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

hal.structure.identifierUnité de recherche sur les Biopolymères, Interactions Assemblages [BIA]
dc.contributor.authorCASTILLO-FRAIRE, Claudia
hal.structure.identifierInstitut des Sciences Chimiques de Rennes [ISCR]
hal.structure.identifierPlate-forme Rennaise d'Imagerie et Spectroscopie Structurale et Métabolique [PRISM]
dc.contributor.authorPOTTIER, Sandrine
hal.structure.identifierInstitut des Sciences Chimiques de Rennes [ISCR]
hal.structure.identifierPlate-forme Rennaise d'Imagerie et Spectroscopie Structurale et Métabolique [PRISM]
dc.contributor.authorBONDON, Arnaud
hal.structure.identifierUniversidad Autónoma de Chihuahua [UACH]
dc.contributor.authorSALAS, Erika
hal.structure.identifierBiologie du fruit et pathologie [BFP]
dc.contributor.authorBERNILLON, Stéphane
hal.structure.identifierUnité de recherche sur les Biopolymères, Interactions Assemblages [BIA]
dc.contributor.authorGUYOT, Sylvain
hal.structure.identifierInsitut Français des Productions Cidricoles [IFPC]
dc.contributor.authorPOUPARD, Pascal
dc.date.issued2022-03
dc.identifier.issn0308-8146
dc.description.abstractEnDuring 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
dc.language.isoen
dc.publisherElsevier
dc.rights.urihttp://hal.archives-ouvertes.fr/licences/copyright/
dc.subject.enphenolic compounds
dc.subject.enCQA dehydrodimers
dc.subject.enchlorogenic acid
dc.subject.enPPO
dc.subject.encaffeicin
dc.subject.enFood Chemistry phenolic compounds
dc.subject.enCQA dehydrodimers
dc.subject.enchlorogenic acid
dc.title.enNMR structural elucidation of dehydrodimers resulting from oxidation of 5-O-caffeoylquinic acid in an apple juice model solution
dc.typeArticle de revue
dc.identifier.doi10.1016/j.foodchem.2021.131117
dc.subject.halChimie/Génie chimique
dc.subject.halSciences du Vivant [q-bio]/Ingénierie des aliments
bordeaux.journalFood Chemistry
bordeaux.page131117
bordeaux.volume372
bordeaux.peerReviewedoui
hal.identifierhal-03349274
hal.version1
hal.popularnon
hal.audienceInternationale
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-03349274v1
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Food%20Chemistry&rft.date=2022-03&rft.volume=372&rft.spage=131117&rft.epage=131117&rft.eissn=0308-8146&rft.issn=0308-8146&rft.au=CASTILLO-FRAIRE,%20Claudia&POTTIER,%20Sandrine&BONDON,%20Arnaud&SALAS,%20Erika&BERNILLON,%20St%C3%A9phane&rft.genre=article


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