Systematic investigation and molecular modelling of complexation between several groups of flavonoids and HP-β-cyclodextrins. (September 2017)

• Record Type: Journal Article
• Authors: Pérez-Abril, Maravillas; Lucas-Abellán, Carmen; Castillo-Sánchez, Julián; Pérez-Sánchez, Horacio; Cerón-Carrasco, José P.; Fortea, Isabel; Gabaldón, José A.; Núñez-Delicado, Estrella
• Is Part Of: Journal of functional foods. Volume 36(2017)
• Page Start: 122
• Page End: 131
• Publication Date: 2017-09
• Subjects: CDs Cyclodextrins -- HP-β-CDs hydroxy-propyl-β-cyclodextrin -- CVD cardiovascular disease -- APIs Active Pharmaceutical Ingredients -- DMSO dimethylsulfoxide -- HPLC high-performance liquid chromatography -- DFT density functional theory; Cyclodextrin -- Flavonoid -- Inclusion complex -- Microencapsulation -- Molecular modelling; Functional foods -- Analysis -- Periodicals; Food -- Biotechnology -- Periodicals; Nutrition -- Periodicals; 613.2
• DOI: 10.1016/j.jff.2017.06.052
• Languages: English
• ISSNs: 1756-4646

Abstract

Highlights: Changes in flavonoid skeleton and active core affects its HP-β-CDs complexation. Conjugation of three elements on the C-ring has a high effect on the complexation. Kaempferol shows the highest complexation capacity of all flavonoids studied. Abstract: 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.