Natural products derived from tea on the solubility of hesperidin by LC-TOF/MS and NMR

Abstract

The application of hesperidin as bioactive compound is limited due to its low water solubility. The effect of natural products derived from black tea (theophylline, theaflavin, and theaflavin-3,3′-digallate) on the solubility of hesperidin was evaluated by liquid chromatography time-of-flight/mass spectrometry and the mechanism was investigated by NMR spectroscopy. As a result, theaflavin-3,3′-gallate was the most effective in improving hesperidin solubility, and had synergistic effect with theaflavin on complexing with hesperidin. The complexation with natural products caused changes in both the chemical shift (0.01–0.29 ppm) and the diffusion coefficient (0.39–1.19) of hesperidin, implying that the proximity of B ring in hesperidin may play an important role in forming a complex with natural products.