Iron-coordination properties of flavonoids

INOR 888

Maolin Guo, mguo@umassd.edu, Carlos Perez, and Yibin Wei. Department of Chemistry and Biochemistry, University of Massachusetts, Dartmouth, 285 Old Westport Road, Dartmouth, MA 02747
Health benefits of cranberries have long been recognized but the mechanisms behind are still poorly understood. An “iron-binding motif” has been identified from the phenolic phytochemicals found in cranberry by examining their chemical structures. We have investigated the iron-coordination properties of a series of phenolic compounds in aqueous media. The strong iron-binding properties have been confirmed for the compounds containing the “iron-binding motif”. The apparent binding constants have been determined to be in the range 106 to 1012 at pH 7.2. Surprisingly, quercetin binds Fe(II) even stronger than the well known Fe(II)-chelator ferrozine at pH 7.2. This may be the first example of an oxygen-based ligand showing stronger Fe(II)-binding affinity than a nitrogen-based strong Fe(II)-chelator. The strong Fe-binding properties of the phenolics argue that they may be effective in modulating cellular iron homeostasis under physiological conditions. This project is supported by NCCAM/NIH.