a HONEI, Centre for Cardiovascular and Metabolic Research, Hull York Medical School , University of Hull , Cottingham , HU6 7RX , Hull , UK.
Crit Rev Food Sci Nutr. 2015;55(10):1352-67. doi: 10.1080/10408398.2012.694497.
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.
人类饮食中含有多种植物来源的类黄酮，其中许多通过 O-或较少见的 C-糖苷键连接进行糖基化。与 O-连接的类黄酮相比，C-糖苷化类黄酮在人类饮食中的分布、数量和生物学效应在文献中受到的关注较少，尽管它们存在于许多常见的食物中。因此，本文综述了 C-糖苷化类黄酮在人类饮食中的结构性质、命名和分布。结果显示，有 43 种饮食类黄酮是 C-糖苷化的，来源于二氢查尔酮、黄酮和黄烷-3-醇骨架，并分布在可食用的水果、谷物、叶子和茎中。C-连接的糖基包括阿拉伯糖、半乳糖、葡萄糖、芦丁糖和木糖，它们经常不止一次出现在单个类黄酮骨架上，偶尔也与 O-连接的葡萄糖或芦丁糖基一起出现。本文还讨论了这些化合物的药代动力学命运，特别是它们与已知影响 O-糖苷化饮食类黄酮命运的水解机制的明显缺乏相互作用，解释了口服后在人尿中出现完整的 C-糖苷化类黄酮代谢物的不寻常但潜在重要的现象。最后，本文综述了这些化合物的潜在生物学意义，描述了它们具有抗糖尿病、抗炎、抗焦虑、抗痉挛和保肝作用的机制。
