Abstract
Selective cleavage of the side chains of various sterols at C-17, giving rise to androsta-l, 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 Streptomyees. The degradation pathway of cholesterol, for example, was shown as follows:
cholesterol→cholest-4-en-3-one→cholesta-1, 4-dien-3-one
↓t↓
andros-4-ene-3, 17-dione→ADD
Other sterols such as campesterol, β-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.
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.
