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

Lee R. Hagey; Genta Kakiyama; Akina Muto; Takashi Iida; Kumiko Mushiake; Takaaki Goto; Nariyasu Mano; Junichi Goto; Cleida A. Oliveira; Alan F. Hofmann

Journal of Lipid Research (Apr 2009)

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

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

Affiliations

Lee R. Hagey: 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
Genta Kakiyama: 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
Akina Muto: 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
Takashi Iida: 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
Kumiko Mushiake: 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
Takaaki Goto: 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
Nariyasu Mano: 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
Junichi Goto: 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
Cleida A. Oliveira: 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
Alan F. Hofmann: 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

Journal volume & issue: Vol. 50, no. 4
pp. 651 – 657

Abstract

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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)-3α,7α-dihydroxy-5β-cholestan-27-oic acid (constituting 22% of biliary bile acids) and (25R)-3α,7α,12α-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,3α,7α-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.

Published in Journal of Lipid Research

ISSN: 0022-2275 (Print); 1539-7262 (Online)
Publisher: Elsevier
Country of publisher: United States
LCC subjects: Science: Chemistry: Organic chemistry: Biochemistry
Website: https://www.journals.elsevier.com/journal-of-lipid-research

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