Conjugation of phenolic steroid ring Dα-ketols in human pregnancy urine

Abstract

Sequential solvolysis, and hydrolysis with β-glucuronidase followed by suitable separation and purification steps has provided some data on the conjugation of phenolic steroid ring Dα-ketols in late pregnancy urine as compared with the pattern for estriol. In 6 experiments i6α-hydroxyestrone was found to be, on the average, 80% in a form hydrolyzable by β-glucuronidase, 2% in a form split by solvolysis (presumably sulfate) and 18% in a form behaving on hydrolysis like a sulfogluco-siduronate. The corresponding values for 16-ketoestradiol-17β (including perhaps some 16β-hydroxyestrone) were 67%, 18% and 15% and for estriol, 94%, 2% and 5%. In 12 experiments the average “non-glucosiduronate” forms of 16α-hydroxyestrone, 16-ketoestradiol-17β and estriol amounted to 21%, 38% and 5% of each, respectively. The “non-glucosiduronate” conjugates of estriol were, by weight, generally greater in amount than those of the ring Da-ketols. Qualitative supporting evidence for the presence of these ring Dα-ketol conjugates was obtained by direct DEAE-Sephadex and Celite partition chromatography followed by suitable enzyme hydrolysis.