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The course of transformations of testosterone and its derivatives, including compounds with an additional C1,C2 double bond and/or a 17α-methyl group, a 17β-acetyl group or without a 19-methyl group, by a Beauveria bassiana culture was investigated. The fungi promoted hydroxylation of these compounds at position 11α, oxidation of the 17β-hydroxyl group, reduction of the C1,C2 or C4,C5 double bonds and degradation of the progesterone side-chain, leading to testosterone. The structure of 4-ene-3-oxo-steroids had no influence on regio- and stereochemistry of hydroxylation. In a similar manner, dehydroepiandrosterone was hydroxylated by Beauveria bassiana at position 11α, however, a small amount of 7α- hydroxylation product was also formed.

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.

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