Chemical synthesis and characterization of epicatechin glucuronides and sulfates: bioanalytical standards for epicatechin metabolite identification

J Nat Prod. 2013 Feb 22;76(2):157-69. doi: 10.1021/np300568m. Epub 2013 Jan 28.

Abstract

The monoglucuronides and sulfates of epicatechin, 3'-O-methylepicatechin, and 4'-O-methylepicatechin, respectively, were synthesized as authentic bioanalytical standards. Reversed-phase HPLC methods capable of baseline separation of the glucuronides and sulfates have been developed. Both the epicatechin glucuronides and sulfates were stable in the solid state when stored under ambient conditions and in aqueous solution when stored refrigerated. These results should prove invaluable to the research community as analytical standards as well as in future studies of the biological and pharmacological effects of epicatechin in humans.

MeSH terms

  • Catechin / analogs & derivatives*
  • Catechin / chemical synthesis
  • Catechin / chemistry
  • Chromatography, High Pressure Liquid
  • Glucuronides / chemical synthesis*
  • Glucuronides / chemistry
  • Humans
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Sulfuric Acid Esters / chemical synthesis*
  • Sulfuric Acid Esters / chemistry

Substances

  • 3'-O-methylepicatechin
  • Glucuronides
  • Sulfuric Acid Esters
  • epicatechin-glucuronide
  • Catechin