13(s)hpotre

13(S)-HpOTrE(γ) is a monohydroxy PUFA produced by the action of soybean lipoxygenase-1 (LO-1) on γ-linolenic acid. Further action of soybean LO-1 converts 13(S)-HpOTrE(γ) to all four isomers of 6,13-DiHOTrE. At concentrations greater than 100 μM, 13(S)-HpOTrE(γ) inhibits the activity of soybean LO-1.

13(S)-HpOTrE is a monohydroperoxy polyunsaturated fatty acid produced in soybeans by the action of soybean LO-2 on esterified α-linolenic acid.[1] Incubation of soybean seedling biomembranes with soybean LO-2 catalyzes the formation of both 9- and 13-HpOTrE in a molar ratio of 10:1.1 In plants, 13(S)-HpOTrE can be metabolized by the hydroperoxide lyase pathway producing aldehyde and oxoacid fragments, or by the hydroperoxide dehydratase pathway producing jasmonic acid.[2],[3],[4] Treatment of tomato leaves with 13-HpOTrE causes induction of proteinase inhibitors, simulating the normal response to wounding.5 This data suggests that in plants 13(S)-HpOTrE may participate in a lipid-based signalling system initiated by insect and pathogen attack.

Etherolenic acid is a divinyl ether oxylipin.1,2It is a metabolite of linolenic acid that is formed in plantsvia13-lipoxygenase-mediated formation of 13(S)-HpOTrE followed by conversion to the divinyl ether by divinyl ether synthase. 1.Grechkin, A.N., Fazliev, F.N., and Mukhtarova, L.S.The lipoxygenase pathway in garlic (Allium sativum L.) bulbs: Detection of the novel divinyl ether oxylipinsFEBS Letters371159-162(1995) 2.Hamberg, M.Biosynthesis of new divinyl ether oxylipins in Ranunculus plantsLipids37(4)427-433(2002)