ent-Prostaglandin E2

Ent-Prostaglandin E2 is the enantiomer of enzymatically-derived prostaglandin E2 (PGE2). Both are optically pure compounds whereas PGE2 derived from the free radical-catalyzed peroxidation of arachidonate is a racemic mixture. Significant amounts of racemic PGE2 are created in vitro in settings of oxidative stress via isoprostane pathway intermediates. Inhibition of COX-2 with Aspirin reportedly reduces thromboxane A2 synthesis by 90% and PGI2 by > 80%, however, the same concentration decreases PGE2 by only 60%; this may be at least partially explained by free radical-catalyzed formation of stereoisomers of PGE2. Ent-Prostaglandin E2 could potentially be used as an analytical standard in the deconvolution of these extremely relevant, but complex biochemical issues.