Fe(III) and Cu(II) Complexes of Chlorogenic Acid: Spectroscopic, Thermal, Anti-/Pro-Oxidant, and Cytotoxic Studies

Kalinowska, Monika; Gryko, Kamila; Gołębiewska, Ewelina; Świderski, Grzegorz; Lewandowska, Hanna; Pruszyński, Marek; Zawadzka, Małgorzata; Kozłowski, Maciej; Sienkiewicz-Gromiuk, Justyna; Lewandowski, W.

doi:10.3390/ma15196832

Cited by 6 publications

(4 citation statements)

References 58 publications

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“…The formation of Cu(II) complexes with catecholamines in aqueous solutions has already been already reported in 1979 by Fazakerley et al [18]. Catechol-containing Cu(II) complexes are still extensively studied due to their interesting properties [19][20][21]. In this paper, the authors, for the first time, propose the reduction of Cu(II) to Cu(I) following the interaction of cupric ions with catecholamines.…”

Section: Interaction Of Catecholamines With Cu(ii): a Uv-vis And Epr ...mentioning

confidence: 57%

Interaction of Redox-Active Copper(II) with Catecholamines: A Combined Spectroscopic and Theoretical Study

et al. 2023

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In this work, attention is focused on the non-essential amino acid L-Tyrosine (TYR) hydroxylated to L-DOPA, which is the precursor to the neurotransmitters dopamine, noradrenaline (norepinephrine; NE) and adrenaline (epinephrine; EP) known as catecholamines and their interactions with redox-active Cu(II). Catecholamines have multiple functions in biological systems, including the regulation of the central nervous system, and free (unbound) redox metal ions are present in many diseases with disturbed metal homeostasis. The interaction between catecholamines and Cu(II) has been studied by means of Electron Paramagnetic Resonance spectroscopy (EPR), EPR spin trapping and UV-vis spectroscopy. The obtained spectroscopic results are supported by Density Functional Theory calculations. Only minor qualitative and quantitative changes in the UV-vis spectra of all the studied compounds have been observed following their interactions with Cu(II) ions. The low-temperature EPR spectra were more convincing and confirmed the interaction between Cu(II) ions and all the studied compounds, involving hydroxyl groups and amino nitrogens. The use of an ABTS assay revealed that the compounds under study possessed radical-scavenging activities against ABTS•+ in the order TYR < EP < DA < NE~L-DOPA. The neurotransmitters DA, NE and EP, following their interaction with Cu(II), exhibit the ability to (partially) reduce Cu(II) to Cu(I) species which was confirmed using the Cu(I) specific chelator neocuproine. EPR spin-trapping experiments revealed the suppressed formation of hydroxyl radicals (•OH) in a copper(II) catalyzed Fenton-like system in the presence of catecholamines. Only in the case of EP was autooxidation in a stock solution observed. Furthermore, the oxidation of EP is enhanced in the presence of Cu(II) ions. In conclusion, it has been confirmed that the oxidation of catecholamines in the presence of copper promotes the redox cycling process, resulting in the formation of ROS, which may, in turn, cause damage to neuronal systems.

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Section: Interaction Of Catecholamines With Cu(ii): a Uv-vis And Epr ...mentioning

confidence: 57%

Interaction of Redox-Active Copper(II) with Catecholamines: A Combined Spectroscopic and Theoretical Study

et al. 2023

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“…5-CQA main cytotoxic effects on cancer cells are triggering apoptosis, suppressing cell proliferation, or inhibiting the cell cycle. Studies show ( S2 Table ) lack of cytotoxicity of 5-CQA towards HaCaT cell line in concentration range of 0.15–1000 nM [ 5 ], HL-60 and Jurkat cells in concentrations of 1–100 μM [ 12 ].…”

Section: Introductionmentioning

confidence: 99%

“…Chlorogenic acid (5-CQA) (S2 Fig) [4], an ester of caffeic acid and (−)-quinic acid, one of the most abundant phenolic acids, is widely distributed in fruits and vegetables like: apples, pears, carrots, or potatoes. Additionally, it can be found in most consumed beverages in the world: wine, tea and coffee [5][6][7]. Notably, chlorogenic acid demonstrates antimicrobial activity against bacteria (S1 Table ) like Gram-negative Escherichia coli (MIC 7.06 mg/mL) [8], Gram-positive Alicyclobacillus acidoterrestris (MIC 2 μg/mL) [9] and fungi Candida albicans with MIC (80 μg/mL) [10].…”

Section: Introductionmentioning

confidence: 99%

Structural characterization and evaluation of antimicrobial and cytotoxic activity of six plant phenolic acids

Kalinowska,

Świsłocka,

Wołejko

et al. 2024

PLoS ONE

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Phenolic acids still gain significant attention due to their potential antimicrobial and cytotoxic properties. In this study, we have investigated the antimicrobial of six phenolic acids, namely chlorogenic, caffeic, p-coumaric, rosmarinic, gallic and tannic acids in the concentration range 0.5–500 μM, against Escherichia coli and Lactobacillus rhamnosus. The antimicrobial activity was evaluated using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide colorimetric assay. Additionally, the cytotoxic effects of these phenolic acids on two cancer cell lines, the colorectal adenocarcinoma Caco-2 cell line and Dukes’ type C colorectal adenocarcinoma DLD-1 cell line was examined. To further understand the molecular properties of these phenolic acids, quantum chemical calculations were performed using the Gaussian 09W program. Parameters such as ionization potential, electron affinity, electronegativity, chemical hardness, chemical softness, dipole moment, and electrophilicity index were obtained. The lipophilicity properties represented by logP parameter was also discussed. This study provides a comprehensive evaluation of the antimicrobial and cytotoxic activity of six phenolic acids, compounds deliberately selected due to their chemical structure. They are derivatives of benzoic or cinnamic acids with the increasing number of hydroxyl groups in the aromatic ring. The integration of experimental and computational methodologies provides a knowledge of the molecular characteristics of bioactive compounds and partial explanation of the relationship between the molecular structure and biological properties. This knowledge aids in guiding the development of bioactive components for use in dietary supplements, functional foods and pharmaceutical drugs.

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“…Caffeic acid and 5-caffeoylquinic acid generally form equimolar complexes with ferric iron [29]. Another study showed that complexes formed by two ferric irons and three 5-caffeoylqinic acid molecules or one Cu-ion and two 5 caffeoylquinic acid molecules are possible [117].…”

Section: Interactions Of Standards Applied To Dietary Supplementsmentioning

confidence: 99%

Thermal processing and storage effects on antioxidant plant compounds and their interaction in model experiments and plant matrices

Engelhardt¹

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Vegetables contain health-promoting compounds, such as vitamins, phenols, and minerals. To assess the potential health benefits, this thesis investigated interactions between individual compounds and their performance in mixtures during thermal processing in model experiments. These results were applied to Urtica dioica L., Aegopodium podagraria L., both neglected wild vegetables, and Amaranthus L. leaves, which were cooked as vegetables and enriched in wheat-rolls.In model experiments, in presence of iron the 2:1 ratio of ascorbic acid and 5-caffeoylquinic acid had strong synergistic effects on the antioxidant activity measured by TEAC, DPPH, and TPC, whereas strong antagonistic effects were observed in the 1:2 ratio. A caffeoylglucaric acid isomer, identified by NMR spectroscopy, and 5-caffeoylquinic acid had similar antioxidant activity, whereas caffeic acid, the assumed bioactive part of both, had a lower antioxidant activity. Added iron can influence the antioxidant activity of the tested substances by complexation. However, other minerals that occur naturally in plants, measured with an ICP, can form a variety of complexes. In closed microtubes, the antioxidant activity of oven-dried A. podagraria L. increased after cooking, whereas of U. dioica L. did not. In model experiments, 5-caffeoylquinic acid protected quercetin-3-rutionoside from degradation, by adding it to U. dioica L. and A. podagraria L. this effect was not detectable. For these species, fridge-storing resulted in the lowest antioxidant activity, compared to not stored and freezer stored samples. The freeze-dried Amaranthus L. genotypes did not differ in their antioxidant activity, neither in cooked nor uncooked samples. However, household cooking experiments, showed that leaching into the cooking water can be neglected and oxidation processes were the main decreasing effects. In wheat-rolls enriched with fresh leaves of Amaranthus L., total phenolic concentrations quantified by HPLC-DAD and identified by HPLC-MS were 51% to 56% lower in baked wheat-rolls than in cooked vegetables and 73% to 76% lower than in freeze-dried plant powder.Thermal processing and storage effects are complex in plant matrices and cannot be explained fully by model experiments with single substances. Interactions between phenols, minerals, proteins, and enzyme activity need to be considered. This thesis highlights advantages and disadvantages of different thermal processing and storage methods by evaluating interactions of vitamins, phenols, and minerals, including the individuality of plants.

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Fe(III) and Cu(II) Complexes of Chlorogenic Acid: Spectroscopic, Thermal, Anti-/Pro-Oxidant, and Cytotoxic Studies

Cited by 6 publications

References 58 publications

Interaction of Redox-Active Copper(II) with Catecholamines: A Combined Spectroscopic and Theoretical Study

Interaction of Redox-Active Copper(II) with Catecholamines: A Combined Spectroscopic and Theoretical Study

Structural characterization and evaluation of antimicrobial and cytotoxic activity of six plant phenolic acids

Thermal processing and storage effects on antioxidant plant compounds and their interaction in model experiments and plant matrices

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