A SYSTEM OF ANALYSIS BY GAS CHROMATOGRAPHY OF 17α- AND 17β-PREGNANE-3,20-DIOLS AND THEIR IDENTIFICATION AS METABOLITES OF PROGESTERONE IN MAN, THE MONKEY, RABBIT AND GUINEA-PIG

Abstract

SUMMARY The relative elution properties of the eight 17β-pregnane-3,20-diols differing in configuration at C-3, 5, and 20 have been determined; a system of analysis is described by which any pregnanediol in this group can be characterized unambiguously. The required information can be obtained by chromatography of the compound, its acyl derivative and its oxidation product on the fluoroalkyl silicone polymer QF-1. The region of elution of the diacetates of the corresponding 17α-pregnanediol group on QF-1 has also been determined, this information was obtained by the synthesis of four of the eight 17α-pregnanediols. The only members of the 17β-pregnanediol diacetate group which are eluted within this region are 5β-pregnane-3α, 20β-diol diacetate and its 3β-epimer. The utility of this analytical approach is demonstrated by the identification of the pregnanediols from a variety of urinary sources. It is shown that the same three pregnanediols are excreted by man, the rabbit and the monkey as end products of progesterone catabolism. In the guinea-pig, the pregnanediol concentrations are very low, even after injection with progesterone, and only 5β-pregnane-3α, 20α-diol has been identified. The same system of gas chromatography has also been used to confirm some of the biochemical transformations previously reported by Cooke, Rogers & Thomas (1963).