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Larvicidal activity of naturally occurring naphthoquinones and derivatives against the West Nile virus vector Culex pipiens

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Abstract

Concentration-dependent mortality effects were observed for three pure synthetic natural products (alkannin, shikonin, and shikalkin) and three acetylated derivatives of shikonin against Culex pipiens (Culicidae: Diptera) for the first time. The larvicidal properties of all naphthoquinones were evaluated under laboratory conditions against the larvae of the mosquito species C. pipiens biotype molestus, the anthropophilic biotype of the C. pipiens mosquito species. Experimental data of the tested toxicity of quinones revealed generally high efficacy where shikonin (3.9 mg/L) was the most active followed by shikalkin (8.73 mg/L) and alkannin (12.35 mg/L). The insecticidal performance of shikonin-acetylated derivatives was also investigated, aiming at the same time in the establishment of the relationships between the structure and the activity of shikonin-type compounds with larvicidal activity against C. pipiens. Results indicated that naphthoquinones, compared with other natural compounds with larvicidal activity, are very toxic against mosquito larvae and could be a potential source of natural larvicidal substances. Finally, bioassays with shikonin derivatives also revealed that although hydroxylic groups seem to play a secondary role in efficacy, the quinone moiety is essential.

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Acknowledgments

This project is cofinanced by the European Social Fund (75%), National Resources (25%)—Greek G.S.R.T. (PENED ‘01), and P. N. Gerolymatos S.A.

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Authors and Affiliations

  1. Laboratory of Agricultural Entomology, Department of Entomology and Agricultural Zoology, Benaki Phytopathological Institute, 8 S. Delta Str, Kifissia, 14561, Athens, Greece

    Antonios Michaelakis

  2. Natural Products Synthesis and Bioorganic Chemistry Lab., Institute of Physical Chemistry, NCSR “Demokritos”, 15310 Ag. Paraskevi, Attiki, P.O. Box 60228, Athens, Greece

    Antonios Michaelakis, Alexandros T. Strongilos, Emmanuel A. Bouzas & Elias A. Couladouros

  3. Chemistry Laboratories, Agricultural University of Athens, Iera Odos 75, Athens, 11855, Greece

    Alexandros T. Strongilos, Emmanuel A. Bouzas & Elias A. Couladouros

  4. Laboratory of Insecticides of Public Health Importance, Benaki Phytopathological Institute, 8 S. Delta Str, Kifissia, 14561, Athens, Greece

    George Koliopoulos

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  1. Antonios Michaelakis
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  2. Alexandros T. Strongilos
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  3. Emmanuel A. Bouzas
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  4. George Koliopoulos
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  5. Elias A. Couladouros
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Correspondence to Antonios Michaelakis or Elias A. Couladouros.

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Michaelakis, A., Strongilos, A.T., Bouzas, E.A. et al. Larvicidal activity of naturally occurring naphthoquinones and derivatives against the West Nile virus vector Culex pipiens . Parasitol Res 104, 657–662 (2009). https://doi.org/10.1007/s00436-008-1242-7

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  • DOI: https://doi.org/10.1007/s00436-008-1242-7

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