Transformations of steroids by Beauveria bassiana.
The course of transformations of testosterone and its derivatives, including compounds with an additional C1,C2 double bond and/or a 17alpha-methyl group, a 17beta-acetyl group or without a 19-methyl group, by a Beauveria bassiana culture was investigated. The fungi promoted hydroxylation of these compounds at position 11alpha, oxidation of the 17beta-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 11alpha, however, a small amount of 7alpha-hydroxylation product was also formed.
Huszcza
Ewa
E
Department of Chemistry, Agricultural University, Norwida 25, 50-375 Wrocław, Poland. huszcza@ozi.ar.wroc.pl
Dmochowska-Gładysz
Jadwiga
J
Bartmańska
Agnieszka
A
D001203:Ascomycota / Q000378:metabolism*; D001711:Biotransformation; D008958:Models, Molecular; D008968:Molecular Conformation; D013256:Steroids / Q000493:pharmacokinetics*; D013739:Testosterone / Q000031:analogs & derivatives / Q000737:chemistry / Q000493:pharmacokinetics
D013256:Steroids; D013739:Testosterone