9Z,11e,13e,15z-octadecatetraenoic acid

cis-Parinaric acid is a naturally occurring polyunsaturated fatty acid containing an unusual conjugated (Z,E,E,Z) tetraene. This chromophore provides for a natural fluorescence at 432 nm with an excitation wavelength at 320 nm. cis-Parinaric acid occurs naturally in the seeds of the Makita tree, a tropical rainforest tree indigenous to Fiji. Makita seeds are inedible, and this toxicity may be due at least in part to the unstable conjugated fatty acids, including cis-parinaric acid, contained within the seed. cis-Parinaric acid has been used for the measurement of phospholipase activity, lipase activity, and as an indicator of lipid peroxidation.

ChEBI: An octadecatetraenoic acid containing a conjugated system of double bonds at positions 9, 11, 13 and 15.

[1] CLAUDE WOLF  Gilbert B  Lucien Sagaert. A sensitive assay of phospholipase using the fluorescent probe 2-parinaroyllecithin[J]. Biochemical and biophysical research communications, 1981, 99 1: Pages 275-283. DOI: 10.1016/0006-291x(81)91742-3
[2] F BEISSON. Use of naturally fluorescent triacylglycerols from Parinari glaberrimum to detect low lipase activities from Arabidopsis thaliana seedlings.[J]. Journal of Lipid Research, 1999, 40 12: 2313-2321.
[3] SUSAN O. MCGUIRE. An esterification protocol for cis-parinaric acid-determined lipid peroxidation in immune cells1,2[J]. Lipids, 1997, 32 2: 219-226. DOI: 10.1007/s11745-997-0028-x
[4] YVETTE C. M. DE HINGH. Direct Measurement of Lipid Peroxidation in Submitochondrial Particles[J]. Biochemistry Biochemistry, 1995, 34 39: 12755-12760. DOI: 10.1021/bi00039a035
[5] KATRIN K HALLING. Cholesterol interactions with fluid-phase phospholipids: effect on the lateral organization of the bilayer.[J]. Biophysical journal, 2008, 95 8: 3861-3871. DOI: 10.1529/biophysj.108.133744