A process is described for the microbial degradation of cholesterol and plant sterols, to produce androsta-1, 4-diene-3, 17-dione and androst-4-ene-3, 17dione, by two newly isolated bacteria designated Mycobacterium sp. NRRL B-3683 and Mycobacterium sp. NRRL B-3805. These myocbacteria produce substantial amounts of 17-ketonic compounds without appreciable degradation of the steroid nucleus. No ring degradation inhibitory agents are necessary. The first microbiological production of 20a-hydroxymethylpregna-1,4-dien-3-one is also reported.
A process is described for the microbial degradation of cholesterol and plant sterols, to produce androsta-1, 4-diene-3, 17-dione and androst-4-ene-3, 17-dione, by two newly isolated bacteria designated
Mycobacterium
sp. NRRL B-3683 and
Mycobacterium
sp. NRRL B-3805. These myocbacteria produce substantial amounts of 17-ketonic compounds without appreciable degradation of the steroid nucleus. No ring degradation inhibitory agents are necessary. The first microbiological production of 20α-hydroxymethylpregna-1, 4-dien-3-one is also reported.
Suinmnry ( f)-A8(12)-15-Dehydro-PGEl (III), ( j-)-A8(l2) could be separated from (V) by partition chromatography.Stereoselective reductions and an o p t i d resolution were thus achieved by these microbial processes.-PGEl (IV), and ( f)-15-efii-A8(l4-PGE, (V) have been synthesized from the readily available starting material (I} , and compound (111) has been stereoselectively reduced by micro-organisms to either (+)-or (-)-(V).
It has been postulated that 3-(3-oxo-7α-methylthio-4-androsten-17α-yl)propionic acid γ-lactone (I) is a key intermediate in the metabolism of the anti-aldosterone agent, spironolactone (3-[3-oxo-7α-acetylthio-17β-hydroxy-4-androsten-17α-yl] propionic acid γ-lactone). In the present study it was found that microbial oxygenation of I by
Chaetomium cochloides
QM 624 gave three metabolites which retained sulfur in their molecules and were found to be identical to the human metabolites of spironolactone.
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