Epoxy Fatty Acids

Cerulenin, a potent, natural inhibitor of fatty acid synthase (FASN), is an epoxide produced by the fungus Cephalosporium caeruleus. Cerulenin inhibits topoisomerase I catalytic activity and augments SN-38-induced apoptosis. Cerulenin has antifungal and antitumor activies.

Manumycin A is a polyketide antibiotic and an inhibitor of thioredoxin reductase 1 (TrxR-1). Manumycin A can inhibit the growth of breast cancer cells and exert its anti-tumor activity through LC3. Manumycin A can downregulate the release of pro-inflammatory cytokines in human monocytes stimulated by TNF α, and has potential anti-inflammatory activity. Manumycin A can inhibit the Ras/Raf/ERK1/2 signaling and hnRNP H1 in castration resistant prostate cancer cells to suppress exosome biogenesis and secretion.

cis-9,10-Epoxystearic acid (cis-9,10-Epoxyoctadecanoic acid) is an endogenous metabolite that can be found in plasma and urine.

(±)11(12)-EET is a NLRP3 inflammasome inhibitor. (±)11(12)-EET can be used for the research of anti-inflammatory, angiogenic and cardioprotective.

5,6-Epoxyeicosatrienoic acid (5,6-EET; (±)5,6-EpETrE) is a fully racemic version of the enantiomeric forms biosynthesized from arachidonic acid by cytochrome P450 enzymes. In solution, 5,6-Epoxyeicosatrienoic acid degrades into 5,6-DiHET and 5,6-δ-lactone, which can be converted to 5,6-DiHET and quantified by GC-MS. In neuroendocrine cells, such as the anterior pituitary and pancreatic islets, 5,6-Epoxyeicosatrienoic acid has been implicated in the mobilization of calcium and hormone secretion. 5,6-Epoxyeicosatrienoic acid is an inhibitor of T-type voltage-gated calcium channels (Cav3) that inhibits isoforms Cav3.1, Cav3.2 (IC₅₀=0.54 μM), and Cav3. and decreases nifedipine-resistant phenylephrine-induced vasoconstriction in isolated mouse mesenteric arteries via Cav3.2 blockade when used at a concentration of 3 μM. In addition, it is a substrate of COX-1 and COX-2.

14S(15R)-EET is an endogenous epoxytrienoic acid derivative that mainly exists in rat organs. By studying its metabolic process, it was found that its stereoselective hydration and formation of chiral diols were significantly affected by epoxidase. Different 14,15-EET enantiomers showed different regions and stereochemistry of hydration reactions, among which 14(R),15(S)-EET showed specific hydration for C15. These findings reveal the important role of epoxidase in the metabolism of endogenous EETs, and the differences in enzyme affinity and reaction rate for individual EET enantiomers may lead to their stereoselective metabolism.

12(R),13(S)-Epoxy-9(S)-hydroxy-10(E)-octadecenoic acid is a nucleoside metabolite.

(±)19(20)-EDP ethanolamide (19,20-DHEA epoxide) (compound 19) is an ω-3 endocannabinoid epoxide with cytokine modulation in neuroinflammation studies, antiangiogenic effects in vascular endothelial cells, and vasodilatory effects on coronary arteries.

(±)14,15-Epoxyeicosatrienoic acid ((±)14(15)-EET) is the Cytochrome P450 metabolite of arachidonic acid. While CYP3A4 may be involved in breast cancer cell growth, (±)14,15-Epoxyeicosatrienoic acid may promote mitosis and anchorage-dependent cloning through STAT3 affected by CYP3A4. (±)14,15-Epoxyeicosatrienoic acid exhibits STAT3-dependent cell growth promotion and may also participate in the autocrine/paracrine pathway that drives cell growth.

FR901464 is a potent spliceosome inhibitor with prominent anti-tumor and anti-cancer effects.

Eicosapentaenoic acid (EPA) is converted to epoxyeicosatetraenoic acids (EpETEs) by several cytochrome P450 isoforms. The major product of this epoxygenase pathway, (±)17(18)-EpETE, relaxes vascular and airway smooth muscle by activating large conductance Ca²⁺-activated K⁺ (BKCa) channels by directly interacting with BKα channel subunits. (±)8(9)-EpETE is an epoxygenase pathway product produced from EPA by CYP450 both in vitro and in vivo.

(17R,18S)-Epoxyeicosatetraenoic acid (17 (R),18 (S)-EETeTr) is a physiologically active fatty acid metabolite and also a vasodilator targeting BKα. (17R,18S)-Epoxyeicosatetraenoic acid activates the outward potassium current mediated by BK channels, and this effect is independent of the BKβ1 subunit, intracellular/extracellular calcium levels, and sarcoplasmic reticulum calcium release regulated by RyR3. (17R,18S)-Epoxyeicosatetraenoic acid is produced by the epoxidation of eicosapentaenoic acid mediated by CYP1A1 variants. (17R,18S)-Epoxyeicosatetraenoic acid is applicable to research related to arrhythmia.

trans-EKODE-(E)-Ib is a biologically active peroxidation product of linoleic acid.

Asukamycin, a manumycin-type metabolite, could be isolated from Streptomyces nodosus subsp. asukaensis. Asukamycin is an antibiotic and has antimicrobial activity. Asukamycin inhibits growth of various tumor cell lines.

(±)17(18)-EpETE-ethanolamide (17,18-EEQ-EA) (compound 17) is an ω-3 endocannabinoid epoxide with cytokine modulation in neuroinflammation studies, antiangiogenic effects in vascular endothelial cells, and vasodilatory effects on coronary arteries.

Coronaric acid (cis-9,10-Epoxy-cis-12-octadecenoic acid) is an ester product.

(5,6)-Epoxytetraene is a precursor of the trapping product in the biosynthesis of lipoxins in human leukocytes.

Eoxin A4 (14,15-Leukotriene A4) is an Arachidonic acid (HY-109590) metabolite. Eoxin A4 forms via the 15-lipoxygenase pathway.

9,10-Epoxy13-hydroxy-11-octadecenoic acid is a fatty acid.

15H-11,12-EETA is a nucleoside metabolite.