Abstract
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.
Similar content being viewed by others
References
Rosenthal, G. A., Sci. Am. 258 (1985) 94. pp. 1–34.
Rosenthal, G. A., in: Herbivores: Their interaction with Secondary Plant Metabolites, 2nd edition, Volume I. Eds M. R. Berenbaum and G. A. Rosenthal.
Balandrin, M. F., Klocke, J. A., Wurtele, E. S., and Bollinger, H. W.. Science228 (1986) 1154.
Chapman, R. F., Bull Entomol. Res.64 (1974) 339.
Chapman, R. F., and Bernays, E. A.. Experientia45 (1989) 215.
Bernays, E. A., and Chapman, R. F., Host-Plant Selection by Phytophagous Insects. Chapman and Hall, New York 1994.
Nitao, J. K., and Zangerl, A. R. Ecology68 (1987) 521.
Stadler, E., and Buser, H. R. Experientia40 (1984) 1157.
Eigenbrode, S. D., Espelie, K. E., and Shelton, A. M. J. chem. Ecol.17 (1991) 1694.
Zobel, A. M., and Brown, S. A. J. nat. Prod.51 (1988) 941.
Zobel, A. M., Wang, J., Mach, R. E., and Brown, S. A., J. chem. Ecol.17 (1991) 1859.
Goffreda, J. C., Mutschler, M. A., Ave, D. A., Tingey W. M., and Steffens, J. C., J. chem. Ecol.15 (1989) 2135.
Pelletier, Y., and Smilowitz, Z., J. chem. Ecol.16 (1990) 1847.
Menetrez, M. L., Spurr, H. W. Jr., Danehower, D. A., and Lawson, D. R., J. chem. Ecol.16 (1990) 1565.
Roeder, E., and Lu, K., Phytochemistry30 (1991) 1734.
Barrero, A. F., Sanchez, J. F., Alvarez-Manzaneda, E. J., and Alvarez-Manzaneda, R., Phytochemistry27 (1988) 1191.
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.
Escoubas, P., Lajide, L., and Mizutani, J., Entomologia exp. appl.66 (1993) 99.
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.
Gelbaum, L. T., Zalkow, L. H., and Hamilton, D., J. nat. Prod.45 (1988) 370.
Yvin, J. C., Chevolot, L., Chevolot-Magueur, A. M., and Cochard, J. C., J. nat. Prod.48 (1985) 814.
Araki, S., Katsumura, N., Kawasaki, K., Butsugan, Y., J. chem Soc., Perkin Trans. 1,3 (1991) 499.
Ogura, M., Cordell, G. A., and Farnsworth, N. R., J. nat. Prod.39 (1976) 255.
Bohlmann, F., Dupre, S., and Nordenstam, B., Phytochemistry29 (1990) 3136.
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.
Turner, A. B., Q. Rev. chem. Sco.18 (1964) 347.
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.
Kubo, I., and Nakanishi, K, in: Host Plant Resistance to Pests, p. 165 Ed. P. A. Hedin. Am. Chem. Soc. Washington D. C. 1977.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Lajide, L., Escoubas, P. & Mizutani, J. Cyclohexadienones-insect growth inhibitors from the foliar surface and tissue extracts ofSenecio cannabifolius . Experientia 52, 259–263 (1996). https://doi.org/10.1007/BF01920719
Received:
Revised:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF01920719