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26) evidenced an overall quasi coplanar topography for the lowest energy conformation of trans-resveratrol; however, different orientations of the phenyl rings were accessible at a low energy cost (ΔE ca. 0.1-1.8 kcal/mol) also including the perpendicular ones with respect to the stilbenic double bond. The cis-configuration of the stilbenic double bond destabilizes the coplanar arrangement and forces one of the phenyl rings in an almost perpendicular orientation with respect to the stilbenic double bond. Analysis of dihydroresveratrol evidenced the presence of several quasi-transoid conformations of comparable energy (ΔE between 0.5 and 1.7 kcal/mol) which were different with respect to the orientation of the phenyl rings. Cisoid conformations for dihydroresveratrol were about 5-9 kcal/mol less stable, depending on the orientation of the phenyl rings. Dihydroresveratrol could therefore be able to mimic trans-resveratrol at a very low energy cost. Higher energy (5-9 kcal/ mol in the AM1 scale) would be required to mimic cis-resveratrol, a value, however, that, at least for some orientations of the phenyl rings, should not prevent the molecule from adopting this conformation if required for activity.
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