Stacking interaction study of trans-resveratrol (trans-3,5,4′-trihydroxystilbene) in solution by nuclear magnetic resonance and Fourier transform infrared spectroscopy

Interactions between aromatic rings or other unsaturated systems, including pi-stacking and face-to-edge complexes, are the origin of many phenomena in both organic and biological chemistry. It is well known that these interactions play an important role in the stabilization of the stereo-structure of DNA and the tertiary structure of many proteins. Trans-resveratrol (trans-3,5,4'-trihydroxystilbene, trans-RSV) is a phytoalexin found in Vitis sp. and in many other plants and food products and has received much attention because of its possible positive health benefits. In this work, the pi-stacking interaction of trans-RSV was studied by nuclear magnetic resonance (NMR) and Fourier transform infrared (FTIR) spectroscopy. In particular, the proton chemical shift dependence of the RSV concentration in the range 2 x 10(-2)-1 x 10(-5) m and temperature were analysed. Moreover, the dynamics of the supramolecular aggregates were studied by nuclear spin relaxation data. Copyright (C) 2008 John Wiley & Sons, Ltd.