Structure-activity relationship of anthocyanin phytochemicals in inhibiting oxidized-stress injury of vascular endothelial cells

易龙; 陈春烨; 金鑫; 糜漫天; 常辉; 凌文华; 朱俊东; 张乾勇; 张婷; 于斌

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Structure-activity relationship of anthocyanin phytochemicals in inhibiting oxidized-stress injury of vascular endothelial cells

更新时间：2026-01-09

- Structure-activity relationship of anthocyanin phytochemicals in inhibiting oxidized-stress injury of vascular endothelial cells
- Journal of Army Medical University Vol. 31, Issue 21, Pages: 2046-2049(2009)
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  CLC： R151.41;R322.12;R329.26
- Published：2009
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易龙,陈春烨,金鑫,糜漫天,常辉,凌文华,朱俊东,张乾勇,张婷,于斌.花色苷类植物化学物抑制血管内皮细胞氧化应激损伤作用的结构-效应关系研究[J].陆军军医大学学报(原第三军医大学学报),2009,31(21):2046-2049.

　YI Long,CHEN Chun-ye,JIN Xin,MI Man-tian,CHANG Hui,LING Wen-hua,ZHU Jun-dong,ZHANG Qian-yong,ZHANG Ting,YU Bin.Structure-activity relationship of anthocyanin phytochemicals in inhibiting oxidized-stress injury of vascular endothelial cells[J].J Amry Med Univ (J Third Mil Med Univ),2009,31(21):2046-2049.
易龙,陈春烨,金鑫,糜漫天,常辉,凌文华,朱俊东,张乾勇,张婷,于斌.花色苷类植物化学物抑制血管内皮细胞氧化应激损伤作用的结构-效应关系研究[J].陆军军医大学学报(原第三军医大学学报),2009,31(21):2046-2049. DOI：

　YI Long,CHEN Chun-ye,JIN Xin,MI Man-tian,CHANG Hui,LING Wen-hua,ZHU Jun-dong,ZHANG Qian-yong,ZHANG Ting,YU Bin.Structure-activity relationship of anthocyanin phytochemicals in inhibiting oxidized-stress injury of vascular endothelial cells[J].J Amry Med Univ (J Third Mil Med Univ),2009,31(21):2046-2049. DOI：

摘要

目的对膳食中常见的21种花色苷抑制血管内皮细胞氧化应激损伤作用进行结构-效应关系研究，探索与花色苷内皮保护作用密切相关的结构特征，筛选出作用较显著的化合物单体。方法不同浓度氧化低密度脂蛋白（ox-LDL，50、100、150、200 μg/ml）处理内皮细胞24 h，MTT法检测细胞活力，确定IC

；以不同浓度（50、100、200 μmol/L）的花色苷预处理内皮细胞2 h后，100 μg/ml的ox-LDL继续处理细胞24 h，MTT法检测各组细胞活力；100 μmol/L花色苷预处理内皮细胞2 h后，100 μg/ml ox-LDL继续处理细胞24 h，按试剂盒说明书测定细胞培养上清液MDA和NO水平；根据各组细胞活力、MDA和NO值，结合不同花色苷的结构特征进行结构-效应关系分析。结果 ox-LDL 能明显抑制内皮细胞活力，并呈浓度依赖关系，IC

为100 μg/ml。不同花色苷对内皮细胞活力、MDA生成和NO释放的影响存在显著相关性。花色苷对内皮细胞氧化应激损伤的抑制作用与其总-OH数量及B环-OH数量呈明显正相关； B环3′

4′-邻苯二羟基和C环3-OH能增强花色苷的抑制作用，而甲基化和糖苷化能明显削弱其作用；A环6-OH可能削弱其抑制作用，B环5′和A环5位-OH对其作用无显著影响；葡萄糖取代与半乳糖取代对花色苷抑制作用的影响无显著差异，而单糖取代较之双糖取代能明显增强其抑制作用。Delphinidin和Delphinidin-3-glucoside分别是2种作用最显著的花色苷元和花色苷。结论 B环3′

4′-邻苯二羟基和C环3-OH是花色苷抑制内皮细胞氧化损伤的重要结构特征。

Abstract

Objective To investigate the structure-activity relationship for 21 anthocyanins in inhibiting oxidized injury of endothelial cells

and explore the structural characteristics of anthocyanins closely related to their effects. Methods Endothelial cells were treated by ox-LDL

at different concentrations of 50

100

150 or 200 μg/ml

and MTT assay was used to determine IC

. After pre-incubated for 2 h with different concentrations (50

100 or 200 μmol/L) of anthocyanins and then treated with 100 μg/ml ox-LDL for another 24 h in endothelial cells

MTT assay was used to detect the cellular viability. After pre-treated for 2 h with different anthocyanins with 100 μmol/L and treated with ox-LDL for another 24 h

MDA and NO level in the culture media were both measured according to the methods of assay kits. Structure-activity relationship was analyzed according to the respective cellular viability

MDA and NO level. Results Cellular viability was significantly inhibited by ox-LDL in a dose-dependent manner

and the IC

was 100 μg/ml. A significant correlation was observed among the effect of anthocyanins on cell viability

MDA production and NO release. The inhibitory effects of anthocyanins in ox-LDL-injured endothelial cells were positively related to the total number of hydroxyl groups and hydroxyl substitutions in B ring. 3′

4′-ortho-dihydroxyl substitution on B-ring and a 3-hydroxyl group on C-ring significantly enhanced the inhibitory effect of anthocyanins

yet methoxylation or glycosylation significantly decreased the effect. 6-hydroxylation substitution might attenuate the inhibitory effect of anthocyanins

while substitution at C5 or C5′ showed no significant influence on the effect of anthocyanins. Anthocyanin with monosaccharose substitution was much stronger than that with disaccharose substitution

while there was no significant difference between anthocyanins with glucoside and that with galacotoside substitution. Delphinidin and delphinidin-3-glucoside were respectively the most effectual anthocyanidin or anthocyanin. Conclusion 3′

4′-ortho-dihydroxyl substitution on B-ring and a 3-hydroxyl group on C-ring are the main structural requirements for anthocyanins in suppressing ox-LDL-induced injury in endothelial cells.

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