Acylglucosylceramides of pig epidermis: structure determination

The acylglucosylceramides of pig epidermis comprise 56% of the total glucosylceramides and 3.3% of the total epidermal lipid by weight. Contrary to an earlier report on this lipid, the amide-linked fatty acid is not a dihydroxypentatriacontadienoic acid; rather, the fatty acids are a series of long...

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Bibliographic Details
Published in:Journal of lipid research 1983-06, Vol.24 (6), p.753-758
Main Authors: Wertz, P.W, Downing, D.T
Format: Article
Language:English
Subjects:
Amides
animal physiology
Animals
Cerebrosides - isolation & purification
Chromatography, Gas
Chromatography, Thin Layer
Fatty Acids - analysis
Glucosylceramides - isolation & purification
Magnetic Resonance Spectroscopy
Skin - analysis
Structure-Activity Relationship
Swine
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Summary:The acylglucosylceramides of pig epidermis comprise 56% of the total glucosylceramides and 3.3% of the total epidermal lipid by weight. Contrary to an earlier report on this lipid, the amide-linked fatty acid is not a dihydroxypentatriacontadienoic acid; rather, the fatty acids are a series of long chain omega-hydroxy acids consisting of 58% saturates, 35% monoenes, and 7% dienes, with predominant chain lengths of 30, 32, and 34 carbons, respectively. The structure of the acylglucosylceramides may therefore be formulated as 1-(3'-O-acyl)-beta-D-glucosyl-N-(omega-hydroxy)acylsphingosines. In accord with the previous report, 74% of the total esterified fatty acids is linoleic acid and the long-chain bases consist of homologous series of sphinganines and sphingenines ranging from 16-22 carbons in length. This unique glycolipid may play a role in epidermal barrier function.
ISSN:0022-2275
1539-7262
DOI:10.1016/S0022-2275(20)37949-9