Acid–Base Properties of Xanthohumol: A Computational and Experimental Investigation,Journal of Natural Products

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Acid–Base Properties of Xanthohumol: A Computational and Experimental Investigation
Journal of Natural Products ( IF 3.3 ) Pub Date : 2017-11-17 00:00:00 , DOI: 10.1021/acs.jnatprod.7b00530
Marta Arczewska ₁ , Daniel M. Kamiński ₂ , Barbara Gieroba ₃ , Mariusz Gagoś ₃

Affiliation

UV–vis spectrophotometry has been applied to determine acid dissociation constants of the prenylated chalcone xanthohumol. The pK_a values were compared with those derived from pH-metric titrations. The order of the deprotonation site in the xanthohumol molecule was estimated by quantum mechanical calculations as 2′-OH, 4′-OH, and 4-OH. Furthermore, the electronic and spectroscopic properties of xanthohumol have been investigated on the basis of the time-dependent density functional theory (TDDFT). The TDDFT method, combined with a hybrid exchange–correlation functional using the B3LYP and CAM-B3LYP levels of theory in conjunction with the SMD solvation model, was used to optimize all geometries and predict the excitation energies of the neutral form and ionized species of the chalcone depending on pH value. The computed results were in good agreement with the experimental data. Consideration of the acid–base profile in conjunction with other molecular properties has a great importance and has the potential to be used to further improve the bioavailability of xanthohumol.

中文翻译：

黄腐酚的酸碱性质：计算和实验研究

紫外可见分光光度法已被用于测定烯丙基查尔酮黄腐酚的酸解离常数。在P ķ_一将这些值与由pH滴定法得出的值进行比较。通过量子力学计算将黄腐酚分子中去质子化位点的顺序估计为2'-OH，4'-OH和4-OH。此外，基于时变密度泛函理论（TDDFT）研究了黄腐酚的电子和光谱性质。TDDFT方法结合使用B3LYP和CAM-B3LYP理论水平以及SMD溶剂化模型的混合交换-相关函数，可以优化所有几何形状并预测中性形式和离子的电离物种的激发能。查尔酮取决于pH值。计算结果与实验数据吻合良好。

更新日期：2017-11-17

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