Antioxidant and antitumor activities of 4-arylcoumarins and 4-aryl-3,4-dihydrocoumarins

被引:36
|
作者
Zhang, Keyun [1 ]
Ding, Weixian [1 ,2 ,3 ]
Sun, Jie [2 ]
Zhang, Bin [1 ]
Lu, Fujiao [1 ]
Lai, Ren [1 ,4 ]
Zou, Yong [2 ,5 ]
Yedid, Gabriel [1 ]
机构
[1] Nanjing Agr Univ, Coll Life Sci, Nanjing 210095, Jiangsu, Peoples R China
[2] Chinese Acad Sci, Guangzhou Inst Chem, Guangzhou 510650, Guangdong, Peoples R China
[3] Kanion Pharmaceut Corp, Natl Key Lab Pharmaceut New Technol Chinese Med, Lianyungang, Peoples R China
[4] Chinese Acad Sci, Kunming Inst Zool, Kunming 650223, Yunnan, Peoples R China
[5] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510006, Guangdong, Peoples R China
基金
美国国家科学基金会;
关键词
Arylcoumarin; Antioxidant; Radical scavenging; Structure-activity relationships; Antitumor; OXYGEN-FREE-RADICALS; COUMARIN DERIVATIVES; NITRIC-OXIDE; METABOLISM; TOXICITY; INSECTS; ASSAY;
D O I
10.1016/j.biochi.2014.03.014
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Five 4-arylcoumarins (1c-g) and twelve 3,4-dihydro-4-arylcoumarins (2a-l) were synthesized and tested for antioxidant activity, antitumor activity, toxicity and structure-activity relationships analysis. 4-Arylcoumarins and 3,4-dihydro-4-arylcoumarins that possess two hydroxyl groups in ortho position, such as 1d, 1f, 2a, 2f, 2g and 2h had stronger radical scavenging properties than that of vitamin C (Vit C) in ABTS(center dot+) assay. Kinetic traces of scavenging ABTS(center dot+) and DPPH radicals showed that all the reaction could reached endpoint in 1 min, which was similar with Vit C. 4-Arylcoumarins with 3'-hydroxyl-4'-methylphenyl structural show more efficient NO center dot radical scavenging activity. Three compounds 2e, 1f and 2a, in particular had superior EC50 for NO center dot scavenging than did Vit C. MTT assay indicated that one compound in particular had a potential antitumor effect, inhibiting proliferation of BGC-823 cells and almost completely killing them at a concentration 62.5 mg/L. With same concentration 100 mu g/mL, hemolytic analysis in rabbit red blood cells showed that only two compounds had hemolytic activity with a little more than 5% hemolysis. Injection and oral toxicity tests on Galleria mellonella larvae showed that none of the tested 4-arylcoumarins significantly affected their appetite, viability and mortality. (C) 2014 Elsevier B.V. and Societe francaise de biochimie et biologie Moleculaire (SFBBM). All rights reserved.
引用
收藏
页码:203 / 210
页数:8
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