Metabolic fate of cholesteryl methyl ether in Mycobacterium phlei

Mycobacterium phlei transformed cholesteryl methyl ether into three metabolites: 3beta-methoxy-dinor-5,17(20)-choladien-22-oic methyl ester (I), 3beta-methoxy-5-androsten-17-one (II), and 3beta-methoxy-dinor-5-cholen-22-ol (III). After isolation with thin-layer chromatography, their structures were elucidated by mass, IR and NMR spectroscopy. Compound II was the major product. Compounds I and III were products of various side reactions. In the presence of 8-hydroxyquinoline that inhibits degradation of the steroid nucleus, 1,4-androstadiene-3,17-dione was formed in addition to the compounds mentioned. This indicates that a moderate splitting of the ether bond takes place.