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Journal of Lipid Research, Vol 31, 125-130, Copyright © 1990 by Lipid Research, Inc.
AN Baer, PB Costello and FA Green
Characterization of the chemical form and stereo-specificity of the fatty
acid derivatives of arachidonic and linoleic acid in psoriatic epidermis is
needed to define the enzymatic origin of these compounds and their possible
role in pathogenesis. In an analysis of psoriatic skin scales, both free
and esterified 13-hydroxyoctadecadienoic acids were the principal fatty
acid derivatives, present in mean concentrations of 115 and 17 ng/mg
scales, respectively. The analysis included reversed-phase high performance
liquid chromatography of the free acid and of its methyl ester, gas
chromatography, gas-liquid chromatography-mass spectrometry of the methyl
ester derivatives, and chiral separation. The free and esterified
13-hydroxyoctadecadienoic acids isolated from the psoriatic scales
contained a mixture of the S/R stereoisomers, averaging 1.9:1 for free 13-
hydroxyoctadecadienoic acid. These findings are not compatible with the
strict S- stereospecificity for oxygen insertion exhibited by mammalian
lipoxygenase but rather could point to the action of a cyclooxygenase. The
demonstration that a hydroxylated fatty acid derivative is esterified in
vivo in psoriatic keratinocytes suggests that the physiology of these cells
may be altered early in the process of keratinization.
ARTICLES
Free and esterified 13(R,S)-hydroxyoctadecadienoic acids: principal oxygenase products in psoriatic skin scales
Department of Medicine, State University of New York, Buffalo.
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