a-Linolenic Acid

α-Linolenic acid (Alpha-Linolenic Acid) 是一种必需脂肪酸，人体无法合成，从种子油中分离得到。α-Linolenic acid 具有提高记忆力、抑制血栓性疾病、降低血脂等作用。

α-Linolenic acid (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.

gamma-Linolenic acid (gamolenic acid) 是一种 omega-6 (n-6)，18 碳 (18C-) 多不饱和脂肪酸 (PUFA)，可以从人乳和植物种子油中提取。

Dihomo-γ-linolenic acid (DGLA) 是一种广泛存在于植物体内的脂肪酸，具有抗肿瘤和抗增殖作用，抑制异种移植肿瘤细胞生长，可用于研究类风湿性关节炎、动脉粥样硬化和特应性皮炎等与炎症相关的疾病。

18:0-18:2 PG (1-Stearoyl-2-linoleoyl-sn-glycero-3-phospho-(1'-rac-glycerol)) sodium 是一种甘油磷脂，包含Stearic acid、Linolenic acid 以及 phospho-rac-(1-glycerol)。

γ-Linolenic Acid methyl ester (Methyl gamma-linolenate) 是一种弱白三烯 B4 (LTB4) 受体拮抗剂。

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-linolenic acid . 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-linolenic acid 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 linolenic acid, 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.

9(E),11(E),13(E)-Octadecatrienoic acid (β-ESA) is a conjugated polyunsaturated fatty acid that is found in plant seed oils and in mixtures of conjugated linolenic acids synthesized by the alkaline isomerization of linolenic acid. It reduces growth of Caco-2 colon cancer cells in a dose-dependent and time-dependent manner. In vitro, β-ESA induces DNA fragmentation and upregulation of pro-apoptotic Bax mRNA. β-ESA decreases protein expression of the apoptosis suppression factor Bcl-2 and induces apoptosis in T24 bladder cancer cells via production of reactive oxygen species. It also inhibits bacterial fatty acid dioxygenase with a Ki value of 49 nM in vitro.

8(E),10(E),12(Z)-Octadecatrienoic acid is a conjugated polyunsaturated fatty acid (PUFA) that has been found inC. officinalisseed oil and has anticancer activity.1,2,3It inhibits the growth of Caco-2 cells when used at concentrations ranging from 10 to 50 μM.28(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.3It 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)

8(S)-HETrE is a monohydroxy polyunsaturated fatty acid produced by rabbit neutrophil lipoxygenase when dihomo-γ-linolenic acid is used as a substrate. Although the biological activities of 8(S)-HETrE have not been well characterized, it is expected to behave similarly to 8(S)-HETE .

8,11,14-Eicosatrienoic acid, also known as dihomo-γ-linolenic acid , is a polyunsaturated fatty acid (PUFA) produced from γ-linolenic acid by the action of fatty acid elongases. It can be metabolized by the cyclooxygenase pathway to produce 1-series prostaglandins (PGs) (e.g., PGE1). (±)14(15)-EpEDE is an EpEDE acid formed from 8,11,14-eicosatrienoic acid. This monoepoxide can be generated from the PUFA, in vitro, by the action of a strong oxidizing agent. Alternatively, this compound may be produced, in vivo, by epoxidation of the PUFA by cytochrome P450 epoxygenases. The biological properties of this compound are poorly understood.

Prostaglandin D1 (PGD1) is the theoretical D-series metabolite of dihomo-γ-linolenic acid (DGLA), but to date it has not been isolated as a natural product. It is an inhibitor of ADP-induced platelet aggregation in humans with an IC50 value of 320 ng/ml, about 1/10 as potent as PGD2. 13,14-dihydro-15-keto Prostaglandin D1 (13,14-dihydro-15-keto PGD1) is the theoretical metabolite of PGD1 via the 15-hydroxy PG dehydrogenase metabolic pathway. No biological studies for this compound have been reported.

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.

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-epi-12-oxo Phytodienoic acid (13-epi-12-oxo PDA) is a lipoxygenase metabolite of α-linolenic acid 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.

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)

9(S)-HOTrE是一种植物代谢物和十八碳三烯酸，由 5-脂氧合酶（5-LO）作用于 α-亚麻酸产生，可用于研究代谢。

9(S)-HpOTrE is a monohydroperoxy polyunsaturated fatty acid produced by the action of 5-lipoxygenase (5-LO) on α-linolenic acid. 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.

Prostaglandin F1α (PGF1α) is the putative metabolite of dihomo-γ-linolenic acid (DGLA) via the cyclooxygenase (COX) pathway. Both PGF1α and PGF2α have been shown to act as priming pheromones for male Atlantic salmon with a threshold concentration of 10-11 M. [1] PGF1α binds to the ovine corpus luteum FP receptor at only 8% of the relative potency of PGF2α. [2] It is only half as active as PGF2α in inducing human respiratory smooth muscle contractions in vitro. [3]

Cholesteryl homo-γ-linolenate is a cholesterol ester. It accumulates in the adrenal gland of rabbits fed a diet high in linolenic acid. Levels of cholesteryl homo-γ-linolenate are decreased and positively correlate with cognitive decline in HIV-infected humans.

γ-Linolenic acid ethyl ester (Ethyl γ-linolenate) 是一种白三烯 B 受体 4(LTB4)的拮抗剂，具有潜在的抗炎作用。

Punicic acid（Trichosanic acid，石榴酸）是一种天然的共轭亚麻酸和多不饱和脂肪酸，通过激活PPARα、PPARβ、PPARγ和抑制NF-κB抗肥胖和抗糖尿病；通过抑制环氧化酶（COX）和脂氧合酶（LOX）抗炎；通过调节PPARγ和PPARδ改善神经炎症；预防骨质疏松。

13(S)-HOTrE, the 15-lipoxygenase (15-LO) metabolite of linolenic acid, is present in cell membranes and as a cholesteryl ester in atherosclerotic lesions, as well as in the biomembranes of soybeans subjected to 15-LO.