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中国茄子花青素及其他衍生物的糖基化模式对人结肠癌细胞系抗氧化效果的影响。

Effect of glycosylation patterns of Chinese eggplant anthocyanins and other derivatives on antioxidant effectiveness in human colon cell lines.

作者信息

Jing Pu, Qian Bingjun, Zhao Shujuan, Qi Xin, Ye Ludan, Mónica Giusti M, Wang Xingya

机构信息

Research Center for Food Safety and Nutrition, Key Lab of Urban Agriculture (South), Bor S. Luh Food Safety Research Center, School of Agriculture & Biology, Shanghai Jiao Tong University, Shanghai 200240, China.

Research Center for Food Safety and Nutrition, Key Lab of Urban Agriculture (South), Bor S. Luh Food Safety Research Center, School of Agriculture & Biology, Shanghai Jiao Tong University, Shanghai 200240, China.

出版信息

Food Chem. 2015 Apr 1;172:183-9. doi: 10.1016/j.foodchem.2014.08.100. Epub 2014 Sep 6.

Abstract

In this study, we compared the scavenging ROS of anthocyanins from Chinese eggplant var. Niu Jiao Qie and other delphinidin derivatives with different glycosylation patterns in HT-29 and HCT-116 cell lines. The eggplant anthocyanins were isolated and identified using LC-MSn and (1)H/(13)C NMR as delphinidin-3-[(4"-trans-p-coumaroyl)-rhamnosyl (1 → 6)glucoside]-5-glucoside, also known as nasunin. Delphinidin derivatives with glycosylation only on C3 (delphinidin-3-glucoside, 3-sambubioside, or 3-rutinoside) exhibited greater effects on ROS reduction as compared to delphinidin derivatives that have glycosylation on C3 and C5 (delphinidin-3,5-diglucoside>delphinidin-3-rutinoside-5-glucoside). Nasunin has glycosylation on C3 and C5 and an acyl group (p-coumaric acid), demonstrated the least effect on ROS reduction. Meanwhile, their ROS reduction activities were consistent with glutathione reductase protein expression levels in HT-29. Although not potent in ROS reduction, nasunin and its deacylated derivatives protected cells from DNA damage in a dose-dependent manner. Taken together, our results suggest that the anthocyanins isolated from Chinese eggplant var. Niu Jiao Qie and other delphinidin have antioxidant activities in colon cancer cells and also protect cells from DNA damage.

摘要

在本研究中,我们比较了来自中国茄子品种牛角茄的花青素以及其他具有不同糖基化模式的飞燕草素衍生物在HT-29和HCT-116细胞系中清除活性氧(ROS)的能力。通过液相色谱-质谱联用(LC-MSn)和氢谱/碳谱核磁共振((1)H/(13)C NMR)对茄子花青素进行分离和鉴定,确定其为飞燕草素-3-[(4"-反式对香豆酰基)-鼠李糖基(1→6)葡萄糖苷]-5-葡萄糖苷,即萘索宁。与在C3和C5上均有糖基化的飞燕草素衍生物(飞燕草素-3,5-二葡萄糖苷>飞燕草素-3-芸香糖苷-5-葡萄糖苷)相比,仅在C3上有糖基化的飞燕草素衍生物(飞燕草素-3-葡萄糖苷、3-接骨木二糖苷或3-芸香糖苷)对ROS的还原作用更强。萘索宁在C3和C5上均有糖基化且含有一个酰基(对香豆酸),对ROS还原的作用最小。同时,它们的ROS还原活性与HT-29细胞中谷胱甘肽还原酶蛋白表达水平一致。尽管萘索宁在还原ROS方面效果不显著,但其及其脱酰基衍生物能以剂量依赖的方式保护细胞免受DNA损伤。综上所述,我们的结果表明,从中国茄子品种牛角茄中分离出的花青素以及其他飞燕草素在结肠癌细胞中具有抗氧化活性,并且还能保护细胞免受DNA损伤。

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