Document Detail


Microbial transformations of steroids--IV. 6,7-Dehydrogenation; a new class of fungal steroid transformation product.
MedLine Citation:
PMID:  2770300     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Microbial steroid dehydrogenation is quite common. The reaction seems to occur mainly in bacteria and usually results in hydrogen abstraction from positions C(1)-C(2) and/or C(4)-C(5) with occasional aromatisation of ring A. We have screened large numbers of fungal cultures for their ability to monohydroxylate steroids at unusual sites and in the course of our investigations we have identified seven fungal strains capable of dehydrogenating ring B of progesterone and androstenedione at positions C(6)-C(7). Microbiological dehydrogenation at this site seems not to have been reported previously. The structures of the metabolites isolated from progesterone, and the producing fungi, are: 6-dehydroprogesterone (Botryodiplodia theobromae), 11 alpha-hydroxy-6-dehydroprogesterone (Botryosphaerica obtusa, Mucor racemosus and Nigrospora sphaerica), 12 alpha-, 15 beta- and 16 alpha-hydroxy-6-dehydroprogesterones (B. obtusa) and 14 alpha-hydroxy-6-dehydroprogesterone (Apiocrea chrysosperma) [1]. From androstenedione we isolated 6-dehydroandrostenedione (Absidia coerulea and Curvularia lunata) and 6-dehydrotestosterone (C. lunata).
Authors:
K E Smith; S Latif; D N Kirk; K A White
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of steroid biochemistry     Volume:  33     ISSN:  0022-4731     ISO Abbreviation:  J. Steroid Biochem.     Publication Date:  1989 Aug 
Date Detail:
Created Date:  1989-09-29     Completed Date:  1989-09-29     Revised Date:  2010-08-25    
Medline Journal Info:
Nlm Unique ID:  0260125     Medline TA:  J Steroid Biochem     Country:  ENGLAND    
Other Details:
Languages:  eng     Pagination:  271-6     Citation Subset:  IM    
Affiliation:
School of Biological Sciences, Queen Mary College (University of London), UK.
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MeSH Terms
Descriptor/Qualifier:
Androstenedione / metabolism*
Biotransformation
Fungi / metabolism*
Hydrogenation
Magnetic Resonance Spectroscopy
Molecular Structure
Progesterone / metabolism*
Testosterone / metabolism*
Grant Support
ID/Acronym/Agency:
//Wellcome Trust
Chemical
Reg. No./Substance:
57-83-0/Progesterone; 58-22-0/Testosterone; 63-05-8/Androstenedione

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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