摘要
考查了不同浓度β-环糊精及3种β-环糊精衍生物存在时橙皮苷(Hes)的相溶解度变化情况,研究了环糊精对Hes的增溶作用及机理。研究结果表明,4种环糊精均可有效增溶Hes,其中七-(2,6-二甲基)-β-环糊精(DM-β-CD)具有最大的增溶作用。DM-β-CD可以与Hes形成1∶1型复合物,促进Hes的溶解。当DM-β-CD浓度为5.0×10^-3 mol·L-1时,Hes的相溶解度可由5.2×10^-5 mol·L-1提高至2.85×10^-4 mol·L-1。红外光谱与X-射线粉末衍射数据均表征了DM-β-CD/Hes复合物的形成。分子对接结果表明,Hes的糖苷部分自大口进入并被复合在DM-β-CD疏水性空腔中,主客体之间存在多个氢键与疏水作用。此外,半经验量子化学计算结果表明,DM-β-CD/Hes复合物的形成过程中体系内能发生了显著降低。复合物具有良好的动力学稳定性,主客体位置在30 ns内未发生较大变化。
In this work,solubility changes of hesperidin(Hes)according to the existence of different concentration ofβ-cyclodextrin and its three derivatives were investigated.Both the effect and mechanism of solubility enhancement of Hes by cyclodextrins were studied.The experimental results show that all four cyclodextrins can enhance the solubility of Hes effectively and heptakis-(2,6-dimethyl)-β-cyclodextrin(DM-β-CD)performs the maximum solubility enhancement effect by forming 1∶1 DM-β-CD/Hes complex.With the existence of 5.0×10^-3 mol·L-1 of DM-β-CD,solubility of Hes could be increased from 5.2×10^-5 mol·L-1 to 2.85×10^-4 mol·L-1.Infrared spectroscopy and X-ray powder diffraction have been adopted to characterize the formation of DM-β-CD/Hes complex.Molecular docking results indicate that the glucoside part of Hes can be complexed into the cavity of DM-β-CD and there are several hydrogen bonding and hydrophobic interactions between the host and the guest.Additionally,semiempirical quantum chemistry calculation was applied to the docking results indicating the formation of the DM-β-CD;Hes complex is spontaneous with a negative system energy change.The structure of the complex is stable enough in a 30 ns molecular dynamics simulation and no large structural deformation or position change is observed.
作者
于湛
王诗榕
李天乐
张新宇
刘丽艳
辛士刚
张洪波
YU Zhan;WANG Shirong;LI Tianle;ZHANG Xinyu;LIU Liyan;XIN Shigang;ZHANG Hongbo(College of Chemistry and Chemical Engineering, Shenyang Normal University, Shenyang 110034, China;Tieling Prefectural High School, Tieling 112000, China;Experimental Teaching Center, Shenyang Normal University, Shenyang 110034, China)
出处
《沈阳师范大学学报（自然科学版）》
CAS
2020年第6期499-504,共6页
Journal of Shenyang Normal University:Natural Science Edition
基金
辽宁省教育厅科学研究经费项目(LJC201902,LJC202009)。
关键词
相溶解度
环糊精
橙皮苷
复合物
分子对接
分子动力学
phase solubility
cyclodextrin
hesperidin
complex
molecular docking
molecular dynamics
