Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Microbial Transformation of (+)- and (-)-2'-Demethoxydehydrogriseofulvin by Streptomyces cinereocrocatus
TAIKO ODAYOSHIHIRO SATO
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Keywords: conformation
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1983 Volume 31 Issue 3 Pages 934-946

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Abstract

To elucidate the microbial activities of Streptomyces cinereocrocatus, (+)- and (-)-2'-demethoxydehydrogriseofulvin (1c and 3c) were synthesized and subjected to microbial transformation. The microbial transformation of the (-)-enantiomer (3c) afforded (+)-2'-demethoxy-2', 3'-dihydrodehydrogriseofulvin (18) as the sole product in a high yield (60%). On the other hand, the microbial transformation of the (+)-enantiomer (1c) gave (+)-2'-demethoxygriseofulvin (6) (12%) and a mixture of (-)-and (+)-2'-demethoxy-2', 3'-dihydrodehydrogriseofulvin (14 and 18) (8%). The results indicate that the microbial transformations take place directly and/or after isomerization with hydrogenations, depending on the kinds of substrates concerned, i.e., (+)- and (-)-2'-demethoxydehydrogriseofulvin analogs. It was concluded that the modes of microbial transformation of dehydrogriseofulvin analogs are greatly influenced by the structure of the substrates, i.e. the substituent at the 2'-position and/or the enantiomeric nature.

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© The Pharmaceutical Society of Japan
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