, Volume 52, Issue 3, pp 259–263 | Cite as

Cyclohexadienones-insect growth inhibitors from the foliar surface and tissue extracts ofSenecio cannabifolius

  • L. Lajide
  • P. Escoubas
  • J. Mizutani
Research Articles


Dewaxed leaf surface extracts of 12 plants from Hokkaido, prepared by dipping fresh leaves in chloroform for 3 min, were used in a choice leaf-disk bioassay against larvae of the tobacco cutwormSpodoptera litura. Activity was found only in the extract ofSenecio cannabifolius, a very successful weed in Hokkaido. Individual fractions of the extract, however, were not active. Incorporation of the individual fractions of the surface extracts as well as fractions of the methanolic extracts of the leaf residue into an artificial diet fed to neonateS. litura led to the isolation of ethyl (1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl) acetate, the major surface compound, as the active principle. This compound was also present in the methanolic extract of the leaf residue together with methyl (1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl) acetate, which had the same growth inhibitory effect on the larvae. The presence of these compounds in the foliar surface and tissue suggests a defensive role against herbivores.

Key words

Senecio cannabifolius Compositae foliar surface chemistry tobacco cutworm Spodoptera litura Lepidoptera Noctuidae growth inhibition ethyl (1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl) acetate methyl (1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl) acetate 


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  1. 1.
    Rosenthal, G. A., Sci. Am. 258 (1985) 94. pp. 1–34.Google Scholar
  2. 2.
    Rosenthal, G. A., in: Herbivores: Their interaction with Secondary Plant Metabolites, 2nd edition, Volume I. Eds M. R. Berenbaum and G. A. Rosenthal.Google Scholar
  3. 3.
    Balandrin, M. F., Klocke, J. A., Wurtele, E. S., and Bollinger, H. W.. Science228 (1986) 1154.Google Scholar
  4. 4.
    Chapman, R. F., Bull Entomol. Res.64 (1974) 339.Google Scholar
  5. 5.
    Chapman, R. F., and Bernays, E. A.. Experientia45 (1989) 215.Google Scholar
  6. 6.
    Bernays, E. A., and Chapman, R. F., Host-Plant Selection by Phytophagous Insects. Chapman and Hall, New York 1994.Google Scholar
  7. 7.
    Nitao, J. K., and Zangerl, A. R. Ecology68 (1987) 521.Google Scholar
  8. 8.
    Stadler, E., and Buser, H. R. Experientia40 (1984) 1157.Google Scholar
  9. 9.
    Eigenbrode, S. D., Espelie, K. E., and Shelton, A. M. J. chem. Ecol.17 (1991) 1694.Google Scholar
  10. 10.
    Zobel, A. M., and Brown, S. A. J. nat. Prod.51 (1988) 941.Google Scholar
  11. 11.
    Zobel, A. M., Wang, J., Mach, R. E., and Brown, S. A., J. chem. Ecol.17 (1991) 1859.Google Scholar
  12. 12.
    Goffreda, J. C., Mutschler, M. A., Ave, D. A., Tingey W. M., and Steffens, J. C., J. chem. Ecol.15 (1989) 2135.Google Scholar
  13. 13.
    Pelletier, Y., and Smilowitz, Z., J. chem. Ecol.16 (1990) 1847.Google Scholar
  14. 14.
    Menetrez, M. L., Spurr, H. W. Jr., Danehower, D. A., and Lawson, D. R., J. chem. Ecol.16 (1990) 1565.Google Scholar
  15. 15.
    Roeder, E., and Lu, K., Phytochemistry30 (1991) 1734.Google Scholar
  16. 16.
    Barrero, A. F., Sanchez, J. F., Alvarez-Manzaneda, E. J., and Alvarez-Manzaneda, R., Phytochemistry27 (1988) 1191.Google Scholar
  17. 17.
    Bohlmann, F., Knoll, K., Zdero, C., Marhanta, P. K., Grenz, M., Suwita, A., Ehlers, D., LeVan, N., Abraham, R. W., and Natu, A. A., Phytochemistry16 (1977) 965.Google Scholar
  18. 18.
    Escoubas, P., Lajide, L., and Mizutani, J., Entomologia exp. appl.66 (1993) 99.Google Scholar
  19. 19.
    Alkofahi, A., Rupprecht, J. K., Anderson, J. E., McLaughlin, J. L., Mikolajczak, K. L., and Scott, B. A., in: Insectides of Plant Origin (ACS Symposium Series, vol. 387) p. 25. Eds. J. T. Arnason, B. J. R. Philogene, and P. Morand. American Chemical Society, Washington D. C. 1989.Google Scholar
  20. 20.
    Gelbaum, L. T., Zalkow, L. H., and Hamilton, D., J. nat. Prod.45 (1988) 370.Google Scholar
  21. 21.
    Yvin, J. C., Chevolot, L., Chevolot-Magueur, A. M., and Cochard, J. C., J. nat. Prod.48 (1985) 814.Google Scholar
  22. 22.
    Araki, S., Katsumura, N., Kawasaki, K., Butsugan, Y., J. chem Soc., Perkin Trans. 1,3 (1991) 499.Google Scholar
  23. 23.
    Ogura, M., Cordell, G. A., and Farnsworth, N. R., J. nat. Prod.39 (1976) 255.Google Scholar
  24. 24.
    Bohlmann, F., Dupre, S., and Nordenstam, B., Phytochemistry29 (1990) 3136.Google Scholar
  25. 25.
    Pettit, G. R., Einck, J. J., Brown, P., Harvey, T. B. III., Ode, R. H., and Page, C. R., J. nat. Prod.43 (1980) 609.Google Scholar
  26. 26.
    Turner, A. B., Q. Rev. chem. Sco.18 (1964) 347.Google Scholar
  27. 27.
    Norris, D. M. in: Chemistry of Plant Protection, p. 97. Eds W. S. Bowers, W. Ebing, T. R. Fukuto, D. Martin, R. Wegler and I. Yamamoto, Springer Verlag, Heidelberg 1986.Google Scholar
  28. 28.
    Kubo, I., and Nakanishi, K, in: Host Plant Resistance to Pests, p. 165 Ed. P. A. Hedin. Am. Chem. Soc. Washington D. C. 1977.Google Scholar

Copyright information

© Birkhäuser Verlag 1996

Authors and Affiliations

  • L. Lajide
    • 1
  • P. Escoubas
    • 1
  • J. Mizutani
    • 1
  1. 1.Plant Ecochemicals ProjectResearch Development Corporation of Japan (JRDC), Eniwa RBPEniwa-Shi, HokkaidoJapan

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