Reduction of prostaglandin E (PGE) with sodium borohydride yielded 2 compounds 1 of which is identical with PGF isolated from the prostate of sheep and the other of which had different physical and biological properties but the same elementary composition. The former was designated PGF1 and the latter PGF2. Experimental data from mass spectrometry and gas-liquid chromatography analyses indicated that the PGE is an unsaturated dihydroxyketocarboxylic acid and that PGF1 and PGF2 are stereoisomeric unsaturated trihydroxycarboxylic acids. PGE contains 1 carboxyl 1 carbonyl (cyclopentanone) 2 hydroxyls 1 double bond (trans) and 1 ring whereas the PGFs contain 1 carboxyl 3 hydroxyls 1 double bond (trans) and 1 ring. (PGE gives a positive spot on test paper with nitrophenylhydrazine for the presence of a carbonyl whereas the 2 PGFs gave negative tests.)
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Bergström et al. (1962) studied this question.
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