8,11,14-Icosatrienoic acid

Campbell, W. B., Gebremedhin, D., Pratt, P. F., and Harder, D. R. 1996. Identification of epoxye-icosatrienoic acids as endothelium-derived hyperpolarizing factors. Circ. Res. 78 415 123. 

Imig, J.D., X. Zhao, J.R. Falck, S. Wei, and J.H. Capdevila (2001). Enhanced renal microvascular reactivity to angiotensin 11 in hypertension is ameliorated by the sulfonimide analt of 11,12-epoxye-icosatrienoic acid. J. Hypertension 19,983-992. 

The common trienoic fatty acids are cis,cis,cis-9,12,15-octadecatrienoic acid (a-linolenic acid), cis,-c/s,cis-6,9,12-octadecatrienoic acid (y-linolenic acid), c/s,c/s,c/s-8,ll,14-icosatrienoic acid (dihomo-y-lino-lenic acid), 5,9,13-eicosatrienoic acid, and 5,9,13-docosatrienoic acid. An example of a tetraenoic fatty acid is ds,ds,ds,ds-5,8,ll,14-icosatetraenoic acid (arachidonic acid). The discovery of new polyunsaturated acids is an ongoing process, with the recent discovery of 5,9-heneicosadienoic acid, 5,9-do-cosadienoic acid, 5,9-tricosadienoic acid, trienoic 5,9,13-eicosatrienoic acid, and 5,9,13-docosatrienoic acid from Stoichactis helianthus. Geranoic acid (systematic name is 3,7,1 l,15-tetramethyl-2,6,10,14-hexadecatetraenoic acid) (Figure 9), nerolic and far-nesoic acids are polyunsaturated fatty acids with branches in their structures. 

Pritchard KA Jr, Wong PY, Stemerman MB (1990) Atherogenic concentrations of low-density lipoprotein enhance endothelial cell generation of epoxye-icosatrienoic acid products. Am J Pathol 136 1383-1391... 

Fang X, WeintraubNL, Spector AA (2003) Differences in positional esterification of 14,15-epoxye-icosatrienoic acid in phosphatidylcholine of porcine coronary artery endothelial and smooth muscle cells. Prostaglandins Other Lipid Mediat 71 33-42... 

Fang X, Kaduce TL, Weintraub NL, Harmon S, Teesch LM, Morisseau C, Thompson DA, Hammock BD, Spector AA (2001) Pathways of epoxye-icosatrienoic acid metabolism in endothelial cells. Implications for the vascular effects of soluble epoxide hydrolase inhibition. J Biol Chem 276 14867-14874... 

Piomelli D, Shapiro E, Zipkin R, Schwartz JH, Feinmark SJ. Formation and action of 8-hydroxy-11,12-epoxy-icosatrienoic acid in Aplysia a possible second messenger in neurons. Proc Natl Acad Sci USA 1989 86 1721-1725. 

This enzyme [EC 6.2.1.15], also known as arachido-nateiCoA ligase, catalyzes the reaction of arachidonate with ATP and coenzyme A to generate arachidonyl-CoA, AMP, and pyrophosphate (or, diphosphate). The enzyme can also use 8,11,14-icosatrienoate as a substrate, but not the other long-chain fatty acids. It should be noted that this enzyme is not identical to long-chain acyl-CoA synthetase [EC 6.2.1.3]. 

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