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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (06): 1024-1028. 上一篇    下一篇

研究论文

橙皮苷半合成5种生物活性黄酮类化合物

单杨*,a,b，李高阳b，汪秋安c，李忠海d   

  1. (a湖南省农产品加工研究所 长沙 410125)
    (b湖南省柑桔工程技术研究中心 长沙 410125)
    (c湖南大学化学化工学院 长沙 410082)
    (d中南林业科技大学食品科学与工程学院 长沙 410004)
  • 收稿日期:2007-07-20 修回日期:2007-12-10 发布日期:2008-06-26
  • 通讯作者: 单杨

Semisynthesis of Five Bioactive Flavonoids from Hesperidin

SHAN Yang*,a,b, LI Gao-Yangb, WANG Qiu-Anc, LI Zhong-Haid   


  1. (b Centre for Citrus Engineering Technology Research in Hunan, Changsha 410125)
    (c College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082)
    (d School of Food Science and Engineering Technology, Central South University of Forestry and Technology,
    Changsha 410004)
  • Received:2007-07-20 Revised:2007-12-10 Published:2008-06-26
  • Contact: SHAN Yang

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被引次数

98 | 9

以橙皮苷为原料, 经糖苷水解、选择性甲基化、脱氢、脱甲基化、O-异戊烯基化和O-法呢烯基化等反应步骤, 分别以总收率60%, 39%, 64%, 16%, 15%半合成了药用类黄酮天然产物桃皮素、木犀草素和新类黄酮化合物7-O-异戊烯基橙皮素、7-O-法呢烯基橙皮素、7,3'-O,O-二法呢烯基橙皮素, 所合成产物通过NMR, IR, MS等波谱方法进行了结构确证. 合成方法原料易得、工艺简便、收率较高, 具有较高的实用价值.

关键词: 橙皮苷, 半合成, 黄酮类化合物, 生物活性

Five bioactive flavonoids persicogenin, luteolin, 7-O-isopentenyl hesperietin, 7-O-farnesyl hesperietin and 7,3'-O,O-difarnesyl hesperietin were semisynthesized by reaction steps including glycoside hydrolysis, selective methylation, dehydrogenation, demethylation, O-prenylation and O-farnesylation respectively. The overall yields were 60%, 39%, 64%, 16% and 15% respectively calculated on the basis of hesperidin as the starting material. Their structures were confirmed by NMR, IR and MS spectra. The synthetic method has the advantages of easy availability of starting materials, simple operation and good yields. So it has considerable practical value.

Key words: semisynthesis, bioactive, flavonoid, hesperidin