柚皮素/β-环糊精超分子体系的包合行为

doi:10.11938/cjmr20182691

摘要/Abstract

摘要： 本文采用超声法制备了柚皮素（NAR）与β-环糊精（βCD）的包合物.粉末-X射线衍射（XRD）和红外吸收光谱（IR）测定均表明形成的包合物具有不同于主客体的新的结构性质.¹H NMR与ROESY核磁共振（NMR）实验表明NAR以苯环端从βCD的宽口端进入，并形成稳定的超分子包合物.量子化学计算分析NAR/βCD包合物的形成过程表明，驱动力源于焓驱动与氢键弱相互作用力；能隙和结合能分析得到的最优包合模式与NMR研究结果一致；ONIOM分层计算验证了上述结果.分子对接模拟出的最优包合模式也与量子化学计算、NMR的分析结果吻合.本文获取了清晰的NAR/βCD包合物构型及其形成机理，为该超分子药物的定量构效关系研究提供了理论参考.

关键词: 核磁共振(NMR), 量子化学计算, 柚皮素, β-环糊精, 包合物

Abstract: An inclusion complex of naringenin (NAR) and β-cyclodextrin (βCD) was prepared with ultrasonication. Powder X-ray diffraction (XRD) and infrared absorption spectroscopy (IR) indicated that the inclusion complex formed had some new physical/chemical properties. ¹H NMR and ROESY spectroscopy revealed that the stable supramolecular inclusion complex was formed by having the benzene ring of NAR introduced into the big end of the βCD. The formation processes of NAR/βCD inclusion complex were also studied by quantum chemical calculations. It was revealed that enthalpy and hydrogen bonding weak interaction force were the driving forces behind the formation. The optimal inclusion mode obtained from energy gap and binding energy analyses were consistent with the most inclusive mode obtained from molecular docking analysis and the NMR results. These results were further confirmed by ONIOM calculation.

Key words: nuclear magnetic resonance (NMR), quantum chemical calculation, naringenin, β-cyclodextrin, inclusion complex

中图分类号:

O482.53

杨云汉, 杜瑶, 应飞祥, 杨俊丽, 夏大真, 夏福婷, 杨丽娟. 柚皮素/β-环糊精超分子体系的包合行为[J]. 波谱学杂志, 2019, 36(3): 319-330.

YANG Yun-han, DU Yao, YING Fei-xiang, YANG Jun-li, XIA Da-zhen, XIA Fu-ting, YANG Li-juan. Inclusion Behavior of Naringenin/β-Cyclodextrin Supramolecular Complex[J]. Chinese Journal of Magnetic Resonance, 2019, 36(3): 319-330.

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