背景:三种多酚化合物的抗氧化性能(鼠尾草酚,环西醇,使用密度泛函理论(DFT)计算在6-311G(d,p)以评估它们的抗氧化活性。与SET-PT相关的反应焓,SPLET,使用CPCM(导体状极化连续体)模型分析了气体和不同溶剂中的HAT机理。对于所有可能的氢供体位点,相应的参数(BDE,AIP,PDE,PA,ETE,HOMO,和LUMO)和反应性指数(IPE,EA,X,η,S,和ω)也进行了评估。计算结果表明,衍生物12-OH,11-OH,4\'-哦,和3'-OH具有最低的抗氧化活性。结果也表明,鼠尾草,环西醇,与抗坏血酸相比,木犀草素具有更高的反应性,可以被认为是更好的抗氧化剂。根据研究,邻苯二酚基团是影响所研究化合物抗氧化活性的关键。在这项工作中,理论上预测的抗氧化剂效率顺序与QSAR(定量结构-活性关系)数据非常吻合。研究结果表明,在真空以及苯介质中。HAT将是最有效的机制;相比之下,极性介质中的热力学平衡方法是SPLET机制。同样,对接建模的结果证实,所选分子对谷胱甘肽-S-转移酶(GSTs)受体具有高抑制活性.此外,它们具有非常重要的药代动力学,化学,和生物概况。最后,所有结果表明,这三种天然分子具有良好的药代动力学特征,特别是对生物膜的生物利用度和渗透性。
方法:本次调查中使用的软件包是Gaussian16,DiscoverystudioVisualizer,和AutoDockvina。这三种化合物(鼠尾草酚,环西醇,以6-311++G(d,P).通过振动分析建立了优化结构(即,频率集中没有虚频率)。所有焓均为零点(ZPE)校正。在298.15K和1个大气压下进行振动频率计算,以确定所研究反应的热力学特性。描述符与真空和各种溶剂中研究分子的抗氧化机制有关。AutoDockvina使用分子对接来评估和评估标题化合物作为利用适当受体蛋白的潜在抗氧化药物的相容性。考虑了在苯(lot=2.27)和水(lot=78.39)介质中的溶剂化作用。此外,还考虑了甲醇溶剂(炭黑=32.61),以与经验数据进行比较.
BACKGROUND: The antioxidant properties of the three polyphenolic compounds (
carnosol, cirsiliol, and luteolin) of Salvia officinalis L. were investigated employing the density functional theory (DFT) calculations at the B3LYP of basis set at 6-311 + + G (d, p) in order to evaluate their antioxidant activity. The enthalpies of reactions associated with the SET-PT, SPLET, and HAT mechanisms were analyzed in gas and in different solvents using the CPCM (conductor-like polarizable continuum) model. For all possible hydrogen donor sites, the corresponding parameters (BDE, AIP, PDE, PA, ETE, HOMOs, and LUMOs) and reactivity indices (IPE, EA, Χ, η, S, and ω) were also evaluated. The calculated results showed that derivatives 12-OH, 11-OH, 4\'-OH, and 3\'-OH had the lowest antioxidant activity. The results showed as well that
carnosol, cirsiliol, and luteolin have higher reactivity compared to ascorbic acid and could be considered better antioxidants. According to research, the catechol group is crucial in influencing the studied compounds antioxidant activity. The theoretically predicted order of antioxidant efficiencies in this work agrees well with the QSAR (quantitative structure-activity relationship) data. The findings show that in the vacuum as well as benzene media. HAT would be the most effective mechanism; in contrast, the thermodynamic equilibrium approach in polar media is the SPLET mechanism. Likewise, the outcomes of the docking modeling confirm that the selected molecules have high inhibitory activity to glutathione-S-transferases (GSTs) receptors. Moreover, they have very important pharmacokinetic, chemical, and biological profiles. Finally, all the results show that the three natural molecules have good pharmacokinetic profiles, particularly the bioavailability and permeability toward biological membranes.
METHODS: The software packages used in this investigation are Gaussian 16, Discovery studio Visualizer, and AutoDock vina. The three compounds (
carnosol, cirsiliol, and luteolin) of Salvia officinalis L. were optimized with DFT/B3LYP of basis set at 6-311 + + G (d, p). The optimized structures were established via vibrational analysis (i.e., no imaginary frequencies in the frequency set). All enthalpies were zero-point (ZPE) corrected. Vibrational frequency calculations were performed at 298.15 K and 1 atmosphere pressure to determine the thermodynamic characteristics of the investigated reactions. The descriptors were associated with the antioxidant mechanisms for investigated molecules in vacuum and in various solvents. The molecular docking was used by AutoDock vina to estimate and evaluate the title compounds compatibility as potential antioxidant drugs utilizing appropriate receptor proteins. The solvation effect in the medium of benzene (ɛ = 2.27) and water (ɛ = 78.39) was taken into account. Furthermore, a methanol solvent (ɛ = 32.61) was also taken into consideration to compare with the empirical data.