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Hydroxyacid derivatives in human epidermis
Author(s) -
Wertz Philip W.,
Downing Donald T.
Publication year - 1988
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02535512
Subject(s) - chemistry , fatty acid , hydrolysis , chromatography , epidermis (zoology) , thin layer chromatography , methanol , organic chemistry , biochemistry , biology , anatomy
The principal objective of this investigation was to examine the ω‐hydroxyacid derivatives in the cornified layer of human skin. Toward this end, sunburn peelings were collected, and the lipids were extracted with chlofoform/methanol. Comparison with authentic standards by thin layer chromatography (TLC) indicated the presence of both N‐(ω‐acyloxy)acylsphingosine (acylceramide) and ω‐acyloxy fatty acid (acyl acid), which accounted for 1.7% and 2.0% of the total lipid, respectively, as estimated by photodensitometry of the charred chromatograms. Each of these lipids was isolated by preparative TLC, hydrolyzed, and the resulting fragments were further analyzed by TLC and by gas liquid chromatography (GLC) of appropriate derivatives. In both of these lipids, the predominant ω‐hydroxyacid proved to be the 30‐carbon saturated species (56–59% of the total), while linoleate was the major ester‐linked fatty acid. Linoleate was more abundant in the acyl acid (38.0%) than in acylceramide (21.4%). These findings represent the first demonstration of acyl acid in human skin and support the proposition that acyl acid, like the other linoleate‐rich ω‐hydroxyacid derivatives, functions as a molecular rivet in maintaining epidermal structure and fucntion.