Chin. J. Org. Chem. ›› 2012, Vol. ›› Issue (03): 560-566.DOI: 10.6023/cjoc1109081 Previous Articles     Next Articles

Articles

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 出版日期:2012-03-25 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 Online:2012-03-25 Published:2012-03-24
  • Supported by:

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

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