Iron-chelation properties of phenolic acids bearing catechol and galloyl groups

Abstract

In this study, the capacity of seven phenolic acids and hydroxytyrosol for complex formation with iron was quantified. A metal-chelation mechanism was described by means of spectrophotometry and calculating the binding constants of the complexes. The influence of phosphate buffer, Hepes buffer, Tris buffer and water on this mechanism was investigated. UV–Vis absorption spectroscopy showed that the absorption of phenolic acids changes upon the addition of Fe 2+, which resulted in several shifts of their spectra. These batochromic shifts were analyzed and evaluated by calculating binding constants. Furthermore, in the presence of different concentrations of EDTA (0–1 mM), a reduction of the constants was observed. However, not all of the phenolic compounds assessed here showed complex formation, those not bearing catechol or galloyl moiety like vanillic acid, syringic acid and ferulic acid, did not show any complex formation in our study. The ability of the phenolic compounds which chelate iron have been ranked in line with the binding constants in ascending order rendering the protocatechuic acid (1.43 M −1) the weakest chelator, followed by hydroxytyrosol (2.66 M −1), gallic acid (4.78 M −1), caffeic acid (8.12 M −1) and chlorogenic acid (20.13 M −1) as the strongest chelator.