Host-guest inclusion complexes of hydroxytyrosol with cyclodextrins: Development of a potential functional ingredient for food application.

Hydroxytyrosol (HT), a potent phenolic phytochemical, exerts positive health effects due to its antioxidant properties. However, it is highly reactive to oxygen, light, and heat and presents high instability. Alpha- and beta-cyclodextrin (α-CD, β-CD) have structures that allow them to encapsulate a variety of hydrophobic molecules. The aim of this study was to examine the outcomes of the inclusion of HT into α-CD and β-CD. Aqueous solutions of HT and either α-CD or β-CD were prepared and freeze-drying was applied for the encapsulation, in 1:1 and 2:1 molar ratios. The produced solid complexes were studied and characterized using NMR spectroscopy, differential scanning calorimetry (DSC) and attenuated total reflection-Fourier transform infrared spectroscopy (ATR-FTIR). Encapsulation efficiency (EE%), stability, and in vitro release of the encapsulated complexes under simulated digestion conditions were also evaluated. In both DSC thermograms and FTIR spectra of the inclusion complexes, absence of the characteristic peaks of HT and shifts of the CDs peaks were observed, showing an interaction between the molecules. NMR suggested a stronger complex formed between β-CD and HT. The EE% of β-CD/HT (1:1 and 2:1) complexes and α-CD/HT (1:1) complex was found to be higher (83%, 76%, 78%, respectively), compared to α-CD/HT (2:1) (51%). Data obtained support the encapsulation of HT in both CDs, revealing a potential interaction between them and an improvement in HT's thermal stability. Regarding the in vitro release study, both CD complexes had similar behavior and a controlled release of HT in the intestinal site was observed. PRACTICAL APPLICATION: The encapsulation of hydroxytyrosol in cyclodextrins resulted in white amorphous food-grade powders with no aroma and taste. Incorporation of these powders in foods could lead to an increase in their antioxidant content and offer an additional nutritional value.