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Transformations of testosterone and related steroids in Absidia glauca culture
Author(s) -
Huszcza Ewa,
DmochowskaGladysz Jadwiga
Publication year - 2003
Publication title -
journal of basic microbiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.58
H-Index - 54
eISSN - 1521-4028
pISSN - 0233-111X
DOI - 10.1002/jobm.200390011
Subject(s) - methyltestosterone , hydroxylation , chemistry , testosterone (patch) , androstenedione , methyl group , incubation , stereochemistry , steroid , double bond , group (periodic table) , organic chemistry , biochemistry , endocrinology , biology , androgen , enzyme , hormone
In the following study, the course of transformations of testosterone and its derivatives with an additional C 1 –C 2 double bond and/or 17α‐methyl group or without 19‐methyl group in Absidia glauca culture was investigated. The fungi were observed to hydroxylate these compounds and to oxidise the 17β‐hydroxyl group. The products of 6β, 7α, 7β, 11α, 12β or 15β hydroxylation were obtained. 19‐Nortestosterone was also hydroxylated at the 10β position. The position and stereochemistry of the introduced hydroxyl group was dependent on the presence of the additional C 1 –C 2 double bond, while hydroxylation at the C‐6β was unaffected. The incubation of testosterone with Absidia glauca gave hydroxyderivatives of androstenedione: 7α‐hydroxyandrostenedione and 6β,11α‐dihydroxyandrostenedione. When 1‐dehydrotestosterone and 1‐dehydro‐17α‐methyltestosterone were used, the products were hydroxylated at 6β, 7β or 15β position while 17α‐methyltestosterone and 19 nortestosterone products were hydroxylated at 6β, 7α, 11α or 12β position. Two metabolites: 6β,11α‐dihydroxyandrostenedione and 6β,12β‐dihydroxy‐17α‐methyltestosterone were dihydroxylated. The presence of 17α‐methyl group in 17α‐methyltestosterone and 1‐dehydro‐17α‐methyltestosterone did not influence the position of hydroxylation.