title: Experimental and molecular docking investigations on the inclusion mechanism of the complex of phloridzin and hydroxypropyl-β-cyclodextrin.
abstract: Phloridzin is a nutraceutical. Its use in food, medicine and cosmetics is limited because of its low aqueous solubility and stability limits, but it can be improved by complexing with cyclodextrins. In this study, we investigated the inclusion mechanism between phloridzin and hydroxylpropyl-β-cyclodextrin (HP-β-CD) using isothermal titration calorimetry (ITC), ultraviolet-visible spectrometry (UV), infrared spectrometry (IR), proton nuclear magnetic resonance spectroscopy ((1)H NMR) and molecular docking simulations. The ITC results found that the equilibrium binding constant of HP-β-CD with phloridzin was higher than that of β-CD. Their inclusion was a spontaneous process with negative ΔG, ΔH and ΔS values. UV spectra showed that the aqueous solubility of phloridzin was enhanced by HP-β-CD. Our IR analysis verified the inclusion complexation of phloridzin into the HP-β-CD cavity. The Autodock determined that the substitution distribution of HP-β-CD influenced not only the orientation and depth degree of phloridzin within the cavity, but also the binding energies.
authors.affiliation: Zhengzhou Fruit Research Institute, Chinese Academy of Agricultural Sciences, Zhengzhou 450009, China. Electronic address: zhangchunling@caas.cn.
authors.forename: Chun-Ling
authors.initials: CL
authors.lastname: Zhang
authors.affiliation: Zhengzhou Fruit Research Institute, Chinese Academy of Agricultural Sciences, Zhengzhou 450009, China. Electronic address: liujiechao@caas.cn.
authors.forename: Jie-Chao
authors.initials: JC
authors.lastname: Liu
authors.affiliation: Zhengzhou Fruit Research Institute, Chinese Academy of Agricultural Sciences, Zhengzhou 450009, China. Electronic address: yangwenbo@caas.cn.
authors.forename: Wen-Bo
authors.initials: WB
authors.lastname: Yang
authors.affiliation: Zhengzhou Fruit Research Institute, Chinese Academy of Agricultural Sciences, Zhengzhou 450009, China. Electronic address: chendalei@caas.cn.
authors.forename: Da-Lei
authors.initials: DL
authors.lastname: Chen
authors.affiliation: Zhengzhou Fruit Research Institute, Chinese Academy of Agricultural Sciences, Zhengzhou 450009, China. Electronic address: jiaozhonggao@caas.cn.
authors.forename: Zhong-Gao
authors.initials: ZG
authors.lastname: Jiao
mesh_terms: D000073738:2-Hydroxypropyl-beta-cyclodextrin; D002151:Calorimetry; D009682:Magnetic Resonance Spectroscopy; D062105:Molecular Docking Simulation; D010695:Phlorhizin / Q000737:chemistry*; D012995:Solubility; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D047392:beta-Cyclodextrins / Q000737:chemistry*
chemical_list: D047392:beta-Cyclodextrins; D000073738:2-Hydroxypropyl-beta-cyclodextrin; D010695:Phlorhizin
keywords: Complex; Hydroxypropyl-β-cyclodextrin; Molecular docking; Phloridzin