Benzoic acids, which are commonly found in food, are also produced by human microbiota from other dietary phenolics. The aim was to investigate the interactions of 8 food-related benzoic acids with the physiological metals iron and copper under different (patho)physiologically relevant pH conditions in terms of chelation, reduction, impact on the metal-based Fenton chemistry, and copper-based hemolysis. Only 3,4-dihydroxybenzoic acid behaved as a protective substance under all conditions. It chelated iron, reduced both iron and copper, and protected against the iron and copper-based Fenton reaction. Conversely, 2,4,6-trihydroxybenzoic acid did not chelate iron and copper, reduced both metals, potentiated the Fenton reaction, and worsened copper-based hemolysis of rat red blood cells. The other tested compounds showed variable effects on the Fenton reaction. Interestingly, prooxidative benzoic acids mildly protected human erythrocytes against Cu-induced lysis. In conclusion, 3,4-dihydroxybenzoic acid seems to have a protective effect against copper and iron-based toxicity under different conditions.

The Department of Chemistry School of Sciences and Engineering The University of Crete University Campus Voutes 70013 Heraklion Crete Greece

The Department of Pharmaceutical Chemistry and Pharmaceutical Analysis Faculty of Pharmacy in Hradec Králové Charles University Akademika Heyrovského 1203 500 03 Hradec Králové Czech Republic

The Department of Pharmacognosy and Pharmaceutical Botany Faculty of Pharmacy in Hradec Králové Charles University Akademika Heyrovského 1203 500 03 Hradec Králové Czech Republic

The Department of Pharmacology and Toxicology Faculty of Pharmacy in Hradec Králové Charles University Akademika Heyrovského 1203 500 03 Hradec Králové Czech Republic

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Synthetic and semi-synthetic antioxidants in medicine and food industry: a review