Antioxidant activity of an inclusion complex between rutin and ß-cyclodextrin: experimental and quantum chemical studies.

This study aims to synthesize a guest-host complex derived from rutin (Rut) and ß-cyclodextrin (ß-CD) (denoted as [Rut⊂ß-CD]). The obtained substance was characterized by the FT-IR and DSC methods, signifying the formation of an inclusion complex between Rut and ß-CD. Complex formation increased the antioxidant activity of rutin corresponding to the decrease of EC50 values from 1.547 × 10-5 mol L-1 to 1.227 × 10-5 mol L-1 according to the DPPH free radical scavenging test. The rutin-ß-CD interaction energies were calculated in the vacuum and various solvents (e.g., water, ethanol, and dimethylsulfoxide) utilizing an accurate and broadly parametrized self-consistent tight-binding quantum chemical method (GFN2-xTB). The calculation results reveal the influence of solvent on the structural formation of the rutin-ß-CD complex. In both the vacuum and aqueous solution, rutin can enter into the small-sized empty cavity of ß-CD, albeit through different terminals, resulting in distinct preferential structures. The presence of organic solvents appears to reduce the interaction between rutin and ß-CD, with the interaction strength following the order: water > ethanol > dimethyl sulfoxide.