Comparative studies of ‘bile salts’. 13. Bile acids of the leopard seal, Hydrurga leptonyx, and of two snakes of the genus Bitis

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Abstract
Bile salts of the leopard seal, Hydrurga leptonyx, and of the Californian sealion, Zalophus californi-anus, have been shown to contain the "B-phocaecholic acid" of Ham-marsten (1909, 1910), which it is now proposed to call "phocaecholic acid". Leopard-seal bile was shown to contain also allo(5a)cholic acid and the 3[alpha]:7[alpha]:12[alpha]:23-tetrahydroxycholanic acid identified by Bergstrom et al. (1959) as Hammarsten''s (1909, 1910) "[alpha]-phocaecholic acid". It is suggested that this name is inapplicable, as the substance is not a "cholic" (trihydroxycholanic) acid. Bile salts of the Gaboon viper, Bitis gabonica, and puff adder, Bitis arietans, contained a new acid, called "bitocholic acid", an unidentified isomer of cholic acid and the same 3[alpha]:7[alpha]:12[alpha]:23-tetrahydroxycholanic acid as was found in seal bile. Bitocholic acid was shown by its properties and by degradation to the known nordeoxycholic acid (3[alpha]:12[alpha]-dihydroxynor-cholanic acid) to be 3[alpha]: 12[alpha]:23-trihydroxycholanic acid. Phocaecholic acid was degraded to norchenodeoxycholic acid (3[alpha]:7[alpha]-dihydroxynor-cholanic acid), also prepared by Wieland-Barbier degradation from chenodeoxycholic acid. This work confirms the constitution suggested for phocaecholic acid by Windaus and van Schoor (1928). In none of the C-23-hydroxylated bile acids described could the optical configuration at C -23 be determined by measurements of [[alpha]]D. Although snakes of the genus Bitis contain C-23-hydroxylated bile acids, previously thought to be confined to the Pinnipedia, the types of bile acids present do not indicate a very close similarity between the bile salts of these snakes and those of Pinnepedia.