New compounds obtained by evolution and oxidation of malvidin 3-O-glucoside in ethanolic medium

J Agric Food Chem. 2008 Jun 25;56(12):4584-91. doi: 10.1021/jf8001872. Epub 2008 May 23.

Abstract

Two new colorless phenolic compounds were formed from malvidin 3- O-glucoside incubated in an ethanolic solution. Their structures were characterized by means of one- and two-dimensional NMR analysis and through electrospray ionization-mass spectrometry. As compared to the structure of the initial anthocyanin skeleton, the first new compound showed the presence of two fused five-membered rings replacing the pyran ring and of a carbonyl function on the 2-position. The first five-membered ring was shown to result from the formation of a new linkage between the B ring 6'-position and the C ring 4-position, while the second was a dihydro furan ring with an oxygenated ether linkage between the 8a-position and the 3-position. The second isolated compound was shown to have similar structure with an ethyl ether moiety in the 3-position instead of the glucose moiety. A mechanism explaining the formation of the isolated compounds involving the passage through the chalcone form of the anthocyanin and an oxidation process is proposed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anthocyanins / chemistry*
  • Chromatography, High Pressure Liquid
  • Ethanol*
  • Glucosides
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Oxidation-Reduction
  • Solutions
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Anthocyanins
  • Glucosides
  • Solutions
  • Ethanol
  • malvidin-3-glucoside