title: A new, major C27 biliary bile acid in the red-winged tinamou (Rhynchotus rufescens):25R-1beta, 3alpha,7alpha-trihydroxy-5beta-cholestan-27-oic acid.
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-3alpha,7alpha-dihydroxy-5beta-cholestan-27-oic acid (constituting 22% of biliary bile acids) and 25R-3alpha,7alpha,12alpha-trihydroxy-5beta-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-1beta, 3alpha, 7alpha-trihydroxy-5beta-cholestan-27-oic acid, a C27 trihydroxy bile acid not previously reported. Although C27 bile acids with a 1beta-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 1beta-hydroxyl group.
authors.affiliation: Department of Medicine, University of California, San Diego, La Jolla, CA 92093-0063, USA.
authors.forename: Lee R
authors.initials: LR
authors.lastname: Hagey
authors.forename: Genta
authors.initials: G
authors.lastname: Kakiyama
authors.forename: Akina
authors.initials: A
authors.lastname: Muto
authors.forename: Takashi
authors.initials: T
authors.lastname: Iida
authors.forename: Kumiko
authors.initials: K
authors.lastname: Mushiake
authors.forename: Takaaki
authors.initials: T
authors.lastname: Goto
authors.forename: Nariyasu
authors.initials: N
authors.lastname: Mano
authors.forename: Junichi
authors.initials: J
authors.lastname: Goto
authors.forename: Cleida A
authors.initials: CA
authors.lastname: Oliveira
authors.forename: Alan F
authors.initials: AF
authors.lastname: Hofmann
mesh_terms: D000818:Animals; D001647:Bile Acids and Salts / Q000737:chemistry* / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D046108:Palaeognathae / Q000378:metabolism*; D021241:Spectrometry, Mass, Electrospray Ionization; D053719:Tandem Mass Spectrometry
chemical_list: D001647:Bile Acids and Salts