Identification and cytotoxic evaluation of the novel rutin–methylglyoxal adducts with dione structures in vivo and in foods

Flavonoids with meta-hydroxyl groups have been proven to react with methylglyoxal (MGO) and form mono- and di-MGO adducts via nucleophilic addition reactions. Rutin, a rutinoside of quercetin with typical meta-phenol structure, is widely distributed in plant-sourced materials. Interestingly, different from the adducts reported between flavonoids and MGO, new rutin-MGO adducts with dione structures on the moiety of MGO were identified and proven to occur in various foods (0.66-6.58 mg/kg in total) and in vivo (up to 5.01 μg/L in plasma of rats administered with 100 mg/kg bodyweight of rutin). The three adducts discovered were assigned as 6-(1,2-propanedione)-8-(1-acetol)-rutin, 6-(1-acetol)-8-(1,2-propanedione)-rutin, and 6-(1,2-propanedione)-8-(1,2-propanedione)-rutin. Cytotoxicity evaluation in different cell lines indicated that the formation of these rutin-MGO adducts remarkably reduced the toxicity of MGO, which provide further promise for the application of rutin as a scavenger of dicarbonyl compounds by dietary supplement and addition in foods.