2-
Arachidonoyl glycerol (2-
AG; ) has been isolated from porcine brain, and has been characterized as the natural endocannabinoid ligand for the CB
1 receptor.
1,2 Incubation of 2-
AG with COX-2 and specific prostaglandin H
2 (PGH
2; ) 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, PGD
2-
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
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.
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).
