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2012 >Issue 03: 560 - 566

DOI: https://doi.org/10.6023/cjoc1109081

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 ,
  • 吴峥 ,
  • 吴进 ,
  • 汪秋安 ,
  • 单杨
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  • 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

  网络出版日期: 2012-03-24

基金资助

湖南省科技计划(No. 2011FJ3214)资助项目.

收起

Synthesis and Biological Activities of Natural Flavonoid Diosmetin and Its Derivatives

  • Cai Shuanglian ,
  • Wu Zheng ,
  • Wu Jing ,
  • Wang Qiuan ,
  • Shan Yang
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  • a College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082;
    b Centre for Citrus Engineering Technology Research in Hunan, Changsha 410125

Received date: 2011-09-08

  Revised date: 2011-10-14

  Online published: 2012-03-24

Supported by

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

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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

本文引用格式

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 , (03) : 560 -566 . DOI: 10.6023/cjoc1109081

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-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

参考文献

[1] Nakanishi, T.; Ogaki, J.; Inada, A.; Murata, H.; Nishi, M. J. Nat.Prod. 1985, 48, 491.  

[2] Zhao, C.-C.; Shao, J.-H.; Cao, D.-D.; Zhang, Y.-W.; Li, X. ChinaJ. China Mater. Med. 2009, 34, 2761 (in Chinese).(赵春超, 邵建华, 曹丹丹, 张玉伟, 李铣, 中国中药杂志, 2009,34, 2761.)

[3] Lin, L. Z.; Harnly, J. M. Food Chem. 2010, 120, 319.  

[4] Desoky, S. K.; Hawas, U. W.; Sharaf, M. Chem. Nat. Compd. 2007,43, 542.  

[5] Epifano, F.; Curini, M.; Genovese, S.; Blaskovich, M.; Hamilton,A.; Sebti, S. M. Bioorg. Med. Chem. 2007, 17, 2639.  

[6] Clark, M. K.; Scott, S. A.; Wojtkowiak, J.; Chirco, R.; Mathieu, P.;Reiners, J. J.; Mattingly, R. R.; Borch, R. F.; Gibbs, R. A. J. Med.Chem. 2007, 50, 3274.  

[7] Shan, Y.; Li, G.-Y.; Wang, Q.-A.; Li, Z.-H. Chin. J. Org. Chem.2008, 28, 1024 (in Chinese).(单阳, 李高阳, 汪秋安, 李忠海, 有机化学, 2008, 28, 1024.)

[8] Zhao, J.; Zhang, Z.-P.; Chen, H.-S.; Zhang, X.-Q.; Chen, X.-H.Acta Pharm. Sin. 1998, 33, 22 (in Chinese).(赵晶, 张致平, 陈鸿珊, 张兴权, 陈湘红, 药学学报, 1998, 33,22.)

[9] Wang, Q.-A.; Wu, Z.; Liu, L.; Zou, L.-H.; Luo, M. Chin. J. Org.Chem. 2010, 30, 1682 (in Chinese).(汪秋安, 吴峥, 刘莉, 邹亮华, 罗茗, 有机化学, 2010, 30, 1682.)
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