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Comparative Studies of 'Bile Salts' 13 352 M. L. DEDMAN, T. H. FARMER AND C. J. 0. R. MORRIS 1961 Farmer, T. H. (1959). Biochem. J. 73, 321. Hill, R. L. & Smith, E. L. (1957). J. biol. (Chem. 228, Farmer, T. H. & Morris, C. J. 0. R. (1956). Nature, Lond., 577. 178, 1465. Morris, C. J. 0. R. (1951). Analy8t, 76, 470. Gross, D. (1956). Nature, Lond., 178, 29. Sayers, M. A., Sayers, G. & Woodbury, L. A. (1948). Hayes, E. E. & White, W. F. (1954). Recent Progr. Hormone Endocrinology, 42, 378. Res. 10, 265. Shepherd, R. G., Wilson, S. D., Howard, K. S., Bell, P. H., Heilmann, J., Barollier, J. & Watzke, E. (1957). Hoppe- Davies, D. S., Davis, S. B., Eigner, E. A. & Shakespeare, Seyl. Z. 30, 219. N. E. (1956). J. Amer. chem. Soc. 78, 5067. Biochem. J. (1961) 78, 352 Comparative Studies of 'Bile Salts' 13. BILE ACIDS OF THE LEOPARD SEAL, HYDRURGA LEPTONYX, AND OF TWO SNAKES OF THE GENUS BITIS* BY G. A. D. HASLEWOOD Guy'8 Ho8pital Medical School, London, S.E. 1 (Received 5 July 1960) In the preliminary survey with which this work the corresponding esters of leopard-seal and began the bile of ten species of snakes was ex- Californian-sealion bile acids. Chromatography on amined. The Boidae (three species) gave pytho- alumina of the ethyl esters of Gaboon-viper bile cholic lactone (3cc: 12a: 16ac-trihydroxycholanic acid acids easily separated the fraction responsible for lactone), six other species yielded cholic acid spot P from a 'spot Q-ethyl cholate' fraction, (3x:7a:12x-trihydroxycholanic acid), but from the described later. Gaboon viper, Biti8 gabonica, no known bile acid The ethyl ester giving spot P was hydrolysed was isolated (Haslewood & Wootton, 1950). An and the (non-crystalline) acid was investigated, investigation of the bile salts of this species by with the clue that it might be related to the bile paper chromatography (Haslewood & Sjovall, acids of Pinnepedia. The characteristic chemical 1954) confirmed their unusual nature. feature of these acids is the C-23 hydroxyl group, The work now reported included a detailed found by Windaus & van Schoor (1928) in 'fi- chemical examination of the bile salts of the phocaecholic acid' (30c:7a:23-trihydroxycholanic Gaboon viper and also those of the puff adder, acid, I). This acid was now isolated from leopard- Biti arietans, a closely related species. It was found that the bile salts of these snakes resembled CH3 23 those of Pinnepedia. For comparison, therefore, CH*CH2*CH(OH)*CO2H the leopard seal, Hydrurga leptonyx, was also in- vestigated. Some knowledge was, incidentally, obtained of the bile acids of the Californian sealion, Zalophus californianu. 13 71 RESULTS HO 'OH Paper chromatograms of the methyl or ethyl (I) esters of Gaboon-viper bile acids showed faint seal and Californian-sealion bile and conditions spots corresponding to those given by methyl or were found by which the -CH(OH) * CO2H grouping ethyl cholate, together with two additional intense could be quantitatively estimated by lead tetra- spots. In the solvent systems used, one of these acetate oxidation. Application of this method to intense spots (P) appeared just behind the methyl the 'spot P' of Gaboon-viper acid gave the same or ethyl cholate spot, and the other (Q) moved result, quantitatively, as had been obtained from only a little way from the start-line. Fortuitously ',B-phocaecholic acid' (I). However, the 'spot P' it was noticed that spots P and Q appeared at the acid did not crystallize with (I), and its specific same places on chromatograms as spots given by rotation was [o]D + 48 5°, in contrast with [a]D + 110 * Part 12: Haslewood & Ogan 959). for 'fl-phocaecholic acid'. These facts, and the Vol. 78 BILE ACIDS OF LEOPARD SEAL AND BITIS SNAKES 353 H COH H 0 1 23 H*-CHCH(OH)*CO,H 10~~~~~1 ,Lead tetra-acetate, acetylation H(C ' CrO,,hydrolysis 0I (II) Bitocholic acid (IILI) 5-0 A _ 40 es b3O30 0 20 S 0 1O B 20 40 60 80 100 1: Vol. of effluent (ml.) Fig. 1. Results of separating the complex (40 mg., m.p. about 2050) of ethyl esters from Gaboon-viper bile by partition chromatography on Celite (10 g.). Peak A is due to the ethyl ester of an isomer of cholic acid and peak B to ethyl 30c:7x:12as:23-tetrahydroxycholanate. Details are as given in the text. 4000 3000 Wavelength (A) Fig. 2. Infrared spectra in KBr of methyl cholate, methyl allo(5a)cholate and the methyl ester of the cholic acid isomer, from Gaboon-viper and puff-adder bile, whose ethyl ester gave peak A (Fig. 1). Spectra were recorded separately and are redrawn together for comparison. In each case the percentage transmittance at 2-5p was above 94. 23 Bioch. 1961, 78 354 G. A. D. HASLEWOOD 1961 finding that the methyl or ethyl esters of the (1909, 1910) has this constitution. The infrared 'spot P' acid ran on chromatograme at the same spectrum of the 'ac-acid' was almost but not quite rate as the corresponding esters of (I), suggested identical with that of the tetrahydroxy acid from that the new acid might be 3cx:12ac:23-trihydroxy- the Gaboon viper. Probably both the acid of cholanic acid (II), which would be expected to Bergstrom et al. (1959) and the Gaboon viper have the properties described. A larger sample of tetrahydroxy acid consist mainly of 3a,:7a:12a,:23- the acid giving spot P was therefore oxidized with tetrahydroxycholanic acid (IV), and elution peak lead tetra-acetate and the product was acetylated B (Fig. 1) is due to ethyl 3a:7x:12a:23-tetra- and further oxidized with chromic acid. From the hydroxycholanate. Some evidence was obtained saponified product there was obtained nordeoxy- that Gaboon-viper bile contained a little cholic cholic acid (III), identical with a sample made from acid. deoxycholic acid (3m: 12cc-dihydroxycholanic acid) An identical complex, m.p. about 2050, was by the method of Riegel, Moffett & McIntosh isolated from the ethyl esters of puff-adder bile (1944). These experiments show that a chief acids and was resolved in the same way and with constituent of Gaboon-viper bile acids is (II), which the same results as shown in Fig. 1. The bile of the it is proposed to call bitocholic acid. Methyl puff adder also yielded methyl bitocholate. bitocholate was readily obtained crystalline as its Leopard-seal and Californian-sealion bile yielded complex with diethyl ether. ',B-phocaecholic acid', and from the leopard-seal For confirmation of the formula (I) of Windaus ethyl esters there was obtained a complex, m.p. & van Schoor (1928), 'p-phocaecholic acid' was about 2050, having almost the same elementary degraded by the above-described methods (as analysis and infrared spectrum as the corresponding II -+ III) to give norchenodeoxycholic acid, also substance from the Gaboon viper. Resolution of prepared by Wieland-Barbier degradation of this complex on Celite gave a result very similar to chenodeoxycholic acid (3x:7a-dihydroxycholanic that shown in Fig. 1, and the ester corresponding to acid). elution peak B (Fig. 1) was also ethyl 3a:7a:12a:23- The 'spot Q-ethyl cholate' fraction mentioned tetrahydroxycholanate. The ester eluted at the above was crystallized from ethyl acetate to give position of peak A (Fig. 1) was, however, ethyl a substance melting constantly at about 2050 and allo(5a)cholate [ethyl 3a:70c: 12a-trihydroxy(5a)- giving an elementary analysis corresponding to a cholanate], previously prepared from cholic acid formula C26H4406 or C26H44O0. Paper chromato- (Anderson & Haslewood, 1960), and there was no graphy of this substance showed it to be a complex evidence for the presence of the ester, m.p. 2250, containing an ester with the mobility of ethyl described above. cholate and another giving spot Q. Separation on Attempts to detect the value and sign of the Celite gave th3 result shown in Fig. 1. contribution to [a]D of the -CH(OH)- group at Elution peak A (Fig. 1) was due to an isomer C-23 in ' -phocaecholic acid' by comparing the (m.p. 2250, [OC]D + 230) of ethyl cholate which gave specific rotations of this acid, its ethyl ester and its a positive Hammarsten (HCI) test. The correspond- acetylated ethyl ester with the rotations of the ing methyl ester had m.p. about 227° and the acid corresponding derivatives of chenodeoxycholic melted at about 2400. The infrared spectra of the acid failed, since, within the limits of experimental new methyl ester, of methyl allo(5ce)cholate and of error, the contribution to [o]D of the asymmetry at methyl cholate are shown in Fig. 2. C-23 could not be detected. Peak B (Fig. 1) was given by an -ester which crystallized as a hydrate, m.p. 1820, [o]D + 360, and on saponification gave an acid with the properties EXPERIMENTAL expected of 3c:7a: 12x:23-tetrahydroxycholanic acid General. Details were as described by Haslewood & (IV). Bergstrom, Krabisch & Lindeberg (1959) Wootton (1951), except that melting-point determinations claim that the 'ac-phocaecholic acid' ofHammarsten and esterification of bile acids were done as by Haslewool (1956). Paper chromatography was as described by H CH3 Haslewood (1956), and partition chromatography on O CH-CH2-CH(OH).CO2H23 Celite as by Haslewood & Ogan (1959). Infrared spectro- scopy in the range 2-5-15-0l was done with aPerkin- Elmer Infracord apparatus, by the KBr-disk method. A solution of the steroid (0561-0 mg.) in acetone (about 0-2 ml.) was dropped on to powdered KBr (320 mg., Merck's 'for infrared spectroscopy') in a mortar and the 13 5 71 solvent was evaporated at 50°.
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