Facile Total Synthesis and Bioactivity of Aspernigerin

doi:10.6023/cjoc201204002

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (08): 1498-1502.DOI: 10.6023/cjoc201204002 Previous Articles Next Articles

Notes

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

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 Qinglai^a, Li Yongqiang^b, Yang Xinling^a, Ling Yun^a

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).

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

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Wu Qinglai, Li Yongqiang, Yang Xinling, Ling Yun. Facile Total Synthesis and Bioactivity of Aspernigerin[J]. Chin. J. Org. Chem., 2012, 32(08): 1498-1502.

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Aspernigerin的简便全合成及生物活性研究

Facile Total Synthesis and Bioactivity of Aspernigerin

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