title: Substituent Inductive Effects on the Electrochemical Oxidation of Flavonoids Studied by Square Wave Voltammetry and Ab Initio Calculations.
abstract: Flavonoids are natural products commonly found in the human diet that show antioxidant, anti-inflammatory and anti-hepatotoxic activities. These nutraceutical properties may relate to the electrochemical activity of flavonoids. To increase the understanding of structure-electrochemical activity relations and the inductive effects that OH substituents have on the redox potential of flavonoids, we carried out square-wave voltammetry experiments and ab initio calculations of eight flavonoids selected following a systematic variation in the number of hydroxyl substituents and their location on the flavan backbone: three flavonols, three anthocyanidins, one anthocyanin and the flavonoid backbone flavone. We compared the effect that the number of -OH groups in the ring B of flavan has on the oxidation potential of the flavonoids considered, finding linear correlations for both flavonols and anthocyanidins ( R 2 = 0.98 ). We analyzed the effects that position and number of -OH substituents have on electron density distributions via ab initio quantum chemical calculations. We present direct correlations between structural features and oxidation potentials that provide a deeper insight into the redox chemistry of these molecules.
authors: Departament of Chemistry, Tecnológico de Monterrey, Av. E. Garza Sada 2501 Sur, Monterrey 64849, N.L., Mexico. narroyo@chem.uscb.edu.
authors: Netzahualcóyotl
authors: N
authors: Arroyo-Currás
authors: Facultad de Ciencias Químicas, Universidad Autónoma de Nuevo León, Av. Pedro de Alba S-N Cd. Universitaria, San Nicolás De Los Garza 66451, N.L., Mexico. rosas.victor@gmail.com.
authors: Víctor M
authors: VM
authors: Rosas-García
authors: Departament of Chemistry, Tecnológico de Monterrey, Av. E. Garza Sada 2501 Sur, Monterrey 64849, N.L., Mexico. mvidea@itesm.mx.|School of Engineering and Science, Tecnológico de Monterrey, Av. E. Garza Sada 2501 Sur, Monterrey 64849, N.L., Mexico. mvidea@itesm.mx.
authors: Marcelo
authors: M
authors: Videa
mesh_terms: D055664:Electrochemical Techniques / Q000379:methods*; D005419:Flavonoids / Q000737:chemistry*; D006801:Humans; D010084:Oxidation-Reduction
chemical_list: D005419:Flavonoids
keywords: ab initio; antioxidants; electron density distribution; flavonoids; voltammetry