New oxandrolone derivatives by biotransformation using Rhizopus stolonifer

M Iqbal Choudhary; Mohammad Yasin Mohammad; Syed Ghulam Musharraf; Masood Parvez; Amal Al-Aboudi; Atta-ur-Rahman

doi:10.1016/j.steroids.2009.08.003

New oxandrolone derivatives by biotransformation using Rhizopus stolonifer

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

Authors

M Iqbal Choudhary¹, Mohammad Yasin Mohammad, Syed Ghulam Musharraf, Masood Parvez, Amal Al-Aboudi, Atta-ur-Rahman

Affiliation

¹ H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, Pakistan. hej@cyber.net.pk

PMID: 19698730
DOI: 10.1016/j.steroids.2009.08.003

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