Microbial transformation of oxandrolone with Macrophomina phaseolina and Cunninghamella blakesleeana
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Elsevier Inc.
Abstract
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. © 2015 Elsevier Inc. All rights reserved.
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Keywords
Anabolic-androgenic compounds, Biotransformation, Cunninghamella blakesleeana, Macrophomina phaseolina, Oxandrolone, Ascomycota, Mucorales, 11beta,17beta dihydroxy 17alpha (hydroxymethyl) 2 oxa 5alpha androstan 3 one, 11beta,17beta dihydroxy 17alpha methyl 2 oxa 5alpha androstan 3 one, 12beta,17beta dihydroxy 17alpha methyl 2 oxa 5alpha androstan 3 one, 17beta hydroxy 17alpha methyl 2 oxa 5alpha 3,11 dione, 5alpha,11beta,17beta trihydroxy 17alpha methyl 2 oxa androstan 3 one, Anabolic agent, Antifungal agent, Unclassified drug, Antifungal activity, Article, Biocatalysis, Carbon nuclear magnetic resonance, Column chromatography, Controlled study, Drug hydroxylation, Drug identification, Drug structure, Drug synthesis, Drug transformation, Heteronuclear multiple bond correlation, High performance liquid chromatography, Melting point, Nonhuman, Optical rotation, Proton nuclear magnetic resonance, Stereochemistry, Thin layer chromatography, Ascomycetes, Metabolism, Physiology