Isolation, synthesis and anti-hepatitis B virus evaluation of p-hydroxyacetophenone derivatives from Artemisia capillaris.
Isolation, synthesis and anti-hepatitis B virus evaluation of p-hydroxyacetophenone derivatives from Artemisia capillaris.
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DOI：
10.1016/j.bmcl.2015.02.024
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发表时间：
2015-04
影响因子：
2.7
通讯作者：
Yong Zhao;Chang-An Geng;Hao Chen;Yun-bao Ma;Xiaoyan Huang;Tuan-wu Cao;K. He;Hao Wang;Xue-mei Zhang;Ji-Jun Chen
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文献类型：
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作者：
Yong Zhao;Chang-An Geng;Hao Chen;Yun-bao Ma;Xiaoyan Huang;Tuan-wu Cao;K. He;Hao Wang;Xue-mei Zhang;Ji-Jun Chen
对羟基苯乙酮（p-HAP）是茵陈中保肝利胆的主要成分，近年来研究发现其具有抗B型肝炎病毒（HBV）的作用。除top-HAP外，还从A中分离出4个p-HAP衍生物。毛细管电泳通过各种色谱方法。对β-HAP及其糖苷进行结构修饰，合成了28个新的衍生物，其中13个化合物具有抑制B肝炎表面抗原（HBsAg）分泌的活性，18个化合物具有抑制HBV DNA复制的活性。一级构效关系（SAR）表明，β-HAP糖苷与取代肉桂酸的共轭衍生物（2a-2 i）对HBV DNA复制有明显的抑制作用，IC_（50）为5.8 ~ 74.4 μM。
p-Hydroxyacetophenone (p-HAP), as a main hepatoprotective and choleretic constituent of Artemisia capillaris, was revealed with anti-hepatitis B virus (HBV) effects in recent investigation. In addition top-HAP, four derivatives ofp-HAP were also isolated fromA. capillarisby various chromatographic methods. Subsequent structural modification onp-HAP and its glycoside led to the synthesis of 28 additional derivatives, of which 13 compounds showed activity inhibiting hepatitis B surface antigen (HBsAg) secretion; and 18 compounds possessed inhibition on HBV DNA replication. The primary structure–activity relationships (SARs) suggested that the conjugated derivatives ofp-HAP glycoside and substituted cinnamic acids (2a–2i) obviously enhanced the activity against HBV DNA replication with IC50values ranged from 5.8 to 74.4 μM.