Inhibition of fatty acid delta 6- and delta 5-desaturation by cyclopropene fatty acids in rat liver microsomes.

delta 6-Desaturation of linoleic acid and delta 5-desaturation of dihomo-gamma-linolenic acid were measured in liver microsomes from rats fed fresh Baobab seed oil containing cyclopropene fatty acids (malvalic acid and sterculic acid) or heated Baobab seed oil practically devoid of these fatty acids or control oil. The presence of cyclopropene fatty acids in the fresh Baobab oil diet highly depressed both desaturations, but delta 6- more than delta 5-desaturation. The decreased capacity of microsomes to desaturate was reflected in the lower arachidonic acid content in microsomal phospholipids from rats fed this oil. However it was also lower in rats fed heated oil although in vitro delta 6- and delta 5-desaturation were not depressed. When liver microsomes prepared from rats fed the control diet were used for the desaturation assays, the presence of free malvalic or sterculic acid in the medium, also highly depressed delta 6- and delta 5-desaturation. The incorporation of arachidonic acid, the product of delta 5-desaturation, into phospholipids was also highly depressed, while that of the precursor dihomo-gamma-linolenic acid was not. This suggests that cyclopropene fatty acids specifically inhibit incorporation of the delta 5-desaturation product into phospholipids or that they specifically inhibit desaturation of the substrate previously incorporated into a membrane phospholipid.