Biotransformation XXXIX. Metabolism of testosterone, androstenedione, progesterone and testosterone derivatives in Absidia coerulea culture.

The strain of Absidia coerulea was used to investigate the transformations of testosterone, androstenedione, progesterone and testosterone derivatives with additional Cl-C2 double bond and/or 17alpha-methyl group. All the examined substrates were transformed, mainly hydroxylated. It was found that the position and stereochemistry of the introduced hydroxyl group, as well as the yield of products, depended on the structure of the substrate. The first three substrates (hormones) underwent hydroxylation at C-14, and additional hydroxylation at 7alpha was observed in progesterone. The presence of the double bond (C1-C2) in 1-dehydrotestosterone did not influence the position of hydroxylation, but the product with additional C14-C15 double bond (at the same site as hydroxylation) was formed. 17alpha-Methyltestosterone was hydroxylated at the 7alpha position, and also the dehydrogenated product (at the same site, with C6-C7 double bond) was obtained. The testosterone derivative with both C1-C2 double bond and 17alpha-methyl group underwent hydroxylation at the 7alpha or 11beta position, and a little amount of 14alpha, 15alpha epoxide was formed.