Microbial Transformation of Lanosterol Derivatives with Mycobacterium sp. (NRRL B-3805)

Incubation of 8 alpha ,9 alpha -epoxytetrahydrolanosterol with Mycobacterium sp. (NRRL B-3805) gave 20(S)-hydroxymethyl-12 alpha -hydroxypregn-4-en-3-one and 20(S)-hydroxymethyl 4,4,14 alpha -trimethylpregna 7,9(11)-dien-3 beta -ol in 5.0% and 1.6% yields, respectively. Incubation of lanosta-7,9(11)...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 1995-08, Vol.58 (8), p.1222-1227
Main Authors: Wang, K. C, You, Bih-Jing, Yan, Jiann-Long, Lee, Shoei-Sheng
Format: Article
Language:English
Subjects:
Mycobacterium
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Summary:Incubation of 8 alpha ,9 alpha -epoxytetrahydrolanosterol with Mycobacterium sp. (NRRL B-3805) gave 20(S)-hydroxymethyl-12 alpha -hydroxypregn-4-en-3-one and 20(S)-hydroxymethyl 4,4,14 alpha -trimethylpregna 7,9(11)-dien-3 beta -ol in 5.0% and 1.6% yields, respectively. Incubation of lanosta-7,9(11)-dien-3 beta -ol resulted in the isolation of two C-19 steroids as the major metabolites that have been isolated previously from the incubation of lanosterol, and methyl 12 alpha -hydroxybisnorchola-4,17(20)-dien-22-oate in low yield. These results indicated that this microorganism is capable of carrying out saturation of a C=C bond, methylation of a carboxyl function, and 12 alpha -hydroxylation in the steroid nucleus, besides earlier reported transformations.
ISSN:0163-3864
1520-6025
DOI:10.1021/np50122a010