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Mechanisms of Steroid Oxidation by Microorganisms

VIII. 3,4-DIHYDROXY-9,10-SECOANDROSTA-1,3,5(10)-TRIENE-9,17-DIONE, AN INTERMEDIATE IN THE MICROBIOLOGICAL DEGRADATION OF RING A OF ANDROST-4-ENE-3,17-DIONE

From the ¹ From the School of Pharmacy, University of Wisconsin, Madison, Wisconsin 53706

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 3a-H-4[3'-propionic acid]-7aß-methylhexahydro-1,5-indanedione. When this catechol was incubated with cell-free extracts of Nocardia restrictus, it was rapidly and completely metabolized to 3a-H-4-[3'-propionic acid]-7aß-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.

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