β-cyclodextrin and caffeine complexes with natural polyphenols from olive and olive oils: NMR, thermodynamic, and molecular modeling studies.
Complexes of β-cyclodextrin (β-CD) and caffeine (Caf) with biophenols present in olive and olive oil (tyrosol, hydroxytyrosol, homovanillic acid, 3,4-dihydroxyphenylacetic acid, and protocatechuic acid) were investigated by NMR spectroscopy and thermodynamical-molecular dynamic studies to verify the formation of supermolecular aggregates. The obtained results indicated that the investigated biophenols form inclusion complexes with β-CD in a molar ratio of 1:1 in aqueous solution having binding constant values from 10- to 40-fold bigger than those of the corresponding complexes with Caf. Then, β-CD preferentially encloses the biophenol molecule, decreasing its bitter taste and, at the same time, preserving it against chemical and physical decomposition reactions that occur during storage.
Dipartimento di Scienze Chimiche, Università di Catania, Viale Andrea Doria 6, 95125 Catania, Italy. arescifina@unict.it
Antonio
A
Rescifina
Ugo
U
Chiacchio
Daniela
D
Iannazzo
Anna
A
Piperno
Giovanni
G
Romeo
D002110:Caffeine / Q000737:chemistry*; D005419:Flavonoids / Q000737:chemistry*; D005503:Food Additives / Q000737:chemistry; D005519:Food Preservation; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008958:Models, Molecular; D008968:Molecular Conformation; D031658:Olea / Q000737:chemistry*; D000069463:Olive Oil; D010636:Phenols / Q000737:chemistry*; D010938:Plant Oils / Q000737:chemistry*; D059808:Polyphenols; D013816:Thermodynamics; D047392:beta-Cyclodextrins / Q000737:chemistry*
D005419:Flavonoids; D005503:Food Additives; D000069463:Olive Oil; D010636:Phenols; D010938:Plant Oils; D059808:Polyphenols; D047392:beta-Cyclodextrins; D002110:Caffeine; C031215:betadex