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NMR structural elucidation of dehydrodimers resulting from oxidation of 5-O-caffeoylquinic acid in an apple juice model solution

Abstract : During apple juice and cider-making processes, phenolic compounds undergo enzymatic 21oxidation. 5-O-caffeoylquinic acid (CQA) is one of the major hydroxycinnamic acid derivatives 22and it is the preferential substrate for polyphenol oxidase (PPO) in apple juices. Consequently, 23CQA dehydrodimers (MW 706 Da) are among the main products resulting from CQA oxidation. 24CQA dehydrodimers were previously synthesized in a biomimetic apple juice model solution. 25Following their purification and characterization using UV-Visible spectra and mass 26spectrometry, the structures of seven CQA dehydrodimers were elucidated using 1H and 13C one- 27and two-dimensional NMR spectroscopy. Six of them exhibited dihydrobenzofuran, 28benzodioxane, or dihydronaphtalene skeletons, which are caffeicin-like structures. Interestingly, 229a new dehydrodicaffeoyldiquinic acid molecule was also characterised for which two novel 30structures showing a symmetric dicatechol skeleton were also proposed
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Soumis le : lundi 20 septembre 2021 - 13:58:38
Dernière modification le : vendredi 5 novembre 2021 - 03:43:47

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Claudia Castillo-Fraire, Sandrine Pottier, Arnaud Bondon, Erika Salas, Stéphane Bernillon, et al.. NMR structural elucidation of dehydrodimers resulting from oxidation of 5-O-caffeoylquinic acid in an apple juice model solution. Food Chemistry, Elsevier, 2022, Food Chemistry, 372, pp.131117. ⟨10.1016/j.foodchem.2021.131117⟩. ⟨hal-03349274⟩

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