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

Food Chem. 2017 Oct 1:232:177-184. doi: 10.1016/j.foodchem.2017.04.027. Epub 2017 Apr 6.

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 (KF=606.65±30.18M-1), the complexation showing a strong dependence on pH and temperature: The complexation constant (KF) 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 1H 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.

Keywords: Cyclodextrins; Fluorescence; Nanoencapsulation; Oxyresveratrol; Resveratrol; Stilbene.

MeSH terms

  • Computational Biology
  • Cyclodextrins / chemistry*
  • Entropy
  • Molecular Docking Simulation
  • Temperature
  • Thermodynamics

Substances

  • Cyclodextrins