(±)-Catechin-A Mass-Spectrometry-Based Exploration Coordination Complex Formation with Fe and Fe

Overview

Journal Cells

Publisher MDPI

Specialties Biochemistry
Biophysics
Cell Biology
Molecular Biology

Date 2022 Mar 25

PMID 35326409

Authors

Lenka Kubicova

Gert Bachmann

Wolfram Weckwerth

Vladimir Chobot

Affiliations

Soon will be listed here.

Abstract

Catechin is an extensively investigated plant flavan-3-ol with a beneficial impact on human health that is often associated with antioxidant activities and iron coordination complex formation. The aim of this study was to explore these properties with Fe and Fe using a combination of nanoelectrospray-mass spectrometry, differential pulse voltammetry, site-specific deoxyribose degradation assay, Fe autoxidation assay, and brine shrimp mortality assay. Catechin primarily favored coordination complex formation with Fe ions of the stoichiometry catechin:Fe in the ratio of 1:1 or 2:1. In the detected Fe-catechin coordination complexes, Fe prevailed. Differential pulse voltammetry, the site-specific deoxyribose degradation, and Fe autoxidation assays proved that coordination complex formation affected catechin's antioxidant effects. In situ formed Fe-catechin coordination complexes showed no toxic activities in the brine shrimp mortality assay. In summary, catechin has properties for the possible treatment of pathological processes associated with ageing and degeneration, such as Alzheimer's and Parkinson's diseases.

Citing Articles

Metal-Flavonoid Interactions-From Simple Complexes to Advanced Systems.

Walencik P, Choinska R, Golebiewska E, Kalinowska M Molecules. 2024; 29(11).

PMID: 38893449 PMC: 11173564. DOI: 10.3390/molecules29112573.

Transcriptome Analysis Reveals Changes in Whole Gene Expression, Biological Process, and Molecular Functions Induced by Nickel in Jack Pine ().

Moy A, Czajka K, Michael P, Nkongolo K Plants (Basel). 2023; 12(15).

PMID: 37571042 PMC: 10421529. DOI: 10.3390/plants12152889.

References

Filosa S, Di Meo F, Crispi S . Polyphenols-gut microbiota interplay and brain neuromodulation. Neural Regen Res. 2018; 13(12):2055-2059. PMC: 6199944. DOI: 10.4103/1673-5374.241429. View

Pierre J, Fontecave M . Iron and activated oxygen species in biology: the basic chemistry. Biometals. 1999; 12(3):195-9. DOI: 10.1023/a:1009252919854. View

de Souza R, De Giovani W . Antioxidant properties of complexes of flavonoids with metal ions. Redox Rep. 2004; 9(2):97-104. DOI: 10.1179/135100004225003897. View

Xuan Y, Scheuermann E, Meda A, Hayen H, von Wiren N, Weber G . Separation and identification of phytosiderophores and their metal complexes in plants by zwitterionic hydrophilic interaction liquid chromatography coupled to electrospray ionization mass spectrometry. J Chromatogr A. 2006; 1136(1):73-81. DOI: 10.1016/j.chroma.2006.09.060. View

Gao J, Zhou Q, Wu D, Chen L . Mitochondrial iron metabolism and its role in diseases. Clin Chim Acta. 2020; 513:6-12. DOI: 10.1016/j.cca.2020.12.005. View

Janda E, Isidoro C, Carresi C, Mollace V . Defective autophagy in Parkinson's disease: role of oxidative stress. Mol Neurobiol. 2012; 46(3):639-61. DOI: 10.1007/s12035-012-8318-1. View

Mahal H, Kapoor S, Satpati A, Mukherjee T . Radical scavenging and catalytic activity of metal-phenolic complexes. J Phys Chem B. 2005; 109(50):24197-202. DOI: 10.1021/jp0549430. View

Ferenczyova K, Kindernay L, Vlkovicova J, Kalocayova B, Rajtik T, Bartekova M . Pharmacology of Catechins in Ischemia-Reperfusion Injury of the Heart. Antioxidants (Basel). 2021; 10(9). PMC: 8465198. DOI: 10.3390/antiox10091390. View

Docampo-Palacios M, Alvarez-Hernandez A, de Fatima A, Liao L, Pasinetti G, Dixon R . Efficient Chemical Synthesis of (Epi)catechin Glucuronides: Brain-Targeted Metabolites for Treatment of Alzheimer's Disease and Other Neurological Disorders. ACS Omega. 2020; 5(46):30095-30110. PMC: 7689943. DOI: 10.1021/acsomega.0c04512. View

10.

Ruidavets J, Teissedre P, Ferrieres J, Carando S, Bougard G, Cabanis J . Catechin in the Mediterranean diet: vegetable, fruit or wine?. Atherosclerosis. 2000; 153(1):107-17. DOI: 10.1016/s0021-9150(00)00377-4. View

11.

Mira L, Fernandez M, Santos M, Rocha R, Florencio M, Jennings K . Interactions of flavonoids with iron and copper ions: a mechanism for their antioxidant activity. Free Radic Res. 2003; 36(11):1199-208. DOI: 10.1080/1071576021000016463. View

12.

Chobot V, Hadacek F, Bachmann G, Weckwerth W, Kubicova L . In Vitro Evaluation of Pro- and Antioxidant Effects of Flavonoid Tricetin in Comparison to Myricetin. Molecules. 2020; 25(24). PMC: 7768484. DOI: 10.3390/molecules25245850. View

13.

Schaffer S, Halliwell B . Do polyphenols enter the brain and does it matter? Some theoretical and practical considerations. Genes Nutr. 2011; 7(2):99-109. PMC: 3316747. DOI: 10.1007/s12263-011-0255-5. View

14.

Grunewald R . Ascorbic acid in the brain. Brain Res Brain Res Rev. 1993; 18(1):123-33. DOI: 10.1016/0165-0173(93)90010-w. View

15.

Perron N, Wang H, Deguire S, Jenkins M, Lawson M, Brumaghim J . Kinetics of iron oxidation upon polyphenol binding. Dalton Trans. 2010; 39(41):9982-7. DOI: 10.1039/c0dt00752h. View

16.

Russell M . Green Rust: The Simple Organizing 'Seed' of All Life?. Life (Basel). 2018; 8(3). PMC: 6161180. DOI: 10.3390/life8030035. View

17.

Shubina V, Kozina V, Shatalin Y . Comparison of Antioxidant Properties of a Conjugate of Taxifolin with Glyoxylic Acid and Selected Flavonoids. Antioxidants (Basel). 2021; 10(8). PMC: 8389318. DOI: 10.3390/antiox10081262. View

18.

Kubicova L, Hadacek F, Weckwerth W, Chobot V . Effects of endogenous neurotoxin quinolinic acid on reactive oxygen species production by Fenton reaction catalyzed by iron or copper. J Organomet Chem. 2015; 782:111-115. PMC: 4396856. DOI: 10.1016/j.jorganchem.2015.01.030. View

19.

Kubicova L, Chobot V . Potential of kynurenine metabolites in drug development against neurodegenerative diseases. Neural Regen Res. 2020; 16(2):308-309. PMC: 7896208. DOI: 10.4103/1673-5374.290897. View

20.

Ojala T, Vuorela P, Kiviranta J, Vuorela H, Hiltunen R . A bioassay using Artemia salina for detecting phototoxicity of plant coumarins. Planta Med. 2000; 65(8):715-8. DOI: 10.1055/s-1999-14049. View