Investigation of the products of metabolism after incubation of deoxycorticosterone with rabbit-liver homogenate

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Abstract
In a large-scale experiment in which deoxycorti-costerone was incubated in air with a suspension of disintegrated rabbit liver with added nicotinamide, about 20% of the added steroid has been accounted for by isolated metabolites and unchanged substrate. The following substances were isolated and fully characterized: 20[alpha], 21-dihydroxypregn-4-en-3-one and its 20[beta]-epimer; 3[alpha],21-dihydroxy-5[alpha]-pregnan-20-one and its 3[beta]-epimer; 3[alpha],21-dihydroxy-5[beta]-pregnan-20-one; unchanged substrate. Evidence is presented for the formation of other metabolites: 21-hydroxy-5[alpha]-pregnane-3,20-dione and its 5[beta]-iso-mer; 6,21-dihydroxypregn-4-ene-3,20-dione; three closely related substances which were probably hydroxylated derivatives of dihydro and tetrahydro reduced deoxycorticosterone; 5[alpha]- or 5[beta]-pregnane-3[alpha],20 , 21-triols. In a "control" experiment 45% of the added steroid was recovered unchanged. The significance of these results is discussed.