Propyl gallate/cyclodextrin supramolecular complexes with enhanced solubility and radical scavenging capacity

This study prepared and investigated the inclusion complexes of propyl gallate (PG) with beta-cyclodextrin (β-CD) and its water-soluble derivatives dimethyl-beta-cyclodextrin (DM-β-CD), hydroxypropyl-beta-cyclodextrin (HP-β-CD), and sulfobutylether-beta-cyclodextrin (SBE-β-CD). Phase solubility studies indicated that the formed complexes were in 1:1 stoichiometry. FT-IR, PXRD, DSC, 1H-NMR, ROESY-NMR, and SEM analysis results confirmed the formation of the complexes. The NMR results indicated that the aromatic ring of PG was embedded into the CD cavity. The aqueous solubility of PG was markedly improved, and that of the PG/DM-β-CD complex increased by 365.3 times. In addition, the results of the antioxidant activity assay showed that the hydroxyl radical and superoxide radical scavenging capacities of the complexes increased by 3-11 times and 1-6.5 times, respectively, compared with those of PG under the same concentration. Therefore, CD/PG inclusion complexes with improved solubility and radical scavenging capacity can be used as water-soluble antioxidants in the food industry.