Mechanism of Antioxidant Activity of Betanin, Betanidin and Respective C15-Epimers via Shape Theory, Molecular Dynamics, Density Functional Theory and Infrared Spectroscopy

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 comparison...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2022-03, Vol.27 (6), p.2003
Main Authors: Ramirez-Velasquez, Iliana María, Velez, Ederley, Bedoya-Calle, Alvaro, Caro-Lopera, Francisco Jose
Format: Article
Language:English
Subjects:
antioxidant mechanisms
Antioxidants
Antioxidants - chemistry
Antioxidants - pharmacology
Betacyanins - chemistry
Density Functional Theory
DFT calculations
Free radicals
Geometry
Hydrogen atoms
Infrared spectra
Infrared spectroscopy
Molecular docking
Molecular Docking Simulation
Molecular dynamics
Molecular Dynamics Simulation
Oxidation
shape theory
Spectrum Analysis
Therapeutic targets
Xanthine oxidase
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Summary: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27062003