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Article

Dehydroflavonolignans from Silymarin Potentiate Transition Metal Toxicity In Vitro but Are Protective for Isolated Erythrocytes Ex Vivo

1
Department of Pharmacognosy, Faculty of Pharmacy in Hradec Králové, Charles University, Heyrovského 1203, 500 05 Hradec Králové, Czech Republic
2
Department of Pharmacology and Toxicology, Faculty of Pharmacy in Hradec Králové, Charles University, Heyrovského 1203, 500 05 Hradec Králové, Czech Republic
3
Department of Analytical Chemistry, Faculty of Pharmacy in Hradec Králové, Charles University, Heyrovského 1203, 500 05 Hradec Králové, Czech Republic
4
Laboratory of Biotransformation, Institute of Microbiology of the Czech Academy of Sciences, Vídeňská 1083, 142 20 Prague, Czech Republic
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Department of Pharmaceutical Chemistry and Pharmaceutical Analysis, Faculty of Pharmacy in Hradec Králové, Charles University, Heyrovského 1203, 500 05 Hradec Králové, Czech Republic
*
Authors to whom correspondence should be addressed.
These authors contributed equally to the study.
Academic Editor: Janusz M. Gebicki
Antioxidants 2021, 10(5), 679; https://doi.org/10.3390/antiox10050679
Received: 15 March 2021 / Revised: 16 April 2021 / Accepted: 23 April 2021 / Published: 27 April 2021
(This article belongs to the Special Issue Biological Activity of Mammalian Metabolites of Antioxidants)
2,3-Dehydrosilybin (DHS) was previously shown to chelate and reduce both copper and iron ions. In this study, similar experiments with 2,3-dehydrosilychristin (DHSCH) showed that this congener of DHS also chelates and reduces both metals. Statistical analysis pointed to some differences between both compounds: in general, DHS appeared to be a more potent iron and copper chelator, and a copper reducing agent under acidic conditions, while DHSCH was a more potent copper reducing agent under neutral conditions. In the next step, both DHS and DHSCH were tested for metal-based Fenton chemistry in vitro using HPLC with coulometric detection. Neither of these compounds were able to block the iron-based Fenton reaction and, in addition, they mostly intensified hydroxyl radical production. In the copper-based Fenton reaction, the effect of DHSCH was again prooxidant or neutral, while the effect of DHS was profoundly condition-dependent. DHS was even able to attenuate the reaction under some conditions. Interestingly, both compounds were strongly protective against the copper-triggered lysis of red blood cells, with DHSCH being more potent. The results from this study indicated that, notwithstanding the prooxidative effects of both dehydroflavonolignans, their in vivo effect could be protective. View Full-Text
Keywords: flavonolignans; silymarin; milk thistle; dehydroflavonolignans; dehydrosilybin; dehydrosilychristin; hydroxyl radical; iron; copper; prooxidation flavonolignans; silymarin; milk thistle; dehydroflavonolignans; dehydrosilybin; dehydrosilychristin; hydroxyl radical; iron; copper; prooxidation
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MDPI and ACS Style

Lomozová, Z.; Tvrdý, V.; Hrubša, M.; Catapano, M.C.; Macáková, K.; Biedermann, D.; Kučera, R.; Křen, V.; Mladěnka, P.; Valentová, K. Dehydroflavonolignans from Silymarin Potentiate Transition Metal Toxicity In Vitro but Are Protective for Isolated Erythrocytes Ex Vivo. Antioxidants 2021, 10, 679. https://doi.org/10.3390/antiox10050679

AMA Style

Lomozová Z, Tvrdý V, Hrubša M, Catapano MC, Macáková K, Biedermann D, Kučera R, Křen V, Mladěnka P, Valentová K. Dehydroflavonolignans from Silymarin Potentiate Transition Metal Toxicity In Vitro but Are Protective for Isolated Erythrocytes Ex Vivo. Antioxidants. 2021; 10(5):679. https://doi.org/10.3390/antiox10050679

Chicago/Turabian Style

Lomozová, Zuzana, Václav Tvrdý, Marcel Hrubša, Maria C. Catapano, Kateřina Macáková, David Biedermann, Radim Kučera, Vladimír Křen, Přemysl Mladěnka, and Kateřina Valentová. 2021. "Dehydroflavonolignans from Silymarin Potentiate Transition Metal Toxicity In Vitro but Are Protective for Isolated Erythrocytes Ex Vivo" Antioxidants 10, no. 5: 679. https://doi.org/10.3390/antiox10050679

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