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Cyclic voltammetric analysis of 2-styrylchromones: Relationship with the antioxidant activity

2008Journal article Open access
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dc.contributor.authorGomes, Ana Sara
dc.contributor.authorFernandes, Eduarda
dc.contributor.authorGarcia, M. Beatriz
dc.contributor.authorSilva, Artur
dc.contributor.authorPinto, Diana
dc.contributor.authorSantos, Clementina M.M.
dc.contributor.authorCavaleiro, José
dc.contributor.authorLima, José Costa
dc.date.accessioned2011-04-12T10:19:26Z
dc.date.available2011-04-12T10:19:26Z
dc.date.issued2008
dc.description.abstract2-Styrylchromones (2-SC) are a chemical family of oxygen heterocyclic compounds, vinylogues of flavones (2-phenylchromones), whose occurrence in nature has been reported. Recently, several 2-SC derivatives were demonstrated to have antioxidant properties, namely, xanthine oxidase inhibition, hepatoprotection against pro-oxidant agents in cellular and non-cellular systems and scavenging activity against reactive oxygen and reactive nitrogen species (ROS and RNS). Considering these antioxidant properties, it may be hypothesised that the electrochemical redox behaviour of 2-SC contributes significantly to their activity. To test this hypothesis, the electrochemical behaviour of different 2-SC was studied, together with a number of flavonoids with well-known antioxidant activities, by cyclic voltammetry, and the results correlated to their ability to scavenge ROS and RNS. The results obtained showed that 2-SC with a catecholic B-ring have a low oxidation peak potential corresponding to the oxidation of the 30,40-OH (catechol) moiety. The compounds with a phenolic B-ring have a common peak, with oxidation potential values of about +0.4/+0.5 V versus Ag/AgCl, corresponding to the oxidation of the 40-OH. The oxidation of the hydroxyl substituents in the A-ring generated peaks of higher potentials (+0.7/+0.8 V vs Ag/AgCl). The results from the scavenging assays were in agreement with those obtained from the cyclic voltammetry, that is, higher scavenging effects corresponded to lower values of oxidation potentials, with significant correlation coefficients. The values obtained for the studied flavonoids are in accordance with the literature, and reflect their relative antioxidant activity, when compared to the studied 2-SC. Thus, in this family of compounds, oxidation potentials obtained by cyclic voltammetry seem to be applicable as a general indicator of radical scavenging activity.por
dc.description.sponsorshipThe authors acknowledge FCT and FEDER financial support for the Project POCI/QUI/59284/2004. Ana Gomes acknowledges FCT and FSE her Ph.D. Grant (SFRH/BD/23299/2005).
dc.identifier.citationGomes, Ana; Fernandes, Eduarda; Garcia, M. Beatriz; Silva, Artur; Pinto, Diana; Santos, Clementina; Cavaleiro, José; Costa Lima, José (2008). Cyclic voltammetric analysis of 2-styrylchromones: Relationship with the antioxidant activity. Bioorganic & Medicinal Chemistry. ISSN 0968-0896. 16: 7, p. 7939-7943por
dc.identifier.doi10.1016/j.bmc.2008.07.072
dc.identifier.urihttp://hdl.handle.net/10198/4011
dc.language.isoengpor
dc.peerreviewedyespor
dc.publisherElsevierpor
dc.subject2-Styrylchromonespor
dc.subjectCyclic voltammetrypor
dc.subjectOxidation mechanismpor
dc.subjectScavenging activitypor
dc.subjectReactive oxygen speciespor
dc.subjectReactive nitrogen speciespor
dc.titleCyclic voltammetric analysis of 2-styrylchromones: Relationship with the antioxidant activitypor
dc.typejournal article
dspace.entity.typePublication
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/POCI/POCI%2FQUI%2F59284%2F2004/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/SFRH/SFRH%2FBD%2F23299%2F2005/PT
oaire.citation.endPage7943por
oaire.citation.startPage7939por
oaire.citation.titleBioorganic & Medicinal Chemistrypor
oaire.fundingStreamPOCI
oaire.fundingStreamSFRH
person.familyNameSantos
person.givenNameClementina M.M.
person.identifier.ciencia-id9018-DB9C-C590
person.identifier.orcid0000-0003-4380-7990
person.identifier.scopus-author-id7201458663
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.rightsopenAccesspor
rcaap.typearticlepor
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relation.isAuthorOfPublication.latestForDiscovery64f662b6-775d-4ea0-bfd7-f527af0ac1a0
relation.isProjectOfPublication1a77f25c-e459-4679-93cb-48bc8c6709ac
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