Mechanisms of Steroid Oxidation by Microorganisms

Abstract

Abstract 3,4-Dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione has been synthesized by a combination of chemical and microbiological methods. While this 3,4-catechol has not yet been isolated as a metabolic product, all of the data suggest that it is an intermediate in the degradation of the aromatic ring of 3-hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione with the eventual formation of 3aα-H-4α[3'-propionic acid]-7aβ-methylhexahydro-1,5-indanedione. When this catechol was incubated with cell-free extracts of Nocardia restrictus, it was rapidly and completely metabolized to 3aα-H-4α-[3'-propionic acid]-7aβ-methylhexahydro-1,5-indanedione. Under similar conditions, 3-hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione and 3,19-dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione were very slowly and incompletely metabolized.