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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 08: 1498 - 1502

DOI: https://doi.org/10.6023/cjoc201204002

Notes

Facile Total Synthesis and Bioactivity of Aspernigerin

  • Wu Qinglai ,
  • Li Yongqiang ,
  • Yang Xinling ,
  • Ling Yun
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  • 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 date: 2012-04-01

  Revised date: 2012-05-03

  Online 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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Abstract

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

Cite this article

Wu Qinglai , Li Yongqiang , Yang Xinling , Ling Yun . Facile Total Synthesis and Bioactivity of Aspernigerin[J]. Chinese Journal of Organic Chemistry, 2012 , 32(08) : 1498 -1502 . DOI: 10.6023/cjoc201204002

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