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Marine-Natural-Product Development: First Discovery of Nortopsentin Alkaloids as Novel Antiviral, Anti-phytopathogenic-Fungus, and Insecticidal Agents

  • Xiaofei Ji
    Xiaofei Ji
    State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071, China
    More by Xiaofei Ji
  • , 
  • Jincheng Guo
    Jincheng Guo
    State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071, China
    More by Jincheng Guo
  • , 
  • Yuxiu Liu
    Yuxiu Liu
    State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071, China
    More by Yuxiu Liu
  • , 
  • Aidang Lu
    Aidang Lu
    State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071, China
    More by Aidang Lu
  • , 
  • Ziwen Wang*
    Ziwen Wang
    Tianjin Key Laboratory of Structure and Performance for Functional Molecules, Key Laboratory of Inorganic−Organic Hybrid Functional Materials Chemistry, Ministry of Education, College of Chemistry, Tianjin Normal University, Tianjin 300387, China
    *E-mail: [email protected]. Tel.: 0086-22-23503792. Fax: 0086-22-23503792 (Z.W.).
    More by Ziwen Wang
  • , 
  • Yongqiang Li
    Yongqiang Li
    State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071, China
    More by Yongqiang Li
  • , 
  • Shaoxiang Yang
    Shaoxiang Yang
    Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, Beijing 100048, China
    More by Shaoxiang Yang
    Orcidhttp://orcid.org/0000-0002-9944-7472
  • , and 
  • Qingmin Wang*
    Qingmin Wang
    State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071, China
    *E-mail: [email protected]. Tel.: 0086-22-23503952. Fax: 0086-22-23503952 (Q.W.).
    More by Qingmin Wang
    Orcidhttp://orcid.org/0000-0002-6062-3766
Cite this: J. Agric. Food Chem. 2018, 66, 16, 4062–4072
Publication Date (Web):April 9, 2018
https://doi.org/10.1021/acs.jafc.8b00507
Copyright © 2018 American Chemical Society
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    Abstract

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    Nortopsentin alkaloids were found to have potent antiviral, anti-phytopathogenic-fungus, and insecticidal activities for the first time. Antiviral-activity tests revealed that these compounds were very sensitive to substituents, so a series of nortopsentin derivatives were designed, synthesized, and systematically evaluated for their antiviral activities against TMV, their fungicidal activities, and their insecticidal activities on the basis of a structural-diversity-derivation strategy. Compounds 2e (in vivo inactivation-, curative-, and protective-activity inhibitory rates of 50, 59, and 56%, respectively, at 500 μg/mL) and 2k (in vivo inactivation-, curative-, and protective-activity inhibitory rates of 60, 58, and 52%, respectively, at 500 μg/mL), with excellent antiviral activities and good physicochemical properties, emerged as new lead compounds for novel-antiviral-agent development. Further fungicidal-activity tests revealed that these alkaloids displayed broad-spectrum fungicidal activities. Compounds 2f, 2h, and 2j emerged as new lead compounds for antifungal-activity research. Additionally, all the compounds displayed good insecticidal activities against five kinds of insects, including Mythimna separate, Helicoverpa armigera, Ostrinia nubilalis, Plutella xylostella, and Culex pipiens pallens.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jafc.8b00507.

    • 1H and 13C NMR and HRMS spectra of nortopsentins in series 1 and 2 and 1H NMR spectra of compounds 4–10 (PDF)

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