A Theoretical Study on the Antioxidant Activity of Piceatannol and Isorhapontigenin Scavenging Nitric Oxide and Nitrogen Dioxide Radicals

The antioxidant activity of naturally occurring stilbene compounds piceatannol (PIC) and isorhapontigenin (ISO) scavenging two free radicals (NO and NO2) were studied using density functional theory (DFT) method. Four reaction mechanisms have been considered: hydrogen atom transfer (HAT), radical ad...

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Bibliographic Details
Published in:PloS one 2017-01, Vol.12 (1), p.e0169773-e0169773
Main Authors: Lu, Yang, Wang, AiHua, Shi, Peng, Zhang, Hui
Format: Article
Language:English
Subjects:
Algorithms
Anti-infective agents
Antioxidants
Antioxidants (Nutrients)
Antioxidants - chemistry
Antioxidants - pharmacology
Biology and Life Sciences
Chemical properties
Density functional theory
DNA damage
Electron transfer
Energy
Engineering
Free Radical Scavengers - pharmacology
Free radicals
Hydrogen
Hydrogen atoms
Models, Molecular
Models, Theoretical
Molecular Conformation
Nitric oxide
Nitric Oxide - chemistry
Nitric Oxide - metabolism
Nitrogen dioxide
Nitrogen Dioxide - chemistry
Nitrogen Dioxide - metabolism
Oxidation
Physical chemistry
Physical Sciences
Piceatannol
Polyphenols
Prevention
Reaction mechanisms
Scavenging
Solvents
Stilbene
Stilbenes - chemistry
Stilbenes - pharmacology
Studies
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Summary:The antioxidant activity of naturally occurring stilbene compounds piceatannol (PIC) and isorhapontigenin (ISO) scavenging two free radicals (NO and NO2) were studied using density functional theory (DFT) method. Four reaction mechanisms have been considered: hydrogen atom transfer (HAT), radical adduct formation (RAF), single electron transfer (SET), and sequential proton loss electron transfer (SPLET). The reaction channels in water solution were traced independently, and the respective thermodynamic and kinetic parameters were obtained. We found PIC and ISO scavenge NO mainly through RAF mechanism, and scavenge NO2 through HAT mechanism. The capacity of PIC scavenging NO2 is much higher than ISO, but the reactivity of scavenging NO is lower than ISO.
ISSN:1932-6203
1932-6203
DOI:10.1371/journal.pone.0169773