Iron binding of 3-hydroxychromone, 5-hydroxychromone, and sulfonated morin: Implications for the antioxidant activity of flavonols with competing metal binding sites

Andrea M. Verdan, Hsiao C. Wang, Carla R. García, William P. Henry, Julia L. Brumaghim

    Research output: Contribution to journalArticlepeer-review

    41 Scopus citations

    Abstract

    The iron binding properties and antioxidant activities of compounds with hydroxy-keto binding sites, 3-hydroxychromone, 5-hydroxychromone, and sulfonated morin were investigated. For these compounds, prevention of iron-mediated DNA damage and kinetics of Fe II oxidation were studied in aqueous solutions close to physiological pH (pH 6). 3-Hydroxychromone and sulfonated morin inhibit iron-mediated DNA damage at lower concentrations than 5-hydroxychromone. All three compounds bind iron, but 3-hydroxychromone and sulfonated morin promote Fe II oxidation much faster than 5-hydroxychromone. These results indicate that DNA damage inhibition by flavonols with competing hydroxy-keto binding sites is primarily due to iron binding at the 3-hydroxy-keto site. Iron oxidation rate also plays a significant role in antioxidant activity. In addition to iron binding and oxidation, reactive oxygen species scavenging occurs at high concentrations for the hydroxychromones. This study emphasizes the importance of iron binding in polyphenol antioxidant behavior and provides insights into the iron binding antioxidant activity of similar flavonols such as quercetin and myricetin.

    Original languageEnglish (US)
    Pages (from-to)1314-1322
    Number of pages9
    JournalJournal of Inorganic Biochemistry
    Volume105
    Issue number10
    DOIs
    StatePublished - Oct 2011

    Keywords

    • Antioxidants
    • DNA damage
    • Hydroxychromones
    • Iron
    • Iron binding
    • Sulfonated morin

    ASJC Scopus subject areas

    • Biochemistry
    • Inorganic Chemistry

    Fingerprint

    Dive into the research topics of 'Iron binding of 3-hydroxychromone, 5-hydroxychromone, and sulfonated morin: Implications for the antioxidant activity of flavonols with competing metal binding sites'. Together they form a unique fingerprint.

    Cite this