Oleoylethanolamide
Encyclopedia
Oleoylethanolamine is an endogenous
peroxisome proliferator-activated receptor alpha
(PPAR-α) agonist
. It is a naturally occurring ethanolamide
lipid that regulates feeding and body weight in vertebrates ranging from mice to pythons.
OEA is the monounsaturated analogue
of the endocannabinoid anandamide
, but unlike anandamide it acts independently of the cannabinoid pathway, regulating PPAR-α activity to stimulate lipolysis
.
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. (illustration). This produces an N-acylphosphatidylethanolamine, which is then split (hydrolyzed) by N-acyl phosphatidylethanolamine-specific phospholipase D
(NAPE-PLD) into phosphatidic acid and OEA.
OEA has recently been demonstrated to bind to the novel cannabinoid receptor
GPR119
. OEA has been suggested to be the receptor's endogenous ligand.
Endogenous
Endogenous substances are those that originate from within an organism, tissue, or cell. Endogenous retroviruses are caused by ancient infections of germ cells in humans, mammals and other vertebrates...
peroxisome proliferator-activated receptor alpha
Peroxisome proliferator-activated receptor alpha
Peroxisome proliferator-activated receptor alpha , also known as NR1C1 , is a nuclear receptor protein that in humans is encoded by the PPARA gene.- Function :...
(PPAR-α) agonist
Agonist
An agonist is a chemical that binds to a receptor of a cell and triggers a response by that cell. Agonists often mimic the action of a naturally occurring substance...
. It is a naturally occurring ethanolamide
Ethanolamide
Ethanolamides are chemical compounds which are amides formed from carboxylic acids and ethanolamine. Some ethanolamides are naturally occurring, such as anandamide which plays a physiological role as a neurotransmitter....
lipid that regulates feeding and body weight in vertebrates ranging from mice to pythons.
OEA is the monounsaturated analogue
Analog (chemistry)
In chemistry, a structural analog , also known as chemical analog or simply analog, is a compound having a structure similar to that of another one, but differing from it in respect of a certain component. It can differ in one or more atoms, functional groups, or substructures, which are replaced...
of the endocannabinoid anandamide
Anandamide
Anandamide, also known as N-arachidonoylethanolamide or AEA, is an endogenous cannabinoid neurotransmitter. The name is taken from the Sanskrit word ananda, which means "bliss, delight", and amide. It is synthesized from N-arachidonoyl phosphatidylethanolamine by multiple pathways...
, but unlike anandamide it acts independently of the cannabinoid pathway, regulating PPAR-α activity to stimulate lipolysis
Lipolysis
Lipolysis is the breakdown of lipids and involves the hydrolysis of triglycerides into free fatty acids followed by further degradation into acetyl units by beta oxidation. The process produces Ketones, which are found in large quantities in ketosis, a metabolic state that occurs when the liver...
.
OEA is produced by the small intestine
Small intestine
The small intestine is the part of the gastrointestinal tract following the stomach and followed by the large intestine, and is where much of the digestion and absorption of food takes place. In invertebrates such as worms, the terms "gastrointestinal tract" and "large intestine" are often used to...
following feeding in two steps. First an N-acyl transferase (NAT) activity joins the free amino terminus of phosphatidylethanolamine
Phosphatidylethanolamine
Phosphatidylethanolamine is a lipid found in biological membranes. It is synthesized by the addition of CDP-ethanolamine to diglyceride, releasing CMP. S-adenosyl methionine can subsequently methylate the amine of phosphatidyl ethanolamine to yield phosphatidyl choline.Cephalin is a phospholipid,...
(PE) to the oleoyl group (one variety of acyl
Acyl
An acyl group is a functional group derived by the removal of one or more hydroxyl groups from an oxoacid, including inorganic acids.In organic chemistry, the acyl group is usually derived from a carboxylic acid . Therefore, it has the formula RCO-, where R represents an alkyl group that is...
group) derived from sn-1-oleoyl-phosphatidylcholine
Phosphatidylcholine
Phosphatidylcholines are a class of phospholipids that incorporate choline as a headgroup.They are a major component of biological membranes and can be easily obtained from a variety of readily available sources such as egg yolk or soy beans from which they are mechanically extracted or chemically...
, which contains the fatty acid
Fatty acid
In chemistry, especially biochemistry, a fatty acid is a carboxylic acid with a long unbranched aliphatic tail , which is either saturated or unsaturated. Most naturally occurring fatty acids have a chain of an even number of carbon atoms, from 4 to 28. Fatty acids are usually derived from...
oleic acid
Oleic acid
Oleic acid is a monounsaturated omega-9 fatty acid found in various animal and vegetable fats. It has the formula CH37CH=CH7COOH. It is an odorless, colourless oil, although commercial samples may be yellowish. The trans isomer of oleic acid is called elaidic acid...
at the sn-1 position. (illustration). This produces an N-acylphosphatidylethanolamine, which is then split (hydrolyzed) by N-acyl phosphatidylethanolamine-specific phospholipase D
N-acyl phosphatidylethanolamine-specific phospholipase D
N-acyl phosphatidylethanolamine phospholipase D is an enzyme that catalyzes the release of N-acylethanolamine from N-acyl-phosphatidylethanolamine . This is a major part of the process that converts ordinary lipids into chemical signals like anandamide and oleoylethanolamine...
(NAPE-PLD) into phosphatidic acid and OEA.
OEA has recently been demonstrated to bind to the novel cannabinoid receptor
Cannabinoid receptor
The cannabinoid receptors are a class of cell membrane receptors under the G protein-coupled receptor superfamily. As is typical of G protein-coupled receptors, the cannabinoid receptors contain seven transmembrane spanning domains...
GPR119
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 :...
. OEA has been suggested to be the receptor's endogenous ligand.