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J. Biochem, 1984, Vol. 96, No. 4 1103-1107
© 1984 Japanese Biochemical Society

research-article

Stereospecific Formation of (24E)-3{alpha}, 7{alpha}, 12{alpha}-Trihydroxy-5ß-Cholest-24-En-26-Oic Acid and (24R,25S)-3{alpha}, 7{alpha}, 12{alpha}, 24-Tetrahydroxy-5ß-Cholestan-26-Oic Acid from Either (25R)-or (25S)-3{alpha}, 7{alpha},12{alpha}-Trihydroxy-5ß-Cholestan-26-Oic Acid by Rat Liver Homogenate1,2

Mizuho UNE, Izumi MORIGAMI, Kenji KIHIRA and Takahiko HOSHITA3

Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine Minami-ku Kasumi, Hiroshima, Hiroshima 734

3 To whom communications should be addressed.

Studies of the stereochemistry of the intermediates, 3{alpha},7{alpha},12{alpha}-trihydroxy-5ß-cholest-24-en-26-oic acid and 3{alpha},7{alpha}, 12{alpha}, 24-tetrahydroxy-5ß-cholestan-26-oic acid, in the biosynthetic sequence between 3{alpha}, 7{alpha}, 12{alpha}, 24-tetrahydroxy-5ß-cholestan-26-oic acid and cholic acid have been undertaken. (25R) or (25S)-3{alpha}, 7{alpha}, 12{alpha}-Trihydroxy-5ß-cholestan-26-oic acid was incubated with rat liver homogenates. The reaction products were converted to p-bromophenacyl ester derivatives and the esters were analyzed by high-performance liquid chromatography. By comparison with authentic samples of two (24E)- and (24Z)-isomers of the {alpha},ß-unsaturated acid and of four isomers at C-24 and C-25 of the ß-hydroxy acid, (24E)-3{alpha},7{alpha},12{alpha}-trihydroxy-5ß-cholestan-26-oic acid and (24R,25S)-3{alpha},7{alpha},12{alpha},24-tetrahydroxy-5ß-cholestan-26-oic acid were found to be formed from either (25R)-or (25S)-3{alpha},7{alpha},12{alpha}-trihydroxy-5ß-cholestan-26-oic acid. No formation of the (24Z)-isomer of the trihydroxycholestenoic acid or the other three isomers of the tetrahydroxycholestanoic acid was detected. The findings are discussed in relation to the assumed pathway for side chain cleavage in cholic acid biosynthesis.

1 This paper is part XXVII of a series entitled ‘Comparative biochemical studies of bile acids and bile alcohols.’ Part XXVI: Kuwabara, M.,Ushiroguchi, T., Kihira, K., Kuramoto, T.,& Hoshita,T. (1984)J. Lipid Res. 25, 361–368.

2 This study was supported in part by a Grant-in-Aid for Scientific Research from the Ministry of Education, Science and Culture of Japan.


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