9ALPHA,15S-DIHYDROXY-11-OXO-PROSTA-5Z,13E-DIEN-1-OIC ACID, 1-GLYCERYL ESTER

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

What are the applications of Application

Prostaglandin D2-1-glyceryl ester is the glycero-ester of PGD2 showing similarity to natural endocannabinoids

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).