Antioxidant activity and enzymatic of lichen substances: A study based on cyclic voltammetry and theoretical

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datacite.alternateIdentifier.citationCHEMICO-BIOLOGICAL INTERACTIONS,Vol.372,,2023
datacite.alternateIdentifier.doi10.1016/j.cbi.2023.110357
datacite.creatorYanez, Osvaldo
datacite.creatorOsorio, Manuel I.
datacite.creatorOsorio, Edison
datacite.creatorTiznado, William
datacite.creatorRuiz, Lina
datacite.creatorGarcia, Camilo
datacite.creatorNagles, Orlando
datacite.creatorSimirgiotis, Mario J.
datacite.creatorCastaneta, Grover
datacite.creatorAreche, Carlos
datacite.creatorGarcia Beltran, Olimpo
datacite.date2023
datacite.subject.englishLichenic substances
datacite.subject.englishAntioxidant
datacite.subject.englishCyclic voltamperograms
datacite.subject.englishDFT methods
datacite.subject.englishCYPs enzymes
datacite.subject.englishNatural products
datacite.titleAntioxidant activity and enzymatic of lichen substances: A study based on cyclic voltammetry and theoretical
dc.date.accessioned2023-06-08T15:48:17Z
dc.date.available2023-06-08T15:48:17Z
dc.description.abstractThe antioxidant activity of nine lichen substances, including methylatrarate (1), methyl haematommate (2), lobaric acid (3), fumarprotocetraric acid (4), sphaerophorin (5), subsphaeric acid (6), diffractaic acid (7), bar-batolic acid (8) and salazinic acid (9) has been determined through cyclic voltammetry. The compounds 1-4 presented slopes close to the Nernst constant of 0.059 V, indicating a 2H+/2e213; relation between protons and electrons, as long as the compounds 5, 6, 7, 8, and 9 present slopes between 0.037 V and 0.032 V, indicating a 1H+/2e/13; relation between protons and electrons. These results show a high free radical scavenging activity by means of the release of H+, suggesting an important antioxidant capacity of these molecules. Theoretical cal-culations of hydrogen bond dissociation enthalpies (BDE), proton affinities (PA), and Proton Transfer (PT) mechanisms, at M06-2x/6-311+G(d,p) level complement the experimental results. Computations support that the best antioxidant activity is obtained for the molecules (3, 4, 5, 6, 7 and 8), that have a carboxylic acid group close to a phenolic hydroxyl group, through hydrogen atomic transfer (HAT) and sequential proton loss electron transfer (SPLET) mechanisms. Additional computations were performed for modelling binding affinity of the lichen substances with CYPs enzymes, mainly CYP1A2, CYP51, and CYP2C9*2 isoforms, showing strong affinity for all the compounds described in this study.
dc.identifier.urihttps://repositoriodigital.uct.cl/handle/10925/5336
dc.language.isoen
dc.publisherELSEVIER IRELAND LTD
dc.sourceCHEMICO-BIOLOGICAL INTERACTIONS
oaire.resourceTypeArticle
uct.indizacionSCI
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