Oleoylethanolamide (OEA) is an
endogenous
Endogenous substances and processes are those that originate from within a living system such as an organism, tissue, or cell.
In contrast, exogenous substances and processes are those that originate from outside of an organism.
For example, es ...
peroxisome proliferator-activated receptor alpha (
PPAR
In the field of molecular biology, the peroxisome proliferator-activated receptors (PPARs) are a group of nuclear receptor proteins that function as transcription factors regulating the expression of genes. PPARs play essential roles in the reg ...
-α)
agonist
An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the ago ...
. It is a naturally occurring
ethanolamide
Ethanolamides are chemical compounds which are amides formed from carboxylic acids and ethanolamine. Some ethanolamides are naturally occurring, such as anandamide, palmitoylethanolamide and prostamides, which play physiological roles as lipid neur ...
lipid that regulates feeding and body weight in
vertebrates ranging from mice to pythons.
OEA is a shorter, 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
The small intestine or small bowel is an organ in the gastrointestinal tract where most of the absorption of nutrients from food takes place. It lies between the stomach and large intestine, and receives bile and pancreatic juice through the p ...
following feeding in two steps. First an
''N''-acyl transferase (NAT) activity joins the free amino terminus of
phosphatidylethanolamine
Phosphatidylethanolamine (PE) is a class of phospholipids found in biological membranes. They are synthesized by the addition of cytidine diphosphate-ethanolamine to diglycerides, releasing cytidine monophosphate. ''S''-Adenosyl methionine can s ...
(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
/ref> This produces an ''N''-acylphosphatidylethanolamine, which is then split (hydrolyzed
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile.
Biological hydrolysis ...
) 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.Caenorhabditis elegans
''Caenorhabditis elegans'' () is a free-living transparent nematode about 1 mm in length that lives in temperate soil environments. It is the type species of its genus. The name is a blend of the Greek ''caeno-'' (recent), ''rhabditis'' (ro ...
'' through interactions with lysomal molecules.
References
External links
Science Magazine
BBC: Fatty foods 'offer memory boost'
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In pharmacology, biological activity or pharmacological activity describes the beneficial or adverse effects of a drug on living matter. When a drug is a complex chemical mixture, this activity is exerted by the substance's active ingredient or ...
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{{Cannabinoid receptor modulators
{{Lysophospholipid signaling modulators
{{PPAR modulators
{{Transient receptor potential channel modulators
Neurotransmitters
Fatty acid amides
Endocannabinoids