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A Siphonotid Millipede (Rhinotus) as the Source of Spiropyrrolizidine Oximes of Dendrobatid Frogs

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Abstract

Poison frogs of the neotropical family Dendrobatidae contain a wide variety of lipophilic alkaloids, which are accumulated from alkaloid-containing arthropods. A small millipede, Rhinotus purpureus (Siphonotidae), occurs microsympatrically with the dendrobatid frog Dendrobates pumilio on Isla Bastimentos, Bocas del Toro Province, Panamá. Methanol extracts of this millipede contain the spiropyrrolizidine O-methyloxime 236, an alkaloid previously known only from skin extracts of poison frogs, including populations of D. pumilio. Thus, R. purpureus represents a likely dietary source of such alkaloids in dendrobatid frogs.

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References

  • Badio, B., Shi, D., Shin, Y., Hutchinson, K. D., Padgett, W. L., and Daly, J. W. 1996. Spiropy-rrolizidines: A new class of blockers of nicotinic receptors. Biochem. Pharmacol. 52:933–939.

    Google Scholar 

  • Daly, J. W., Andriamaharavo, N. R., Andriantsiferana, M., and Myers, C. W. 1996. Mada-gascan poison frogs (Mantella) and their skin alkaloids. Am. Mus. Novitates 3177:1–34.

    Google Scholar 

  • Daly, J. W., Garraffo, H. M., Jain, P., Spande, T. F., Snelling, R. R., Jaramillo, C., and Rand, A. S. 2000. Arthropod-frog connection: Decahydroquinoline and pyrrolizidine alkaloids common to microsympatric myrmicine ants and dendrobatid frogs. J. Chem. Ecol. 26:73–85.

    Google Scholar 

  • Daly, J. W., Garraffo, H. M., Pannell, L. K., and Spande, T. F. 1990. Alkaloids from Australian frogs (Myobatrachidae): Pseudophrynamines and pumiliotoxins. J. Nat. Prod. 53:407–421.

    Google Scholar 

  • Daly, J. W., Garraffo, M. H., Spande, T. F., Jaramillo, C., and Rand, S. A. 1994. Dietary source for skin alkaloids of poison frogs (Dendrobatidae)?. J. Chem. Ecol. 20:943–955.

    Google Scholar 

  • Daly, J. W., Kaneko, T., Wilham, J., Garraffo, M. H., Spande, T. F., Espinosa, A., and Donnelly, M. A. 2002. Bioactive alkaloids of frog skins: Combinatorial bioprospecting reveals that pumiliotoxins have an arthropod source. Proc. Natl. Acad. Sci. U.S.A. 99:13996–14001.

    Google Scholar 

  • <bib-book type="handbook">Eisner, T., Alsop, D., Hicks, K., and Meinwald, J. 1978. Defensive secretions of millipedes, pp. 41–72. in: Handbook of Experimental Pharmacology. Vol. 4. S. Bertini (ed.). Springer Verlag, Berlin, Germany.

    Google Scholar 

  • Garraffo, H. M., Spande, T. F., Daly, J. W., Baldessari, A., and Gros, E. G. 1993. Alkaloids from bufonid toads (Melanophyrniscus): Decahydroquinolines, pumiliotoxins and homopumiliotoxins, indolizidines, pyrrolizidines, and quinolizidines. J. Nat. Prod. 56:357–373.

    Google Scholar 

  • Meinwald, J., Smolanoff, J., Mcphail, A. T., Miller, R. W., Eisner, T., and Hicks, K. 1975. Nitropolyzonamine: A spirocyclic nitro compound from the defensive glands of a millipede (Poly-zonium rosalbum). Tetrahedon Lett. 28:2367–2370.

    Google Scholar 

  • Schildknecht, H., Maschwitz, U., and Wenneis, W. F. 1967. Neue Stofe aus dem Wehrsekret der Diplopodengattung Glomeris. Naturwissenschaften 16:196–197.

    Google Scholar 

  • Wood, W. F., Hanke, F. J., Kubo, I., Carroll, J. A., and Crews, P. 2000. Buzonamine, a new alkaloid from the defensive secretions of the millipede, Buzonium crassipes. Biochemi. Syst. Ecol. 28:305–312.

    Google Scholar 

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Correspondence to J. W. Daly.

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Saporito, R.A., Donnelly, M.A., Hoffman, R.L. et al. A Siphonotid Millipede (Rhinotus) as the Source of Spiropyrrolizidine Oximes of Dendrobatid Frogs. J Chem Ecol 29, 2781–2786 (2003). https://doi.org/10.1023/B:JOEC.0000008065.28364.a0

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  • DOI: https://doi.org/10.1023/B:JOEC.0000008065.28364.a0

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