α-Linolenicacid (ALA) is an essential fatty acid found in leafy green vegetables. ALA, as part of a low saturated fat diet, helps prevent cardiovascular disease. ALA decreases blood pressure, serum cholesterol levels, and platelet aggregation.
Ethyl dihomo-γ-linolenicacid ethyl ester (ethyl DGLA), an ω-6 fatty acid intermediate ester form, elevates prostaglandin E1(PGE1) and PGE2 secretion in rabbit renal papilla when administered dietarily at a dosage of 1 g kg per day for 25 days. Additionally, this dosage of ethyl DGLA increases triglyceride levels and enhances the proportion of 20:3ω6 and 20:4ω6 phospholipids in the renal medulla of rabbits. Ethyl DGLA formulations have been employed in managing eczema and inflammatory disorders.
1,2,3-Tri-γ-linolenoyl glycerol, a polyunsaturated triacylglycerol featuring γ-linolenoyl side chains at the C-1, C-2, and C-3 positions, occurs in multiple plant species such as blackcurrant, redcurrant, and borage.
Jacaric acid is a conjugated polyunsaturated fatty acid first isolated from seeds of Jacaranda plants. Structurally, it is an 18-carbon ω-6 triene isomer of γ-linolenicacid . Jacaric acid induces cell cycle arrest and apoptosis in a variety of cancer cell lines (GI50 = 1-5 μM). It increases the production of reactive oxygen species, and cytotoxicity is abolished by the antioxidant α-tocopherol, suggesting that apoptosis results from oxidative stress. Jacaric acid is metabolized in vivo to conjugated linoleic acid , which is also cytotoxic to cancer cells. Jacaric acid inhibits cyclooxygenase-1 in vitro (Ki = 1.7 μM) and, with long term feeding, decreases stearoyl-CoA desaturase expression and activity in mice.
A1-Phytoprostane-I is a cyclopentenone isoprostane produced by the action of reactive oxygen species on α-linolenicacid in plants. There are two A1-phytoprostanes, both having the single ketone group on the ring structure. This isoform results from cyclization between carbons 9 and 13 of linolenicacid, as opposed to carbons 3 and 7 in A1-phytoprostane-II. A1-Phytoprostanes induce the expression of glutathione-S-transferase, increase phytoalexin biosynthesis, and trigger the expression of several genes involved in primary and secondary metabolism in plants.
13(S)-HpOTrE is a monohydroperoxy polyunsaturated fatty acid produced in soybeans by the action of soybean LO-2 on esterified α-linolenicacid.[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.
13-epi-12-oxo Phytodienoic acid (13-epi-12-oxo PDA) is a lipoxygenase metabolite of α-linolenicacid in the leaves of green plants such as corn. ω-3 and ω-6 polyunsaturated fatty acids in plants are substrates for plant lipoxygenases. 12-oxo PDA is one of the best studied end metabolites of this enzymatic pathway. While the initial enzymatic product and major isomer of 12-oxo PDA contains side chains in the cis position, both being β to the ring, the upper side chain attached at C-13, can and frequently does, isomerize when 12-oxo PDA is extracted, isolated, or stored. 13-epi-12-oxo PDA is the product of this isomerization.
9(S)-HpOTrE is a monohydroperoxy polyunsaturated fatty acid produced by the action of 5-lipoxygenase (5-LO) on α-linolenicacid. It can be further metabolized to colnelenic acid by a divinyl ether synthase activity found in garlic and potato microsomal fractions. 9(S)-HpOTrE also serves as a substrate for further oxidation by both soybean and potato LOs, resulting in the formation of 9,16-dihydroperoxy acid. The suicide inactivation of LOs when 9(S)-HpOTrE is used as a substrate is thought to occur via formation of an unstable epoxide.