Interactions of Natural Flavones with Iron Are Affected by 7-O-Glycosylation, but Not by Additional 6″-O-Acylation
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.
| Main Authors: | , , , , , |
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| Format: | Article/Letter to editor biblioteca |
| Language: | English |
| Subjects: | 7-O-glycosides, Apium graveolens, apiin, complexation, ferrous, glycosylated flavonoids, ligand-to-metal charge transfer, metal chelation, oxidation, polyphenol, |
| Online Access: | https://research.wur.nl/en/publications/interactions-of-natural-flavones-with-iron-are-affected-by-7-o-gl |
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