The Occurrence, Fate and Biological Activities of C-glycosyl Flavonoids in the Human Diet.

The human diet contains a wide variety of plant-derived flavonoids, many of which are glycosylated via an O- or less commonly a C-glycosidic linkage. The distribution, quantity, and biological effects of C-glycosyl flavonoids in the human diet have received little attention in the literature in comparison to their O-linked counterparts, however, despite being present in many common foodstuffs. The structural nature, nomenclature, and distribution of C-glycosyl flavonoids in the human diet are, therefore, reviewed. Forty-three dietary flavonoids are revealed to be C-glycosylated, arising from the dihydrochalcone, flavone, and flavan-3-ol backbones, and distributed among edible fruits, cereals, leaves, and stems. C-linked sugar groups are shown to include arabinose, galactose, glucose, rutinose, and xylose, often being present more than once on a single flavonoid backbone and occasionally in tandem with O-linked glucose or rutinose groups. The pharmacokinetic fate of these compounds is discussed with particular reference to their apparent lack of interaction with hydrolytic mechanisms known to influence the fate of O-glycosylated dietary flavonoids, explaining the unusual but potentially important appearance of intact C-glycosylated flavonoid metabolites in human urine following oral administration. Finally, the potential biological significance of these compounds is reviewed, describing mechanisms of antidiabetic, antiinflammatory, anxiolytic, antispasmodic, and hepatoprotective effects.