Mechanism of Resveratrol Dimers Isolated from Grape Inhibiting 1O2 Induced DNA Damage by UHPLC-QTOF-MS2 and UHPLC-QQQ-MS2 Analyses.

Qingjun Kong,Hongxi Xiao,Jia Yu,Qingzhi Zeng,Jun Lu,Xueyan Ren

doi:10.3390/biomedicines9030271

Qingjun Kong, Hongxi Xiao + Show 4 more

Open Access

https://doi.org/10.3390/biomedicines9030271

Copy DOI

Abstract

Resveratrol dimers have been extensively reported on due to their antioxidative activity. Previous studies revealed that resveratrol dimer has been shown to selectively quench singlet oxygen (1O2), and could protect DNA from oxidative damage. The mechanism of resveratrol dimers protecting DNA against oxidative damage is still not clear. Therefore, in this project, the reactants and products of resveratrol dimers protecting guanine from oxidative damage were qualitatively monitored and quantitatively analyzed by UHPLC-QTOF-MS2 and UHPLC-QQQ-MS2. Results showed that when guanine and resveratrol dimers were attacked by 1O2, mostly resveratrol dimers were oxidized, which protected guanine from oxidation. Resveratrol dimers’ oxidation products were identified and quantified at m/z 467.1134 [M-H]− and 467.1118 [M-H]−, respectively. The resorcinol of resveratrol dimers reacted with singlet oxygen to produce p-benzoquinone, protecting guanine from 1O2 damage. Therefore, it is hereby reported for the first time that the resorcinol ring is the characteristic structure in stilbenes inhibiting 1O2 induced-DNA damage, which provides a theoretical basis for preventing and treating DNA damage-mediated diseases.

Highlights

Oxidative stress refers to the condition in which the oxidative and anti-oxidative effects in the body are out of balance, and free radicals produce negative effects
Resveratrol dimers can prevent 1 O2 induced-DNA damage by replacing guanine to be oxidized by 1 O2
The mechanism is different from the resveratrol monomer, when guanine is attacked by 1 O2

Summary

Introduction

Oxidative stress refers to the condition in which the oxidative and anti-oxidative effects in the body are out of balance, and free radicals produce negative effects It may cause metabolic dysregulation or oxidative damage to cells, tissues, and organs [1]. 1 O2 , as an excited oxygen molecule (1 ∆g ), can be produced by biologically relevant processes in vivo, and by photosensitized oxidations in vitro. This can occur with two of the optogenetic sensitizers, aryloxazinones and thiopurines, which generate 1 O2 at a specific wavelength of UV irradiation.

Methods

Results

Discussion

Conclusion