URINARY EXCRETION OF C-20-REDUCTION PRODUCTS OF CORTICOSTERONE.

1. A 200 mg. portion of corticosterone was ingested by a healthy man and the urine collected. Part of the urine was treated with the gastric juice of Helix pomatia and extracted with ethyl acetate, and the extract fractionated with Girard T. Paper-chromatographic separation of the non-ketonic fraction in the Bush (1952) system B(5) revealed the presence of two unknown polar components. 2. The unknown compounds did not possess a reducing (blue tetrazolium) or a reducible (potassium borohydride) grouping. Both contained a terminal alpha-glycollic fragment as shown by the formation of formaldehyde, and of a non-volatile aldehyde on oxidation with sodium bismuthate. 3. Unknown compound (I) had paper-chromatographic mobilities identical with those of 5beta-pregnane-3alpha,11beta,20beta,21-tetraol. The oxidation product of compound (I) had a retention time (gas-liquid chromatography) on an SE30 column identical with that of 3alpha,11beta-dihydroxy-21-nor-5beta-pregnan-20-al. The retention times of various derivatives agreed with those produced in an identical manner on the standard, and accordingly compound (I) is formulated as 5beta-pregnane-3alpha,11beta,20xi,21-tetraol. 4. Unknown compound (II) had a higher R(F) than compound (I), and its oxidation product had a longer retention time than that of compound (I). From the group effects observed in paper and gas-liquid chromatography, compound (II) is tentatively formulated as 5alpha-pregnane-3alpha,11beta,20xi,21-tetraol. The 5alpha/5beta ratio found was about 2.0.