From Wikipedia, the free encyclopedia
Oleoylethanolamide
Names
Preferred IUPAC name
(9Z )-N -(2-Hydroxyethyl)octadec-9-enamide
Identifiers
ChEBI
ChemSpider
ECHA InfoCard
100.003.532
UNII
InChI=1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9-
N Key: BOWVQLFMWHZBEF-KTKRTIGZSA-N
N InChI=1/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9-
Key: BOWVQLFMWHZBEF-KTKRTIGZBW
CCCCCCCC\C=C/CCCCCCCC(=O)NCCO
Properties
C 20 H 39 N O 2
Molar mass
325.537 g·mol−1
Appearance
White solid
Melting point
59–60 °C (138–140 °F; 332–333 K)
Solubility in ethanol and DMSO
Soluble
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Oleoylethanolamide (OEA ) 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.
[1]
[2]
[3]
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 .
[4]
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.
[5] 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 .
[6]
OEA has been demonstrated to bind to the novel
cannabinoid receptor
GPR119 .
[7] OEA has been suggested to be the receptor's endogenous ligand.
[8]
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 " during the hibernation season together with the alteration of the endocannabinoid system required for the metabolic changes for hibernation.
[9]
OEA has been reported to lengthen the life span of the roundworm
Caenorhabditis elegans through interactions with lysomal molecules.
[10]
References
^ Gaetani S, Oveisi F, Piomelli D (2003).
"Modulation of meal pattern in the rat by the anorexic lipid mediator oleoylethanolamine" . Neuropsychopharmacology . 28 (7): 1311–6.
doi :
10.1038/sj.npp.1300166 .
PMID
12700681 .
^ Lo Verme J, Gaetani S, Fu J, Oveisi F, Burton K, Piomelli D (2005).
"Regulation of food intake by oleoylethanolamine" . Cell. Mol. Life Sci . 62 (6): 708–16.
doi :
10.1007/s00018-004-4494-0 .
PMID
15770421 .
S2CID
26838764 .
^ Giuseppe Astarita; Bryan C. Rourke; Johnnie B. Andersen; Jin Fu; Janet H. Kim; Albert F. Bennett; James W. Hicks & Daniele Piomelli (2005-12-22).
"Postprandial increase of oleoylethanolamine mobilization in small intestine of the Burmese python (Python molurus)" . Am J Physiol Regul Integr Comp Physiol . 290 (5): R1407–R1412.
doi :
10.1152/ajpregu.00664.2005 .
PMID
16373434 .
S2CID
11852711 .
^ Gaetani S, Kaye WH, Cuomo V, Piomelli D (September 2008).
"Role of endocannabinoids and their analogues in obesity and eating disorders" . Eat Weight Disord . 13 (3): e42–8.
PMID
19011363 .
^
illustration
^ Magotti P, Bauer I, Igarashi M, Babagoli M, Marotta R, Piomelli D, Garau G (Dec 2014).
"Structure of Human N-Acylphosphatidylethanolamine-Hydrolyzing Phospholipase D: Regulation of Fatty Acid Ethanolamide Biosynthesis by Bile Acids" . Structure . 23 (3): 598–604.
doi :
10.1016/j.str.2014.12.018 .
PMC
4351732 .
PMID
25684574 .
^ Overton HA, Babbs AJ, Doel SM, Fyfe MC, Gardner LS, Griffin G, Jackson HC, Procter MJ, Rasamison CM, Tang-Christensen M, Widdowson PS, Williams GM, Reynet C (2006).
"Deorphanization of a G protein-coupled receptor for oleoylethanolamide and its use in the discovery of small-molecule hypophagic agents" . Cell Metab . 3 (3): 167–175.
doi :
10.1016/j.cmet.2006.02.004 .
PMID
16517404 .
^ Brown AJ. (2007).
"Novel cannabinoid receptors" . Br J Pharmacol . 152 (5): 567–575.
doi :
10.1038/sj.bjp.0707481 .
PMC
2190013 .
PMID
17906678 .
^ Boyer C, Cussonneau L, Brun C, Deval C, Pais de Barros JP, Chanon S, Bernoud-Hubac N, Daira P, Evans AL, Arnemo JM, Swenson JE, Gauquelin-Koch G, Simon C, Blanc S, Combaret L, Bertile F, Lefai E (2020).
"Specific shifts in the endocannabinoid system in hibernating brown bears" . Frontiers in Zoology . 17 (1): 35.
doi :
10.1186/s12983-020-00380-y .
PMC
7681968 .
PMID
33292302 .
^ Folick A, Oakley HD, Yu Y, Armstrong EH, Kumari M, Sanor L, Moore DD, Ortlund EA, Zechner R, Wang MC (2015).
"Aging. Lysosomal signaling molecules regulate longevity in Caenorhabditis elegans" . Science . 347 (6217): 83–6.
doi :
10.1126/science.1258857 .
PMC
4425353 .
PMID
25554789 .
External links
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