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

Biomedicines ◽  
2021 ◽  
Vol 9 (3) ◽  
pp. 271
Author(s):  
Qingjun Kong ◽  
Qingzhi Zeng ◽  
Jia Yu ◽  
Hongxi Xiao ◽  
Jun Lu ◽  
...  

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.

The Analyst ◽  
2021 ◽  
Author(s):  
Jing Zhou ◽  
Dan Yang ◽  
Guohui Liu ◽  
Siying Li ◽  
Wennan Feng ◽  
...  

Guanine (G) oxidation products, such as 8-hydroxy-2′-deoxyguanosine (8-OHdG) and 8-oxo-guanine (8-OXOG), have been widely studied as promising biomarkers for DNA oxidative damage.


2007 ◽  
Vol 189 (15) ◽  
pp. 5504-5514 ◽  
Author(s):  
Signe Saumaa ◽  
Andres Tover ◽  
Mariliis Tark ◽  
Radi Tegova ◽  
Maia Kivisaar

ABSTRACT Oxidative damage of DNA is a source of mutation in living cells. Although all organisms have evolved mechanisms of defense against oxidative damage, little is known about these mechanisms in nonenteric bacteria, including pseudomonads. Here we have studied the involvement of oxidized guanine (GO) repair enzymes and DNA-protecting enzyme Dps in the avoidance of mutations in starving Pseudomonas putida. Additionally, we examined possible connections between the oxidative damage of DNA and involvement of the error-prone DNA polymerase (Pol)V homologue RulAB in stationary-phase mutagenesis in P. putida. Our results demonstrated that the GO repair enzymes MutY, MutM, and MutT are involved in the prevention of base substitution mutations in carbon-starved P. putida. Interestingly, the antimutator effect of MutT was dependent on the growth phase of bacteria. Although the lack of MutT caused a strong mutator phenotype under carbon starvation conditions for bacteria, only a twofold increased effect on the frequency of mutations was observed for growing bacteria. This indicates that MutT has a backup system which efficiently complements the absence of this enzyme in actively growing cells. The knockout of MutM affected only the spectrum of mutations but did not change mutation frequency. Dps is known to protect DNA from oxidative damage. We found that dps-defective P. putida cells were more sensitive to sudden exposure to hydrogen peroxide than wild-type cells. At the same time, the absence of Dps did not affect the accumulation of mutations in populations of starved bacteria. Thus, it is possible that the protective role of Dps becomes essential for genome integrity only when bacteria are exposed to exogenous agents that lead to oxidative DNA damage but not under physiological conditions. Introduction of the Y family DNA polymerase PolV homologue rulAB into P. putida increased the proportion of A-to-C and A-to-G base substitutions among mutations, which occurred under starvation conditions. Since PolV is known to perform translesion synthesis past damaged bases in DNA (e.g., some oxidized forms of adenine), our results may imply that adenine oxidation products are also an important source of mutation in starving bacteria.


Biomolecules ◽  
2019 ◽  
Vol 9 (7) ◽  
pp. 268
Author(s):  
Qingjun Kong ◽  
Xueyan Ren ◽  
Jianrui Qi ◽  
Jia Yu ◽  
Jun Lu ◽  
...  

Stilbenes, particularly resveratrol and resveratrol dimers, could effectively quench singlet oxygen (1O2). It was reported that both resorcinol and carbon-carbon double bond quenching 1O2 can participate in the mechanism. However, it is still not clear which structure plays a dominant role in quenching 1O2. To investigate the characteristic structure in the mechanism of quenching 1O2, the resveratrol, pterostilbene and piceatannol quenching 1O2 abilities were compared by UHPLC-QTOF-MS2 and UHPLC-QQQ-MS2. Results showed that catechol, carbon-carbon double bond and resorcinol participated in the quenching of 1O2. Catechol ring plays a leading role in the mechanism, and the contribution of the structures in quenching 1O2 activity are as follows: catechol ring > carbon-carbon double bond > resorcinol ring, which is supported by the calculation of energy. Our findings will contribute to the future screening of stilbenes with higher activity, and those stilbenes may have great therapeutic potential in 1O2-mediated diseases.


Toxicology ◽  
2013 ◽  
Vol 314 (2-3) ◽  
pp. 229-237 ◽  
Author(s):  
Ratan Singh Ray ◽  
Syed Faiz Mujtaba ◽  
Ashish Dwivedi ◽  
Neera Yadav ◽  
Ankit Verma ◽  
...  

1996 ◽  
Vol 17 (5) ◽  
pp. 1183-1185 ◽  
Author(s):  
Lucymara F. Agnez ◽  
Regina L.Costa de Oliveira ◽  
Paolo Di Mascio ◽  
Carlos F.M. Menck

2016 ◽  
Vol 2016 ◽  
pp. 1-7 ◽  
Author(s):  
Jelena Petrović ◽  
Dušanka Stanić ◽  
Gordana Dmitrašinović ◽  
Bosiljka Plećaš-Solarović ◽  
Svetlana Ignjatović ◽  
...  

Sedentary lifestyle is highly associated with increased risk of cardiovascular disease, obesity, and type 2 diabetes. It is known that regular physical activity has positive effects on health; however several studies have shown that acute and strenuous exercise can induce oxidative stress and lead to DNA damage. As magnesium is essential in maintaining DNA integrity, the aim of this study was to determine whether four-week-long magnesium supplementation in students with sedentary lifestyle and rugby players could prevent or diminish impairment of DNA. By using the comet assay, our study demonstrated that the number of peripheral blood lymphocytes (PBL) with basal endogenous DNA damage is significantly higher in rugby players compared to students with sedentary lifestyle. On the other hand, magnesium supplementation significantly decreased the number of cells with high DNA damage, in the presence of exogenous H2O2, in PBL from both students and rugby players, and markedly reduced the number of cells with medium DNA damage in rugby players compared to corresponding control nonsupplemented group. Accordingly, the results of our study suggest that four-week-long magnesium supplementation has marked effects in protecting the DNA from oxidative damage in both rugby players and in young men with sedentary lifestyle. Clinical trial is registered at ANZCTR Trial Id:ACTRN12615001237572.


2007 ◽  
Vol 2 ◽  
pp. 117739010700200 ◽  
Author(s):  
Tamara Zoltan ◽  
Franklin Vargas ◽  
Carla Izzo

We have determined and quantified spectrophotometrically the capacity of producing reactive oxygen species (ROS) as 1O2 during the photolysis with UV-A light of 5 new synthesized naphthyl ester derivates of well-known quinolone antibacterials (nalidixic acid (1), cinoxacin (2), norfloxacin (3), ciprofloxacin (4) and enoxacin (5)). The ability of the naphthyl ester derivatives (6-10) to generate singlet oxygen were detecting and for the first time quantified by the histidine assay, a sensitive, fast and inexpensive method. The following tendency of generation of singlet oxygen was observed: compounds 7 >10 > 6 > 8 > 9 >> parent drugs 1-5.


2007 ◽  
Vol 62 (11-12) ◽  
pp. 833-838 ◽  
Author(s):  
Violeta B. Velikova ◽  
Aglika M. Edreva ◽  
Tsonko D. Tsonev ◽  
Hamlyn G. Jones

This paper demonstrates for the first time that plant metabolites of the phenylamide type, conjugates of putrescine with hydroxycinnamic acids (p-coumaric, caffeic and ferulic), possess 1O2 quenching properties. Data were obtained confirming that their acidic parent compounds were also able to quench 1O2, as did polyamines (putrescine, spermidine and spermine), and that this ability depends on the number of amino groups. Potentiation of the 1O2 quenching ability of the conjugates relative to both parent components was established. The importance of polyamines and phenylamides in the plant non-enzymatic antioxidant defence at sites of intensive 1O2 generation, such as the photosynthetic centers, was suggested.


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