Docosatetraenoic acid explained

Docosatetraenoic acid designates any straight chain 22:4 fatty acid. (See Essential fatty acid for nomenclature.)

One isomer is of particular interest:

• all-cis-7,10,13,16-docosatetraenoic acid is an ω-6 fatty acid with the common name adrenic acid (AdA). This is a naturally occurring polyunsaturated fatty acid formed through a 2-carbon chain elongation of arachidonic acid. It is one of the most abundant fatty acids in the early human brain.^[1] This unsaturated fatty acid is also metabolized by cells to biologically active products viz., dihomoprostaglandins,^[2] and epoxydocosatrienoic acids (EDTs, also known as dihomo-EETs).^{[3] [4] [5]} In addition to being endothelium-derived hyperpolarizing factors, EDTs have demonstrated anti-endoplasmic reticulum stress and anti-nociceptive activities. They are hydrolyzed by the soluble epoxide hydrolase (sEH) to dihydroxydocosatrienoic acids (DHDTs) and hence might play a role in the efficacy of sEH inhibitors.

See also

• Polyunsaturated fat

Further reading

• Ferretti, A., Flanagan, V.P. Mass spectrometric evidence for the conversion of exogenous adrenate to dihomo-prostaglandins by seminal vesicle cyclo-oxygenase. A comparative study of two animal species. J Chromatogr 383 241-250 (1986).
• Sprecher, H., VanRollins, M., Sun, F., et al. Dihomo-prostaglandins and -thromboxane. A prostaglandin family from adrenic acid that may be preferentially synthesized in the kidney. J Biol Chem 257 3912-3918 (1982).

Notes and References

1. Martinez M . Tissue levels of polyunsaturated fatty acids during early human development . J Pediatr . 120 . 4 Pt 2 . S129–38 . 1992 . 1532827 . 10.1016/S0022-3476(05)81247-8.
2. Campbell WB, Falck JR, Okita JR, Johnson AR, Callahan KS. John R. Falck . Synthesis of dihomoprostaglandins from adrenic acid (7,10,13,16-docosatetraenoic acid) by human endothelial cells . Biochim. Biophys. Acta . 837 . 1 . 67–76 . 1985 . 3931686 . 10.1016/0005-2760(85)90086-4.
3. Kopf PG, Zhang DX, Gauthier KM, Nithipatikom K, Yi XY, Falck JR, Campbell WB . Adrenic acid metabolites as endogenous endothelium-derived and zona glomerulosa-derived hyperpolarizing factors . Hypertension . 55 . 2 . 547–54 . 2010 . 20038752 . 2819927 . 10.1161/HYPERTENSIONAHA.109.144147 .
4. Am J Physiol Heart Circ Physiol . May 2007. 292. 5. H2265–74 . Metabolism of adrenic acid to vasodilatory 1alpha,1beta-dihomo-epoxyeicosatrienoic acids by bovine coronary arteries. . Yi XY, Gauthier KM, Cui L, Nithipatikom K, Falck JR, Campbell WB . 17209008 . 10.1152/ajpheart.00947.2006.
5. ACS Omega . March 2021. 6. 10. 7165–7174 . Adrenic Acid-Derived Epoxy Fatty Acids Are Naturally Occurring Lipids and Their Methyl Ester Prodrug Reduces Endoplasmic Reticulum Stress and Inflammatory Pain. . Singh N, Barnych B, Wagner KM, Wan D, Morisseau C, Hammock BD . 10.1021/acsomega.1c00241. 7970556. free. 33748630.