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天然黄酮香叶木素类及其衍生物的合成与生物活性研究
引用本文:蔡双莲,吴峥,吴进,汪秋安,单杨.天然黄酮香叶木素类及其衍生物的合成与生物活性研究[J].有机化学,2012,32(3):560-566.
作者姓名:蔡双莲  吴峥  吴进  汪秋安  单杨
作者单位:1. 湖南大学化学化工学院 长沙410082
2. 湖南省柑桔工程技术研究中心 长沙410125
基金项目:湖南省科技计划(No.2011FJ3214)资助项目~~
摘    要:以橙皮苷为原料,经脱氢、选择性甲基化、糖苷水解、相转移催化下的糖苷化反应、异戊烯基化和法呢烯基化等反应步骤,分别合成了3’-O-甲基香叶木素(1),香叶木素-7-O-β-D-葡萄糖苷(2),香叶木素-7-O-β-D-半乳糖苷(3),3’-O-甲基香叶木素-7-O-β-D-葡萄糖苷(4)4种天然产物及3’-O-甲基香叶木素-7-O-β-D-半乳糖苷(5),香叶木素-7-O-β-D-乙酰葡萄糖苷(6)、香叶木素-7-O-β-D-乙酰半乳糖苷(7),3’-O-甲基香叶木素-7-O-β-D-乙酰葡萄糖苷(8),3’-O-甲基香叶木素-7-O-β-D-乙酰半乳糖苷(9),7-O-异戊基香叶木素(10),7-O-异戊烯基-3’-O-甲基香叶木素(11)和7-O-法呢烯基-3’-O-甲基香叶木素(12)8种新的香叶木素衍生物.所合成化合物的结构已由核磁共振谱、红外光谱和质谱所证实,并用比色法MTT3-(4,5-二甲基噻唑-2)-2,5-二苯基四氮唑溴盐]蛋白染色法对所合成的目标化合物进行了体外抗肿瘤细胞生物活性测试,发现化合物6,10和11对肝癌细胞(SMMC-7721)、乳腺癌细胞(MCF-7)和结肠癌细胞(SW480)有一定的抑制活性.

关 键 词:黄酮类  橙皮苷  香叶木素  合成  生物活性

Synthesis and Biological Activities of Natural Flavonoid Diosmetin and Its Derivatives
Cai, Shuanglian , Wu, Zheng , Wu, Jing , Wang, Qiuan , Shan, Yang.Synthesis and Biological Activities of Natural Flavonoid Diosmetin and Its Derivatives[J].Chinese Journal of Organic Chemistry,2012,32(3):560-566.
Authors:Cai  Shuanglian  Wu  Zheng  Wu  Jing  Wang  Qiuan  Shan  Yang
Institution:Cai,Shuangliana Wu,Zhenga Wu,Jinga Wang,Qiuan,a Shan,Yangb(aCollege of Chemistry and Chemical Engineering,Hunan University,Changsha 410082)(bCentre for Citrus Engineering Technology Research in Hunan,Changsha 410125)
Abstract:Four natural flavonoids 3’-O-methyldiosmetin(1),diosmetin-7-O-β-D-glucoside(2),diosmetin-7-O-β-D-galactoside(3),3’-O-methyldiosmetin-7-O-β-D-glucoside(4),and eight new diosmetin derivatives 3’-O-methyldiosmetin-7O-β-D-galactoside(5),diosmetin-7-O-β-D-acetylglucoside(6),diosmetin-7-O-β-D-acetylgalactoside(7),3’-O-methyl-diosmetin-7-O-β-D-acetylglucoside(8),3’-O-methyldiosmetin-7-O-β-D-galactoside(9),7-O-isopentyldiosmetin(10),7-O-prenyldiosmetin(11) and 7-O-farnesyl-3’-O-methyldiosmetin(12) were synthesized from hesperidin by reaction steps including dehydrogenation,selective methylation,glycoside hydrolysis,glycosylation under phase transfer catalytic condition,O-prenylation and O-farnesylation,respectively.Their structures were confirmed by NMR,IR and MS techniques.The synthesized compounds were evaluated for biological activity against four human cancer cell lines by the standard MTT 3-(4,5-dimethylthiazol-2-y1)-2,5-diphenytetrazolium bromide] method,and the results showed that 6,10 and 11 exhibited moderate cytotoxicity against SMMC-7721,MCF-7 and SW480 cancer cell lines.
Keywords:flavonoid  hesperidin  diosmetin  synthesis  biological activity
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