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Interactions of Calcium with Chlorogenic and Rosmarinic Acids: An Experimental and Theoretical Approach

Abstract : Chlorogenic (CA) and rosmarinic (RA) acids are two natural bioactive hydroxycinnamic acids whose antioxidant properties can be modulated by the chelation of metal ions. In this work, the interactions of these two carboxylic phenols with calcium ions and the impact of such interactions on their antioxidant activity were investigated. UV-Vis absorbance, mass spectroscopy and 1 H and 13 C liquid NMR were used to identify complexes formed by CA and RA with calcium. Antioxidant activities were measured by the Bois method. Density functional theory (DFT) calculations were performed to evaluate the most stable configurations and correlated with NMR data. Taken together, these data suggest that calcium ions mainly interact with the carboxylate groups of both molecules but that this interaction modifies the reactivity of the catechol groups, especially for RA. These results highlight the complex interplay between metal chelation and antioxidant properties of natural carboxylic phenols.
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Submitted on : Friday, August 28, 2020 - 9:46:54 AM
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Estelle Palierse, Cédric Przybylski, Dalil Brouri, Claude Jolivalt, Thibaud Coradin. Interactions of Calcium with Chlorogenic and Rosmarinic Acids: An Experimental and Theoretical Approach. International Journal of Molecular Sciences, MDPI, 2020, 21 (14), pp.4948. ⟨10.3390/ijms21144948⟩. ⟨hal-02924443⟩

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