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The effect of flavonoids on the reduction of cupric ions, the copper-driven Fenton reaction and copper-triggered haemolysis
Abstract
Flavonoids are considered beneficial, but they may exhibit pro-oxidative effects likely due to metal reducing properties. For the first time, 24 structurally related flavonoids were compared for copper reduction, and modulation of the copper-triggered Fenton reaction and lysis of erythrocytes. The vast majority of flavonoids reduced cupric ions; their behaviour ranged from progressive gradual reduction through bell-shaped, neutral, to a blockade of spontaneous reduction. Similarly, different behaviours were observed with the Fenton reaction. Flavone was the only flavonoid that potentiated copper-triggered haemolysis (155 ± 81 % at twice the amount of Cu 2+), while 18 flavonoids were at least partly protective in some concentrations. Only 5-hydroxyflavone did not reduce Cu 2+ and behaved as an antioxidant in both assays (reduction of 60 ± 10 % and 88 ± 1%, respectively, at an equimolar ratio with Cu 2+). In conclusion, relatively subtle structural differences resulted in very different anti/prooxidant behaviour depending on the model.
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“Antioxidant properties of flavonoids predominantly depend on the number and position of hydroxyl groups and their metal-chelating ability (Fig. 12) (Lomozova et al. 2022; Simunkova et al. 2021).”
From Reactive Oxygen Species, Toxicity, Oxidative Stress, and Antioxidants: Chronic Diseases and Aging (2023) · cites this paper as Lomozova et al. 2022
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Reactive Oxygen Species, Toxicity, Oxidative Stress, and Antioxidants: Chronic Diseases and Aging
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Metadata
- Authors
- Lomozová, Z., Hrubša, M., Conte, P. F., Papastefanaki, E., Moravcová, M., Catapano, M. C., Proietti Silvestri, I., Karlíčková, J., Kučera, R., Macáková, K., & Mladěnka, P.
- Affiliations
- Charles University (CZ)
- University of Rome Tor Vergata (IT)
- University of Crete (GR)
- Corresponding author
- Mladěnka, Přemysl
- ORCID
- Venue
- Food Chemistry
- Publisher
- Elsevier BV
- Published
- 2022-11
- Volume
- 394
- Pages
- 133461
- ISSN
- 0308-8146 (ISSN-L)
- OpenAlex
- W4282553177
- Cited by
- 44
- References
- 40
- Citations by year
- 2026: 7 · 2025: 13 · 2024: 14 · 2023: 9 · 2022: 1
- FWCI
- 4.84
- Type
- journal article
- Language
- en
- Open access
- closed
- Licence
- Locations
- Food Chemistry (publishedVersion)
- PubMed (publishedVersion)
- Funders
- Charles University (CZ.02.2.69/0.0/0.0/19_073/0016935)
- Topics
- Health Sciences › Medicine › Biochemistry (medical) › Phytochemicals and Antioxidant Activities
- Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
- Physical Sciences › Chemistry › Organic Chemistry › Synthesis of Organic Compounds
- Keywords
- flavonoids, copper reduction, hemolysis, pro-oxidant activity, antioxidant activity, flavones, 5-hydroxyflavone, dietary flavonoids
- MeSH terms
- Antioxidants, Copper, Flavonoids, Hemolysis, Humans, Ions, Oxidation-Reduction
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