Transformations of testosterone and related steroids in Absidia glauca culture.
In the following study, the course of transformations of testosterone and its derivatives with an additional C(1)-C(2) double bond and/or 17alpha-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 17beta-hydroxyl group. The products of 6beta, 7alpha, 7beta, 11alpha, 12beta or 15beta hydroxylation were obtained. 19-Nortestosterone was also hydroxylated at the 10beta 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-6beta was unaffected. The incubation of testosterone with Absidia glauca gave hydroxyderivatives of androstenedione: 7alpha-hydroxyandrostenedione and 6beta,11alpha-dihydroxyandrostenedione. When 1-dehydrotestosterone and 1-dehydro-17alpha-methyltestosterone were used, the products were hydroxylated at 6beta, 7beta or 15beta position while 17alpha-methyltestosterone and 19 nortestosterone products were hydroxylated at 6beta, 7alpha, 11alpha or 12beta position. Two metabolites: 6beta,11alpha-dihydroxyandrostenedione and 6beta,12beta-dihydroxy-17alpha-methyltestosterone were dihydroxylated. The presence of 17alpha-methyl group in 17alpha-methyltestosterone and 1-dehydro-17alpha-methyltestosterone did not influence the position of hydroxylation.
Huszcza
Ewa
E
Department of Chemistry, Agricultural University, Norwida 25, 50-375 Wrocław, Poland. huszcza@ozi.ar.wroc.pl
Dmochowska-Gladysz
Jadwiga
J
D020095:Absidia / Q000378:metabolism*; D001711:Biotransformation; D013739:Testosterone / Q000378:metabolism*
D013739:Testosterone