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Journal of Lipid Research, Vol. 50, 651-657, April 2009
Copyright © 2009 by American Society for Biochemistry and Molecular Biology

A new, major C₂₇ biliary bile acid in the Red-winged tinamou (Rhynchotus rufescens):(25R)-1β,3,7-trihydroxy-5β-cholestan-27-oic acid^*

Lee R. Hagey^*, Genta Kakiyama, Akina Muto, Takashi Iida^1,, Kumiko Mushiake, Takaaki Goto, Nariyasu Mano^**, Junichi Goto^**, Cleida A. Oliveira and Alan F. Hofmann^1,*

^* Department of Medicine, University of California, San Diego, La Jolla, CA 92093-0063
Department of Chemistry, College of Humanities & Sciences, Nihon University, Sakurajousui, Setagaya, Tokyo 156-8550, Japan
Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, Japan
^** Division of Pharmaceutical Sciences, Tohoku University Hospital, Seiryocho, Sendai 980-8574, and Japan
Department of Morphology, Federal University of Minas Gerais, Belo Horizonte, MG, Brazil

^* This work was supported by National Institutes of Health Grant AM 64891 (to A.F.H.) and by a Grant-in-Aid for Young Scientists (B) (to G.K., Grant 20,750,141) for 2008–2009; a Grant-in-Aid for Scientific Research (C) (to T.I., Grant 19,510,223) for 2007–2008 from the Ministry of Education, Sciences, Sports, and Culture of Japan; and Nihon University Multidisciplinary Research Grant (to T.I.) for 2008.

Published, JLR Papers in Press, November 14, 2008.

¹ To whom correspondence should be addressed. e-mail: takaiida{at}chs.nihon-u.ac.jp (T.I., chemical aspects); ahofmann{at}ucsd.edu (A.F.H., biological aspects)

The chemical structures of the three major bile acids present in the gallbladder bile of the Red-winged tinamou (Rhynchotus rufescens), an early evolving, ground-living bird related to ratites, were determined. Bile acids were isolated by preparative reversed-phase HPLC. Two of the compounds were identified as the taurine N-acylamidates of (25R)-3,7-dihydroxy-5β-cholestan-27-oic acid (constituting 22% of biliary bile acids) and (25R)-3,7,12-trihydroxy-5β-cholestan-27-oic acid (constituting 51%). The remaining compound, constituting 21% of biliary bile acids, was an unknown C₂₇ bile acid. Its structure was elucidated by LC/ESI-MS/MS and NMR and shown to be the taurine conjugate of (25R)-1β,3,7-trihydroxy-5β-cholestan-27-oic acid, a C₂₇ trihydroxy bile acid not previously reported. Although C₂₇ bile acids with a 1β-hydroxyl group have been identified as trace bile acids in the alligator, this is the first report of a major biliary C₂₇ bile acid possessing a 1β-hydroxyl group.

Supplementary key words 1β-hydroxylation • C₂₇ bile acids • 1β,3,7-trihydroxy-5β-cholestan-27-oic acid • taurine conjugate • LC-MS • NMR

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