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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概要

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• 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.

• 公益社団法人日本薬学会の論文
• 2006-06-01

著者

• Hashimoto T

  Faculty Of Pharmaceutical Sciences Hokuriku University

• 橋本 忠

  北陸大・薬

• 橋本 忠

  北陸大学薬学部

• HASHIMOTO Toshihiro

  Faculty of Pharmaceutical Sciences, Tokushima Bunri University

• ASAKAWA Yoshinori

  Faculty of Pharmaceutical Sciences, Tokushima Bunri University

• Asakawa Y

  Fac. Of Pharmaceutical Sciences Tokushima Bunri Univ.

• NOMA Yoshiaki

  Faculty of Domestic Sciences, Tokushima Bunri University

• Hashimoto Tadashi

  Faculty Of Pharmaceutical Sciences Hokuriku University

• Hashimoto T

  Hokuriku Univ. Kanazawa Jpn

• Noma Y

  Faculty Of Human Life Sciences Tokushima Bunri University

• Noma Yoshiaki

  Faculty Of Domestic Sciences Tokushima Bunri University

• Asakawa Y

  Tokushima Bunri Univ. Tokushima Jpn

• Asakawa Yoshinori

  Faculty Of Pharmaceutical Sciences Tokushima Bunri University

• Hashimoto Toshihiro

  Faculty Of Pharmaceutical Sciences Tokushima Bunri University

• Hashimoto Toshihiro

  Fac. Of Pharmaceutical Sciences Tokushima Bunri Univ.

• FURUSAWA Mai

  Faculty of Pharmaceutical Sciences, Tokushima Bunri University

• Hashimoto Tadashi

  Drug Metabolism Laboratories Drug Development Division Yamanouchi Pharmaceutical Co. Ltd.

• Furusawa Mai

  Faculty Of Pharmaceutical Science Tokushima Bunri University

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