A new class of blue anthocyanin-derived pigments isolated from red wines

J Agric Food Chem. 2003 Mar 26;51(7):1919-23. doi: 10.1021/jf020943a.


Two newly formed anthocyanin-derived pigments that revealed unique spectroscopic features, showing maximum absorption in their UV-vis spectra at 575 nm, were isolated by TSK Toyopearl HW-40 (S) gel column chromatography and semipreparative HPLC from an aged Port red wine. Further characterization by ESI/MS and NMR ((1)H, gCOSY) showed them to belong to a new class of pigments described here for the first time, the structure of which consisted of a pyranoanthocyanin moiety linked to a flavanol by a vinyl bridge. The extended conjugation of the pi electrons throughout all the pigment molecule is likely to confer a higher stability on it and is probably the origin of the intense blue color. The formation of these pigments was found to arise from the reaction between anthocyanin-pyruvic acid adducts and vinyl-flavanol adducts.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anthocyanins / analysis*
  • Anthocyanins / chemistry
  • Chromatography, High Pressure Liquid
  • Color
  • Flavonoids / analysis
  • Flavonols
  • Magnetic Resonance Spectroscopy
  • Pigments, Biological / analysis*
  • Pigments, Biological / chemistry
  • Pyruvic Acid / chemistry
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry
  • Vinyl Compounds / chemistry
  • Wine / analysis*


  • Anthocyanins
  • Flavonoids
  • Flavonols
  • Pigments, Biological
  • Vinyl Compounds
  • Pyruvic Acid