title: Major biliary bile acids of the medaka (Oryzias latipes): 25R- and 25S-epimers of 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoic acid.
abstract: The biliary bile salts of the medaka, the Japanese rice fish (Oryzias latipes) were isolated and identified. Only bile acids were present, and all were N-acylamidated with taurine. Three bile acids, constituting 98% of total bile acids, were isolated by chromatography and their structure inferred from their properties compared to those of synthetic standards when analyzed by liquid chromatographytandem mass spectrometry. The dominant bile acid was the 25R-epimer (82%) of 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-27-oic acid. The 25S-epimer was also present (11%), as was cholic acid (5%). Complete (1)H and (13)C NMR signal assignments of the C-25 epimers were made by using a combination of several 1D- and 2D-NMR techniques. The (1)H and (13)C NMR chemical shifts and spectral patterns of the hydrogen and carbon atoms, being close to the asymmetric centered at C-25, provided confirmatory evidence in that they distinguished the two epimeric diastereomers. The medaka is the first fish species identified as having C(27) biliary bile acids as dominant among its major bile salts.
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: Takashi
authors.initials: T
authors.lastname: Lida
authors.forename: Hideyuki
authors.initials: H
authors.lastname: Tamegai
authors.forename: Shoujiro
authors.initials: S
authors.lastname: Ogawa
authors.forename: Mizuho
authors.initials: M
authors.lastname: Une
authors.forename: Kiyoshi
authors.initials: K
authors.lastname: Asahina
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: Matthew D
authors.initials: MD
authors.lastname: Krasowski
authors.forename: Alan F
authors.initials: AF
authors.lastname: Hofmann
mesh_terms: D000818:Animals; D001646:Bile / Q000737:chemistry*; D001647:Bile Acids and Salts / Q000737:chemistry* / Q000378:metabolism*; D002777:Cholestanols / Q000737:chemistry* / Q000378:metabolism*; D015394:Molecular Structure; D009990:Oryzias / Q000235:genetics / Q000502:physiology*; D010802:Phylogeny
chemical_list: D001647:Bile Acids and Salts; D002777:Cholestanols; C009561:3,7,12-trihydroxycoprostane