Synthesis, discovery, and quantitation of dihomo-isofurans: biomarkers for in vivo adrenic acid peroxidation

Angew Chem Int Ed Engl. 2014 Jun 10;53(24):6249-52. doi: 10.1002/anie.201402440. Epub 2014 May 18.

Abstract

The growing importance of lipidomics, and the interest of non-enzymatic metabolites of polyunsaturated fatty acids (PUFAs) prompted us to initiate the synthesis of novel dihomo-IsoF compounds. Such metabolites of adrenic acid, the main PUFA in white matter, were synthesized using a divergent approach based on an orthoester cyclization. LC-MS/MS investigation on pig brains showed the potential of this novel biomarker for the first time, as a powerful new tool for brain lipid peroxidation assessment.

Keywords: biomarkers; lipids; mass spectrometry; oxidation; total synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Fatty Acids, Unsaturated / chemical synthesis*
  • Fatty Acids, Unsaturated / chemistry
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Lipid Peroxidation

Substances

  • Fatty Acids, Unsaturated
  • Furans
  • adrenic acid