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Chinese Journal of Organic Chemistry >

2012 >Issue 03: 560 - 566

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

Articles

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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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

Cite this article

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

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