The inclusion complex of oxyresveratrol in modified cyclodextrins: A thermodynamic, structural, physicochemical, fluorescent and computational study.

Food Chem

Department of Biochemistry and Molecular Biology-A, Faculty of Biology, University of Murcia, Campus de Espinardo, 30071 Murcia, Spain. Electronic address:

Published: October 2017

AI Article Synopsis

  • The study investigated how oxyresveratrol interacts with modified cyclodextrins (CDs), specifically noting that they form a stable 1:1 complex, with MβCD being the most effective.
  • The stability of the complex is affected by pH and temperature, showing that higher pH and temperature reduce the affinity (as indicated by a lower complexation constant).
  • Thermodynamic analysis revealed negative changes in entropy, enthalpy, and Gibbs free energy, while fluorescence tests indicated enhanced emission of oxyresveratrol upon MβCD addition, and additional structural insights were gained through H NMR and molecular docking studies.

Article Abstract

The interaction between oxyresveratrol (a type of stilbene with high biological activity) and modified cyclodextrins (CDs) was studied. Using HPLC-RP, was seen to form a 1:1 complex with all the CDs tested. The best CD in this respect was MβCD (K=606.65±30.18M), the complexation showing a strong dependence on pH and temperature: The complexation constant (K) decreased as the pH and temperature increased. The thermodynamic parameters studied (ΔH°, ΔS° and ΔG°) showed negative entropy, enthalpy and Gibbs free energy change at 25°C. In addition, fluorescence signal of oxyresveratrol increased when MβCD was added. The oxyresveratrol emission and excitation spectra were obtained for first time. A H NMR was carried out to study the structure of the complex and, DSC studied demonstrated the complexation. A computational study by molecular docking was made to complement the structural study.

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Source
http://dx.doi.org/10.1016/j.foodchem.2017.04.027DOI Listing

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