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Experimental and computational studies of naringin/cyclodextrin inclusion complexation

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Abstract

This study investigated inclusion formation and the physicochemical properties of naringin/cyclodextrin through a combined computational and experimental approach. Molecular dynamics simulations were applied to investigate the thermodynamics and geometry of naringin/cyclodextrin cavity docking. The complexes were investigated by UV, FT-IR, DSC, XRD, SEM, 2D-NOSEY and 1H-NMR analyses. Clearly visible protons belonging to naringin and chemical shift displacements of the H3 and H5 protons in cyclodextrin were anticipated in the formation of an inclusion complex. Naringin solubility increased linearly with increasing cyclodextrin concentration (displaying an AL profile). The simulations indicated that the phenyl group of naringin was located deep within the cyclodextrin cavity, while the glycoside group of naringin was on the plane of the wider rim of cyclodextrin. The simulation and molecular modeling results indicate that (2-hydroxypropyl)-β-cyclodextrin (HP-β-CD) provided the more stable inclusion complex. This result was also in good concordance with the stability constants that had been determined by the phase solubility method. The consistency of the computational and experimental results indicates their reliability.

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Acknowledgements

This work was supported by the Program for Chang jiang Scholars and Innovative Research Team in University (No. IRT13095), the National Natural Science Foundation of China (Nos. 21442006, 21262043 and 20902079). The authors thank the High Performance Computing Center at Yunnan University for use of the high performance computing platform.

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    Authors and Affiliations

    1. Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), The Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, People’s Republic of China

      Hui-Huan Yan, Jian-Qiang Zhang, Si-Hao Ren, Xiao-Guang Xie, Yi Jin & Jun Lin

    2. Advanced Analysis and Measurement Center, Yunnan University, Kunming, 650091, People’s Republic of China

      Rong Huang

    3. Department of Biology and Chemistry, Puer College, Puer, 665000, Yunnan, People’s Republic of China

      Jian-Qiang Zhang

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    Correspondence to Rong Huang, Yi Jin or Jun Lin.

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    Hui-Huan Yan, Jian-Qiang Zhang have contributed equally to this work.

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    Yan, HH., Zhang, JQ., Ren, SH. et al. Experimental and computational studies of naringin/cyclodextrin inclusion complexation. J Incl Phenom Macrocycl Chem 88, 15–26 (2017). https://doi.org/10.1007/s10847-017-0704-x

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