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

Molecules

Ederley Velez¹  Francisco Jose Caro-Lopera¹  Alvaro Bedoya-Calle¹  Iliana María Ramirez-Velasquez² 

[1]Faculty of Basic Sciences, University of Medellin, Cra. 8730-65, Medellín 050026, Colombia

[2]Faculty of Exact and Applied Sciences, Instituto Tecnológico Metropolitano ITM, Cll. 7376A-354, Medellín 050034, Colombia

关键词: antioxidant mechanisms;    DFT calculations;    shape theory;    molecular docking;   

DOI  :  10.3390/molecules27062003

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown