Microbial transformation of mesterolone.
The microbial transformation of mesterolone (= (1alpha,5alpha,17beta)-17-hydroxy-1-methylandrostan-3-one; 1), by a number of fungi yielded (1alpha,5alpha)-1-methylandrostane-3,17-dione (2), (1alpha,3beta,5alpha,17beta)-1-methylandrostane-3,17-diol (3), (5alpha)-1-methylandrost-1-ene-3,17-dione (4), (1alpha,5alpha,15alpha)-15-hydroxy-1-methylandrostane-3,17-dione (5), (1alpha,5alpha,6alpha,17beta)-6,17-dihydroxy-1-methylandrostan-3-one (6), (1alpha,5alpha,7alpha,17beta)-7,17-dihydroxy-1-methylandrostan-3-one (7), (1alpha,5alpha,11alpha,17beta)-11,17-dihydroxy-1-methylandrostan-3-one (8), (1alpha,5alpha,15alpha, 17beta)15,17-dihydroxy-1-methylandrostan-3-one (9), and (5alpha,15alpha,17beta)-15,17-dihydroxy-1-methylandrost-1-en-3-one (10). Metabolites 5-10 were found to be new compounds. All metabolites, except 2, 3, 6, and 7, exhibited potent anti-inflammatory activity. The structures of these metabolites were characterized on the basis of spectroscopic studies, and the structure of 5 was also determined by single-crystal X-ray-diffraction analysis.
Choudhary
M Iqbal
MI
H.E.J. Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Karachi-75270, Pakistan. hej@cyber.net.pk
Sultan
Sadia
S
Jalil
Saima
S
Anjum
Shazia
S
Rahman
Azhar Abdul
AA
Fun
Hoong-Kun
HK
D001711:Biotransformation; D018360:Crystallography, X-Ray; D005658:Fungi / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008655:Mesterolone / Q000737:chemistry / Q000493:pharmacokinetics*; D013045:Species Specificity
D008655:Mesterolone