1999 Fiscal Year Final Research Report Summary
Development of the Detection and Measurement of Bile Acid Ester Glycosides as Markers of Liver Diseases in Humans
| Project/Area Number |
10640597
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
分離・精製・検出法
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| Research Institution | Nihon University |
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Principal Investigator |
IIDA Takashi College of Humanities and Sciences, Nihon University, Professor, 文理学部, 教授 (60060125)
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| Project Period (FY) |
1998 – 1999
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| Keywords | Steroid / Bile acid / Unusual bile acid / Hepatobiliary disease / Bile acid ester glycoside / Acyl glycoside / 2-Chloro-1,3,5-trinitrobenzene |
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| Research Abstract |
An efficient synthesis of the carboxyl-linked glucosides of bile acids was described. Direct esterification of unprotected bile acids with 2,3,4,6-tetra-O-benzyl-D-glucopyranose in pyridine in the presence of 2-chloro-1,3,5-trinitrobenzene as a coupling agent afforded a mixture of the α- and β-anomers (ca. 1 : 4) of the 1-O-acyl-D-glucoside benzyl ethers of bile acids, which was effectively separated on a C_<18> reversed-phase chromatography. Subsequent hydrogenolysis of the α- and β-acyl glucoside benzyl ethers on a 10% Pd/C catalyst at atomospheric pressure gave the corresponding free esters. A facile hydrolysis and transesterification of the acyl glucosides in various solvents were also revealed.
A method for the separation of a mixture of different series of ionic, high polar, and hydrophilic conjugates of bile acid ester glucosides by indusion high performance liquid chromatography (HPLC) with methyl β-cyclodextrin or by ion-pair HPLC with an ion-pair chromatographic reagent, di-n-butylamine acetate (DBAA), as mobile phase additives. Satisfactory chromatographic separation and column performance were attained by the indusion HPLC and ion-pair HPLC methods. The present methods provide an insight into the separation and structural elucidation of biologically important bile acid ester glucosides.
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