Description
19(R)-
Hydroxylated prostaglandins occur in μg/ml concentrations in the semen of certain mammalian species, especially primates. In the case of humans, the compounds are primarily of the PGE series, and the hydroxyl stereochemistry is 15(S),19(R).
1 19(R)-
Hydroxylated prostaglandins are also found in the seminal plasma of marsupials, where F-
type compounds of the 1 and 2-
series predominate.
2 The 15(R)-
hydroxy epimer of these 19-
hydroxylated prostaglandins is the inverse or “unnatural” isomer at C-
15. The biological role of 19(R)-
hydroxylated prostaglandins is not well established. In the E-
series, 19(R)-
hydroxylation has been identified with EP
2 receptor subtype selectivity.
3
References
1. Cooper, I., and Kelly, R.W.
The measurement of E and 19-hydroxy E prostaglandins in human seminal plasma Prostaglandins 10(3),507-514(1975).
2. Marley, P.B., Rodger, J.C., White, I.G., et al.
19-Hydroxylated prostaglandins in the semen of the marsupial Trichosurus vulpecula (brush-tailed possum) Comp. Biochem. Physiol. B Biochem. Mol. Biol. 70(3),619-621(1981).
3. Woodward, D.F., Protzman, C.E., Krauss, A.H.P., et al.
Identification of 19(R)-OH prostaglandin E2 as a selective prostanoid EP2-receptor agonist Prostaglandins 46(4),371-383(1993).
