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Systematic investigation and molecular modelling of complexation between several groups of flavonoids and HP-β-cyclodextrins
- Pérez-Abril, Maravillas, Lucas-Abellán, Carmen, Castillo-Sánchez, Julián, Pérez-Sánchez, Horacio, Cerón-Carrasco, José P., Fortea, Isabel, Gabaldón, José A., Núñez-Delicado, Estrella
- Journal of functional foods 2017 v.36 pp. 122-131
- bioavailability, chemical structure, hydrogen bonding, hydrophobicity, kaempferol, molecular models, oxygen, pharmaceutical industry, water solubility
- Flavonoids play an important role in the food and pharmaceutical industries and its molecular structure is responsible for their bioavailability and activity. Their very low water-solubility reduces their bioavailability. HP-β-cyclodextrins have been used to improve this parameter. Our results permit a better understanding of the influence of flavonoid molecular skeletons on the cyclodextrin complexation process. Molecular docking analysis showed that the most stable complex with HP-β-CD is that formed by kaempferol, being its stability mainly due to the hydrogen bonds network established between oxygen at positions 3, 4, 5 and 7 and to the hydrophobic stabilization of its aromatic scaffold within the inner cavity of HP-β-CD. The highest relative effect of the different substructures on inclusion efficacy is, primarily, the result of the conjugation between three elements on the flavonoid C-ring: the carbonyl group in C-4 position, the double bond C2C3 and the hydroxyl group in C-3 position.