15-deoxy-δ12,14-Prostaglandin J2-2-glycerol ester

15-deoxy-δ^12,14-Prostaglandin J₂-2-glycerol ester (15-deoxy-δ^12,14-PGJ₂-2-glycerol ester) is formed from PGD₂ by the elimination of two molecules of water. It binds selectively to PPARγ with an EC₅₀ value of 2 µM in a murine chimera system.^1,2 15-deoxy-δ^12,14-PGJ₂-2-glycerol ester is more potent than PGD₂, δ¹²-PGJ₂, and PGJ₂ in stimulating lipogenesis in C3H10T1/2 cells. The EC₅₀ value for induction of adipocyte differentiation in cultured fibroblasts is 7 µM.¹ PG glycerol esters are generated by the action of cyclooxygenase-2 on the endocannabinoid 2-arachidonyl glycerol.³ The biosynthesis of PGH, PGD, PGE, PGF, and TXA-2-glyceryl ester compounds have all been documented. While the stability and metabolism of these PG products has been investigated,⁴ little is known about their intrinsic biological activity.

1.Kliewer, S.A., Lenhard, J.M., Willson, T.M., et al.A prostaglandin J2 metabolite binds peroxisome proliferator-activated receptor γ and promotes adipocyte differentiationCell83(5)813-819(1995) 2.Forman, B.M., Tontonoz, P., Chen, J., et al.15-Deoxy-δ12,14-prostaglandin J2 is a ligand for the adipocyte determination factor PPARγCell83(5)803-812(1995) 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 ethanolamidesJ. 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 vivoThe Journal of Biological Chemisty276(40)36993-36998(2001)