Complexations of -cyclodextrins with naringenin, naringin and catechin: thermodynamic parameters and regulation of mitochondrial functions in vitro
PHYSICS AND CHEMISTRY OF LIQUIDS(2023)
摘要
Flavonoids are exogenous phytochemicals with high antioxidative potential. The present work provides the mechanism of the complexations of low water-soluble flavanone naringenin, its glycosylated form naringin, and water-soluble flavan-3-ol catechin with beta-cyclodextrin (beta CD) and hydroxypropyl-beta-cyclodextrin (HP beta CD). The flavonoids studied showed high affinity in the interactions with HP beta CD (the association constants K and the stoichiometry N were equal to 8500 +/- 950 M-1 and 0.85 +/- 0.05, 9400 +/- 1200 M-1 and 1.7 +/- 0.10, 7550 +/- 600 M-1 and 1.25 +/- 0.05 in the case of naringenin, naringin and catechin, respectively). The formations of the complexes with beta-cyclodextrins markedly increased the water solubility of naringenin and naringin. The flavonoid-HP beta CD complexations were exothermic (Delta H < 0) and spontaneous (Delta G < 0). The naringenin and naringin complexations with HP beta CD were entropy-driven, and the catechin complexation was enthalpy-driven. Flavonoid molecules dispersed in the HP beta CD structure during complexations. The flavonoid-HP beta CD associations demonstrated enthalpy-entropy compensation. Naringenin (5-50 mu M) and, to a lesser extent, catechin inhibited the respiration of isolated rat liver mitochondria. Naringenin, naringin and catechin (5-25 mu M) increased the rate of Ca2+-induced mitochondrial permeability transition. The complexations with HP beta CD did not significantly influence the effects of the flavonoids on respiration and enhanced the effects on mitochondrial permeability transition.
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关键词
Naringenin,naringin,catechin,beta-cyclodextrins,microcalorimetry,mitochondria
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