Determination of stoichiometric coefficients and apparent formation constants for beta-cyclodextrin complexes of trans-resveratrol using reversed-phase liquid chromatography

J Chromatogr A. 2006 Dec 1;1135(2):158-65. doi: 10.1016/j.chroma.2006.09.013. Epub 2006 Nov 2.

Abstract

The complexation of trans-resveratrol with beta-cyclodextrin (beta-CD) was investigated using reversed-phase liquid chromatography and mobile phases to which beta-CD was added. The decrease in the retention times with increasing concentrations of beta-CD (0-2.5 mM) showed that trans-resveratrol forms a 1:1 complex with beta-CD, while the apparent formation constants (K(F)) were strongly dependent of the water-methanol proportion of the mobile phase employed. A slight decrease in K(F) was observed at 50-55% water in the mobile phase but a large increase from 55 to 70% water. The values of K(F) for the trans-resveratrol-beta-CD interaction decreased when the temperature was raised from 20 to 37 degrees C. In order to gain information about the mechanism aspect of the trans-resveratrol affinity for beta-CD, the thermodynamic parameters of the complexation were obtained. Complex formation of trans-resveratrol with beta-CD (DeltaG degrees =-17.01 kJ/mol) is largely driven by enthalpy (DeltaH degrees = -30.62 kJ/mol) and slightly entropy changes (DeltaS degrees = -45.68 J/mol K).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, High Pressure Liquid / methods*
  • Methanol
  • Resveratrol
  • Spectrophotometry, Ultraviolet
  • Stilbenes / chemistry*
  • Thermodynamics
  • Water
  • beta-Cyclodextrins / chemistry*

Substances

  • Stilbenes
  • beta-Cyclodextrins
  • Water
  • betadex
  • Resveratrol
  • Methanol