New oxandrolone derivatives by biotransformation using Rhizopus stolonifer

Steroids. Nov-Dec 2009;74(13-14):1040-4. doi: 10.1016/j.steroids.2009.08.003. Epub 2009 Aug 19.

Abstract

Structural transformation of the steroidal lactone, oxandrolone (1), by suspended-cell cultures of the plant pathogen fungus Rhizopus stolonifer, resulted in the production of three new metabolites. These metabolites were identified as 11alpha-hydroxyoxandrolone (2), 6alpha-hydroxyoxandrolone (3) and 9alpha-hydroxyoxandrolone (4), by different spectroscopic methods and single-crystal X-ray diffraction analysis for metabolite 2. Compounds 1 and 3 showed a significant beta-glucuronidase inhibitory activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biotransformation
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / metabolism
  • Enzyme Inhibitors / pharmacology
  • Glucuronidase / antagonists & inhibitors*
  • Oxandrolone / analogs & derivatives*
  • Oxandrolone / chemistry
  • Oxandrolone / metabolism
  • Oxandrolone / pharmacology
  • Rhizopus / metabolism*
  • Spectrophotometry, Ultraviolet
  • X-Ray Diffraction

Substances

  • 11-hydroxyoxandrolone
  • 6-hydroxyoxandrolone
  • 9-hydroxyoxandrolone
  • Enzyme Inhibitors
  • Oxandrolone
  • Glucuronidase