Studies on Metabolism of 3-Deoxysteroids. VIII. Isolation and Characterization of Conjugated Metabolites of 3-Deoxyestrone

Isolation and characterization of the conjugated metabolites formed from 3-deoxyestrone have been carried out. The urine of rabbit with a large dosage of the steroid was collected and extracted with n-butanol. The extract was in turn chromatographed on Sephadex LH-20 to give 2-hydroxy-3-deoxyestrone glucuronide (Conjugate I). This procedure, however, failed to separate the remaining conjugates and therefore the glucuronides were transformed into the acetate-methyl esters. Upon column chromatography on alumina 17α-estradiol 17-glucuronide (Conjugate II), 6βA-hydroxy-3-deoxyestrone glucuronide (Conjugate III) and 16, 17-epiestriol 3, 17 (or 3, 16)-diglucuronide (Conjugate IV) were isolated as their derivatives and the structures were elucidated by dcgradative means (see Chart 1). The biochemical significance of the occurrence of these conjugates has been discussed.