Journal of Lipid Research, Vol. 9, 27-33, January 1968
Copyright © 1968 by Lipid Research, Inc.

6-Acyl galactosyl ceramides of pig brain: structure and fatty acid composition

Yasuo Kishimoto , Martha Wajda , and Norman S. Radin

Mental Health Research Institute, University of Michigan, Ann Arbor, Michigan 48104

Two glycolipids were isolated from pig brain and were shown to be the fatty acid esters of kerasin and cerebron in which the second fatty acid moiety is attached to the 6-position of the galactose. The point of attachment was shown in two ways: by permethylation and by cleavage with periodate. Methanolysis of the permethylated cerebroside esters yielded O-methyl sphingosines, methyl esters of nonhydroxy or 2-methoxy acids, and methyl 2,3,4-trimethyl galactoside. Cleavage of the cerebron ester with periodate, followed by treatment with sodium borohydride and dilute HCl, yielded ceramide plus 1-monoglyceride. The ester-linked fatty acids were primarily 16:0, 18:0, and 18:1, while the amide-linked fatty acids showed the wide assortment of chain lengths typical of brain cerebrosides. The methylation step, with silver oxide and methyl iodide, yielded two derivatives with the cerebroside esters, but the structural explanation for the difference was not elucidated. The galactose in the cerebron ester was shown to exist in the ßbeta;-pyranoside form.

Supplementary key words 6-acyl cerebrosides • ester-type glycolipids • structure determination • sphingosine derivatives

Submitted on June 8, 1967
Accepted on September 11, 1967

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