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Proc Natl Acad Sci U S A. 1973 Mar;70(3):899-903.

Detection and isolation of an endoperoxide intermediate in prostaglandin biosynthesis.

Abstract

An earlier proposed endoperoxide intermediate in the biosynthesis of prostaglandins was detected in short-time incubations of arachidonic acid with the microsomal fraction of homogenates of sheep vesicular glands. Conversion of the endoperoxide into prostaglandin E(2) was stimulated by reduced glutathione but suppressed by p-mercuribenzoate and N-ethylmaleimide. The methyl ester of an unknown compound was isolated by solvent extraction and thin-layer chromatography after short-time incubation of arachidonic acid with the microsomal fraction and p-mercuribenzoate. This derivative was identical to the methylester of the endoperoxide, as shown by its conversion into the methyl esters of 11-dehydroprostaglandin F(2alpha) and prostaglandin E(2) by spontaneous rearrangement and its conversion into the methyl ester of prostaglandin F(2alpha) by mild chemical reduction. The smooth muscle-stimulating activity of the endoperoxide ester on the isolated rabbit aortas trip was 4- to 8-times higher than that of the methyl ester of prostaglandin E(2).

PMID:
4514999
PMCID:
PMC433384
DOI:
10.1073/pnas.70.3.899
[Indexed for MEDLINE]
Free PMC Article

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