The isolation of 16β-hydroxyoestrone and 16-oxo-oestradiol-17β from the urine of pregnant women

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Abstract
A ketonic neutral-phenolic fraction obtained from enzymically hydrolyzed late-pregnancy urine was subjected to partition chromatography and then paper chromatography. By means of the Folin-Ciocalteu reagent spots corresponding in their mobilities to those of 16 [alpha]-hydroxyestrone, 16-oxoestradiol-17 [beta] and 16 [beta]-hydroxyestrone were detected. By using similar methods on a large scale 3 semicrystalline concentrates believed to contain the three a -ketolic estrogen derivatives respectively were prepared from 200 1 of late-pregnancy urine. Acetylation of these concentrates yielded 3 crystalline acetates which were identified as those of 16 a-hydroxyestrone, 16-oxoestradiol-17 [beta] and 16 [beta]-hydroxyestrone by melting points, mixed melting points and infrared spectrometry. This demonstration of the concurrence of 16 [beta]-hydroxyestrone in urine is compatible with the previously expressed view (Marrian, G. F., Watson, E.J.D. and Panattoni, M. (1957). Biochem. J. 65, 12); (Marrian, G. F., Loke, K. H., Watson, E.J.D. and Panattoni, M. (1957). Biochem. J. 66, 60), that this compound is the intermediate in the metabolic conversion of estrone into 16-epiestriol. Since the isolation procedure employed was unlikely to have caused artifactual formation of 16-oxoestradiol-17 [beta] by rearrangement of 16 [alpha]-hydroxyestrone or 16 [alpha]-hydroxyestrone, this work supports the view of Levitz, M., Spitzer, J. R. and Twombly, G. H. (1958). J. Biol. Chem. 231, 787. that 16-oxoestradiol-17 [beta] is a naturally occurring estrogen metabolite.