FORMATION OF 6α, 1 1β-DIHYDROXY-Δ4-ANDROSTENE3,17-DIONE AND OTHER C19-COMPOUNDS BY A COW ADRENAL HOMOGENATE PREPARATION

Abstract

6[alpha]-Hydroxy and 6[beta]-hydroxy-[DELTA]4-androstene-3,17-dione were incubated with an adrenal residue preparation. From the incubation of the former the new steroid 6[alpha], 11[beta]-dihydroxyandrostenedione (XIII) was identified as the major transformation product. A number of more polar compounds (VIII, XIV, XV, XVI, XVII) were isolated and possible structures were discussed. The occurrence of the less polar compounds 6 -ketoandrosteredione (DC) and 5[alpha]-androstane-3,6,17-trione (XII) is ascribed to the presence in the preparation of steroid 6-hydroxy-dehydrogenase (s) and a steroid 6[alpha]-hydroxy-[DELTA]4-isomerase, respectively. It is suggested that the steroid 11[beta]-hydroxylating enzyme approaches the nucleus from the same side (front or [beta]-side) where eventually the hydroxyl substituent becomes attached. The preparation of [DELTA]4-androstene is described in an appendix.