ISOLATION OF URINARY 3α, 16α-DIHYDROXYANDROST-5-EN-17-ONE IN ADRENAL CARCINOMA

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Abstract
3α,16α-Dihydroxyandrost-5-en-17-one was first isolated by YoungLai & Solomon (1967) as a major radioactive urinary metabolite after administration of [7-3H]16α-hydroxydehydroepiandrosterone (16α-hydroxy DHA) to two human subjects. We have isolated this metabolite after glucuronidase hydrolysis and chloroform extraction of a urine sample from a patient who had an inoperable asymptomatic adrenal carcinoma and who excreted about 5 mg of each of this compound and 16α-hydroxy DHA/24 h. The isolated steroid gave a purple colour with blue tetrazolium salt, characteristic of an α-ketol group. On a silica gel plate approximately 3 μg of this steroid could be visualized with picric acid reagent (Eberlein, 1965) specific for 5-ene-3-hydroxysteroids. The free and acetylated steroid could not be distinguished from authentic standards by gas—liquid chromatography (g.l.c.) using SE-30 and QF-1 columns. Mass spectra obtained by g.l.c. linked to mass spectrometry of the trimethylsilyl ether of authentic and isolated steroid confirmed its identity. The spectrum

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