四种白藜芦醇衍生物分子的光谱和抗氧化性质计算研究
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摘要
使用密度泛函理论B3LYP-D3方法,对四种白藜芦醇衍生物的分子结构、红外光谱、电子吸收光谱及抗氧化活性进行计算研究,并基于Tomasi的极化统一场模型(PCM)讨论电子吸收光谱及抗氧化活性的溶剂效应。结果表明,四种化合物电子吸收光谱都是π-π~*跃迁,随着溶剂极性的增大,λ_(max)变化不明显,电离能(IP)在逐渐减小,抗氧化活性增强;对白藜芦醇分子中C=C烷基化修饰后的衍生物降低了分子的共平面性,提高了分子的电离能(IP)和能隙(E_(gap)),使得化合物a、b、c、d抗氧化活性略低于白藜芦醇,但具有更好的稳定性。
The molecular structures, IR spectra, electronic absorption spectra and antioxidant activity of four kinds of resveratrol derivatives were calculated by using the density functional theory B3LYP-D3 method. The polarized continuum models(PCM) of Tomasi were used to discuss the solvent effects. The computational results showed that, the absorption spectra could be assigned to a charge transfer(CT) state with a π-π~* character. With the increase of solvent polarity, the change of λ_(max) is not obvious, the ionization energy(IP) decreased gradually, and the antioxidant activity increased. Alkylation of C = C reduced the coplanarity of the molecule, meanwhile, it increased the ionization energy(IP) and energy gap(Egap), resulted in the antioxidant activity of compounds a, b, c and d was slightly lower than resveratrol, but with better stability.
The molecular structures, IR spectra, electronic absorption spectra and antioxidant activity of four kinds of resveratrol derivatives were calculated by using the density functional theory B3LYP-D3 method. The polarized continuum models(PCM) of Tomasi were used to discuss the solvent effects. The computational results showed that, the absorption spectra could be assigned to a charge transfer(CT) state with a π-π~* character. With the increase of solvent polarity, the change of λ_(max) is not obvious, the ionization energy(IP) decreased gradually, and the antioxidant activity increased. Alkylation of C = C reduced the coplanarity of the molecule, meanwhile, it increased the ionization energy(IP) and energy gap(Egap), resulted in the antioxidant activity of compounds a, b, c and d was slightly lower than resveratrol, but with better stability.
引文
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[3]Keylor Mitchell H.,Matsuura Bryan S.,Stephenson Corey R.J.Chemistry and Biology of Resveratrol-Derived Natural Products[J].Chem.Rev.2015,115:8976-9027.
[4]杜成,任玉杰,王庆伟,等.白藜芦醇衍生物的合成及抑制宫颈癌HeLa细胞肿瘤活性[J].有机化学,2013,33:1279-1283.
[5]陈笑,金欣.白藜芦醇类似物及衍生物的研究进展[J].绍心文理学院学报,2015,35(9):46-50.
[6]Akihiro H.,Kazuo T.,Kiyoshi F.Pharmaceutical composition for prophylaxis and/or treatment of corneal and conjunctival diseases or presbyopia containing stilbene compound as active ingredient:US,20170246122A1[P]2017.8.31.
[7]邵学广,朱维良,吴海龙,等.计算(机)化学学科进展(2011~2013)[J].化学通报,2014,77(7):692-698.
[8]Goerigk Lars.How Do DFT-DCP,DFT-NL,and DFT-D3 Compare for the Description of London-Dispersion Effects in Conformers and General Thermochemistry?[J].Journal of Chemical Theory and Computation,2014,10(3):968-980.
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