Sugar moiety has a synergistic effect on hydroxylated xanthone for better antioxidant activity of mangiferin

Sugar moiety has a synergistic effect on hydroxylated xanthone for better antioxidant activity of mangiferin

The structure–antioxidant relationship of mangiferin was elucidated by means of quantum chemistry calculations. The density functional theory level of theory was used for antioxidant pharmacophore selection. According to the obtained geometry by using the DFT/B3LYP/6-31+G(d,p) values, HOMO, ionizati...

Full description

Saved in:
Bibliographic Details
Published in:Medicinal chemistry research Vol. 27; no. 4; pp. 1276 - 1282
Main Authors: da Veiga, Andrex Augusto Silva, de Jesus Chaves Neto, Antonio Maia, da Silva, Albérico Borges Ferreira, Herculano, Anderson Manoel, Oliveira, Karen Renata Matos, dos Santos Borges, Rosivaldo
Format: Journal Article
Language:English
Published: New York Springer US 01-04-2018
Springer Nature B.V
Subjects:
Antioxidants
Biochemistry
Biomedical and Life Sciences
Biomedicine
Catechol
Cell Biology
Density distribution
Density functional theory
Electron transfer
Energy distribution
Energy of dissociation
Free energy
Heat of formation
Hydrogen
Hydrogen bonds
Ionization
Ionization potentials
Original Research
Pharmacology
Pharmacology/Toxicology
Quantum chemistry
Resorcinol
Sugar
Synergistic effect
Mangiferin derivatives
DFT
Xanthones
Antioxidant
Mangiferin
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The structure–antioxidant relationship of mangiferin was elucidated by means of quantum chemistry calculations. The density functional theory level of theory was used for antioxidant pharmacophore selection. According to the obtained geometry by using the DFT/B3LYP/6-31+G(d,p) values, HOMO, ionization potential, bond dissociation energy, stabilization energy, and spin density distribution, the catechol moiety is more important for the antioxidant capacity than the resorcinol moiety. However, the sugar is a strong electron-withdrawing group due to its hydrogen bond formation with the resorcinol moiety of xanthone ring. The hydrogen transfer is more important for the antioxidant activity than the electron transfer. The hydrogen abstractions in the ortho positions are more favored than the meta positions. Thus, our results show a synergistic effect between xanthone and sugar rings.
ISSN:1054-2523
1554-8120
DOI:10.1007/s00044-018-2147-3