Transformations of steroid esters by Fusarium culmorum

Z Naturforsch C J Biosci. 2006 Nov-Dec;61(11-12):809-14. doi: 10.1515/znc-2006-11-1207.

Abstract

The course of transformations of the pharmacological steroids: testosterone propionate, 4-chlorotestosterone acetate, 17beta-estradiol diacetate and their parent alcohols in Fusarium culmorum AM282 culture was compared. The results show that this microorganism is capable of regioselective hydrolysis of ester bonds. Only 4-ene-3-oxo steroid esters were hydrolyzed at C-17. 17beta-Estradiol diacetate underwent regioselective hydrolysis at C-3 and as a result, estrone--the main metabolite of estradiol--was absent in the reaction mixture. The alcohols resulting from the hydrolysis underwent oxidation at C-17 and hydroxylation. The same products (6beta- and 15alpha-hydroxy derivatives) as from testosterone were formed by transformation of testosterone propionate, but the quantitative composition of the mixtures obtained after transformations of both substrates showed differences. The 15alpha-hydroxy derivatives were obtained from the ester in considerably higher yield than from the parent alcohol. The presence of the chlorine atom at C-4 markedly reduced 17beta-saponification in 4-chlorotestosterone acetate. Only 3beta,15alpha-dihydroxy-4alpha-chloro-5alpha-androstan-17-one (the main product of transformation of 4-chlorotestosterone) was identified in the reaction mixture. 6beta-Hydroxy-4-chloroandrostenedione, which was formed from 4-chlorotestosterone, was not detected in the extract obtained after conversion of its ester.

MeSH terms

  • Biotransformation
  • Estradiol / analogs & derivatives*
  • Estradiol / metabolism*
  • Fusarium / growth & development
  • Fusarium / metabolism*
  • Steroids / metabolism*
  • Testosterone / analogs & derivatives
  • Testosterone / metabolism
  • Testosterone Propionate / metabolism*

Substances

  • Steroids
  • estradiol-3,17-diacetate
  • Testosterone
  • Estradiol
  • Testosterone Propionate