R. A. Mendes, S.K.C. Almeida, I.N. Soares, C.A. Barboza, R.G. Freitas, A. Brown, and G.L.C. de Souza*
Journal of Molecular Modeling, 24, 133.
Publication year: 2018

In this work, we present a computational study on the antioxidant potential of myricetin 3,4′-di-O-α-L-rhamnopyranoside (Compound M). A density functional theory (DFT) approach with the B3LYP and LC-ωPBE functionals and with both the 6-311G(d,p) and 6-311+G(d,p) basis sets was used. The focus of the investigation was on the structural and energetic parameters including both bond dissociation enthalpies (BDEs) and Ionization Potentials (IPs), which provide information on the potential antioxidant activity. The properties computed were compared with BDEs and IPs available in the literature for myricetin, a compound well known for presenting antioxidant activity (and the parent molecule of the compound of interest in the present work). Myricetin 3,4′-di-O-α-L-rhamnopyranoside presented the lowest BDE to be 79.13 kcal/mol (as determined using B3LYP/6-311G(d,p) in water) while myricetin has quite similar value (within 3.4 kcal/mol). IPs computed in the gas phase [B3LYP/6- 311G(d,p)] are 157.18 kcal/mol and 161.4 kcal/mol for myricetin 3,4′-di-O-α-L- rhamnopyranoside and myricetin, respectively. As the values of BDEs are considerably lower than the ones probed for IPs (in the gas phase or in any given solvent environment), the hydrogen atom transfer mechanism is preferred over the single electron transfer mechanism. The BDEs obtained suggest that myricetin 3,4′-di-O-α-L-rhamnopyranoside can present antioxidant potential as good as the parent molecule myricetin (a well known antioxidant). Therefore, experimental tests on the antioxidant activity of Compound M are encouraged.