Microbial transformation of oxandrolone with Macrophomina phaseolina and Cunninghamella blakesleeana

[Display omitted] •Oxandrolone (1) was subjected to biotransformation with two fungi.•Four new metabolites 2–5 were obtained on incubation with M. phaseolina.•One new metabolite 6 was isolated on fermentation with C. blakesleeana.•C-5, C-11, C-12, and C-20 were the common sites of functional group m...

Full description

Saved in:
Bibliographic Details
Published in:Steroids 2015-10, Vol.102, p.39-45
Main Authors: Smith, Colin, Wahab, Atia-tul, Khan, Mahwish Shafi Ahmed, Ahmad, Malik Shoaib, Farran, Dina, Iqbal Choudhary, M., Baydoun, Elias
Format: Article
Language:English
Subjects:
Anabolic-androgenic compounds
Ascomycota - metabolism
Biotransformation
Biotransformation - physiology
Cunninghamella blakesleeana
Macrophomina phaseolina
Mucorales - metabolism
Oxandrolone
Oxandrolone - metabolism
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:[Display omitted] •Oxandrolone (1) was subjected to biotransformation with two fungi.•Four new metabolites 2–5 were obtained on incubation with M. phaseolina.•One new metabolite 6 was isolated on fermentation with C. blakesleeana.•C-5, C-11, C-12, and C-20 were the common sites of functional group modification. Microbial transformation of oxandrolone (1) was carried out by using Cunninghamella blakesleeana and Macrophomina phaseolina. Biotransformation of 1 with M. phaseolina yielded four new metabolites, 11β,17β-dihydroxy-17α-(hydroxymethyl)-2-oxa-5α-androstan-3-one (2), 5α,11β,17β-trihydroxy-17α-methyl-2-oxa-androstan-3-one (3), 17β-hydroxy-17α-methyl-2-oxa-5α-androstan-3,11-dione (4), and 11β,17β-dihydroxy-17α-methyl-2-oxa-5α-androstan-3-one (5). Whereas a new metabolite, 12β,17β-dihydroxy-17α-methyl-2-oxa-5α-androstan-3-one (6), was obtained through the microbial transformation of oxandrolone (1) with C. blakesleeana. The structures of isolated metabolites were characterized on the basis of MS and NMR spectroscopic data.
ISSN:0039-128X
1878-5867
DOI:10.1016/j.steroids.2015.06.008