Quinolone and isoquinolone alkaloids: the structural-electronic effects and the antioxidant mechanisms
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ORIGINAL RESEARCH
Quinolone and isoquinolone alkaloids: the structural-electronic effects and the antioxidant mechanisms Nguyen Tien Dung 1 & Do Minh Thanh 2 & Nguyen Thi Huong 3 & Phan Thi Thuy 4 & Nguyen Thi Hoan 5 & Dinh Thi Mai Thanh 6 & Nguyen Van Trang 2 & Ninh The Son 7 Received: 1 May 2020 / Accepted: 28 July 2020 # Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract Quinolone and isoquinolone alkaloids, which were found in the plant kingdom, are now potential antioxidants. In this case study, a quantum calculated procedure utilizing the density functional theory (DFT)-B3LYP method coupled with basis set 6–311++ G(d,p) was used to investigate free-radical quenching activity of alkaloidal quinolone viridicatol (1) and alkaloidal isoquinolone 5-hydroxy-8-methoxy-4-phenylisoquinolin-1(2H)-one (2). On the basis of thermodynamic perspective and from the findings, the powerful antioxidative potential of these two title compounds in the liquids water, methanol, and especially DMSO was mostly driven by the proton affinity (PA), consistent with the SPLET (sequential proton loss electron transfer) mechanism. The environmental effect has also been investigated, and the antioxidative action caused by O–H bond disruption is easier than that of N–H bond in both the gaseous phase and liquids. In the gaseous phase, the combinations of two studied compounds and •OOH/ DPPH radicals are kinetic evidence, including two intermediates and one transition state. From thermodynamic and kinetic viewpoints, compound 2 can be seen as a therapeutically useful agent in antioxidative treatment because of the role of a 5hydroxy group. Keywords Quinolone . Isoquinolone . Density functional theory . Antioxidative
Introduction Reactive oxygen species (ROS) has considerably shown as a chemical species consisting of oxygen. The well-known radical agents, such as hydroxyls, peroxides, superoxide, singlet oxygen, or alpha-oxygen, are now presenting in inside and outside living organisms [1]. ROS is recognized to be caused by brain injury after ischemic stroke or apoptosis after cerebral
ischemia [2]. ROS cellular overproduction may claim for oxidative stress occurrences and biomolecule damage of normal cells and tissues [3]. Historic documents have contained numerous notes indicating that the application of synthetic substances as traditional antibiotics was often associated with high costs, long treatment durations, and drug failures [4]. Hence, searching for novel antioxidants from medicinal plants
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11224-020-01602-z) contains supplementary material, which is available to authorized users. * Nguyen Van Trang [email protected]
3
Faculty of Chemical Technology, Hanoi University of Industry, 298 Cau Dien, North District Tu Liem, Hanoi, Vietnam
* Ninh The Son [email protected]
4
School of Natural Sciences Education, Vinh University, Vinh, Vietnam
5
Centre for Informatics and Computing, VAST, 18 Hoang Qu
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