Antioxidant activity and enzymatic of lichen substances: A study based on cyclic voltammetry and theoretical
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Date
Authors
GARCIA SANHUEZA, CAMILO ANDRES
Yañez, Osvaldo
Osorio, Manuel Isaías
Osorio, Edison H.
Tiznado, William A.
Ruíz, Lina María
García, Camilo
Nagles, Edgar
Simirgiotis, Mario Juan
Castañeta, Grover
Areche, Carlos
Yañez, Osvaldo
Osorio, Manuel Isaías
Osorio, Edison H.
Tiznado, William A.
Ruíz, Lina María
García, Camilo
Nagles, Edgar
Simirgiotis, Mario Juan
Castañeta, Grover
Areche, Carlos
Authors
Date
Datos de publicación:
10.1016/j.cbi.2023.110357
Keywords
Antioxidant - Cyclic Voltamperograms - Cyps Enzymes - Dft Methods - Lichenic Substances - Natural Products - Hydrogen - Phenol - Proton - Sterol 14alpha Demethylase - Antioxidants - Hydrogen - Protons - Barbatolic Acid - Carboxylic Acid - Cytochrome P450 1a2 - Cytochrome P450 2c9 - Diffractaic Acid - Fumarprotocetraric Acid - Hydrogen - Lichen Substance - Lobaric Acid - Methyl Haematommate - Methylatrarate - Natural Product - Organic Compound - Phenol - Proton - Salazinic Acid - Sphaerophorin - Sterol 14alpha Demethylase - Subsphaeric Acid - Unclassified Drug - Antioxidant - Active Transport - Antioxidant Activity - Article - Binding Affinity - Calculation - Chemical Structure - Controlled Study - Cyclic Voltammetry - Cyclic Voltamperogram - Dissociation - Electron - Electron Transport - Enzyme Activity - Free Radical Scavenging Assay - Human - Hydrogen Atomic Transfer - Hydrogen Bond - Lichen (organism) - Mathematical Computing - Nonhuman - Proton Transport - Reversal Potential - Slope Factor - Theoretical Sample - Chemistry - Thermodynamics - Antioxidants - Electron Transport - Hydrogen - Lichens - Protons - Thermodynamics - Sustancias Líquenicas - Antioxidante - Voltammogramas Cíclicos - Métodos Dft - Enzimas Cyps - Productos Naturales
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Abstract
The 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), barbatolic 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+/2e? 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? 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 calculations 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. © 2023 Elsevier B.V., All rights reserved.
Description
Keywords
Antioxidant , Cyclic Voltamperograms , Cyps Enzymes , Dft Methods , Lichenic Substances , Natural Products , Hydrogen , Phenol , Proton , Sterol 14alpha Demethylase , Antioxidants , Hydrogen , Protons , Barbatolic Acid , Carboxylic Acid , Cytochrome P450 1a2 , Cytochrome P450 2c9 , Diffractaic Acid , Fumarprotocetraric Acid , Hydrogen , Lichen Substance , Lobaric Acid , Methyl Haematommate , Methylatrarate , Natural Product , Organic Compound , Phenol , Proton , Salazinic Acid , Sphaerophorin , Sterol 14alpha Demethylase , Subsphaeric Acid , Unclassified Drug , Antioxidant , Active Transport , Antioxidant Activity , Article , Binding Affinity , Calculation , Chemical Structure , Controlled Study , Cyclic Voltammetry , Cyclic Voltamperogram , Dissociation , Electron , Electron Transport , Enzyme Activity , Free Radical Scavenging Assay , Human , Hydrogen Atomic Transfer , Hydrogen Bond , Lichen (organism) , Mathematical Computing , Nonhuman , Proton Transport , Reversal Potential , Slope Factor , Theoretical Sample , Chemistry , Thermodynamics , Antioxidants , Electron Transport , Hydrogen , Lichens , Protons , Thermodynamics , Sustancias Líquenicas , Antioxidante , Voltammogramas Cíclicos , Métodos Dft , Enzimas Cyps , Productos Naturales
Citation
10.1016/j.cbi.2023.110357