A scalable biomimetic synthesis of resveratrol dimers and systematic evaluation of their antioxidant activities

Angew Chem Int Ed Engl. 2015 Mar 16;54(12):3754-7. doi: 10.1002/anie.201409773. Epub 2015 Feb 4.

Abstract

An efficient synthetic route to the resveratrol oligomers quadrangularin A and pallidol is reported. It features a scalable biomimetic oxidative dimerization that proceeds in excellent yield and with complete regioselectivity. A systematic evaluation of the natural products and their synthetic precursors as radical-trapping antioxidants has revealed that, contrary to popular belief, this mode of action is unlikely to account for their observed biological activity.

Keywords: antioxidants; biomimetic synthesis; quinone methides; resveratrol; total synthesis.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry*
  • Antioxidants / metabolism
  • Biological Products / chemical synthesis
  • Biological Products / chemistry
  • Biomimetics
  • Cell Line
  • Dimerization
  • Humans
  • Indolequinones / chemistry
  • Oxidation-Reduction
  • Polycyclic Compounds / chemical synthesis*
  • Polycyclic Compounds / chemistry
  • Polycyclic Compounds / metabolism
  • Resveratrol
  • Stereoisomerism
  • Stilbenes / chemical synthesis*
  • Stilbenes / chemistry*
  • Stilbenes / metabolism

Substances

  • Antioxidants
  • Biological Products
  • Indolequinones
  • Polycyclic Compounds
  • Stilbenes
  • pallidol
  • quadrangularin A
  • quinone methide
  • Resveratrol