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.

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.

(±)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.

(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.

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.

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

(±)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.