A comprehensive investigation of guaiacyl-pyranoanthocyanin synthesis by one-/two-dimensional NMR and UPLC-DAD-ESI-MS(n)

Food Chemistry
Anna Vallverdú-QueraltChristine Le Guernevé

Abstract

In red and rosé wines, the grape anthocyanins are progressively converted to more stable pigments, including phenylpyranoanthocyanins. One-/two-dimensional NMR and UPLC-DAD-ESI-MS(n) measurements were used to monitor the synthesis of guaiacylpyranomalvidin 3-O-glucoside from malvidin 3-O-glucoside and vinylguaiacol in model solutions and identify the products formed during the reaction. The highest conversion rates (30%, determined by (1)H qNMR) were obtained with a small excess of vinylguaiacol in methanol/water (70/30) at pH 3 and 35°C. Two reaction pathways competed with the formation of guaiacylpyranomalvidin 3-O-glucoside. The first one only concerns malvidin 3-O-glucoside and consists in C-ring cleavage with formation of malvone and smaller molecular weight breakdown products. This pathway is favored at higher pH and incubation temperature. At lower pH values or in the presence of large vinylguaiacol excess, faster consumption of malvidin 3-O-glucoside resulted from the formation of more complex pyranoanthocyanins substituted by vinylguaiacol oligomers.

References

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Citations

Nov 10, 2016·International Journal of Molecular Sciences·Anna Vallverdú-QueraltOlivier Dangles
Dec 6, 2019·Journal of the Science of Food and Agriculture·Alexandra Olmo-CunilleraMaria Pérez
Aug 9, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Olivier Dangles, Julie-Anne Fenger
Jun 24, 2017·ChemistryOpen·Anna Vallverdú-QueraltVéronique Cheynier
Mar 2, 2018·Frontiers in Chemistry·Mónica BuenoVicente Ferreira

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