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

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 alcoho...

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Published inJournal of lipid research Vol. 35; no. 9; pp. 1646 - 1651
Main Authors YOSHII, M, UNE, M, KIHIRA, K, KURAMOTO, T, AKIZAWA, T, YOSHIOKA, M, BUTLER, VP, HOSHITA, T
Format Journal Article
LanguageEnglish
Published BETHESDA LIPID RESEARCH INC 01.09.1994
Elsevier
Subjects
Animals
Bile Acids and Salts - biosynthesis
Bile Acids and Salts - chemistry
Bile Acids and Salts - isolation & purification
Biochemistry & Molecular Biology
Bufo marinus - metabolism
Bufonidae - metabolism
Cholestanols - chemistry
Cholestanols - isolation & purification
Cholestanols - metabolism
Chromatography, Gas
Gas Chromatography-Mass Spectrometry
Life Sciences & Biomedicine
Molecular Structure
Science & Technology
Species Specificity
BUFO MARINUS
MASS SPECTROMETRY
BILE ALCOHOLS
GAS-LIQUID CHROMATOGRAPHY
BIOSYNTHESIS
BILE ACIDS
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Summary: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 C-27 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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ISSN:0022-2275
DOI:10.1016/s0022-2275(20)41162-9