Hydroxy-eicosatrienoic acid

Figure 1. Metabolic pathway for linoleic acid. COX, Cycloozygenase, LOX, Lipoxygenase, PGEi, Prostaglandin Ej, PGE2, Prostaglandin E2, PGI2, Prostaglandin l2,TXA2, Thromboxane A2, 15-HETrE, 15-hydroxy eicosatrienoic acid, LTB4, Leukotriene B4.

The role of unsaturated fatty acids in inducing an inflammatory response of the endothelium has been explored and the results are contradictory (71-73). In one study, unsaturated fatty acids, by inducing an oxidative stress-like state, did promote an inflammatory response (71). However, this study could not have observed an anti-inflammatory effect because cells were not exposed to (proinflammatory) cytokines. Indeed, unsaturated fatty acids reduce the inflammatory response to cytokines in endothelial cells in vitro (72). 13-Oxo-octadecadienoic acid inhibits the cytokine-de-pendent expression of inducible cyclooxygenase in macrophages (74). As a result, the resolution of inflammation of the arterial wall would be impaired and this would favor atherosclerosis. By contrast, 13-hydroxy-octadecadienoic and 15-hydroxy-eicosatrienoic acids inhibit the cytokine-induced... 

Strain ALA2 converted y-linolenic acid (18 3 all ds-6,9,12) to several products including 12,17 13,17-diepoxy-6,9-octadecadienoic acid 12,13,17-trihydroxy-6(Z),9(Z)-octadecadienoic acid and 12-hydroxy-13,16-epoxy-6(Z),9(Z)-octadecadienoic acid as depicted in the top half of Figure 16.2 (Hosokawa et al, 2003a). Strain ALA2 also converted the substrate arachidonic acid (20 4 all civ-5,8,11,13) to cyclic and trihydroxyl fatty acids as reported previously (Hosokawa et al., 2003a). These reactions resulted in compounds 14,19 15,19-diepoxy-5(Z),8(Z),ll(Z)-eicosatrienoic acid 14-hydroxy-15,18-epoxy-5(Z),... 

Iodohexadecanal Gyclic adenosine monophosphate 6-Iodo-5-hydroxy-8,l 1, l4-eicosatrienoic acid 6-lactone Deoxyrihonucleic acid Epidermal growth factor Fihrohlast growth factor Gas chromatography-mass spectrometry... 

Hydroxy-13,16-epoxy-6(Z),9(Z)-octadecadienoic acid 14-Hydroxy-15,18-epoxy-5(Z),8(Z),11 (Z)-eicosatrienoic acid... 

Among common foodstuffs, onion and garlic have been reported to contain a heat-stable, lipid soluble factor that inhibits platelet aggregation [183-186], This factor inhibits thromboxane synthesis in platelets from exogenous [ C]arachidonic acid. Along with the decreased thromboxane formation, a new metabolite of arachidonic acid appeared, 10-hydroxy-11,12-epoxy-5,8,14-eicosatrienoic acid, probably via the platelet lipoxygenase pathway [185],... 

The results in Table 6 were obtained when both the overall rates of chain elongation and the condensation reaction were measured with 16 0 CoA, 6,9-18 2 CoA and 6,9,12-18 3 CoA as substrates The 8-hydroxy acyl-CoA dehydrase reaction was assayed only with the CoA derivatives of DL-8-hydroxy-stearic acid (8-OH-18 0 CoA) and DL-8-hydroxy-8,11-eicosadienoic acid (8-OH-8,11-20 2 CoA). The 2-trans-enoyl-CoA reductase reaction was assayed with the CoA derivatives of 2-trans-octadecenoic acid (2 trans-18 1 CoA) and 2-trans-8,ll-eicosatrienoic acid (2-trans-8,11-20 3 CoA) All reactions were assayed with the microsomes from rats raised on both a chow diet and a fat-free diet. Both the rates of the condensation reaction and the overall chain elongation reaction were depressed when rats were fed a chow diet These depressed rates of conversion were more pronounced when 16 0 CoA was used as substrate than when 6,9-18 2 CoA or 6,9,12-18 3 CoA were used as substrates. These results support our N-ethylmaleimide inhibition studies and are consistent with the concept that rat liver microsomes contain at least two different condensing enzymes. One condensing enzyme would preferentially utilize saturated substrates while another would act on unsaturated substrates. 

Epoxy-5,11,14-eicosatrienoic acid, E-60016 8a, 13 R-Epoxy-6)9-hydroxy-14-labden-11 -one, in E-80037... 

Pace-Asciak CR, Granstrom E, Samuelsson B. Arachidonic acid epoxides. Isolation and structure of two hydroxy epoxide intermediates in the formation of 8,11 >12- and 10,11,12-trihydroxy-eicosatrienoic acids. J Biol Chem 1983 258 6835-6840. 

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