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Hydrolysis, Extraction, and Fractionation of the Biliary Androgens in the Female Bovine¹

Department of Dairy Husbandry, University of Missouri, Columbia

ABSTRACT

A systematic procedure has been developed for the hydrolysis, extraction, and fractionation of the androgens in the bile of the female bovine. The procedure described includes the following methods: (a) hydrolysis of the bile; (b) extraction of the hydrolysate; (c) separation of the ether-soluble material into acidic and neutral fractions; (d) separation of the neutral fraction into the alcoholic and nonalcoholic fractions; (e) separation of the neutral alcoholic fraction into the ketonic and nonketonic fractions; and (f) digitonin separation of the neutral hydroxyketones into alpha and beta fractions.

The fractionation procedure identified a digitonin-precipitable and a digitonin-nonprecipitable hydroxyketonic androgen from the neutral, saponifiable material of bile from the female bovine. Both androgens gave the purple Zimmermann color characteristic of 17-ketosteroids. The digitonin-precipitable androgen is tentatively regarded as an androstane (ene) derivative containing a 3ß-hydroxyl group and a 17-keto group. Similarly, the digitonin-nonprecipitable androgen is tentatively regarded as an androstane (ene) derivative containing a 3-hydroxyl group and a 17-keto group.

The experimental evidence established that the biliary androgens in the female bovine are in a conjugated state, whereas the fecal androgens are in an unconjugated state.

The fact that the biliary androgens are hydroxyketones, as compared to the diketonic fecal androgens, suggests an enterohepatic recycling of the androgens in the bovine or alteration by the microorganisms of the gastro-intestinal tract.

¹ Contribution from the Missouri Agricultural Experiment Station, Journal Series No. 2278. Approved by the Director.

² Post-doctoral Research Fellow of the National Institute of Arthritis and Metabolic Diseases, National Institutes of Health, U. S. Public Health Service.

³ Aided in part by a grant from the U. S. Atomic Energy Commission [Contract No. AT(11-1-301].