Journal of Lipid Research, Vol 35, 1646-1651, Copyright © 1994 by Lipid Research, Inc.
Bile salts of the toad, Bufo marinus: characterization of a new unsaturated higher bile acid, 3 alpha,7 alpha,12 alpha,26-tetrahydroxy- 5 beta-cholest-23-en-27-oic acid
M Yoshii, M Une, K Kihira, T Kuramoto, T Akizawa, M Yoshioka, VP Butler Jr and T Hoshita
Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, Japan.
The bile salts present in gallbladder bile of the toad, Bufo marinus, were
found to consist of a mixture of bile alcohol sulfates and unconjugated
bile acids. The major bile alcohol was 5 beta-bufol; 5 alpha- and 5
beta-cholestane-3 alpha,7 alpha,12 alpha, 26-tetrols occurred as the minor
bile alcohols. Bile acids of Bufo marinus were cholic acid, allocholic
acid, 3 alpha,7 alpha,12 alpha-trihydroxy-5 alpha- and 5
beta-cholestan-26-oic acids, 3 alpha,7 alpha,12 alpha- trihydroxy-5 alpha-
and 5 beta-cholest-23-en-26-oic acids, 3 alpha,7 alpha,12 alpha,
26-tetrahydroxy-5 beta-cholestan-27-oic acid, and a C27 bile acid which has
not been previously described. By chromatographic behavior, mass spectral
data, and identification of the products of catalytic hydrogenation and
ozonolysis, the structure of the new higher bile acid was elucidated as 3
alpha,7 alpha,12 alpha,26-tetrahydroxy-5 beta-cholest-23-en-27-oic acid.
The bile salt pattern of Bufo marinus closely resembles that of Bufo
vulgaris formosus, except for the absence of 3 alpha,7 alpha,12
alpha-trihydroxy-5 beta-cholest-22-ene-24- carboxylic acid, the major bile
acid of the latter toad.
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