biostudies-literatureUnknown3(6)Bijlsma JIn 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 ACS food science & technology1111-1121https://www.ebi.ac.uk/biostudies/studies/S-EPMC10278068biostudies-literatureInteractions of Natural Flavones with Iron Are Affected by 7-O-Glycosylation, but Not by Additional 6″-O-Acylation.PMC10278068Koppelaar JSanders MGVincken JPde Bruijn WJCVelikov KPBijlsma JfalseInteractions 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 2023-01-01T00:00:00Z2023 Jun2025-04-26T09:04:14.072Z2025-04-06T12:56:33.056ZS-EPMC102780683734223810.1021/acsfoodscitech.3c00112