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有机化学
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有机化学 ›› 2012, Vol. 32 ›› Issue (08): 1498-1502.DOI: 10.6023/cjoc201204002 上一篇    下一篇

研究简报

Aspernigerin的简便全合成及生物活性研究

吴清来a, 李永强b, 杨新玲a, 凌云a   

  1. a 中国农业大学理学院应用化学系 农业部农药化学与应用重点开放实验室 北京 100193;
    b 南开大学元素有机化学国家重点实验室 天津 300071
  • 收稿日期:2012-04-01 修回日期:2012-05-03 发布日期:2012-05-11
  • 通讯作者: 凌云 E-mail:lyun@cau.edu.cn
  • 基金资助:

    国家高技术研究发展计划(863计划)(No. 2011AA10A202)、国家自然基金(No. 21072222)资助项目.

Facile Total Synthesis and Bioactivity of Aspernigerin

Wu Qinglaia, Li Yongqiangb, Yang Xinlinga, Ling Yuna   

  1. a Key Laboratory of Pesticide Chemistry and Application, Ministry of Agriculture, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193;
    b State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071
  • Received:2012-04-01 Revised:2012-05-03 Published:2012-05-11
  • Supported by:

    Project supported by the National High-Tech R&D Program of China (863 Program) (No. 2011AA10A202) and the National Natural Science Foundation of China (No. 21072222).

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Aspernigerin是从狗牙根内生菌Aspergillus niger IFB-E003的培养液中分离得到的天然产物, 对癌细胞具有较强的活性. 设计了一条全新的合成路线, 以1,2,3,4-四氢喹啉和氯乙酰氯为主要原料, 经过两步反应合成了Aspernigerin, 总收率80.3%, 较文献报道的合成路线的总收率提高了33%. 首次对Aspernigerin进行农用生物活性测试, 结果表明, Aspernigerin具有一定的杀菌、杀虫活性和除草活性, 在600和200 μg/mL的浓度下对小菜蛾的杀虫活性分别为100%和75%, 在500 μg/mL的浓度下对稗草、小麦、黄瓜的根、茎的生长抑制率都在90%以上.

关键词: Aspernigerin, 天然产物, 全合成, 1,2,3,4-四氢喹啉, 氯乙酰氯, 生物活性

Aspernigerin is a natural product originally isolated from the extract of a culture of aspergillus niger IFB-E003, an endophyte in cyndon dactylon, and has been shown to be cytotoxic to the tumor cell lines. A facile total synthetic method for preparing aspernigerin from starting material 1,2,3,4-tetra-hydroquinoline and chloroacetyl chloride in two steps was reported. The total yield was 80.3% which increased 33% compared with the method of reference. The pesticide biological activity of aspernigerin was tested for the first time. The result indicated that aspernigerin exhibited certain fungicidal activities, insecticidal activities and herbicidal activities. Especially, the insecticidal activities against Plutella xylostella were 100% and 75% at the concentration of 600 and 200 μg/mL, respectively. The herbicidal activities against Echinochloa Crusgalli, Triticum aestivum and Cucumis sativus were all higher than 90% at the concentration of 500 μg/mL.

Key words: aspernigerin, natural product, total synthesis, 1,2,3.4-tetra-hydroquinoline, chloroacetyl, bioactivity