Inclusion Behavior of Naringenin/β-Cyclodextrin Supramolecular Complex

doi:10.11938/cjmr20182691

Abstract

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

CLC Number:

O482.53

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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