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Eicosanoid


DATA No : XPR7086 INFORMANT : Keizo Waku

NAME : 2-Mono((all Z)-5', 8', 11', 14'-eicosatetraenoyl)glycerol

COMMON NAME: 2-Arachidonoylglycerol
SYMBOL: 2-AG
FORMULA: C23H38O4 MOL.WT (average) : 378.545


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BIOLOGICAL ACTIVITY
Effect of 2-arachidonoylglycerol on the specific binding of CP55940 to rat synaptosomal membrane. Ki= 3.1pmM (Ref. 7014)The increase of [Ca2+]in NG108-15 neuroblastoma x glioma hybrid cells by 2-arachidonoylglycerol is demonstrated as follows. (Ref. 7014)
[Table 7086]
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:soluble in the organic solvent(Ref. 0014)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA
2-arachidonoylglycerol was purified by TLC using petroleum ether:diethylether:acetic acid(20:80:1) as the solvent system (Rf, 0.23). (Ref. 7014)
SOURCE
This compound was distributed in rat brain (Ref. 7014) and canine gut (Ref. 7017).
CHEMICAL SYNTHESIS
2-Arachidonoyl-1,3-benzylidene-sn-glycerol was synthesized from 1,3-benzylidine-sn-glycerol and arachidonic anhydride. 2-arachidonoylglycerol was synthesized by treatment the above compound by boric acid and boric acid trimethyl ester at 85degC under vacuum for 3 min. (Ref. 7014)
METABOLISM
2-arachidonoylglycerol was easily hydrolyzed in the rat brain to arachidonic acid and glycerol.(Ref. 7013)
GENETIC INFORMATION

NOTE

REFERENCES
[0014]
AUTHOR:Whittle, B. J., and Moncada, S.
TITLE:Pharmacological interactions between prostacyclin and thromboxanes PubMed ID:6313114
JOURNAL:Br Med Bull.
VOL:39 PAGE : 232-238 (1983)
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[7013]
AUTHOR:T. Sugiura, S. Kondo, A. Sukagawa, S. Nakane, A. Shinoda, K. Itoh, A. Yamashita and K. Waku
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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[7014]
AUTHOR:T. Sugiura, T. Kodaka, S. Nakane, T. Miyashita, S. Kondo, Y. Suhara, H. Takayama, K. Waku, C. Seki, N. Baba et al.
TITLE:Evidencethat the Cannabinoid CBl 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 -2801 (1999)
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[7017]
AUTHOR:Mechoulam, R., Ben-Shabat, S., Hanus, L., Ligumsky, M., Kaminski, N. E., Schatz, A. R., Gopher, A., Almog, S., Martin, B. R., Compton, D. R., et al.
TITLE:Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors PubMed ID:7605349
JOURNAL:Biochem Pharmacol.
VOL:50 PAGE : 83-90 (1995)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.