槲皮素-3-氧-酰基酯的合成及其生物活性

doi:10.16178/j.issn.0528-9017.20180303

浙江农业科学 ›› 2018, Vol. 59 ›› Issue (3): 363-369.DOI: 10.16178/j.issn.0528-9017.20180303

槲皮素-3-氧-酰基酯的合成及其生物活性

汪雷, 马琛, 高海立, 徐涛^*

浙江理工大学生命科学学院,浙江杭州 310018

收稿日期:2018-01-11 出版日期:2018-03-11
通讯作者: 徐涛(1964—),男,甘肃天水人,教授,博士,从事天然药物栽培及化学成分提取方面的研究工作,E-mail:xutao1998cn@163.com。
作者简介:汪雷(1989—),男,河南信阳人,硕士研究生,从事植物生理学方面的研究工作,E-mail:1157130668@qq.com。
基金资助:
国家自然科学基金(30772712)

Received:2018-01-11 Online:2018-03-11

摘要/Abstract

摘要： 槲皮素是一种具有多种生物活性的黄酮类化合物。以槲皮素为先导物,选择性地对C环3位羟基进行结构修饰。以廉价的芦丁为原料,经苄基化保护、酸水解得到中间体1(7,3',4'-氧-三苄基槲皮素),中间体1与羧酸发生Steglich酯化反应,再经Pd/C催化加氢脱苄基得到7种槲皮素-3-氧-酰基酯,目标产物结构经红外光谱(IR)、¹H核磁共振(NMR)、¹³C NMR、电喷雾-质谱(ESI-MS)确证。采用邻二氮菲法和DPPH法考查7种目标化合物的抗氧化活性,结果显示,槲皮素3位羟基以2~3个碳原子的羧酸取代能提高其抗氧化活性。采用MTT法初步评价了7种目标化合物对人食管癌细胞(EC109)、人食管鳞癌细胞(EC9706)、人胃癌细胞(MGC-803)和人前列腺癌细胞(PC-3)的抑制作用。结果表明,槲皮素3位羟基以7个碳原子以上羧酸取代能显著提高其对MGC-803细胞的抑制作用。

关键词: 槲皮素, 槲皮素酯类衍生物, 抗氧化活性, 抗肿瘤活性

中图分类号:

汪雷, 马琛, 高海立, 徐涛. 槲皮素-3-氧-酰基酯的合成及其生物活性[J]. 浙江农业科学, 2018, 59(3): 363-369.

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槲皮素-3-氧-酰基酯的合成及其生物活性

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