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.
D000730:Androstadienes / Q000378:metabolism; D000737:Androstenols / Q000096:biosynthesis; D001673:Biodegradation, Environmental; D055598:Chemical Phenomena; D002621:Chemistry; D002770:Cholenes / Q000096:biosynthesis; D002784:Cholesterol / Q000031:analogs & derivatives* / Q000378:metabolism; D005285:Fermentation; D008738:Methyl Ethers; D009161:Mycobacterium / Q000378:metabolism*; D009168:Mycobacterium phlei / Q000378:metabolism*; D015125:Oxyquinoline
D000730:Androstadienes; D000737:Androstenols; D002770:Cholenes; D008738:Methyl Ethers; D015125:Oxyquinoline; D002784:Cholesterol