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.
journal_name
Food Chemjournal_title
Food chemistryauthors
Vallverdú-Queralt A,Meudec E,Ferreira-Lima N,Sommerer N,Dangles O,Cheynier V,Le Guernevé Cdoi
10.1016/j.foodchem.2015.12.089subject
Has Abstractpub_date
2016-05-15 00:00:00pages
902-10eissn
0308-8146issn
1873-7072pii
S0308-8146(15)30366-6journal_volume
199pub_type
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