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Acylglycerol


DATA No : NAG5233 INFORMANT : Nobuo Ueta

NAME : Glycerol 2-(5,8,11,14-eicosatetraenoate)

COMMON NAME: 2-Arachidonoyl-sn-glycerol
SYMBOL:
FORMULA: C23H38O4 MOL.WT (average) : 378.545


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BIOLOGICAL ACTIVITY
Increases intracellular free Ca2+ concentrations in NG108-15 cells through a cannabinoid CB1 receptor-dependent mechanism.(Ref. 5118)
PHYSICAL AND CHEMICAL PROPERTIES
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CHROMATOGRAM DATA

SOURCE
A rat brain contains a significant amount of arachidonoylglycerol. (Ref. 5128)
CHEMICAL SYNTHESIS
1,3-Benzylidene-sn-glycerol is prepared from glycerol and benzaldehyde using sulfosalicylic acid as a catalyst. Arachidonoyl anhydride is prepared from arachidonic acid by treatment with dicyclohexylcarbodiimide. 2-Acyl-1,3-benzylideneglycerol is synthesized from 1,3-benzylidenglycerol and arachidonoyl anhydride using dimethylaminopyridine as a catalyst. This compound is purified by TLC, and then treated with boric acid and boric acid trimethyl ester, at 85degC under vacuum for 3min, to yield 2-arachidonoyl-sn-glycerol. The product is purified by TLC and boric acid-impregnated TLC. (Ref. 5118)
METABOLISM

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FATTY ACID COMPOSITION
REFERENCES
[5118]
AUTHOR:Sugiura,T., Kodaka,T., Nakane,S., Miyasita,T., Kondo,S., Suhara,Y., Takayama,H., and Waku,K.
TITLE:Evidence that the Cannabinoid CB1 Receptor is a 2-Arachidonoylglycerol Receptor: Structure-Activity Relationship of 2-Arachidonoylglycerol, Ether-linked Analogues and Related Compounds. PubMed ID:9915812
JOURNAL:J. Biol. Chem.
VOL:274 PAGE : 2794 -801 (1999)
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[5128]
AUTHOR:Sugiura,T., Kondo,S., Sukagawa,A., Nakane,S., Shinoda,A., Itoh,K., Yamashita,A., and Waku,K.
TITLE:2-Arachidonoylglycerol: a possible endogenous cannabinoid receptor ligand in brain.PubMed ID:7575630
JOURNAL:Biochem. Biophys. Res. Commun.
VOL:215 PAGE : 89 -97 (1995)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.