黄芩素磺化物的合成、抗氧化活性及其与DNA作用的研究

天然产物研究与开发 ›› 2010, Vol. 23 ›› Issue (6): 961-964.

黄芩素磺化物的合成、抗氧化活性及其与DNA作用的研究

何清^1,2，王彦昌¹，贺云¹，张尊听^1*，张小清³

¹陕西师范大学化学与材料科学学院，西安 710062； ²温州大学化学与材料工程学院，温州 325027；³西安医学院，西安 710021

收稿日期:2009-05-26 出版日期:2011-01-10 发布日期:2011-10-19
通讯作者: zhangzt@snnu.edu.cn
基金资助:
教育部重点项目(107138)；陕西省自然科学基金资助(SJ08B19)

Synthesis of Sulfonated Baicalein and Its Antioxidative Activity and Interaction with DNA

HE Qing ^1,2 , WANG Yan-chang¹, HE Yun¹, ZHANG Zun-ting^1*, ZHANG Xiao-qing³

¹School of Chemistry and Materials Science, Shaanxi Normal University, Xi'an 710062, China; ²College of Chemistry and Materials Science, Wenzhou University, Wenzhou 325027, China; 3Xi’an Medical University, Xi'an 710061, China

Received:2009-05-26 Online:2011-01-10 Published:2011-10-19

摘要/Abstract

摘要：

以黄芩素为先导化合物利用磺化反应首次合成水溶性黄酮——黄芩素-8-磺酸钠，采用IR、¹H NMR和元素分析对黄芩素-8-磺酸钠结构进行了表征；同时，对磺化反应条件进行了优化。通过DPPH（1,1-二苯基-2-苦肼基自由基）法对黄芩素-8-磺酸钠清除自由基作用进行了研究；以溴化乙錠（EB）为荧光探针，研究了黄芩素-8-磺酸钠与CT-DNA的相互作用。实验结果表明：最佳的磺化反应条件为：黄芩素与浓硫酸比例1:8（g/mL），100 ℃时反应12 h。黄芩素-8-磺酸钠具有强抗氧化活性，与DNA结合作用显著。

关键词: 黄芩素, 黄芩素-8-磺酸钠, 抗氧化活性, CT-DNA

Abstract:

A sulfonate was introduced to the molecular structure of baicalein by sulfonation reaction and water-soluble flavone sodium baicalein-8-sulfonate was synthesized. Sodium baicalein-8-sulfonate was characterized by IR, ¹H NMR, and elemental analyses. And the conditions of sulfonation reaction were optimized. The antioxidative activity of sodium baicalein-8-sulfonate was tested by the method of DPPH (1,1-diphenyl-2-picrylhydrazyl free radical). Furthermore, the interaction of sodium baicalein-8-sulfonate with DNA was studied by fluorescent spectroscopy of EB as a spectral probe in Tris-HCl buffer (pH = 7.4). The result indicated that the optimal sulfonation reaction conditions are the ratio of baicalein and sulphuric acid=1:8 (g/mL), temperature 100 ℃, and time 12 h. The antioxidative activity of sodium baicalein-8-sulfonate was stronger than baicalein, and its interaction with DNA was higher.

Key words: baicalein, sodium baicalein-8-sulfonate, antioxidative activity, CT-DNA

何清，王彦昌，贺云，张尊听，张小清. 黄芩素磺化物的合成、抗氧化活性及其与DNA作用的研究[J]. 天然产物研究与开发, 2010, 23(6): 961-964.

HE Qing, WANG Yan-Chang, HE Yun, ZHANG Zun-Ting, ZHANG Xiao-Qing. Synthesis of Sulfonated Baicalein and Its Antioxidative Activity and Interaction with DNA[J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2010, 23(6): 961-964.

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