Journal article
Major biliary bile acids of the Medaka (Oryzias latipes): 25R- and 25S-epimers of 3α,7α,12α-trihydroxy-5β-cholestanoic Acid
Zoological science, Vol.27(7), pp.565-573
07/2010
DOI: 10.2108/zsj.27.565
PMCID: PMC2901895
PMID: 20608845
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
-acyl amidated 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 chromatography-tandem mass spectrometry. The dominant bile acid was the 25
R
-epimer (82%) of 3α,7α,12α-trihydroxy-5β-cholestan-27-oic acid. The 25
S
-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 its major bile salts.
Details
- Title: Subtitle
- Major biliary bile acids of the Medaka (Oryzias latipes): 25R- and 25S-epimers of 3α,7α,12α-trihydroxy-5β-cholestanoic Acid
- Creators
- Lee R Hagey - Department of Medicine, University of California, San Diego, La Jolla, CA 92093-0063, USATakashi Iida - Department of Chemistry, College of Humanities & Sciences, Nihon University, Sakurajousui, Setagaya, Tokyo 156-8550, JapanHideyuki Tamegai - Department of Chemistry, College of Humanities & Sciences, Nihon University, Sakurajousui, Setagaya, Tokyo 156-8550, JapanShoujiro Ogawa - Department of Chemistry, College of Humanities & Sciences, Nihon University, Sakurajousui, Setagaya, Tokyo 156-8550, JapanMizuho Une - Faculty of Pharmaceutical Sciences, Hiroshima International University, Kure, Hiroshima 737-0112, JapanKiyoshi Asahina - Department of Marine Science and Resources, College of Bioresouce Sciences, Nihon University, Kameino, Fujisawa, Kanagawa 274-8555, JapanKumiko Mushiake - Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, JapanTakaaki Goto - Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, JapanNariyasu Mano - Division of Pharmaceutical Sciences, Tohoku University Hospital, Seiryocho, Sendai 980-8574, JapanJunichi Goto - Division of Pharmaceutical Sciences, Tohoku University Hospital, Seiryocho, Sendai 980-8574, JapanMatthew D Krasowski - Department of Pathology, University of Iowa Hospital and Clinics, Iowa City, IA 52242, USAAlan F Hofmann - Department of Medicine, University of California, San Diego, La Jolla, CA 92093-0063, USA
- Resource Type
- Journal article
- Publication Details
- Zoological science, Vol.27(7), pp.565-573
- DOI
- 10.2108/zsj.27.565
- PMID
- 20608845
- PMCID
- PMC2901895
- NLM abbreviation
- Zoolog Sci
- ISSN
- 0289-0003
- eISSN
- 0289-0003
- Language
- English
- Date published
- 07/2010
- Academic Unit
- Pathology
- Record Identifier
- 9984047852202771
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