Δ4-3-KETOPREGNENE-20α-OL AND Δ4-3-KETOPREGNENE-20β-OL, TWO NATURALLY OCCURRING METABOLITES OF PROGESTERONE. ISOLATION, IDENTIFICATION, BIOLOGIC ACTIVITY AND CONCENTRATION IN HUMAN TISSUES*

Abstract

Delta4-3-ketopregnene-20[alpha]-ol and delta4-3-ketopregnene-20[beta]-ol have been isolated from human ripe follicles, corpora lutea, placentae and fat tissue. Both compounds are metabolites of progesterone. Both compounds have progestational activity by Hooker-Forbes and Clauberg tests and are therefore to be regarded as gesta-gens. The relative concentrations of both compounds in the placenta in the second to the tenth month of pregnancy and in the ovary during the menstrual cycle and pregnancy have been quantitatively determined and compared to progesterone levels in these tissues. Neither progesterone nor the delta4-3-ketopregnene-20-ol fraction could be found in either uterine muscle or mucosa within the limits of the method used. A compound was found in placental blood which is probably identical with delta4-3-ketopregnene-20-ol.