisynthesis of acutissimins and their occurrence in wine 115 4.3.2 Condensation reaction between vescalagin and glutathione 118 4.3.3 Hemisynthesis of anthocyano-ellagitannins: possible influence on wine color 119 4.3.4 Oxidative conversion of acutissimin A into mongolicain A 120 4.4 Biological activity of C-glucosidic ellagitannins 122 4.4.1 Antiviral activity of C-glucosidic ellagitannins 123 4.4.2 Antitumor activity of C-glucosidic ellagitannins 124 4.5 Conclusion 125 4.6 Acknowledgments 126 4.7 References 126 5 Strategies to Optimize the Flavonoid Content of Tomato Fruit 138 Arnaud G. Bovy, Victoria Gomez-Roldan, and Robert D. Hall 5.1 Introduction 138 5.2 The metabolic route to flavonoids in tomato fruit 140 5.3 The natural biodiversity of flavonoids in tomato 141 5.3.1 Flavonoid biodiversity I: commercially available genotypes 142 5.3.2 Flavonoid biodiversity II: wild tomato species 142 5.3.3 Flavonoid biodiversity III: information from specific tomato mutants 143 5.4 Metabolic engineering of the flavonoid pathway 145 5.4.1 Exploitation of the transgenic approach using up regulation of structural genes 145 5.4.2 Using RNAi to block targeted steps in the flavonoid pathway 146 5.4.3 Production of novel tomato flavonoids by introducing new branches of the flavonoid pathway: flavonoid-related stilbenes 147 5.4.4 Production of novel tomato flavonoids by introducing new branches of the flavonoid pathway: deoxychalcones 148 5.4.5 Production of novel tomato flavonoids by introducing new branches of the flavonoid pathway: flavones, isofl avones, and aurones 149 5.4.6 Modifying the flavonoid pathway using regulatory genes 150 5.5 Metabolomics-assisted breeding 154 5.6 Conclusions and future prospects 156 5.7 Acknowledgments 156 5.8 References 156 6 Biological Activity of Phenolics in Plant Cells 163 Luc P.R. Bidel, Marc Coumans, Yves Baissac, Patrick Doumas, and Christian Jay-Allemand 6.1 Introduction 163 6.2 Synthesis and transports 164 6.2.1 Metabolic channeling at the endoplasmic reticulum (ER) level 164 6.2.2 Endomembrane carriers 165 6.2.3 Vesicle trafficking 166 6.2.4 Long-distance transport 166 6.3 Phenolics interact with plasmalemma components 167 6.3.1 Biophysical interactions with phospholipid bilayers 167 6.3.2 Interactions with plasma membrane-associated proteins 169 6.3.3 Flavonoids prevent and alleviate oxidative burst 172 6.3.4 Phenolics modulate plasma membrane carriers 172 6.4 Phenolics in apoplast 175 6.4.1 Phenolics as a major player in mechanical tissue rigidification 175 6.4.2 Phenolics as major components of apoplastic chemical protection 175 6.4.3 Phenolics as apoplastic allelochemical signals 177 6.5 Phenolics in hyaloplasm 177 6.5.1 Phenolics interact with cytoskeleton 178 6.5.2 Phenolics inhibit carbohydrate catabolism 178 6.5.3 Many fl avonoids prevent and alleviate oxidative and nitrosative stresses 178 6.5.4 Salicylic acid promotes oxidative stress signaling pathway 179 6.6 Phenolics in vacuoles 180 6.6.1 Sunscreen role for vacuolar phenolics 180 6.6.2 Are vacuolar phenolics effective buffers? 180 6.6.3 Are vacuolar phenolics effective chelators? 182 6.7 Phenolics in mitochondria and chloroplasts 183 6.7.1 Inhibitory effects 183 6.7.2 Protecting effects 183 6.7.3 Putative phenolic photoreceptors 183 6.8 Phenolics have many emergent roles within the nucleus 184 6.8.1 Presence of phenolics within the nucleus 184 6.8.2 Flavonoids prevent DNA damages 184 6.8.3 Prooxidative actions of phenolics on DNA 186 6.8.4 Flavonoids affect histone acetylation and phosphorylation 186 6.8.5 Flavonoids inhibit DNA methylation 187 6.8.6 Phenolics affect cell cycle 187 6.8.7 Phenolics inhibit replication 188 6.8.8 Phenolics promote or repress transcription 189 6.9 Conclusion 190 6.10 References 191 7 Muriel Wheldale Onslow and the Rediscovery of Anthocyanin Function in Plants 206 Kevin S. Gould 7.1 Introduction 206 7.1.1 Muriel Wheldale Onslow: a brief biography 208 7.2 Functional hypotheses for anthocyanins in vegetative tissues 211 7.3 A modern spin on some old ideas 213 7.3.1 Photoprotection revisited 213 7.3.2 Anthocyanins, sugars, and autumn leaves 217 7.4 Concluding remarks 218 7.5 Acknowledgments 219 7.6 References 219 8 Plant Phenolic Compounds Controlling Leaf Movement 226 Minoru Ueda and Yoko Nakamura 8.1 Introduction 226 8.2 Endogenous bioactive substance controlling nyctinasty 227 8.3 The chemical mechanism of the rhythm in nyctinasty 228 8.4 Bioorganic studies of nyctinasty using functionalized leaf-movement factors as molecular probes 230 8.4.1 Fluorescence studies on nyctinasty 230 8.4.2 Photoaffinity labeling of the target protein for the leaf-movement factor 231 8.4.3 Are leaf-movement target proteins common to the same plant genus? 234 8.5 References 235 9 Red Clover Derived Isoflavones: Metabolism and Physiological Effects in Cattle and Sheep and their Concentration in Milk Produced for Human Consumption 238 Juhani Taponen, Eeva A. Mustonen, Lea Kontio, Ilkka Saastamoinen, Aila Vanhatalo, Hannu Saloniemi, and Kristiina Wahala 9.1 Introduction 238 9.2 Phytoestrogens in ruminant feeds 238 9.3 Red clover as a source of isoflavones 239 9.4 Metabolism of isofl avones in ruminants 241 9.5 Equol: the most important metabolite 243 9.6 Physiological effects and regulatory mechanisms of endogenous estrogens 245 9.7 Effects of phytoestrogens in sheep reproduction 247 9.7.1 Classical clover disease 247 9.7.2 Temporary subfertility 247 9.7.3 Permanent infertility 247 9.8 Effects of phytoestrogens in cattle reproduction 248 9.9 Antioxidant capacity of isoflavones 249 9.10 New outlook 249 9.11 References 250 10 Polyphenols as Biomarkers in Nutrition Research: Resveratrol Metabolome a Useful Nutritional Marker of Moderate Wine Consumption 255 Raul Zamora-Ros and Cristina Andres-Lacueva 10.1 Introduction 255 10.2 Characteristics of nutritional biomarkers 256 10.3 Strengths and limitations of biological biomarkers over dietary estimation 261 10.4 Resveratrol: a useful biomarker of wine consumption 262 10.5 References 265 11 Translation of Chemical Properties of Polyphenols into Biological Activity with Impact on Human Health 269 Joao Laranjinha 11.1 Introduction 269 11.2 Polyphenols as antioxidants: the earlier notions 270 11.2.1 The infl uence of redox potentials 270 11.2.2 Redox cycles of polyphenols with vitamins E and C: the influence of solubility 272 11.3 Beyond "global" antioxidation: alternate biological activities for polyphenols with impact on human health 274 11.3.1 Modulation of redox signaling pathways 274 11.3.2 Modulation of nitric oxide metabolism 276 11.4 References 278 12 Mitigation of Oxidative Stress and Infl ammatory Signaling by Fruit and Walnut Polyphenols: Implications for Cognitive Aging 283 James A. Joseph, Barbara Shukitt-Hale, and Lauren M. Willis 12.1 Introduction 283 12.2 Oxidative stress/infl ammatory interactions 284 12.2.1 Oxidative stress 284 12.2.2 Inflammation 284 12.2.3 Intracellular signaling 285 12.2.4 Calcium buffering capacity 286 12.2.5 Neurogenesis 286 12.2.6 Membrane changes 287 12.3 Nutritional interventions 287 12.3.1 Fruit polyphenols as neuroprotective agents 287 12.3.2 Polyunsaturated fatty acids and cognition: animal studies 289 12.4 References 291 13 Antiatherosclerotic Effects of Dietary Flavonoids: Insight into their Molecular Action Mechanism at the Target Site 299 Junji Terao, Kaeko Murota, and Yoshichika Kawai 13.1 Introduction 299 13.2 Flavonoids in the diet and their antioxidant/prooxidant activity 300 13.3 Absorption and metabolism of dietary flavonoids in the digestive system 304 13.4 Oxidative LDL theory and antioxidant activity of fl avonoids in plasma 307 13.5 Antioxidant and "beyond" antioxidant activity of flavonoids in the artery 309 13.6 Activated macrophages as potential targets of dietary flavonoids as antiatherosclerotic factors 312 13.7 Conclusion 313 13.8 References 314 Index 319

巻冊次

v. 3 ISBN 9781444337464

内容説明

Plant polyphenols are secondary metabolites that constitute one of the most common and widespread groups of natural products. They express a large and diverse panel of biological activities including beneficial effects on both plants and humans. Many polyphenols, from their structurally simplest representatives to their oligo/polymeric versions (also referred to as vegetable tannins) are notably known as phytoestrogens, plant pigments, potent antioxidants, and protein interacting agents. Sponsored by Groupe Polyphenols, this publication, which is the third volume in this highly regarded Recent Advances in Polyphenol Research series, is edited by Veronique Cheynier, Pascale Sarni-Manchado, and Stephane Quideau (the current President of Groupe Polyphenols). Like their predecessors, they have once again put together an impressive collection of cutting-edge chapters written by expert scientists internationally respected in their respective field of polyphenol sciences. This Volume 3 provides the latest information and opinion on the following major research topics about polyphenols: Organic chemistry and physical chemistry Biosynthesis, genetics and metabolic engineering The role of polyphenols in plants and ecosystems Health and nutrition Analysis and metabolomics Chemists, biochemists, plant scientists, pharmacognosists and pharmacologists, biologists, ecologists, food scientists and nutritionists will all find this book an invaluable resource. Libraries in all universities and research institutions where these disciplines are studied and taught should have copies on their bookshelves.

目次

Contributors xv Preface xix 1 Plant Phenolics: A Biochemical and Physiological Perspective 1 Vincenzo Lattanzio, Angela Cardinali and Vito Linsalata 1.1 The general phenolic metabolism in plants 1 1.2 Effect of non-freezing low temperature stress on phenolic metabolism in crop plants 6 1.3 Plant phenolics as defence compounds 11 1.4 Diversion of carbon skeletons from primary to phenolic-related secondary metabolism 19 References 26 2 Polyphenols: From Plant Adaptation to Useful Chemical Resources 41 Alain-Michel Boudet 2.1 The emergence of phenolic metabolism and the adaptation of plants to a terrestrial environment 41 2.2 The shikimate pathway: a complex and subtle interface between primary metabolism and phenolic metabolism 47 2.3 Plant (poly)phenols: a diversified reservoir of useful chemicals 56 2.4 Concluding remarks 63 Acknowledgments 64 References 64 3 Fifty Years of Polyphenol-Protein Complexes 71 Ann E. Hagerman 3.1 Introduction 71 3.2 Precipitable complexes 74 3.3 Soluble complexes 76 3.4 Proline-rich proteins 78 3.5 Mechanisms of binding 79 3.6 Stoichiometry of binding 80 3.7 Protein conformation 82 3.8 Covalent tannin-protein complexes 83 3.9 Conclusions 90 Acknowledgments 91 References 91 4 Chemistry of Flavonoids in Color Development 99 Kumi Yoshida, Kin-ichi Oyama and Tadao Kondo 4.1 Introduction 99 4.2 Synthetic studies on anthocyanins toward polyacylated pigments 103 4.3 Synthesis of copigments for studying blue color development 109 4.4 Conclusion 122 Abbreviations 123 Acknowledgments 124 References 124 5 Colouring up Plant Biotechnology 131 Cathie Martin, Yang Zhang, Laurence Tomlinson, Kalyani Kallam, Jie Luo, Jonathan D.G. Jones, Antonio Granell, Diego Orzaez and Eugenio Butelli 5.1 Introduction 131 5.2 Plant production of anthocyanins 132 5.3 Engineering anthocyanin production in plants 137 5.4 Conclusions 139 Acknowledgements 139 References 139 6 Anthocyanin Biosynthesis, Regulation, and Transport: New Insights from Model Species 143 Lucille Pourcel, Andres Bohorquez-Restrepo, Niloufer G. Irani and Erich Grotewold 6.1 Anthocyanins and related pigments in model plant species 143 6.2 Transcriptional regulation of anthocyanin biosynthetic genes 147 6.3 Anthocyanin transport and subvacuolar localization 151 6.4 Concluding remarks 154 References 154 7 Shedding Light on the Black Boxes of the Proanthocyanidin Pathway with Grapevine 161 Yung-Fen Huang, Veronique Cheynier and Nancy Terrier 7.1 Tools available on grape to study PA biosynthesis 161 7.2 Biosynthesis 167 7.3 Regulation of the pathway 176 References 182 8 Phenolic Compounds in Plant Defense and Pathogen Counter-defense Mechanisms 191 Fouad Daayf, Abdelbasset El Hadrami, Ahmed F. El-Bebany, Maria A. Henriquez, Zhen Yao, Holly Derksen, Ismail El-Hadrami and Lorne R. Adam 8.1 Introduction 191 8.2 Plant defenses and pathogen counter-defenses 192 8.3 Phenolic-related plant responses to pathogens 194 8.4 Pathogens counter-defense against plants' phenolic-related defenses 200 8.5 Concluding remarks 202 Acknowledgments 203 References 203 9 Absorption and Metabolism of Dietary Chlorogenic Acids and Procyanidins 209 Gary Williamson and Angelique Stalmach 9.1 Introduction 209 9.2 Procyanidins 210 9.3 Chlorogenic acids and hydroxycinnamates 214 References 218 10 Extra-Virgin Olive Oil-Healthful Properties of Its Phenolic Constituents 223 Francesco Visioli and Elena Bernardini 10.1 Introduction 223 10.2 Epidemiological studies 225 10.3 In vitro studies on olive oil's phenolics 225 10.4 In vivo studies 228 10.5 Olive oil and cancer 231 10.6 Potential mechanisms of action of olive phenols-to be elucidated 232 10.7 Focus on hydroxytyrosol 233 10.8 Olive mill waste water as a source of olive phenols 236 10.9 Conclusions 240 Acknowledgments 244 References 244 11 Analysis and Characterisation of Flavonoid Phase II Metabolites 249 Celestino Santos-Buelga, Susana Gonzalez-Manzano, Montserrat Duenas and Ana M. Gonzalez-Paramas 11.1 Introduction 249 11.2 Flavonoid metabolism 251 11.3 Preparation of metabolites 253 11.4 Characterisation of flavonoid metabolites 258 11.5 Extraction and preparation 263 11.6 Analysis of metabolites in biological samples 268 Acknowledgments 277 References 277 12 High-speed Countercurrent Chromatography in the Separation of Polyphenols 287 Andrew Marston 12.1 Foreword 287 12.2 High-speed countercurrent chromatography 288 12.3 Separations of polyphenols 291 12.4 Extensions of the basic countercurrent chromatography method 302 References 307 13 Strategies for the Controlled Synthesis of Oligomeric Polyphenols 311 Scott A. Snyder 13.1 Introduction 311 13.2 Serial oligomer families 313 13.3 Oligomer families with diverse bond connections 319 13.4 Conclusion 345 Acknowledgments 345 References 346 Index 353 A color plate section is located between pages 12 and 13. 2

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詳細情報

• NII書誌ID(NCID): BA87560744
• ISBN:
  • 9781405158374
  • 9781405193993
  • 9781444337464
  • 9781118329672
  • 9781118883266
  • 9781119427933
• LCCN: 2008006133
• 出版国コード: uk
• タイトル言語コード: eng
• 本文言語コード: eng
• 出版地: Oxford ; Ames, Iowa
• ページ数/冊数: v.
• 大きさ: 25 cm
• 分類:
  • LCC : QK898.P764
  • DC22 : 572/.2
• 件名:
  • LCSH : Polyphenols -- Research