Microbial hydroxylation of hydroxyprogesterones and α-glucosidase inhibition activity of their metabolites

Abstract

Microbial transformation of 11α-hydroxyprogesterone (1) with Cunninghamella elegans, Gibberella fujikuroi, Fusarium lini, and Candida albicans yielded 11α,15α,16α-trihydroxypregn-4-ene-3,20-dione (3), 11α-hydroxy-5α-pregnane-3,20-dione (4), 6β,11α- dihydroxypregn-4-ene-3,20-dione(5), 11α-hydroxypregna-1,4-diene-3,20-dione (6), 11α,17β-dihydroxyandrost-4-en-3-one (7), and 11α,15α-dihydroxypregn-4-ene-3,20-dione (8). On the other hand, microbial transformation of 17α-hydroxyprogesterone (2) with Cunninghamella elegans and Fusarium Uni yielded 11α,17α- dihydroxypregn-4-ene-3,20-dione (9), and 17α-hydroxypregna-1,4-diene-3,20- dione (10). The structures of the metabolites 3-10 were deduced on the basis of spectroscopic methods. Compound 3 was identified as a new metabolite, which exhibited a promising inhibitory activity against the α-glucosidase enzyme. © 2007 Verlag der Zeitschrift für Naturforschung.