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

International Journal of Molecular Sciences

Cédric Przybylski¹  Thibaud Coradin²  Estelle Palierse²  Claude Jolivalt³  Dalil Brouri³ 

[1] CNRS, Institut Parisien de Chimie Moléculaire (IPCM), Sorbonne Université, 4 place Jussieu, 75005 Paris, France;CNRS, Laboratoire de Chimie de la Matière Condensée de Paris (LCMCP), Sorbonne Université, 4 place Jussieu, 75005 Paris, France;CNRS, Laboratoire de Réactivité de Surface (LRS), Sorbonne Université, 4 place Jussieu, 75005 Paris, France;

关键词: chlorogenic acid;    rosmarinic acid;    calcium;    antioxidant;    Density Functional Theory;   

DOI  :  10.3390/ijms21144948

来源: DOAJ

【 摘 要 】

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 ¹H and ¹³C 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.

【 授权许可】

Unknown