Microbial Hydroxylation of 16α, 17α-Epoxyprogesterone by Penicillium Decumbens.

Abstract

Microbial transformation has been successfully applied in the production of steroid intermediates with therapeutic use and commercial value in pharmaceutical industry due to its high regio- and stereo-selectivity. As such, it is still important to screen microbial strains with novel activity or more efficient abilities in the development of the commercial steroid industry. Biotransformation of steroid: 16α, 17α-epoxyprogesterone (1). using Penicilliumdecumbens as biocatalyst was investigated and selective hydroxylation of 1 was observed. The products were separated by silica gel column chromatography, and the structure determination was performed by MS, NMR, and X-ray crystallography. Biotransformation of 1 afforded 7β-hydroxy-16α, 17α-epoxyprogesterone (2). and 7β,11α-dihydroxy-16α,17α- epoxyprogesterone (3). The two novel metabolic products 2 and 3 were reported for the first time. Moreover, the identified C7β- and C11-αhydroxylation is a novel reaction of microbial transformation of steroids by P.decumbens.