Remarkable biomimetic chemoselective aerobic oxidation of flavano-ellagitannins found in oak-aged wine

Angew Chem Int Ed Engl. 2013 Oct 25;52(44):11530-3. doi: 10.1002/anie.201305839. Epub 2013 Sep 13.


Under the auspices of Bacchus! Acutissimins, natural flavano-ellagitannins, occur in oak-aged wine as a result of a diastereoselective condensation reaction of the flavan-3-ol catechin, a component of grapes, with the C-glucosidic ellagitannin vescalagin, found in oak. The acutissimins are further converted into natural mongolicains and analogues of camelliatannin G in a remarkably chemoselective fashion by simple aerobic oxidation.

Keywords: biosynthesis; chemoselectivity; oxidation; tannins; wine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anticarcinogenic Agents / pharmacokinetics*
  • Antioxidants / pharmacokinetics*
  • Biomimetics
  • Diet
  • Humans
  • Hydrolyzable Tannins / chemistry*
  • Oxidation-Reduction
  • Wine / analysis*


  • Anticarcinogenic Agents
  • Antioxidants
  • Hydrolyzable Tannins
  • ellagitannin