title: Interaction of cinnamic acid derivatives with β-cyclodextrin in water: experimental and molecular modeling studies.
abstract: Cyclodextrins (CDs) can be used to improve the solubility and stability of cinnamic acid derivatives (CAs). However, there was no detailed report about understanding the effects of the substituent groups in the benzene ring on the inclusion behavior between CAs and CDs in aqueous solution. Here, the interaction of β-CD with CAs, including caffeic acid, ferulic acid, and p-coumaric acid, in water was investigated by phase-solubility method, UV, fluorescence, and (1)H NMR spectroscopy, together with ONIOM (our Own N-layer Integrated Orbital molecular Mechanics)-based QM/MM (Quantum Mechanics/Molecular Mechanics) calculations. Experimental results demonstrated that CAs could form 1:1 stoichiometric inclusion complex with β-CD by non-covalent bonds, and that the maximum apparent stability constants were found in caffeic acid (176M(-1)) followed by p-coumaric acid (160M(-1)) and ferulic acid (133M(-1)). Moreover, our calculations reasonably illustrated the binding orientations of β-CD with CAs determined by experimental observations.
authors.affiliation: School of Food Science, Henan Institute of Science and Technology, Xinxiang 453003, PR China; Key Laboratory of Biorheological Science and Technology, Ministry of Education, School of Bioengineering, Chongqing University, Chongqing 400044, PR China.
authors.forename: Benguo
authors.initials: B
authors.lastname: Liu
authors.affiliation: School of Food Science, Henan Institute of Science and Technology, Xinxiang 453003, PR China.
authors.forename: Jie
authors.initials: J
authors.lastname: Zeng
authors.affiliation: Key Laboratory of Biorheological Science and Technology, Ministry of Education, School of Bioengineering, Chongqing University, Chongqing 400044, PR China.
authors.forename: Chen
authors.initials: C
authors.lastname: Chen
authors.affiliation: Key Laboratory of Biorheological Science and Technology, Ministry of Education, School of Bioengineering, Chongqing University, Chongqing 400044, PR China.
authors.forename: Yonglan
authors.initials: Y
authors.lastname: Liu
authors.affiliation: School of Food Science, Henan Institute of Science and Technology, Xinxiang 453003, PR China.
authors.forename: Hanjun
authors.initials: H
authors.lastname: Ma
authors.affiliation: School of Food Science, Henan Institute of Science and Technology, Xinxiang 453003, PR China.
authors.forename: Haizhen
authors.initials: H
authors.lastname: Mo
authors.affiliation: Key Laboratory of Biorheological Science and Technology, Ministry of Education, School of Bioengineering, Chongqing University, Chongqing 400044, PR China. Electronic address: gzliang@cqu.edu.cn.
authors.forename: Guizhao
authors.initials: G
authors.lastname: Liang
mesh_terms: D002934:Cinnamates / Q000737:chemistry*; D003505:Cyclodextrins / Q000737:chemistry*; D008958:Models, Molecular; D014867:Water / Q000737:chemistry*
chemical_list: D002934:Cinnamates; D003505:Cyclodextrins; D014867:Water; C029010:cinnamic acid
keywords: Cinnamic acid derivatives (CAs); Inclusion complex; ONIOM (our Own N-layer Integrated Orbital molecular Mechanics) calculations; β-Cyclodextrin (β-CD)