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-Chuan Wang, Carla R. García, William P. Henry, Julia L. Brumaghim

Research output: Contribution to journalArticle

20 Citations (Scopus)

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 1 2011
Externally publishedYes

Fingerprint

Flavonols
Iron
Antioxidants
Metals
Binding Sites
Iron Compounds
DNA Damage
Oxidation
DNA
Quercetin
Polyphenols
morin
3-hydroxychromone
Scavenging
Reactive Oxygen Species
Kinetics

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry

Cite this

Iron binding of 3-hydroxychromone, 5-hydroxychromone, and sulfonated morin : Implications for the antioxidant activity of flavonols with competing metal binding sites. / Verdan, Andrea M.; Wang, Hsiao-Chuan; García, Carla R.; Henry, William P.; Brumaghim, Julia L.

In: Journal of Inorganic Biochemistry, Vol. 105, No. 10, 01.10.2011, p. 1314-1322.

Research output: Contribution to journalArticle

Verdan, Andrea M. ; Wang, Hsiao-Chuan ; García, Carla R. ; Henry, William P. ; Brumaghim, Julia L. / Iron binding of 3-hydroxychromone, 5-hydroxychromone, and sulfonated morin : Implications for the antioxidant activity of flavonols with competing metal binding sites. In: Journal of Inorganic Biochemistry. 2011 ; Vol. 105, No. 10. pp. 1314-1322.
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