Transformations of steroids by Beauveria bassiana

Z Naturforsch C J Biosci. 2005 Jan-Feb;60(1-2):103-8. doi: 10.1515/znc-2005-1-219.

Abstract

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.

MeSH terms

  • Ascomycota / metabolism*
  • Biotransformation
  • Models, Molecular
  • Molecular Conformation
  • Steroids / pharmacokinetics*
  • Testosterone / analogs & derivatives
  • Testosterone / chemistry
  • Testosterone / pharmacokinetics

Substances

  • Steroids
  • Testosterone