Mechanism of Antioxidant Activity of Betanin, Betanidin and Respective C15-Epimers via Shape Theory, Molecular Dynamics, Density Functional Theory and Infrared Spectroscopy
Open Access
Abstract
Betanin and betanidin are compounds with extensive interest; they are effectively free radical scavengers. The present work aims to elucidate the differences between the mechanism of the antioxidant activity of betanin, betanidin, and their respective C15-epimers. Shape Theory establishes comparisons between the molecules’ geometries and determines parallelisms with the descriptors BDE, PA, ETE IP, PDE, and infrared spectra (IR) obtained from the molecule simulations. Furthermore, the molecules were optimized using the B3LYP/6-31+G(d,p) protocol. Finally, the molecular docking technique analyzes the antioxidant activity of the compounds in the complex with the therapeutic target xanthine oxidase (XO), based on a new proposal for the geometrical arrangement of the ligand atoms in the framework of Shape Theory. The results obtained indicate that the SPLET mechanism is the most favorable in all the molecules studied and that the first group that loses the hydrogen atom in the four molecules is the C17COOH, presenting less PA the isobetanidin. Furthermore, regarding the molecular docking, the interactions of these compounds with the target were favorable, standing out to a greater extent the interactions of isobetanidin with XO, which were analyzed after applying molecular dynamics.Keywords
This publication has 66 references indexed in Scilit:
- Biosynthesis of betalains: yellow and violet plant pigmentsTrends in Plant Science, 2013
- Generalised Shape Theory Via Pseudo-Wishart DistributionSankhya A, 2013
- Febuxostat inhibition of endothelial-bound XO: Implications for targeting vascular ROS productionFree Radical Biology and Medicine, 2011
- Substrate Orientation and Catalytic Specificity in the Action of Xanthine OxidaseJournal of Biological Chemistry, 2010
- AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreadingJournal of Computational Chemistry, 2009
- AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibilityJournal of Computational Chemistry, 2009
- An Au(III) complex of glycyl- S -serine: a linear polarized IR and 1H- and 13C-NMR investigationJournal of Coordination Chemistry, 2007
- A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to isotropic and anisotropic dielectricsThe Journal of Chemical Physics, 1997
- VMD: Visual molecular dynamicsJournal of Molecular Graphics, 1996
- Multivariate Aspects of Shape TheoryThe Annals of Statistics, 1993