5,7,4'-三羟基异黄酮基-8-对偶氮苯磺酸的合成及其抗氧化活性研究  

Synthesis and antioxidant activities of 5,7,4′-tri(hydroxyl) isoflavonyl-8-azophenylsulfonic acid

作　　者：吕沙沙[1] 李利平[1] 徐爽[1] 郭蓉[1] 延玺[1] 

机构地区：[1]北京师范大学化学学院,北京100875

出　　处：《中国药物化学杂志》2012年第5期364-368,共5页Chinese Journal of Medicinal Chemistry

基　　金：国家自然科学基金项目(20271008);北京市重点学科基金项目(0503)

摘　　要：目的合成未见文献报道的化合物5,7,4'-三羟基异黄酮基-8-对偶氮苯磺酸,并探讨其抗氧化活性。方法采用IR、1H-NMR、元素分析对其结构进行表征。利用荧光光谱法研究目标物对羟基自由基的清除活性,采用紫外光谱法研究目标物对超氧阴离子自由基和1,1-二苯基-2-苦肼基自由基(DPPH·)的清除活性。结果与结论目标化合物对1,1-二苯基-2-苦肼基自由基、羟基自由基和超氧阴离子自由基都有良好的清除活性,而且对羟基自由基的清除活性远高于对超氧阴离子自由基和1,1-二苯基-2-苦肼基自由基的清除活性。Free radicals are known to be the major cause of various chronic and degenerative diseases,inclu- ding aging, coronary heart disease, inflammation, stroke, diabetes mellitus and cancer. Reactive oxygen spe- cies（ ROS）, including free radicals such as superoxide anion radical（ 02）,hydrogen peroxide（ H202 ） and hydroxyl radical（-HO）, can cause cellular injuries and initiate peroxidation of polyunsaturated fatty acids in biological membranes. Moreover, it has been suggested that lipid peroxyl radicals contribute to the oxidation of lipids, increasing the risk of atherosclerosis, which is an awful disease of the artery wall for human. Isofla- vones, the naturally occurring compounds, are capable of Scavenging free radicals and inhibiting lipids oxida- tion in vivo, which possess potential cardioprotective effects. However, the poor solubility of these com- pounds limits their bioavailability in vivo. In order to improve the bioavailability, a novel antioxidant isofla- vone derivative, 5,7,4＇-tri （ hydroxyl ） isoflavonyl-8-azophenylsulfonic acid （ 1 ） was designed and synthe- sized and its structure was characterized by IR, 1H-NMR and elemental analysis. The scavenging activities of the title compound on hydroxyl radicals （. OH） were detected by fluorescent spectrophotometry, while its scavenging activities on superoxide anion free radicals＇（ 02 ） and 1,1-diphenyl-2-picrylhydrazyl free radical （DPPH.） were measured by ultraviolet spectrophotometry. The experimental results showed that the title compound could scavenge superoxide anion free radicals, DPPH. and hydroxyl radicals effectively with IC50 values of （ 11.88 ± 0. 1 ） μmol. L - 1, （ 36.2 ± 0. 3 ） μmol. L - 1 and （2. 12 ± 0. 1 ） 10 - 7 mol- L - 1, respec- tively. The scavenging activity on hydroxyl radicals was better than that on superoxide anion free radicals and DPPH..

关 键 词：异黄酮衍生物 抗氧化活性 自由基 荧光光谱 紫外光谱 

分 类 号：R914[医药卫生—药物化学]