匙萼金丝桃化学成分及镇痛与抗疟活性研究

刘健, 肖朝江, 崔淑君, 李阳, 董相, 姜北

中国药学杂志 ›› 2019, Vol. 54 ›› Issue (8) : 614-619.

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中国药学杂志 ›› 2019, Vol. 54 ›› Issue (8) : 614-619. DOI: 10.11669/cpj.2019.08.004
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匙萼金丝桃化学成分及镇痛与抗疟活性研究

  • 刘健, 肖朝江, 崔淑君, 李阳, 董相, 姜北*
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Chemical Constituents of Hypericum uralum and the Analgesic and Antimalarial Activities

  • LIUJian, XIAOChao-jiang, CUIShu-jun, LIYang, DONGXiang, JIANGBei*
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摘要

目的 对匙萼金丝桃(Hypericum uralum)化学成分进行分离鉴定;对部分成分的镇痛与β-羟高铁血红素形成抑制活性进行测试。方法 利用硅胶、Sephadex LH-20等材料柱色谱和现代波谱技术对匙萼金丝桃体积分数95%乙醇提取物乙酸乙酯部分化学成分进行分离和结构鉴定;采用小鼠乙酸扭体法、热水甩尾法和β-羟高铁血红素形成抑制实验对部分单体化合物进行生物活性测试。结果 从匙萼金丝桃体积分数95%乙醇提取物乙酸乙酯部位中分离得到13个化合物,分别鉴定为(-)-圣草素(1),3,4,5-三羟基酮(2),1,7-二羟基酮(3),4-羟基-2,3-二甲氧基酮(4),toxyloxanthone B(5),1,3,6,7-四羟基酮(6),2,3-二甲氧基酮(7),1,5,6-三羟基-3-甲氧基酮(8),hyperielliptone HD(9),3,3′,4,4′-四羟基联苯(10),莽草酸(11),槲皮素-3-O-(4″-甲氧基)-α-L-鼠李糖(12)和原花青素A-2(13)。镇痛活性测试结果表明,化合物3和12具有一定的外周镇痛活性;同时,化合物1表现出较强的β-羟高铁血红素形成抑制活性。结论 化合物1~13均为首次从该植物中分离得到;匙萼金丝桃镇痛与抗疟活性具有相应物质基础。

Abstract

OBJECTIVE To study the chemical constituents of Hypericum uralum were isolated and identified and test the analgesic activity and β-hematin formation inhibitory activity of some selected compounds. METHODS The compounds were isolated and purified by column chromatography padded with the separating material including silica gel and Sephadex LH-20, and their structures were elucidated based on the analyses of modern spectrum technology. Analgesic and antimalarial activities of selected compounds from H. uralum were evaluated by acetic acid-induced writhing, hot water tail-flick test in mice, and β-hematin formation inhibition method, respectively. RESULTS Thirteen compounds were isolated from ethyl acetate portion of 95% ethanol extract of H. uralum and identified as (-)-eriodictyol (1), 3,4,5-trihydroxyxanthone (2), 1,7-dihydroxyxanthone (3), 4-hydroxy-2,3-dimethoxyxanthone (4), toxyloxanthone B (5), 1,3,6,7-tetrahydroxyxanthone (6), 2,3-dimethoxyxanthone (7), 1,5,6-trihydroxy-3-methoxyxanthone (8), hyperielliptone HD (9), 3,3′,4,4′-tetrahydroxybiphenyl (10), shikimic acid (11), quercetin-3-O-(4″-methoxy)-α-L-rahmnopyranosyl (12), and proanthocyanidin A-2 (13). The analgesic activity test indicated that compounds 3 and 12 had certain peripheral analgesic activity, while compound 1 exhibited strong β-hematin formation inhibitory activity. CONCLUSION All the compounds are obtained from this plant for the first time.The analgesic and antimalarial activities of H. uralum have corresponding material basis.

关键词

匙萼金丝桃 / (-)-圣草素 / 1 / 7-二羟基 / 镇痛活性 / β-羟高铁血红素形成抑制活性 / 抗疟活性

Key words

Hypericum uralum / (-)-eriodictyol / 1,7-dihydroxyxanthone / analgesic activity / β-hematin formation inhibitory activity / antimalarial activity

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刘健, 肖朝江, 崔淑君, 李阳, 董相, 姜北. 匙萼金丝桃化学成分及镇痛与抗疟活性研究[J]. 中国药学杂志, 2019, 54(8): 614-619 https://doi.org/10.11669/cpj.2019.08.004
LIUJian, XIAOChao-jiang, CUIShu-jun, LIYang, DONGXiang, JIANGBei. Chemical Constituents of Hypericum uralum and the Analgesic and Antimalarial Activities[J]. Chinese Pharmaceutical Journal, 2019, 54(8): 614-619 https://doi.org/10.11669/cpj.2019.08.004
中图分类号: R965   

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基金

国家自然科学基金项目资助(81460532,81641187)
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