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 (EP) using Penicillium decumbens as biocatalyst was investigated and selective hydroxylation of EP was observed. The products were separated by flash chromatography, and the structure determination were performed by MS, NMR, and X-ray crystallography. Biotransformation of EP afforded 7β-hydroxy-16α, 17α-epoxyprogesterone 1 and 7β, 11α-dihydroxy-16α, 17α-epoxyprogesterone 2. The two novel metabolic products 1 and 2 were reported for the first time. Moreover, the identified C7β- and C11-α hydroxylation is a novel reaction of microbial transformation of steroids by P. decumbens. This indicated that P. decumbens was a potential strains to produce the valuable pharmaceutical ingredients and precursors.