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

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.