Mechanism of the Side Chain Degradation of Progesterone by Microorganisms.

Abstract

The degradation of the side chain of progesterone by Aspergillus flavus and Penicillium lilacinum has been studied. A. flavus cleaves the side chain via an enzymatic Bayer-Williger-oxidation of progesterone to testosterone acetate. This intermediate is then hydrolyzed to acetic acid and testosterone. The testosterone is then oxidized to [DELTA]4 -androstene-3,17-dlone. P. lilacinum more directly oxidizes progesterone to [DELTA]4-androstene-3,17-dione and no testosterone acetate is formed. P. lilacinum easily oxidizes 17a-hydroxyprogesterone to 4-androstene-3,17-dione, while A. flavus leaves this steroid unaffected.