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Spruce Budworm Larval Processing of Piperidine Alkaloids from Spruce Needles

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Abstract

New needle bundles of Picea englemannii (Engelmann spruce) and Picea pungens (blue spruce) contain disubstituted piperidine alkaloids. No alkaloids were found in western spruce budworm larvae (Choristoneura occidentalis), which were feeding on the needles, but needle alkaloids were present in the budworm frass. Excretion of the alkaloids by the budworm larvae, either intact or after a metabolic change, was the common processing pathway. No sequestration could be demonstrated.

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REFERENCES

  • Attygalle, A. B., Xu, S.-C., McCormick, K. D., Meinwald, J., Blankespoor, C. L., and Eisner, T. 1993. Alkaloids of the Mexican bean beetle, Epilachna varivestis. Tetrahedron 49:9333–9342.

    Google Scholar 

  • Brattsen, L. B. 1992. Metabolic defenses against plant allelochemicals, pp. 205–209, in G. A. Rosenthal and M. R. Berenbaum (eds.). Herbivores: Their Interactions with Secondary Plant Metabolites, Vol. 2. Academic Press, San Diego.

    Google Scholar 

  • Brown, W. V., and Moore, B. P. 1982. The defensive alkaloids of Cryptolaemus montrouzieri (Coleoptera: Coccinellidae). Aust. J. Chem. 35:1255–1261.

    Google Scholar 

  • Brown, K. S., Jr., and Trigo, J. R. 1995. The ecological activity of alkaloids, pp. 227–354, in G. A. Cordell (ed.). The Alkaloids: Chemistry and Pharmacology. Vol. 47. Academic Press, San Diego.

    Google Scholar 

  • Cranshaw, W., Leatherman, D., and Kondratieff, B. 1993. Insects that feed on Colorado trees and shrubs. Bulletin 506A. Colorado State University Cooperative Extension, Fort Collins.

    Google Scholar 

  • Eisner, T., Goetz, M., Aneshansley, D., Ferstandig-Arnold, G., and Meinwald, J. 1986. Defensive alkaloid in blood of Mexican bean beetle (Epilachna varivestis). Experientia 42:204–207.

    Google Scholar 

  • Fodor, G. B., and Colasanti, B. 1985. The pyridine and piperidine alkaloids: Chemistry and pharmacology, pp. 4–79, in S. W. Pelletier (ed.). Alkaloids: Chemical and Biological Perspectives, Vol. 3. John Wiley, New York.

    Google Scholar 

  • Hart, N. K., Johns, S. R., and Lamberton, J. A. 1967. (+)-9-Aza-1-methylbicyclo[3.3.1]nonane, a new alkaloid from Euphorbia atoto Frost. Aust. J. Chem. 20:561–563.

    Google Scholar 

  • Hartmann, T. 1991. Alkaloids, pp. 79–123, in G. A. Rosenthal and M. R. Berenbaum (eds.). Herbivores: Their Interactions with Secondary Plant Metabolites, Vol. 1. Academic Press, San Diego.

    Google Scholar 

  • Johnson, W. T., and Lyon, H. H. 1988. Insects that Feed on Trees and Shrubs. Cornell University Press, Ithaca.

    Google Scholar 

  • Jones, T. H., Blum, M. S., and Robertson, H. G. 1990. Novel dialkylpiperidines in the venom of the ant Monomorium delagoense. J. Nat. Prod. 53:429–435.

    Google Scholar 

  • Kamm, C. D. 1997. Alkaloids in conifers and lousewort and insect processing. Ph.D. dissertation. Colorado State University, Fort Collins.

    Google Scholar 

  • MacConnell, J. G., Blum, M. S., and Fales, H. M. 1971. The chemistry of fire ant venom. Tetrahedron 27:1129–1139.

    Google Scholar 

  • Mody, N. V., Henson, R., Hedin, P. A., Kokpol, U., and Miles, D. H. 1976. Isolation of the insect paralyzing agent coniine from Sarracenia flava. Experientia 32:829–830.

    Google Scholar 

  • Proksch, P., Witte, L., Wray, V., and Hartmann, T. 1993. Ontogenetic variation of defensive alkaloids in the Mexican bean beetle Epilachna varivestis (Coleoptera: Coccinellidae). Entomol. Gener. 18:1–7.

    Google Scholar 

  • Roberts, M. F. 1975. γ-Coniceine reductase in Conium maculatum. Phytochemistry 14:2393–2395.

    Google Scholar 

  • Saunders, J. A., O'Neill, N. R., and Romeo, J. T. 1991. Alkaloid chemistry and feeding specificity of insect herbivores, pp. 151–196, in S. W. Pelletier (ed.). Alkaloids: Chemical and Biological Perspectives, Vol. 8. Pergamon Press, Oxford.

    Google Scholar 

  • Schneider, M. J. 1996. Pyridine and piperidine alkaloids: An update, pp. 155–300, in S. W. Pelletier (ed.). Alkaloids: Chemical and Biological Perspectives, Vol. 10. Pergamon Press, Oxford.

    Google Scholar 

  • Schneider, M. J., and Stermitz, F. R. 1990. Uptake of host plant alkaloids by root parasitic Pedicularis species. Phytochemistry 29:1811–1814.

    Google Scholar 

  • Schneider, M. J., Montali, J. A., Hazen, D., and Stanton, C. E. 1991. Alkaloids of Picea. J. Nat. Prod. 54:905–909.

    Google Scholar 

  • Schneider, M. J., Brendze, S., and Montali, J. A. 1995. Alkaloids of Picea breweriana. Phytochemistry 39:1387–1390.

    Google Scholar 

  • Sinclair, W. A., Lyon, H. H., and Johnson, W. T. 1987. Diseases of Trees and Shrubs. Cornell University Press, Ithaca.

    Google Scholar 

  • Stermitz, F. R., Miller, M. M., and Schneider, M. J. 1990. The stereochemistry of (−)-pinidinol, a piperidine alkaloid from Picea engelmannii. J. Nat. Prod. 53:1019–1020.

    Google Scholar 

  • Stermitz, F. R., Tawara, J. T., Boeckl, M., Pomeroy, M., Foderaro, T. A., and Todd, F. G. 1994. Piperidine alkaloid content of Picea (spruce) and Pinus (pine). Phytochemistry 35:951–953.

    Google Scholar 

  • Tawara, J. N., Blokhin, A., Foderaro, T. A., and Stermitz, F. R. 1993. Toxic piperidine alkaloids from pine (Pinus) and spruce (Picea) trees. New structures and a biosynthetic hypothesis. J. Org. Chem. 58:4813–4818.

    Google Scholar 

  • Tawara, J. N., Stermitz, F. R., and Blokhin, A. V. 1995. Alkaloids of young Ponderosa pine seedlings and late steps in the biosynthesis of pinidine. Phytochemistry 39:705–708.

    Google Scholar 

  • Todd, F. R. 1994. Potentially toxic compounds of Convolvulaceae and piperidine alkaloids of Picea. PhD dissertation, Colorado State University, Fort Collins.

    Google Scholar 

  • Todd, F. R., Stermitz, F. R., and Blokhin, A. V. 1995. Piperidine alkaloid content of Picea pungens (Colorado blue spruce). Phytochemistry 40:401–406.

    Google Scholar 

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Kamm, C.D., Tawara, J.N. & Stermitz, F.R. Spruce Budworm Larval Processing of Piperidine Alkaloids from Spruce Needles. J Chem Ecol 24, 1153–1160 (1998). https://doi.org/10.1023/A:1022490701358

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