Identification and cytotoxic evaluation of the novel rutin-methylglyoxal adducts with dione structures in vivo and in foods
Identification and cytotoxic evaluation of the novel rutin-methylglyoxal adducts with dione structures in vivo and in foods
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DOI：
10.1016/j.foodchem.2021.132008
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发表时间：
2022-01-06
期刊：
影响因子：
8.8
通讯作者：
Zheng, Jie
中科院分区：
文献类型：
--
作者：
Chen, Min;Zhou, Hua;Zheng, Jie
具有间羟基的类黄酮已被证明与甲基乙二醛（MGO）反应，并通过亲核加成反应形成单和双MGO加合物。芦丁是槲皮素的一种芦丁苷，具有典型的间酚结构，广泛存在于植物源材料中。有趣的是，与报道的黄酮类化合物和MGO之间的加合物不同，在MGO的大部分上发现并证明了新的具有二酮结构的芦丁-MGO加合物存在于各种食物中（总计0.66-6.58 mg/kg）和体内（给药100 mg/kg体重的大鼠血浆中高达5.01 μ g/L）。发现的三个加合物分别被命名为6-（1,2-丙二酮）-8-（1-乙酰醇）-芦丁、6-（1-乙酰醇）-8-（1,2-丙二酮）-芦丁和6-（1,2-丙二酮）-8-（1,2-丙二酮）-芦丁。不同细胞系的细胞毒性评价表明，这些芦丁-MGO加合物的形成显著降低了MGO的毒性，这为芦丁作为二羰基化合物的清除剂通过膳食补充和食品添加的应用提供了进一步的希望。
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 mu g/L in plasma of rats administered with 100 mg/kg bodyweight of rutin). The three adducts discovered were assigned as 6-(1,2propanedione)-8-(1-acetol)-rutin, 6-(1-acetol)-8-(1,2-propanedione)-rutin, and 6-(1,2-propanedione)-8-(1,2propanedione)-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.