Oleoylethanolamide (OEA) is an endogenous

peroxisome proliferator-activated receptor alpha Peroxisome proliferator-activated receptor alpha (PPAR-α), also known as NR1C1 (nuclear receptor subfamily 1, group C, member 1), is a nuclear receptor protein functioning as a transcription factor that in humans is encoded by the ''PPARA'' gene ...

( PPAR-α) agonist. It is a naturally occurring ethanolamide lipid that regulates feeding and body weight in

vertebrates Vertebrates () comprise all animal taxa within the subphylum Vertebrata () (chordates with backbones), including all mammals, birds, reptiles, amphibians, and fish. Vertebrates represent the overwhelming majority of the phylum Chordata, with c ...

ranging from mice to pythons. OEA is a shorter, monounsaturated analogue of the

endocannabinoid Cannabinoids () are several structural classes of compounds found in the cannabis plant primarily and most animal organisms (although insects lack such receptors) or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tet ...

anandamide Anandamide (ANA), also known as ''N''-arachidonoylethanolamine (AEA), is a fatty acid neurotransmitter. Anandamide was the first endocannabinoid to be discovered: it participates in the body's endocannabinoid system by binding to cannabinoid r ...

, but unlike anandamide it acts independently of the cannabinoid pathway, regulating PPAR-α activity to stimulate

lipolysis Lipolysis is the metabolic pathway through which lipid triglycerides are hydrolyzed into a glycerol and free fatty acids. It is used to mobilize stored energy during fasting or exercise, and usually occurs in fat adipocytes. The most important ...

. 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 In chemistry, an acyl group is a moiety derived by the removal of one or more hydroxyl groups from an oxoacid, including inorganic acids. It contains a double-bonded oxygen atom and an alkyl group (). In organic chemistry, the acyl group (IUPAC ...

group) derived from ''sn''-1-oleoyl-phosphatidylcholine, which contains the

fatty acid In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, ...

oleic acid Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish. In chemical terms, oleic acid is classified as a monounsaturated omeg ...

at the sn-1 position.illustration
/ref> This produces an ''N''-acylphosphatidylethanolamine, which is then split ( hydrolyzed) by ''N''-acyl phosphatidylethanolamine-specific phospholipase D (NAPE-PLD) into

phosphatidic acid Phosphatidic acids are anionic phospholipids important to cell signaling and direct activation of lipid-gated ion channels. Hydrolysis of phosphatidic acid gives rise to one molecule each of glycerol and phosphoric acid and two molecules of fatty ac ...

and OEA. The biosynthesis of OEA and other bioactive lipid amides is modulated by bile acids. OEA has been demonstrated to bind to the novel

cannabinoid receptor Cannabinoid receptors, located throughout the body, are part of the endocannabinoid system a class of cell membrane receptors in the G protein-coupled receptor superfamily. As is typical of G protein-coupled receptors, the cannabinoid recep ...

GPR119 G protein-coupled receptor 119 also known as GPR119 is a G protein-coupled receptor that in humans is encoded by the ''GPR119'' gene. GPR119, along with GPR55 and GPR18, have been implicated as novel cannabinoid receptors. Pharmacology GPR119 ...

. OEA has been suggested to be the receptor's endogenous ligand. OEA has been hypothesized to play a key role in the inhibition of food seeking behavior and in the lipolysis of brown bears "

ursus arctos The brown bear (''Ursus arctos'') is a large bear species found across Eurasia and North America. In North America, the populations of brown bears are called grizzly bears, while the subspecies that inhabits the Kodiak Islands of Alaska is kno ...

" during the hibernation season together with the alteration of the endocannabinoid system required for the metabolic changes for hibernation. OEA has been reported to lengthen the life span of the roundworm '' Caenorhabditis elegans'' through interactions with lysomal molecules.

References

External links

Science Magazine

BBC: Fatty foods 'offer memory boost'
{{Navboxes , title = Biological activity , titlestyle = background:#ccccff , list1 = {{Cannabinoid receptor modulators {{Lysophospholipid signaling modulators {{PPAR modulators {{Transient receptor potential channel modulators Neurotransmitters Fatty acid amides Endocannabinoids