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dc.contributor.authorVásquez-Espinal, Alejandro
dc.contributor.authorYáñez, Osvaldo
dc.contributor.authorOsorio, Edison H.
dc.contributor.authorAreche, Carlos
dc.contributor.authorGarcía-Beltrán, Olimpo
dc.contributor.authorRuíz, Lina María
dc.contributor.authorCassels, Bruce
dc.contributor.authorTiznado, William A.
dc.date.accessioned2021-02-24T14:14:15Z
dc.date.available2021-02-24T14:14:15Z
dc.date.issued2021-01-14
dc.identifier10.1039/d0nj04028b
dc.identifier.issn11440546
dc.identifier.urihttps://hdl.handle.net/20.500.12728/8619
dc.description.abstractPrevious experimental results on the free radical-scavenging properties of boldine, one of the most potent natural antioxidants, suggested that the benzylic hydrogen, neighboring a nitrogen lone electron pair, might be the key to its protective and antioxidant effect, in contrast to the usually assumed labile phenolic hydrogen atoms. Our computations suggest that both boldine and glaucine can undergo two successive hydrogen transfers under attack by an oxidizing radical (from C-6a-H and C-7-H). The hydroxyl groups of boldine could also participate via the HAT mechanism, although to a lesser extent. In the case of quaternary N-methylated derivatives, the sharing of the nitrogen lone pair makes the transfer of the C-6a hydrogen energetically unfeasible, supporting the earlier proposal based on experimental evidence. The hydroxyl groups of boldine and its derivatives could contribute to antioxidant activity via the sequential proton loss electron transfer mechanism, although this would only be relevant at higher pH values.es_ES
dc.language.isoenes_ES
dc.publisherRoyal Society of Chemistryes_ES
dc.subjectAtomses_ES
dc.subjectElectron transitionses_ES
dc.subjectElectron transport propertieses_ES
dc.subjectFree radical reactionses_ES
dc.subjectFree radicalses_ES
dc.subjectHydrogenes_ES
dc.titleStructure-antioxidant activity relationships in boldine and glaucine: a DFT studyes_ES
dc.typeArticlees_ES


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