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.
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.
Furusawa
Mai
M
Faculty of Pharmaceutical Science, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan.
Hashimoto
Toshihiro
T
Noma
Yoshiaki
Y
Asakawaa
Yoshinori
Y
D001230:Aspergillus / Q000378:metabolism; D001711:Biotransformation; D002708:Chlorella / Q000378:metabolism*; D003521:Cyclopropanes / Q000378:metabolism; D004354:Drug Screening Assays, Antitumor; D035926:Hepatophyta / Q000378:metabolism; D009089:Mucor / Q000378:metabolism; D012717:Sesquiterpenes / Q000378:metabolism
D003521:Cyclopropanes; D012717:Sesquiterpenes; C063982:1,1-dimethylcyclopropane