Identification of 10-methylsphinganine in cerebrosides of the guinea pig harderian gland.
A large amount of branched long chain bases was detected in the cerebrosides of guinea pig Harderian gland. The long chain bases of cerebrosides were analyzed by GLC as trimethylsilyl derivatives. The branched long chain bases were separated into four peaks (I, II, III, IV) according to the number of carbon atoms and the position of branching. In the present work, the structures of long chain bases in the four peaks were analyzed by GLC and GC-MS after conversion of them to aldehydes, alcohols, and fatty acids. Furthermore the main component of long chain bases (Peak II) was isolated by HPLC as N-acetyl derivatives and analyzed by NMR. The structures of branched long chain bases in Peaks I, II, III, and IV are as follows. Branched long chain bases of Peak I are 2-amino-10- (main component), 2-amino-9-, and 2-amino-8-methylhexadecane-1,3-diol. Branched long chain bases of Peak II also consist of a mixture of 2-amino-10-, 2-amino-9-, and 2-amino-8-methyl-heptadecane-1,3-diol. The branched long chain base of Peak III is 2-amino-10-methyl-octadecane-1,3-diol, while that of Peak IV is 2-amino-16-methyloctadecane-1,3-diol. Among these branched long chain bases, 10-methylsphinganines are dominant though the chain lengths are different. These branched long chain bases, in which the substituted positions exist in the middle part of aliphatic chain (10-, 9-, or 8-methylsphinganine) are novel long chain bases in mammals.
Yasugi
E
E
Department of Physiological Chemistry and Nutrition, Faculty of Medicine, University of Tokyo.
Kasama
T
T
Seyama
Y
Y
D000818:Animals; D002554:Cerebrosides / Q000302:isolation & purification; D055598:Chemical Phenomena; D002621:Chemistry; D002849:Chromatography, Gas; D002851:Chromatography, High Pressure Liquid; D005260:Female; D008401:Gas Chromatography-Mass Spectrometry; D006168:Guinea Pigs; D006243:Harderian Gland / Q000032:analysis*; D007765:Lacrimal Apparatus / Q000032:analysis*; D009682:Magnetic Resonance Spectroscopy
D002554:Cerebrosides