2-Arachidonoylglycerol

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Template:Chembox E number
2-Arachidonoylglycerol
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Names
IUPAC name
1,3-Dihydroxy-2-propanyl (5Z,8Z,11Z,14Z)-5,8,11,14-eicosatetraenoate
Other names
2-AG, 2-arachidonoylglycerol
Identifiers
3D model (JSmol)
ChemSpider
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Properties
C23H38O4
Molar mass 378.3 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

2-Arachidonoylglycerol (2-AG) is an endocannabinoid, an endogenous agonist of the CB1 receptor.[1][2] It is an ester formed from the omega-6 fatty acid arachidonic acid and glycerol.

Discovery

2-AG was a known chemical compound but its occurrence in mammals and its affinity for the cannabinoid receptors were first described in 1994-1995. A research group at Teikyo University reported the affinity of 2-AG for the cannabinoid receptors in 1994-1995,[3][4] but the isolation of 2-AG in the canine gut was first reported in 1995 by the research group of Raphael Mechoulam at the Hebrew University of Jerusalem, which additionally characterized its pharmacological properties in vivo.[5]

Occurrence

2-AG, unlike anandamide (another endocannabinoid), is present at relatively high levels in the central nervous system; it is the most abundant molecular species of monoacylglycerol found in mouse and rat brain (~5-10 nmol/g tissue).[2][6] Detection of 2-AG in brain tissue is complicated by the relative ease of its isomerization to 1-AG during standard lipid extraction conditions.

It has been found in maternal bovine and human milk.[7]

Pharmacology

Unlike anandamide, formation of 2-AG is calcium-dependent and is mediated by the activities of phospholipase C (PLC) and diacylglycerol lipase (DAGL).[2] 2-AG acts as a full agonist at the CB1 receptor.[8] At a concentration of 0.3 nM, 2-AG induces a rapid, transient increase in intracellular free calcium in NG108-15 neuroblastoma X glioma cells through a CB1 receptor-dependent mechanism.[2] 2-AG is hydrolyzed in vitro by monoacylglycerol lipase (MAGL), fatty acid amide hydrolase (FAAH), and the uncharacterized serine hydrolase enzymes ABHD6 and ABHD12.[9] The exact contribution of each of these enzymes to the termination of 2-AG signaling in vivo is unknown, though it is estimated that MAGL is responsible for ~85% of this activity.

See also

References

Footnotes

  1. ↑ Stella N, Schweitzer P, Piomelli D (1997). "A second endogenous cannabinoid that modulates long-term potentiation". Nature. 388 (6644): 773–8. doi:10.1038/42015. PMID 9285589. Unknown parameter |month= ignored (help)
  2. ↑ 2.0 2.1 2.2 2.3 Sugiura T, Kodaka T, Nakane S; et al. (1999). "Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compounds". The Journal of biological chemistry. 274 (5): 2794–801. doi:10.1074/jbc.274.5.2794. PMID 9915812. Unknown parameter |month= ignored (help)
  3. ↑ Sugiura T, Itoh K, Waku K, Hanahan DJ (1994) Proceedings of Japanese conference on the Biochemistry of Lipids, 36, 71-74 (in Japanese)
  4. ↑ Sugiura T, Kondo S, Sukagawa A; et al. (1995). "2-Arachidonoylglycerol: a possible endogenous cannabinoid receptor ligand in brain". Biochem. Biophys. Res. Commun. 215 (1): 89–97. doi:10.1006/bbrc.1995.2437. PMID 7575630. Retrieved 2009-01-27. Unknown parameter |month= ignored (help)
  5. ↑ Mechoulam R, Ben-Shabat S, Hanuš L; et al. (1995). "Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors". Biochemical pharmacology. 50 (1): 83–90. doi:10.1016/0006-2952(95)00109-D. PMID 7605349. Unknown parameter |month= ignored (help)
  6. ↑ Kondo S, Kondo H, Nakane S; et al. (1998). "2-Arachidonoylglycerol, an endogenous cannabinoid receptor agonist: identification as one of the major species of monoacylglycerols in various rat tissues, and evidence for its generation through Ca2+-dependent and -independent mechanisms". FEBS letters. 429 (2): 152–6. doi:10.1016/S0014-5793(98)00581-X. PMID 9650580. Unknown parameter |month= ignored (help)
  7. ↑ Fride E, Bregman T, Kirkham TC. (2005). "Endocannabinoids and food intake: newborn suckling and appetite regulation in adulthood" (PDF). Experimental Biology and Medicine. 230 (4): 225–234. doi:10.1371/journal.pbio.0020286. PMID 15792943. Unknown parameter |month= ignored (help)
  8. ↑ Savinainen JR, Järvinen T, Laine K, Laitinen JT (2001). "Despite substantial degradation, 2-arachidonoylglycerol is a potent full efficacy agonist mediating CB(1) receptor-dependent G-protein activation in rat cerebellar membranes". British journal of pharmacology. 134 (3): 664–72. doi:10.1038/sj.bjp.0704297. PMC 1572991. PMID 11588122. Unknown parameter |month= ignored (help)
  9. ↑ Blankman JL, Simon GM, Cravatt BF (2007). "A comprehensive profile of brain enzymes that hydrolyze the endocannabinoid 2-arachidonoylglycerol". Chemistry & biology. 14 (12): 1347–56. doi:10.1016/j.chembiol.2007.11.006. PMC 2692834. PMID 18096503. Unknown parameter |month= ignored (help)

General references

Dinh TP, Carpenter D, Leslie FM; et al. (2002). "Brain monoglyceride lipase participating in endocannabinoid inactivation". Proceedings of the National Academy of Sciences of the United States of America. 99 (16): 10819–24. doi:10.1073/pnas.152334899. PMC 125056. PMID 12136125. Unknown parameter |month= ignored (help)

de:2-Arachidonylglycerol it:Arachidonoilglicerolo fi:2-arakidonyyliglyseroli

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