NMR and HPLC-MS/MS analysis of synthetically prepared linoleic acid diol glucuronides

Jie Yang, Martha D. Morton, Dennis W. Hill, David F. Grant

Research output: Contribution to journalArticle

3 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)75-87
Number of pages13
JournalChemistry and Physics of Lipids
Volume140
Issue number1-2
DOIs
StatePublished - Apr 2006

Keywords

  • Glucuronides
  • HPLC-MS/MS
  • Hydroxylated fatty acids
  • Linoleic acid diols
  • NMR

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Cell Biology

Fingerprint Dive into the research topics of 'NMR and HPLC-MS/MS analysis of synthetically prepared linoleic acid diol glucuronides'. Together they form a unique fingerprint.

  • Cite this