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

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

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/ESIMS/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 1b-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 1b-hydroxyl group.

Original languageEnglish
Pages (from-to)651-657
Number of pages7
JournalJournal of lipid research
Volume50
Issue number4
DOIs
Publication statusPublished - 2009 Mar

Keywords

  • 1β,3α,7α-trihydroxy-5β-cholestan-27-oic acid
  • 1β-hydroxylation
  • C bile acids
  • LC-MS
  • NMR
  • taurine conjugate

ASJC Scopus subject areas

  • Biochemistry
  • Endocrinology
  • Cell Biology

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