Biotransformation XLV. Transformations of 4-ene-3-oxo steroids in Fusarium culmorum culture

Add time:07/27/2019    Source:sciencedirect.com

The course of transformations of five 4-ene-3-oxo steroids with varying substituents at C-17 i.e.: 4-androsten-3-one, androstenedione, testosterone, progesterone and 17α-hydroxyprogesterone in Fusarium culmorum culture was investigated. All the substrates were hydroxylated either at 12β and 15α, or at 15α or 6β positions, depending on the structure of the substrate. The main product of 4-androsten-3-one transformation was 12β,15α-diol. A similar 12β,15α-diol was obtained from progesterone, but the main product of transformation of this substrate was 15α-hydroxyprogesterone. The products of hydroxylation at 6β or 15α positions were isolated from 17α-hydroxyprogesterone. The androstenedione and testosterone transformation mixtures contained the same products (6β-hydroxyandrostenedione, 6β-hydroxytestosterone, 15α-hydroxyandrostenedione and 15α-hydroxytestosterone), but the quantities of 6β- and 15α-alcohols varied, depending on the substrate used. During transformations of these two substrates, apart from hydroxylation, ketone–alcohol interconversion at C-17 occurred.

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