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Microbial Transformation of Sterols
Authors:Kei Arima  Michitaro Nagasawa  Moo Bae  Gakuzo Tamura
Institution:Department of Agricultural Chemistry, The University of Tokyo
Abstract:Cholesterol decomposing ability of 1589 microbial strains was examined. Two hundreds and thirty six strains from actinomycetes, bacteria, molds, and yeasts were found capable of oxidizing cholesterol into cholestenone. Cholesta-1,4-dien-3-one was produced by 5 strains of Streptomyces. The complete decomposition of cholesterol molecule was observed in the genera: Arthrobacter, Bacillus, Brevibacterium, Corynebacterium, Microbacterium, Mycobacterium, Nocardia, Protaminobacter, Serratia, and Streptomyces. α,α′-Dipyridyl and arsenite inhibited decomposing enzymes giving rise to cholestenone, cholesta-1,4-dien-3-one, and an intermediate probably devoid of the sterol side chain.

Selective cleavage of the side chains of various sterols at C-17, giving rise to androsta-1,4-diene-3,17-dione (ADD), occurred in the presence of α,α′-dipyridyl by microorganisms of the following genera: Arthrobacter, Bacillus, Brevibacterium, Corynebacterium, Microbacterium, Mycobacterium, Nocardia, Protaminobacter, Serratia, and Streptomyces. The degradation pathway of cholesterol, for example, was shown as follows:  /></span></p>Other sterols such as campesterol, <i>β</i>-sitosterol, stigmasterol and 7-dehydrocholesterol were degraded by the same sequence. The pathway exemplified in cholesterol is considered to be the general degradation pathway of sterols by their decomposing microorganisms.</p>It was further demonstrated that ADD thus formed from sterols was converted into 3-hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione.</td>
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