| NMR and HPLC-MS/MS analysis of synthetically prepared linoleic acid diol glucuronides. | |
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MedLine Citation:
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PMID: 16500631 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Hydroxylated fatty acids are important mediators of many physiological and pathophysiological processes in a variety of human tissues. Recent evidence shows that in humans many of these are ultimately excreted in the urine as the glucuronide conjugates. In this paper we describe a general approach for the chemical synthesis of glucuronide conjugate derivatives of fatty acids. The synthesis strategy employs three steps (epoxidation, hydrolysis and glucuronidation) using methyl linoleate as a model non-hydroxylated starting compound. Hydroxylated starting compounds would require only the glucuronidation step. NMR and HPLC-MS/MS experiments were used to help determine the structure of the synthesized glucuronide conjugates and to identify fragmentation product ions useful for discriminating positional isomers in biological samples. This synthetic strategy should prove useful for generating analytical standards in order to identify and quantify glucuronide metabolites of hydroxylated fatty acids in humans. |
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Authors:
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Jie Yang; Martha D Morton; Dennis W Hill; David F Grant |
Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural; Research Support, U.S. Gov't, Non-P.H.S. Date: 2006-02-09 |
Journal Detail:
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Title: Chemistry and physics of lipids Volume: 140 ISSN: 0009-3084 ISO Abbreviation: Chem. Phys. Lipids Publication Date: 2006 Apr |
Date Detail:
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Created Date: 2006-04-03 Completed Date: 2006-07-05 Revised Date: 2008-11-21 |
Medline Journal Info:
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Nlm Unique ID: 0067206 Medline TA: Chem Phys Lipids Country: Ireland |
Other Details:
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Languages: eng Pagination: 75-87 Citation Subset: IM |
Affiliation:
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Department of Pharmaceutical Sciences, University of Connecticut, Storrs, CT 06269, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Chemistry, Physical Chromatography, High Pressure Liquid / methods Glucuronides* / chemical synthesis, chemistry Linoleic Acids* / chemical synthesis, chemistry Magnetic Resonance Spectroscopy / methods*, standards Mass Spectrometry / methods Molecular Structure Physicochemical Phenomena Reference Standards Sensitivity and Specificity Stereoisomerism Steroids* / chemical synthesis, chemistry |
| Grant Support | |
ID/Acronym/Agency:
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ES 011630/ES/NIEHS NIH HHS; GM 56708/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Glucuronides; 0/Linoleic Acids; 0/Steroids |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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