8(E),10(E),12(Z)-Octadecatrienoic Acid (Synonyms: α-Calendic Acid, Calendic Acid, Calendulic Acid, trans,trans,cis-8,10,12-Octadecatrienoic Acid)

8(E),10(E),12(Z)-Octadecatrienoic acid is a conjugated polyunsaturated fatty acid (PUFA) that has been found in C. officinalis seed oil and has anticancer activity.^1,2,3 It inhibits the growth of Caco-2 cells when used at concentrations ranging from 10 to 50 µM.² 8(E),10(E),12(Z)-Octadecatrienoic acid (10 µM) induces formation of thiobarbituric acid reactive substances (TBARS) and apoptosis in DLD-1 colorectal adenocarcinoma cells.³ It also inhibits prostaglandin biosynthesis in sheep vesicular gland microsomes (IC₅₀ = 31 µM).⁴

1.Crombie, L., and Holloway, S.J.The biosynthesis of calendic acid, octadeca-(8E,10E, 12Z)-trienoic, acid, by developing marigold seeds: origins of (E,E,Z) and (Z,E,Z) conjugated triene acids in higher plantsJ. Chem. Soc. Perk. T. 12425-2434(1985) 2.Yasui, Y., Hosokawa, M., Kohno, H., et al.Growth inhibition and apoptosis induction by all-trans-conjugated linolenic acids on human colon cancer cellsAnticancer Res.26(3A)1855-1860(2006) 3.Shinohara, N., Ito, J., Tsuduki, T., et al.Jacaric acid, a linolenic acid isomer with a conjugated triene system, reduces stearoyl-CoA desaturase expression in liver of miceJ. Oleo Sci.61(8)433-441(2012) 4.Nugteren, D.H., and Christ-Hazelhof, E.Naturally occurring conjugated octadecatrienoic acids are strong inhibitors of prostaglandin biosynthesisProstaglandins33(3)403-417(1987)