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

International Journal of Molecular Sciences
Estelle PalierseThibaud Coradin

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 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.

References

Oct 15, 1996·Physical Review. B, Condensed Matter·G Kresse, J Furthmüller
Oct 28, 1996·Physical Review Letters·J P PerdewM Ernzerhof
Mar 21, 2002·Journal of Agricultural and Food Chemistry·Hiroe KikuzakiHisaji Taniguchi
Nov 13, 2004·Journal of Pharmacological Sciences·Hyun Pyo KimSam Sik Kang
Sep 30, 2005·Journal of Agricultural and Food Chemistry·Bin ShanHarold Corke
Feb 3, 2007·Toxicology in Vitro : an International Journal Published in Association with BIBRA·Keiko MurakamiMasataka Yoshino
Nov 11, 2008·The Journal of Physical Chemistry. a·Jean-Paul CornardCyrille Allet-Bodelot
Feb 3, 2009·Cell Biochemistry and Biophysics·Nathan R Perron, Julia L Brumaghim
Feb 1, 2011·Fitoterapia·D ProcházkováN Wilhelmová
May 20, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yuanzhen Liu, Mingquan Guo
Aug 19, 2015·Journal of Agricultural and Food Chemistry·Véronique CheynierKumi Yoshida
Oct 30, 2016·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Mariola Samsonowicz, Ewa Regulska
Jan 6, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Bence KutusPál Sipos
Jun 20, 2017·Chemico-biological Interactions·Mariola SamsonowiczMonika Kalinowska
Oct 24, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jing YangLeif H Skibsted
Feb 7, 2018·International Journal of Molecular Sciences·Monika KalinowskaWłodzimierz Lewandowski
Mar 14, 2019·Journal of Analytical Methods in Chemistry·Zhaofeng Fu, Rui Chen
Mar 25, 2019·Expert Opinion on Drug Discovery·Prasad DandawateBernhard Biersack
Jul 25, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Renata ŚwisłockaWłodzimierz Lewandowski
May 27, 2020·International Journal of Food Science·Mohammed Sharif SwallahHansong Yu
Jun 11, 2020·Food Research International·Magdalena A OlszewskaManuel Simões

❮ Previous
Next ❯

Methods Mentioned

BETA
NMR

Software Mentioned

ACDLab
Thermo [UNK]
VASP
MAPS

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.