Microbial transformation of mesterolone

Abstract

The microbial transformation of mesterolone (=(1α,5α,17β)-17-hydroxy-1-methylandrostan-3-one; 1), by a number of fungi yielded (1α,5α)-1-methylandrostane-3,17-dione (2), (1α,3β,5α,17β)-1-methylandrostane-3-17-diol (3), (5α)-1-methylandrost-1-ene-3,17-dione (4), (1α,5α,15α)-15-hydroxy-1-methylandrostane-3,17-dione (5), (1α,5α,6α,17β)-6,17-dihydroxy- 1-methylandrostan-3-one (6), (1α,5α,7α,17β)-7,17-dihydroxy- 1-methylandrostan-3-one (7), (1α,5α,11α,17β)-11,17-dihydroxy-1 -methylandrostan-3-one (8), (1α,5α,15α, 17β)-15,17-dihydroxy-1 -methylandrostan-3-one (9), and (5α,15α,17β)-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. © 2005 Verlag Helvetica Chimica Acta AG, Zürich.