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有机化学
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有机化学 ›› 2012, Vol. ›› Issue (03): 560-566.DOI: 10.6023/cjoc1109081 上一篇    下一篇

研究论文

天然黄酮香叶木素类及其衍生物的合成与生物活性研究

蔡双莲a, 吴峥a, 吴进a, 汪秋安a, 单杨b   

  1. a 湖南大学化学化工学院 长沙 410082;
    b 湖南省柑桔工程技术研究中心 长沙 410125
  • 收稿日期:2011-09-08 修回日期:2011-10-14 发布日期:2012-03-24
  • 通讯作者: 汪秋安 E-mail:wangqiuan@yahoo.com
  • 基金资助:

    湖南省科技计划(No. 2011FJ3214)资助项目.

Synthesis and Biological Activities of Natural Flavonoid Diosmetin and Its Derivatives

Cai Shuangliana, Wu Zhenga, Wu Jinga, Wang Qiuana, Shan Yangb   

  1. a College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082;
    b Centre for Citrus Engineering Technology Research in Hunan, Changsha 410125
  • Received:2011-09-08 Revised:2011-10-14 Published:2012-03-24
  • Supported by:

    Project supported by the Science and Technology Planning Project of Hunan Province (No. 2011FJ3214).

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被引次数

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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MTT[3-(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

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-7-O-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.

Key words: flavonoid, hesperidin, diosmetin, synthesis, biological activity