Microbial transformation of (+)-androsta-1 ,4-diene-3,17-dione by Cephalosporium aphidicola

Nat Prod Lett. 2002 Dec;16(6):377-82. doi: 10.1080/10575630290033132.

Abstract

Fermentation of (+)-androsta-1,4-diene-3,17-dione ([structure: see text]) with Cephalosporium aphidicola for 8 days yielded oxidative and reductive metabolites, androst-4-ene-3,17-dione ([structure: see text]), 17beta-hydroxyandrosta-1,4-diene-3-one ([structure: see text]), 11alpha-hydroxyandrosta-1,4-diene-3,17-dione ([structure: see text]), 11alpha-hydroxyandrost-4-ene-3,17-dione ([structure: see text]), 11alpha,17beta-dihydroxyandrost-4-ene-3-one ([structure: see text]) and 11alpha,17beta-dihydroxyandrosta-1,4-diene-3-one ([structure: see text]). The fermentation of [structure: see text] with Fusarium lini also yielded metabolites [structure: see text]. The structures of these metabolites were elucidated on the basis of spectroscopic techniques.

MeSH terms

  • Acremonium / metabolism*
  • Androstadienes / chemistry*
  • Androstadienes / metabolism*
  • Cholesterol / chemistry
  • Fermentation
  • Fusarium / metabolism
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Sitosterols / chemistry
  • Spectrophotometry, Infrared
  • Spectroscopy, Fourier Transform Infrared
  • Stereoisomerism

Substances

  • Androstadienes
  • Sitosterols
  • 1,4-androstadiene-3,17-dione
  • gamma-sitosterol
  • Cholesterol