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Sequestration of ingested [14C]senecionineN-oxide in the exocrine defensive secretions of chrysomelid beetles

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Oreina cacaliae (Chrysomelidae) sequesters in its elytral and pronotal defensive secretion theN-oxides of pyrrolizidine alkaloids (PAN-oxides) from its food plantAdenostyles alliariae (Asteraceae). [14C]SenecionineN-oxide was applied for detailed studies of PAN-oxide sequestration. An average of 11.4% of total radioactivity is taken up by individual beetles which had received [14C]senecionineN-oxide with their food leaves 8 days before. An average of 28.9% of the ingested radioactivity could be recovered from the defensive secretions collected twice, i.e., 5 and 8 days after tracer feeding. The tracer transfer into the secretion seems to be a slow but progressive process as indicated by the high percentage of tracer still recovered from the secretion sampled after 8 days. Chromatographic analysis revealed that [14C]senecionineN-oxide is the only labeled compound in the defensive secretion. Beetles that fed on tertiary [14C]senecionine sequestered only trace amounts of radioactivity (exclusively present as labeled IV-oxide) in their secretions.O. speciosissima, a species also adapted to PA containing food plants, was shown to sequester [14C]senecionineN-oxide with the same efficiency asO. cacaliae. O. bifrons, a specialist feeding onChaerophyllum hirsutum (Apiaceae), rejected PA treated leaf samples already at very low PA concentrations (10 nmol/leaf piece). In bothO. cacaliae andO. speciosissima, [14C]senecionineN-oxide applied by injection into the hemolymph is rapidly transferred into the glands.O. bifrons, not adapted to pyrrolizidine alkaloid containing plants was unable to sequester [14C]-senecionineN- oxide in the secretion but rapidly eliminated the tracer with the frass. Again, only traces of labeled [14C]senecionineN-oxide were found in the defensive secretions of the two PA adapted species if labeled senecionine was injected. It is suggested that the beetles are adapted to theN-oxide form of PAs, similarly as their food plants, and that they lack the ability to efficientlyN-oxidize tertiary PAs. No indication forde novo PA synthesis by the beetles was found in tracer feeding experiments with the biogenetic PA precursor putrescine.

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References

  • Boppré, M. 1986. Insect pharmacophagously utilize defensive plant chemicals (pyrrolizidine alkaloids).Naturwissenschaften 73:17–26.

    Google Scholar 

  • Boppré, M. 1990. Lepidoptera and pyrrolizidine alkaloids; exemplification of complexity in chemical ecology.J. Chem. Ecol. 16:165–185.

    Google Scholar 

  • Brown, K.S. 1984. Adult-obtained pyrrolizidine alkaloids defend ithomiine butterflies against a spider predator.Nature 309:707–709.

    Google Scholar 

  • Ehmke, A., von Borstel, K., andHartmann, T. 1988. AlkaloidN-oxides as transport and vacuolar storage compounds of pyrrolizidine alkaloids inSenecio vulgaris L.Planta 176:83–90.

    Google Scholar 

  • Ehmke, A., Witte, L., Biller, A., andHartmann, T. 1990. Sequestration,N-oxidation and transformation of plant pyrrolizidine alkaloids by the arctiid mothTyria jacobaeae L.Z. Naturforsch. 45c:1185–1192.

    Google Scholar 

  • Ferguson, J.E., andMetcalf, R.L. 1985. Cucurbitacins. Plant-derived defense compounds for Diabroticites (Coleoptera: Chrysomelidae).J. Chem. Ecol. 11:311–317.

    Google Scholar 

  • Hartmann, T., andToppel, G. 1987. SenecionineN-oxide, the primary product of pyrrolizidine alkaloid biosynthesis in root cultures ofSenecio vulgaris.Phytochemistry 26:1639–1643.

    Google Scholar 

  • Hartmann, T., Sander, H., Adolph, R., andToppel, G. 1988. Metabolic links between the biosynthesis of pyrrolizidine alkaloids and polyamines in root cultures ofSenecio vulgaris.Planta 175:82–90.

    Google Scholar 

  • Hartmann, T., Ehmke, A., Eilert, U. V., Borstel, K., andTheuring, C. 1989. Sites of synthesis, translocation and accumulation of pyrrolizidine alkaloidN-oxides inSenecio vulgaris L.Planta 177:98–107.

    Google Scholar 

  • Hartmann, T., Biller, A., Witte, L., Ernst, L., andBoppré, M. 1990. Transformation of plant pyrrolizidine alkaloids into novel insect alkaloids by arctiid moths (Lepidoptera).Biochem. Syst. Ecol. 18:549–554.

    Google Scholar 

  • Pasteels, J.M., Rowell-Rahier, M., Randoux, T., Braekman, J.C., andDaloze, D. 1988a. Pyrrolizidine alkaloids of propable host-plant origin in the protonal and elytral secretion of the leaf beetleOreina cacaliae.Entomol. Exp. Appl. 49:55–58.

    Google Scholar 

  • Pasteels, J.M., Rowell-Rahier, M., andRaupp, M.J. 1988b. Plant-derived defense in chrysomelid beetles, pp. 235–272,in P. Barbosa and D. Letourneau (eds.). Novel Aspects of Insect-Plant Interactions. J. Wiley & Sons, New York.

    Google Scholar 

  • Rowell-Rahier, M.,Witte, L.,Ehmke, A.,Hartmann, T., andPasteels, J.M. 1991. Sequestration of plant pyrrolizidine alkaloids by chrysomelid beetles and selective transfer into the defensive secretions.Chemoecology. In press.

  • Schneider, D. 1987. The strange fate of pyrrolizidine alkaloids, pp. 123–142,in R.F. Chapman, E.A. Bernays, and J.G. Stoffolano (eds.). Perspectives in Chemoreception and Behavior. Springer, New York.

    Google Scholar 

  • vanOycke, S., Braekman, J.C., Daloze, J.C., andPasteels, J.M. 1987. Cardenolide biosynthesis in chrysomelid beetles.Experientia 43:460–462.

    Google Scholar 

  • van Oycke, S., Rendoux, T., Braekman, J.C., Daloze, D., andPasteels, J.M. 1988. New cardenolide glycosides from the defense glands of chrysolinina beetles (Coleoptera: Chrysomelidae).Bull. Soc. Chim. Belg. 97:297–311.

    Google Scholar 

  • von Nickisch-Rosenegk, E., Schneider, D., andWink, M. 1990. Time-course of pyrrolizidine alkaloid processing in the alkaloid expoiting arctiid moth,Creatonotos transiens.Z. Naturforsch. 45c:881–889.

    Google Scholar 

  • Wagner, J., Danzin, C., andMamont, P. 1986. Reversed-phase ion-pair liquid Chromatographic procedure for the simultaneous analysis of S-adenosylmethionine, its metabolites and the natural polyamines.J. Chromatogr. 227:349–368.

    Google Scholar 

  • Wink, M., andSchneider, D. 1988. Carrier-mediated uptake of pyrrolizidine alkaloids in larvae of the aposematic and alkaloid-exploiting moth,Creatonotos. Naturwissenschaften 75:524–525.

    Google Scholar 

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Ehmke, A., Rowell-Rahier, M., Pasteels, J.M. et al. Sequestration of ingested [14C]senecionineN-oxide in the exocrine defensive secretions of chrysomelid beetles. J Chem Ecol 17, 2367–2379 (1991). https://doi.org/10.1007/BF00994588

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