올레아마이드엠이에이

올레아마이드엠이에이 속성

올레아마이드엠이에이 C화학적 특성, 용도, 생산

개요

Oleoyl ethanolamide (OEA) is an analog of the endocannabinoid AEA found in brain tissue and in chocolate. It is one of the long chain fatty acid ethanolamides that accumulates rapidly in infarcted tissue, but its biosynthesis is reduced in the intestine of rats following food deprivation. OEA is an endogenous, potent agonist for PPARα, exhibiting an EC₅₀ value of 120 nM in a transactivation assay. Systemic administration of OEA suppresses food intake and reduces weight gain in rats (10 mg/kg intraperitoneally) and PPARα wild-type mice, but not in PPARα knockout mice. These data indicate that OEA regulates food intake by a PPARα-mediated mechanism.

용도

N-Oleoyl Ethanolamide is an agonist of peroxisome proliferator-activated receptor-α (PPAR-α). N-Oleoyl Ethanolamide generates an intestinal signal that stimulates central dopamine activity establishing a link between caloric-homeostatic and hedonic-homeostatic controllers. Oleoyl Ethanolamide has been implicated as the molecular mechanism associated with gastric bypass success. N-Oleoyl Ethanolamide is a selective GPR55 agonist.

정의

ChEBI: Oleoyl ethanolamide is an N-(long-chain-acyl)ethanolamine that is the ethanolamide of oleic acid. The monounsaturated analogue of the endocannabinoid anandamide. It has a role as a PPARalpha agonist, an EC 3.5.1.23 (ceramidase) inhibitor and a geroprotector. It is a N-(long-chain-acyl)ethanolamine, an endocannabinoid and a N-acylethanolamine 18:1. It is functionally related to an oleic acid.

주요 응용

N-Oleoyl Ethanolamide has been used to study its effects on glucagon-like peptide (GLP)-1RA-mediated anorectic signaling and weight loss.

Biosynthesis

Oleoylethanolamide (OEA) is produced by the small intestine following feeding in two steps. First an N-acyl transferase (NAT) activity joins the free amino terminus of phosphatidylethanolamine (PE) to the oleoyl group (one variety of acyl group) derived from sn-1-oleoyl-phosphatidylcholine, which contains the fatty acid oleic acid at the sn-1 position. This produces an N-acylphosphatidylethanolamine, which is then split (hydrolyzed) by N-acyl phosphatidylethanolamine-specific phospholipase D (NAPE-PLD) into phosphatidic acid and OEA. The biosynthesis of OEA and other bioactive lipid amides is modulated by bile acids.

Biological Functions

N-Oleoyl Ethanolamide 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-Oleoyl Ethanolamide 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-Oleoyl Ethanolamide because this leads to increased formation of ceramide. There are numerous studies in which N-Oleoyl Ethanolamide 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-Oleoyl Ethanolamide decreases ceramide levels in JB6 P+ cells by an unknown mechanism. Recently, N-Oleoyl Ethanolamide 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-Oleoyl Ethanolamide are of significance for neuroprotection is not known, but it indicates that nonendocannabinoid NAEs are also bioactive molecules with potential for cerebral actions.

일반 설명

Oleoylethanolamide (OEA) is an endogenous fatty acid ethanolamine. Small intestine cells, adipose tissues, neurons and astrocytes produces OEA.

생물학적 활성

Lipid 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.

Biochem/physiol Actions

Oleoylethanolamide (OEA) is a lipid mediator, which helps to control various biological functions, like food intake. It modulates the gene expression in the small intestine. OEA has the ability to initiate several receptors, such as cannabinoid receptor type 1 (CB1), peroxisome proliferator-activated receptors (PPARs) and G protein-coupled receptor 119 (GPR119).

효소 저해제

This endocannabinoid-related metabolite (N-Oleoyl Ethanolamide; 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.
N-Oleoyl Ethanolamide 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.

올레아마이드엠이에이 준비 용품 및 원자재

원자재

준비 용품

올레아마이드엠이에이 공급 업체

공급자	전화	이메일	국가	제품 수	이점
PNP Biotech Co. Ltd	+8618516098983	sales@pnpbiotech.com	China	1001	58
GIHI CHEMICALS CO.,LIMITED	+8618058761490	info@gihichemicals.com	China	49999	58
Hebei Yanxi Chemical Co., Ltd.	+8617531190177	peter@yan-xi.com	China	5993	58
Shandong Juchuang Chemical Co., LTD	+86-18885615001 +86-18885615001	admin@juchuangchem.com	China	387	58
airuikechemical co., ltd.	+undefined86-15315557071	sales02@airuikechemical.com	China	994	58
CONTIDE BIOTECH CO.,LTD	+85253358525	xena@healthtide-api.com	China	500	58
BINBO BIOLOGICAL CO.,LTD	+8618629063126	info@binbobiological.com	China	282	58
Henan Tianfu Chemical Co.,Ltd.	+86-0371-55170693 +86-19937530512	info@tianfuchem.com	China	21691	55
Hangzhou FandaChem Co.,Ltd.	008657128800458; +8615858145714	fandachem@gmail.com	China	9348	55
Shanghai Zheyan Biotech Co., Ltd.	18017610038	zheyansh@163.com	CHINA	3620	58

올레아마이드엠이에이 관련 검색: