Interactions of Natural Flavones with Iron Are Affected by 7-O-Glycosylation, but Not by Additional 6″-O-Acylation

Judith Bijlsma, Wouter J.C. de Bruijn, Jamie Koppelaar, Mark G. Sanders, Krassimir P. Velikov, Jean Paul Vincken*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

1 Citation (Scopus)


In iron-fortified bouillon, reactivity of the iron ion with (acylated) flavone glycosides from herbs can affect product color and bioavailability of iron. This study investigates the influence of 7-O-glycosylation and additional 6″-O-acetylation or 6″-O-malonylation of flavones on their interaction with iron. Nine (6″-O-acylated) flavone 7-O-apiosylglucosides were purified from celery (Apium graveolens), and their structures were elucidated by mass spectrometry (MS) and nuclear magnetic resonance (NMR). In the presence of iron, a bathochromic shift and darker color were observed for the 7-O-apiosylglucosides compared to the aglycon of flavones that only possess the 4-5 site. Thus, the ability of iron to coordinate to the flavone 4-5 site is increased by 7-O-glycosylation. For flavones with an additional 3′-4′ site, less discoloration was observed for the 7-O-apiosylglucoside compared to the aglycon. Additional 6″-O-acylation did not affect the color. These findings indicate that model systems used to study discoloration in iron-fortified foods should also comprise (acylated) glycosides of flavonoids.

Original languageEnglish
Pages (from-to)1111-1121
JournalACS Food Science and Technology
Issue number6
Early online date2 May 2023
Publication statusPublished - 16 Jun 2023


  • 7-O-glycosides
  • apiin
  • Apium graveolens
  • complexation
  • ferrous
  • glycosylated flavonoids
  • ligand-to-metal charge transfer
  • metal chelation
  • oxidation
  • polyphenol


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