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N-Oleoylethanolamine

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N-Oleoylethanolamine Basic information
N-Oleoylethanolamine Chemical Properties
Safety Information
  • Hazard Codes Xi
  • Risk Statements 36/37/38
  • Safety Statements 26-36
  • WGK Germany 2
  • HazardClass IRRITANT
N-Oleoylethanolamine Usage And Synthesis
  • Biological FunctionsN-Oleoylethanolamine is also a predominant NAE species in the injured rat brain, and it has also been found to be the major NAE species in a human brain that has suffered a hemispheric stroke. As early as 1975, N-oleoylethanolamine was synthesized as an inhibitor of ceramidase, the enzyme that degrades ceramide. Ceramide is involved in the regulation of apoptosis and cell proliferation. Cannabinoid-induced apoptosis in glioma cells is mediated via formation of ceramide. On a tentative basis, it can be suggested that anandamide-induced apoptosis may be aggravated by the presence of N-oleoylethanolamine because this leads to increased formation of ceramide. There are numerous studies in which N-oleoylethanolamine has been shown to facilitate the apoptosis-inducing effect of different compounds mediated via increased ceramide levels. However, it has also been reported that N-oleoylethanolamine decreases ceramide levels in JB6 P+ cells by an unknown mechanism. Recently, N-oleoylethanolamine has been shown to have a CB1-receptor-independent anorexic effect by inhibiting some intestinal neuronal functions in the rat, and it also causes vasodilation in rat mesenteric arterial segments by an unknown receptor mechanism. Whether these recently discovered biological effects of N-oleoylethanolamine are of significance for neuroprotection is not known, but it indicates that nonendocannabinoid NAEs are also bioactive molecules with potential for cerebral actions.
  • DefinitionChEBI: An N-(long-chain-acyl)ethanolamine that is the ethanolamide of oleic acid. The monounsaturated analogue of the endocannabinoid anandamide
  • Biological ActivityLipid mediator and analog of anandamide (N-(2-Hydroxyethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide ) that is involved in peripheral regulation of feeding. Selective GPR55 agonist (EC 50 values are 0.44, >30 and >30 μ M at GPR55, CB 1 and CB 2 respectively) and PPAR α agonist (EC 50 = 120 nM). Induces satiety through activation of PPAR α and is also a ceramidase inhibitor. Also endogenous agonist at the GPR119 receptor.
  • Enzyme inhibitorThis endocannabinoid-related metabolite (FW = 325.54 g/mol; CAS 111- 58-0; Symbol: NOE and OEA; Soluble in Ethanol, Chloroform, or Methanol) is widely employed to inhibit acid and neutral ceramidases (IC50 ~ 500 μM) that cleave fatty acids from ceramide, producing sphingosine (SPH), which is then enzymatically phosphorylated to form the receptorsensed metabolite, sphingosine-1-phosphate, or S1P. NOE also inhibits the glucosylation of naturally occurring ceramides. In CHP-100 neuroepithelioma cells treated with N-hexanoylsphingosine (C6-Cer; 30 μM), NOE affected only marginally short-chain glucocerebroside accumulation, but markedly decreased accumulation of glucocerebrosides originating from glucosylation of a long-chain ceramide (Lc-Cer) produced upon C6-Cer treatment. NOE also inhibits fatty acid hydrolase (or FAAH), an integral membrane hydrolase possessing an unusual catalytic triad Ser-Ser-Lys. FAAH catalysis is based on the formation of a tetrahedral intermediate, which is a product of the nucleophilic attack of Ser241 on the carbonyl group of the substrate. In the presence of NOE, TNFa leads to a sustained accumulation of ceramide and induces DNA fragmentation in renal mesangial cells. Membrane & Receptor Interactions: NOE forms stable complexes with phospholipid vesicles, lowering diphenylhexatriene polarization ratios in dimyristoylphosphatidylcholine and dipalmitoylphosphatidylcholine uni- and multilamellar bilayer vesicles. Once incorporated into the lipid bilayer of phospholipid vesicles, N-oleoylethanolamine partitions preferentially into more fluid areas, producing a concentration-dependent decrease in their phase transitions. N-Oleoylethanolamine is also an effective inhibitor of mitochondrial swelling, but does not inhibit phospholipase A2 or ruthenium red-induced Ca2+ release. Moreover, among naturally occurring Nacylethanolamines, only NOE (at 10 μM) inhibits the accumulation of Narachidonoylethanolamine (or Anandamide, AEA), a putative endogenous ligand of the cannabinoid receptor, into cerebellar granule cells occurs by means of facilitated diffusion. Ethanolamides of palmitic acid and linolenic acid are inactive at 10 μM. Role as an Anorexic Lipid Mediator: NOleoylethanolamine is a structural analogue of the endogenous cannabinoid anandamide, but does not activate cannabinoid receptors. NOE biosynthesis in rat small intestine is increased by feeding and reduced by fasting. NOE decreases food intake in food-deprived rats via a mechanism that requires intact sensory fibers. Such results suggest that OEA may contribute to the peripheral regulation of feeding. NOE may contribute to regulation of satiety, providing a chemical scaffold for the design of novel appetitesuppressing medications. Despite its designation as endocannabinoidlike compound, NOE is unable to bind with significant affinity to either CB1 or CB2 cannabinoid receptors. SIRT6 Activation: N-Oleoylethanolamine binds to and activates Sirtuin 6 (EC50 = 3.1 μM), an NAD+-dependent histone deacetylase that selectively deacylates H3K9Ac and H3K56Ac, but acts preferentially on long-chain fatty acyl groups over acetyl groups in vitro. (See also Oleamide; N-Oleoyl-2-amino-1,3-propanediol; Oleoyl-Nhydroxylamide)
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