Fatty Acids

11R(12S)-EET is a cis-epoxytrienoic acid (EETs) derivative that is metabolized by cytoplasmic cyclooxygenases. Studies have shown that 14(R), 15(S)-, 11(S),12(R)-, and 8(S),9(R)-EETs are metabolized at significantly higher rates than their enantiomers. Enzyme-catalyzed hydration revealed that water addition was non-regioselective for the 11,12-EET enantiomers, whereas water addition occurred primarily at the C9 position for both enantiomers of 8,9-EET. These results suggest that the metabolic properties of 11R(12S)-EET and other EET enantiomers in enzyme-catalyzed processes are significantly affected by their stereostructures.

11S(12R)-EET is a dominant enantiomer of epoxytrienoic acid (EET) that is metabolized at a higher rate in rat organs. It shows enantiomeric-dependent reaction selectivity in hydration, especially in the case of 11,12-EET, where water addition is non-regioselective, while in 8,9-EET, water addition occurs mainly at the C9 position. In addition, 11S(12R)-EET generates diol products with specific stereochemistry through enzymatic hydration reactions, which are affected by the selective recognition of epoxidases, reaction conversion rates, and substrate binding parameters.

4-oxo Docosahexaenoic acid (4-oxo DHA) is a putative metabolite of Docosahexaenoic acid (HY-B2167) with antiproliferative and PPARγ agonist activity. It inhibits the growth of several triple negative breast cancer cell lines (MCF-10F, trMCF, bsMCF, MDA-MB-231, and BT549) at 50-100 μM, however it increased proliferation of MCF-7 cells. 4-oxo DHA binds covalently to PPARγ and activates gene transcription in luciferase reporter assays and in dendritic cells with EC₅₀ values of approximately 8-16 μM.

Arachidonamide is substrate of anandamide amidohydrolase.

9(E),12(Z)-Octadecadienoic acid is an ω-6 polyunsaturated fatty acid and an isomer of linoleic acid (HY-N0729) that contains a trans double bond at the C9 position. It has been found as a minor component of bovine milk fat and in partially hydrogenated vegetable oils. 9(E),12(Z)-Octadecadienoic acid levels increase in rabbit meat following supplementation with heated sunflower oil, α-tocopheryl acetate, and zinc.

cis-13-Octadecenoic acid is a monounsaturated fatty acid that has been found in bovine milk fat.

cis-9-Heptadecenoic acid is a monounsaturated fatty acid that is a major constituent of ruminant fat and milk. The levels of cis-9-heptadecenoic acid in milk are negatively correlated with methane production in cows fed a high-lipid diet.

cis-8-Octadecenoic acid is a monounsaturated fatty acid and an isomer of oleic acid (HY-N1446), trans-vaccenic acid (HY-113427), trans-petroselinic acid, and cis-petroselinic acid. It has been found in partially hydrogenated vegetable oil and milk fat.

Anandamide (AEA) is an endogenous cannabinoid that binds to both central cannabinoid (CB1) and peripheral cannabinoid (CB2) receptors. The biological actions of AEA are terminated by cellular uptake and hydrolysis of the amide bond by the enzyme fatty acid amide hydrolase. Arachidonoyl-N-methyl amide is an analog of anandamide that binds to the human central cannabinoid (CB1) receptor with a Ki of 60 nM. It inhibits rat glial gap junction cell-cell communication 100% at a concentration of 50 μM.

Very long chain polyunsaturated fatty acids (VLCPUFA) are present in retina, sperm, and brain. Though little is known of their biosynthesis or functional roles in these tissues, recent studies using the elongation of very long-chain FA-4 protein suggest a unique role for VLCPUFA in retinal development and macular degeneration. Dotriaconta-14,17,20,23,26,29-hexaenoic acid is a C32:6 VLCPUFA whose specific biological actions are largely unknown, but are thought to involve normal photoreceptor cell function in the retina.

13(R)-HODE is the opposite enantiomer of the 13(S)-HODE produced when linoleic acid is incubated with soybean lipoxygenase. The presence of 13(R)-HODE in the supernatants and membranes of cultured bovine endothelial cells has been attributed to COX metabolism.1 13(R)-HODE is a weak (IC₅₀=2.7 μM) inhibitor of U-46619-induced platelet aggregation.

8(Z)-Eicosenoic acid is a cis-unsaturated free fatty acid with a 20-carbon chain. It potentiates acetylcholine (ACh) receptor channel currents without depression and enhances PCKε phosphorylation of a substrate peptide in Xenopus oocytes. 8(Z)-Eicosenoic acid constitutes 6% of the fatty acid pool in seed oil isolated from B. collina.

9(R)-HODE is a monohydroxy fatty acid and metabolite of linoleic acid. It is formed from linoleic acid by COX and lipoxygenase (LO).9(R)-HODE induces chemotaxis, increases the levels of chemokine (C-C motif) receptor 9 (CCR9) and chemokine (C-X-C motif) receptor 4 (CXCR4), and inhibits IL-6 release in primary human monocytes. It inhibits CD3α- and CD28-induced proliferation of isolated human peripheral blood lymphocytes when used at a concentration of 25 μg/mL.

12,15-epoxy-13-methyl-12,14-Eicosadienoic acid is a furan fatty acid originally isolated from northern pike (E. lucius).1 Levels of 12,15-epoxy-13-methyl-12,14-eicosadienoic acid are increased in the liver of starving cod.

7-epi Jasmonic acid is the isomer of (±)-Jasmonic acid (HY-122464). (±)-Jasmonic acid is a plant growth regulator and a derivative of α-linolenic acid. (±)-Jasmonic acid decreases chlorophyll levels in green and etiolated barley leaf segments and inhibits elongation of rice seedlings.

11-Dodecenyl acetate is a insect sex pheromone, which is involved in attraction behavior of male moths.

(E,E)-9,11-Tetradecadienyl acetate is a female sex pheromone isolated from light-induced isomerization products in female coastal noctuid moths.

(E,Z)-4,7-Tridecadienyl acetate is a sex pheromone that can be isolated from potato tuber moths (Phthorimaea opercucella).

(E,Z)-3,13-Octadecadienyl acetate (E3,Z13-18:Ac) is an insect sex pheromone that elicits attraction in male lesser peachtree borers (Lesser Peachtree Borer), which can be isolated from female lesser peachtree borers.