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Impact of phenolic compounds in strecker aldehyde formation in wine model systems: target and untargeted analysis

2020Journal article Restricted access
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dc.contributor.authorMonforte, A.R.
dc.contributor.authorMartins, S.I.F.S.
dc.contributor.authorFerreira, A.C. Silva
dc.date.accessioned2021-01-29T16:38:50Z
dc.date.available2021-01-29T16:38:50Z
dc.date.issued2020
dc.description.abstractThe Strecker degradation of phenylalanine has been studied in a phenolic compound/phenylalanine wine model system. Six phenolic compounds (3,4-dihydroxybenzoic acid, gallic acid, caffeic acid, ferulic acid, catechin, and epicatechin) were compared in the formation of phenylacetaldehyde when in the presence of glucose or methylglyoxal (MG). The addition of glucose reduced the formation of Strecker aldehyde, independently of the phenolic compound. The addition of MG, on the other hand, increased phenylacetaldehyde formation for hydroxybenzoic acids and decreased phenylacetaldehyde formation for flavan-3-ols, confirming their capacity to trap the dicarbonyl compound. As a target phenolic compound, catechin was chosen to perform kinetic studies to further understand the reaction intermediates involved in the mechanism of phenylacetaldehyde formation, in particular, catechin o-quinone and catechin–MG adduct. The addition of glucose and MG increased the consumption of catechin, while a reduction in the respective o-quinone was observed, suggesting that these substrates have an impact in other reactions involving catechin. In that regard, for the first time, it was demonstrated that the catechin–MG adduct was capable of oxidizing and forming a new o-quinone, contributing to wine instability promoted by oxidation reactions.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationMonforte, A.R., Martins, S.I.F.S., Ferreira, A.C.S. (2020). Impact of phenolic compounds in strecker aldehyde formation in wine model systems: target and untargeted analysis. Journal of agricultural and food chemistry, 68(38), 10281-10286pt_PT
dc.identifier.doi10.1021/acs.jafc.9b02674pt_PT
dc.identifier.eid85091553862
dc.identifier.eissn1520-5118
dc.identifier.issn0021-8561
dc.identifier.pmid31274314
dc.identifier.urihttp://hdl.handle.net/10400.14/31817
dc.identifier.wos000575685800005
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherAmerican Chemical Societypt_PT
dc.relationCentre for Biotechnology and Fine Chemistry
dc.relationChemiomics: A systems chemistry approach to unravel the interface pathways between oxidation and Maillard mechanism responsible for flavour modulation during wine storage.
dc.subjectStrecker degradationpt_PT
dc.subjectPhenylacetaldehydept_PT
dc.subjectCatechinpt_PT
dc.subjectO-quinonespt_PT
dc.subjectMethylglyoxalpt_PT
dc.titleImpact of phenolic compounds in strecker aldehyde formation in wine model systems: target and untargeted analysispt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleCentre for Biotechnology and Fine Chemistry
oaire.awardTitleChemiomics: A systems chemistry approach to unravel the interface pathways between oxidation and Maillard mechanism responsible for flavour modulation during wine storage.
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UID%2FMulti%2F50016%2F2019/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/POR_NORTE/SFRH%2FBD%2F111889%2F2015/PT
oaire.citation.endPage10286pt_PT
oaire.citation.issue38pt_PT
oaire.citation.startPage10281pt_PT
oaire.citation.titleJournal of agricultural and food chemistrypt_PT
oaire.citation.volume68pt_PT
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStreamPOR_NORTE
person.familyNameMonforte
person.familyNameSilva Ferreira
person.givenNameAna Rita
person.givenNameAntonio Cesar
person.identifier.ciencia-id471B-600E-ABC5
person.identifier.ciencia-id931A-48DA-23A8
person.identifier.orcid0000-0003-2627-2656
person.identifier.orcid0000-0002-1188-1021
person.identifier.scopus-author-id55622494400
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsrestrictedAccesspt_PT
rcaap.typearticlept_PT
relation.isAuthorOfPublication20143552-b796-4417-b119-eb2ffc40b264
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relation.isProjectOfPublication1f76a7db-2520-482f-b56b-7e01ea36dd1f
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