title: Separation and analysis of novel polyunsaturated mycolic acids from a psychrophilic, acid-fast bacterium, Gordona aurantiaca.
abstract: More than 30 molecular species of highly unsaturated mycolic acids, ranging from C60 to C78 and possessing between two and seven double bonds, have been obtained from a new genus of acid-fast bacteria, Gordona aurantiaca. They were fully separated and identified as their trimethylsilyl ether derivatives by a combination of silica gel thin-layer chromatography (TLC), argentation thin-layer chromatography and gas chromatography/mass spectrometry (GC/MS). On silica gel thin-layer chromatography two adjacent spots, corresponding to mycolic acids possessing different structures of straight-chain and alpha-alkyl branch, were detected. The lower spot was separated by argentation TLC into four subclasses: monoenoic (including a small amount of saturated), dienoic, trienoic and tetraenoic mycolic acids ranging from C62 to C74 and possessing a C16:0, C18:0 or C20:0 alkyl branch at the C-2 position. The upper spot was separated by argentation TLC into five subclasses: dienoic (including a small amount of monoenoic), trienoic, tetraenoic, pentaenoic and hexaenoic (heptaenoic) acids ranging from C64 to C78 and possessing a C18:1 or C20:1 alkyl branch at the C-2 position. These types of mycolic acid structure differ from those reported previously in Mycobacteria and Nocardia, in the numbers of both carbon atoms and double-bonds and the intermediate length of the alpha-alkyl branch. The characteristic polyenoic structure of the straight-chain alkyl unit was also confirmed by GC/MS analysis of the meromycolaldehydes obtained after pyrolysis of the methyl mycolates. The major aldehydes obtained from the lower-spot mycolic acids were C44, C46, C48, C50 and C52, while those from the upper-spot mycolic acids were C48, C50, C52, C54 and C56, centering at C54. These aldehydes were also shown to possess between two and four double bonds in the lower-spot and between two and seven double bonds in the higher-spot mycolic acids, respectively. The physiological role of such highly polyunsaturated mycolic acids in psychrophilic acid-fast bacteria is discussed.
mesh_terms: D055598:Chemical Phenomena; D002621:Chemistry; D002849:Chromatography, Gas; D002855:Chromatography, Thin Layer; D008401:Gas Chromatography-Mass Spectrometry; D006358:Hot Temperature; D009161:Mycobacterium / Q000032:analysis*; D009171:Mycolic Acids / Q000302:isolation & purification*; D009170:Nontuberculous Mycobacteria / Q000032:analysis* / Q000254:growth & development
chemical_list: D009171:Mycolic Acids