Abstract
The role of the position of the cis-double bond in monounsaturated fatty acids on their metabolic behavior was studied by feeding rats triacylglycerols containing high levels of petroselinic (Δ6-cis-octadecenoic acid, n-12 18:1) or oleic acid (Δ9-cis-octadecenoic acid, n-9 18:1). Petroselinic acid from dietary triacylglycerols (coriander oil) was extensively esterified into lipids of rat liver. Chain elongation of petroselinic acid to Δ8-cis-eicosenoic acid (n-12 20:1) as well as chain shortening to Δ4-cis-hexadecenoic acid (n-12 16:1) were the major metabolic reactions, whereas products resulting from desaturation/chain elongation of petroselinic acid were not detectable, suggesting that this fatty acid is a dead-end metabolite of this pathway. In contrast, distinctly detectable proportions of desaturation/chain elongation products of oleic acid, e.g. Δ5,8,11-all cis-eicosatrienoic acid (n-9 20:3, Mead's acid) were found in the liver lipids of rats fed a high-oleic sunflower oil. Dietary petroselinic acid inhibited desaturation/chain elongation reactions of linoleic acid (Δ9,12-cis,cis-octadecadienoic acid, n-6 18:2) which resulted in reduced levels of arachidonic acid (Δ5,8,11,14-all cis-eicosatetraenoic acid, n-6 20:4) in liver lipids. It is envisaged that petroselinic acid having a Δ6-double bond mimics a product of Δ6-desaturase and thus induces pseudo-product mediated inhibition of the desaturase. Copyright © 1996 Elsevier Science Inc.
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