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Interactions of di- and trihydroxybenzenes with transition metals and their biological consequences

Z. Lomozová,P. Harčárová,Bohdan Adler,Jana Karlíčková,R. Kučera,P. Mladěnka

Published 2025 in Free radical research

ABSTRACT

Abstract Small dihydroxy- and trihydroxybenzenes are polyphenolic compounds found in plant-based materials and formed by the human gut microbiota from other dietary phenolics. This study aimed to explore how 5 structurally related hydroxybenzenes interact with the biologically relevant metals iron and copper under various (patho)physiological pH conditions, focusing on their chelating and reducing abilities, influence on the metal-driven Fenton reactions, and their role in copper-induced hemolysis. Only compounds with hydroxyl groups in an ortho-position, specifically pyrogallol and 4-methylcatechol, were able to strongly chelate Fe2+ at neutral pH and exhibited the largest capacity to reduce Fe³+ and Cu2+. However, the ability to chelate metals did not translate into inhibition of the Fenton reaction. Only 2,4-dihydroxyacetophenone and resorcinol, compounds with hydroxyl groups in a meta-position that lack chelating capability, were effective in suppressing hydroxyl radical formation triggered by the Fe2+-driven Fenton reaction. Interestingly, pyrogallol, despite its strong pro-oxidant properties, was the only compound that protected human erythrocytes from Cu-induced lysis. In conclusion, solely pyrogallol seems to have a protective effect against copper-induced toxicity under biologically relevant conditions. KEY POLICY HIGHLIGHTS Only hydroxybenzenes with hydroxyl groups in an ortho-position could achieve strong chelation and reduction. Solely 2,4-dihydroxyacetophenone and resorcinol blocked the Fe2+-induced Fenton reaction. The ability to chelate metal ions was unrelated to the inhibition of hydroxyl radical production from the Fenton reaction. Only pyrogallol protected against Cu-based hemolysis.

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