Biotransformation of Aristolane- and 2,3-Secoaromadendrane-Type Sesquiterpenoids Having a 1,1-Dimethylcyclopropane Ring by <i>Chlorella fusca</i> var. <i>vacuolata</i>, <i>Mucor</i> Species, and <i>Aspergillus niger</i>
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- Furusawa Mai
- Faculty of Pharmaceutical Science, Tokushima Bunri University
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- Hashimoto Toshihiro
- Faculty of Pharmaceutical Science, Tokushima Bunri University
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- Noma Yoshiaki
- Faculty of Human Life Sciences, Tokushima Bunri University
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- Asakawaa Yoshinori
- Faculty of Pharmaceutical Science, Tokushima Bunri University
Bibliographic Information
- Other Title
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- Biotransformation of Aristolane- and 2,3-Secoaromadendrane-Type Sesquiterpenoids Having a 1,1-Dimethylcyclopropane Ring by Chlorella fusca var. vacuolata, Mucor Species, and Aspergillus niger
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Abstract
Biotransformation of the aristolane-type sesquiterpene hydrocarbon (+)-1(10)-aristolene (1) from the crude drug Nardostachys chinensis and of the 2,3-secoaromadendrane-type sesquiterpene lactone plagiochilide (2) from the liverwort Plagiochila fruticosa by three microorganisms, Chlorella fusca var. vacuolata, Mucor species, and Aspergillus niger was investigated. C. fusca var. vacuolata and Mucor sp. introduced oxygen function into the cyclohexane ring of aristolene while A. niger oxidized stereoselectively one methyl of the 1,1-dimethyl group on the cyclopropane ring of aristolanes and 2,3-secoaromadendrane to give C-12 primary alcohol and C-12 carboxylic acid. The possible metabolic pathway of the formation of new metabolites is discussed. The stereostructures of new metabolites were established by a combination of NMR spectroscopy including HMBC and NOESY, X-ray crystallographic analysis, and chemical reaction.
Journal
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- Chemical and Pharmaceutical Bulletin
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Chemical and Pharmaceutical Bulletin 54 (6), 861-868, 2006
The Pharmaceutical Society of Japan
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Details 詳細情報について
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- CRID
- 1390001204171129216
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- NII Article ID
- 110004836393
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- NII Book ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- NDL BIB ID
- 7921152
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- Text Lang
- en
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- Data Source
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- JaLC
- NDL
- Crossref
- CiNii Articles
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- Abstract License Flag
- Disallowed