(Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid

Description

8-iso-13,14-dihydro-15-keto Prostaglandin F_2α (8-iso-13,14-dihydro-15-keto PGF_2α) is a metabolite of the isoprostane, 8-isoprostane (8-iso PGF_2α), in rabbits, monkeys and humans.¹ 8-iso PGF_2α is a PG-like product of non-specific lipid peroxidation.² In both humans and monkeys, exogenously infused 8-isoprostane is converted primarily to metabolites having 2 or 4 carbon atoms removed from the top side chain by β-oxidation.¹ A similar pattern is observed when tritiated 8-isoprostane is infused into rabbits.³ Early in the infusion (within 10 minutes) 8-iso-13,14-dihydro-15-keto PGF_2α was a significant component of the metabolite profile, which was comprised mostly of dinor 8-isoprostane metabolites. 8-iso-13,14-dihydro-15-keto PGF_2α weakly inhibits the U-46619 or collagen-induced aggregation of human platelets, although a number of the E-series isoprostanes are much more potent in this assay.⁴

References

1. Chiabrando, C., Valagussa, A., Rivalta, C., et al. Identification and measurement of endogenous β-oxidation metabolites of 8-epi-prostaglandin F_2α J. Biol. Chem. 274(3),1313-1319(1999).
2. Morrow, J.D., Hill, K.E., Burk, R.F., et al. A series of prostaglandin F2-like compounds are produced in vivo in humans by a non-cyclooxygenase, free radical-catalyzed mechanism Proc. Natl. Acad. Sci. USA 87(23),9383-9387(1990).
3. Basu, S. Metabolism of 8-iso-prostaglandin F_2α FEBS Lett. 428(112),32-36(1998).
4. Cranshaw, J.H., Evans, T.W., and Mitchell, J.A. Charcterization of the effects of isoprostanes on platelet aggregation in human whole blood Br. J. Pharmacol. 132,1699-1706(2001).