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Journal of Lipid Research, Vol. 47, 1551-1558, July 2006
Copyright © 2006 by American Society for Biochemistry and Molecular Biology

Identification of a novel bile acid in swans, tree ducks, and geese: 3,7,15-trihydroxy-5ß-cholan-24-oic acid

Genta Kakiyama^*, Takashi Iida^*, Takaaki Goto, Nariyasu Mano, Junichi Goto, Toshio Nambara, Lee R. Hagey, Claudio D. Schteingart^** and Alan F. Hofmann^1,

^* Department of Chemistry, College of Humanities and Sciences, Nihon University, Sakurajousui, Setagaya, Tokyo 156-8550, Japan
Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, Japan
Department of Medicine, University of California, San Diego, La Jolla, CA 92093-0813
^** Department of Chemistry, Ferring Research Institute, San Diego, CA 92121

Published, JLR Papers in Press, April 28, 2006.

¹ To whom correspondence should be addressed. e-mail: ahofmann{at}ucsd.edu

By HPLC, a taurine-conjugated bile acid with a retention time different from that of taurocholate was found to be present in the bile of the black-necked swan, Cygnus melanocoryphus. The bile acid was isolated and its structure, established by ¹H and ¹³C NMR and mass spectrometry, was that of the taurine N-acyl amidate of 3,7,15-trihydroxy-5ß-cholan-24-oic acid. The compound was shown to have chromatographic and spectroscopic properties that were identical to those of the taurine conjugate of authentic 3,7,15-trihydroxy-5ß-cholan-24-oic acid, previously synthesized by us from ursodeoxycholic acid. By HPLC, the taurine conjugate of 3,7,15-trihydroxy-5ß-cholan-24-oic acid was found to be present in 6 of 6 species in the subfamily Dendrocygninae (tree ducks) and in 10 of 13 species in the subfamily Anserinae (swans and geese) but not in other subfamilies in the Anatidae family. It was also not present in species from the other two families of the order Anseriformes. 3,7,15-Trihydroxy-5ß-cholan-24-oic acid is a new primary bile acid that is present in the biliary bile acids of swans, tree ducks, and geese and may be termed 15-hydroxy-chenodeoxycholic acid.

Supplementary key words Anseriformes • bile acid evolution • bile acid conjugation

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				G. Kakiyama, H. Tamegai, T. Iida, K. Mitamura, S. Ikegawa, T. Goto, N. Mano, J. Goto, P. Holz, L. R. Hagey, et al. Isolation and chemical synthesis of a major, novel biliary bile acid in the common wombat (Vombatus ursinus): 15{alpha}-hydroxylithocholic acid J. Lipid Res., December 1, 2007; 48(12): 2682 - 2692. [Abstract] [Full Text] [PDF]