| Identification | Back Directory | [Name]
9ALPHA,15S-DIHYDROXY-11-OXO-PROSTA-5Z,13E-DIEN-1-OIC ACID, 1-GLYCERYL ESTER | [CAS]
309260-52-4 | [Synonyms]
PGD2-1-GLYCERYL ESTER
PROSTAGLANDIN D2-1-GLYCERYL ESTER
9ALPHA,15S-DIHYDROXY-11-OXO-PROSTA-5Z,13E-DIEN-1-OIC ACID, 1-GLYCERYL ESTER
Prosta-5,13-dien-1-oic acid, 9,15-dihydroxy-11-oxo-, 2-hydroxy-1-(hydroxymethyl)ethyl ester, (5Z,9α,13E,15S)- | [Molecular Formula]
C23H38O7 | [MDL Number]
MFCD05863733 | [MOL File]
309260-52-4.mol | [Molecular Weight]
426.54 |
| Hazard Information | Back Directory | [Description]
2-Arachidonoyl glycerol (2-AG; ) has been isolated from porcine brain, and has been characterized as the natural endocannabinoid ligand for the CB1 receptor.1,2 Incubation of 2-AG with COX-2 and specific prostaglandin H2 (PGH2; ) isomerases in cell cultures and isolated enzyme preparations results in prostaglandin glycerol ester formation.3 The biosynthesis of PGH, PGD, PGE, PGF, and TXA-2-glyceryl ester compounds have all been documented. In RAW 264.7 cells, PGD2-2-glyceryl ester is the main COX metabolite.3 The 2-glyceryl ester moiety equilibrates rapidly (within minutes) with the more stable 1-glyceryl ester, producing a 10:90 mixture of the 1- and 2-glyceryl esters in typical aqueous media. While the stability and metabolism of these PG products have been investigated, little is known about their intrinsic biological activity.4 | [Definition]
ChEBI: Prostaglandin D2 1-glyceryl ester is a 1-monoglyceride resulting from the condensation of the carboxy group of prostaglandin D2 with the 1-hydroxy group of glycerol. It has a role as a human metabolite. It is a prostaglandins D, an alicyclic ketone, a 1-monoglyceride and a secondary allylic alcohol. It is functionally related to a prostaglandin D2. | [References]
1. Sugiura, T., Kodaka, T., Kondo, S., et al. 2-Arachidonoylglycerol, a putative endogenous cannabinoid receptor ligand, induces rapid, transient elevation of intracellular free Ca2+ in neuroblastoma X glioma hybrid NG108-15 cells Biochem. Biophys. Res. Commun. 229,58-64(1996).
2. Sugiura, T., Kodaka, T., Kondo, S., et al. Is the cannabinoid CB1 receptor a 2-arachidonoylglycerol receptor? Structural requirements for triggering a Ca2+ transient in NG108-15 cells J. Biochem. 122(4),890-895(1997).
3. Kozak, K.R., Crews, B.C., Morrow, J.D., et al. Metabolism of the endocannabinoids, 2-arachidonylgycerol and anandamide, into prostaglandin, thromboxane, and prostacyclin glycerol esters and ethanolamides J. Biol. Chem. 277(47),44877-44885(2002).
4. Kozak, K.R., Crews, B.C., Ray, J.L., et al. Metabolism of prostaglandin glycerol esters and prostaglandin ethanolamides in vitro and in vivo J. Biol. Chem. 276(40),36993-36998(2001). |
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