Epoxy Fatty Acids

(±)8(9)-EET is one of the main metabolites produced by the metabolism of arachidonic acid (HY-109590) through the cytochrome P450 epoxide pathway. (±)8(9)-EET is an effective substrate for COX-1 and COX-2. (±)8(9)-EET activates PPARα in HEK293 cells and inhibits the activity of NF-κB induced by IL-1β in a PPARα-dependent and -independent manner. The (8S,9R)-isomer of (±)8(9)-EET ([(8S,9R)-EET]) causes vasoconstriction, thereby reducing renal plasma flow and glomerular filtration rate.

cis-Coronaric acid is the 9,10-cis epoxide of linoleic acid, generated by neutrophils during the oxidative burst. It has been recovered from the lungs of hyperoxic rats and from humans with acute respiratory distress syndrome. Mitochondrial dysfunction is the main feature of cis-Coronaric acid cytotoxicity, which may be due to the diol metabolites as well as the parent epoxide.

14R(15S)-EET (14R(15S)-EpETrE) is an oxylipin and a metabolite of Arachidonic acid (HY-109590).

8,9-Epoxyeicosatrienoic acid has an unique protective effect on glomeruli. 8,9-Epoxyeicosatrienoic acid blocks the increase in glomerular albumin permeability caused by circulating permeability factor (FSPF). 8,9-Epoxyeicosatrienoic acid can be used for the research of glomerular dysfunction.

8(S),9(R)-EET is an eicosanoid product of Arachidonic acid (AA; HY-109590) by cytochromes P450. 8(S),9(R)-EET dilates canine epicardial arterioles in a concentration-dependent manner with an EC₅₀ value of 121 nM.

FR901465 is a potent anti-cancer and anti-tumor agent. FR901465 can be used for cancer research.

5R(6S)-EET is the metabolite of Arachidonic acid (HY-109590). 5R(6S)-EET activates the synthesis of endogenous prostaglandin (PGE2), which inhibits the Na⁺ absorption, increases the intracellular Ca²⁺, and promotes the depolarization of transmembrane voltage. 5R(6S)-EET exhibits stereoselectivity with less effectness than 5S(6R)-EET (HY-168382A).

(±)11(12)-EpETE ((±)11,12-EEQ) is an EPA hydroxyl product. EPA is a major component of Omega-3 polyunsaturated fatty acids (PUFAs).

8(9)-EET is one of the main metabolites produced by the metabolism of arachidonic acid (HY-109590) through the cytochrome P450 epoxide pathway. 8(9)-EET is an effective substrate for COX-1 and COX-2. 8(9)-EET activates PPARα in HEK293 cells and inhibits the activity of NF-κB induced by IL-1β in a PPARα-dependent and -independent manner. The (8S,9R)-isomer of 8(9)-EET ([(8S,9R)-EET]) causes vasoconstriction, thereby reducing renal plasma flow and glomerular filtration rate.

(±)14(15)-EpEDE is a a polyunsaturated fatty acid and can be found in DCU (HY-W013989) -treated porcine coronary endothelial cells.

cis-12,13-Epoxy-9(Z)-octadecenoic acid is an ester product.

12(S),13(R)-Epoxy-9(Z)-octadecenoic acid is an ester product.

cis-6,7-Epoxy-octadecanoic acid is an ester product.

cis-14,15-Epoxy-11(Z)-eicosenoic acid is an ester product.

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.