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Benzoyl cyanide and mandelonitrile benzoate in the defensive secretions of millipedes

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Abstract

Analyses of the defensive secretions of 17 species of polydesmoid millipedes show that other chemicals besides HCN and benzaldehyde are liberated during cyanogenesis. Several members of the families Polydesmidae, Paradoxosomatidae, and Euryuridae are shown to secrete both phenol and guaiacol, with one paradoxosomatid also producing ethyl benzoate and benzoic acid. Also, members of the family Xystodesmidae commonly produce the three following compounds: benozoic acid, mandelonitrile benzoate, and benzoyl cyanide. Benzoyl cyanide has not been found previously as a natural product. The defensive role of these additional natural products as antipredator and antibiotic agents is discussed. For certain predators benzoyl cyanide in particular seems to possess anaesthetic properties. Our studies provide an initial chemotaxonomic basis for distinguishing between various polydesmoid taxa.

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References

  • Barbetta, M., Casnati, G., andPavan, M. 1966. The presence of D(+)-mandelonitrile in the defensive secretion of the myriapodeGomphodesmus pavani.Mem. Soc. Entomol. Ital. 45:169–176.

    Google Scholar 

  • Blum, M.S. 1974. Deciphering the communicative Rosetta Stone.Bull. Entomol. Soc. Am. 20:30–35.

    Google Scholar 

  • Blum, M.S., andWoodring, J.P. 1962. Secretion of benzaldehyde and hydrogen cyanide by the millipedePachydesmus crassicatus. Science 138:512–513.

    Google Scholar 

  • Blum, M.S., Macconnell, J.G., Brand, J.M., Duffield, R.M., andFales, H.M. 1973. Phenol and benzaldehyde in the defensive secretion of a strongylosomid millipede.Ann. Entomol. Soc. Am. 66:235.

    Google Scholar 

  • Booth, J., andBoyland, E. 1958. Metabolism of polycyclic compounds 13. Enzymic hydroxylation of naphthalene by rat-liver microsomes.Biochem. J. 70:681–688.

    Google Scholar 

  • Casnati, G., Nencini, G., Quilico, A., Pavan, M., Ricca, A., andSalvatori, T. 1963. The secretion of the myriapod,Polydesmus collaris collaris. Experientia 19:409–411.

    Google Scholar 

  • Cloudsley-Thompson, J.L. 1968. Millipedes, Chapter 2,in Spiders, Scorpions, Centipedes and Mites, J. L. Cloudsley-Thompson (ed.), Pergamon Press, Oxford.

    Google Scholar 

  • Davenport, D., Wootton, D.M., andCushing, J.E. 1952. The biology of the Sierra luminous millipede.Luminodesmus sequoiae Loomis and Davenport.Biol. Bull. 102:100–110.

    Google Scholar 

  • Dornow, A., andTheidel, H. 1954. Uber Acylierungen mit α-Ketonitrilen.Angew. Chem. 66:605.

    Google Scholar 

  • Duffey, S.S., Underhill, E.W., andTowers, G.H.M. 1974. Intermediates in the biosynthesis of HCN and benzaldehyde by a polydesmid millipede,Harpaphe haydeniana (Wood).Comp. Biochem. Physiol. 47B:753–766.

    Google Scholar 

  • Duffield, R.M., Blum, M.S., andBrand, J.M. 1974. Guaiacol in the defensive secretions of polydesmid millipedes.Ann. Entomol. Soc. Am. 67:821–822.

    Google Scholar 

  • Eisner, H.E., Eisner, T., andHurst, J.J. 1963a. Hydrogen cyanide and benzaldehyde produced by millipedes.Chem. Ind. 1963:124–125.

    Google Scholar 

  • Eisner, H.E., Wood, W.F., andEisner, T. 1975. Hydrogen cyanide production in North American and African polydesmoid millipeds.Psyche 82:20–23.

    Google Scholar 

  • Eisner, T. 1970. Arthropod defenses, Chapter 8,in Chemical Ecology, E. Sondheimer and J.B. Simeone (eds.), Academic Press, New York.

    Google Scholar 

  • Eisner, T., Eisner, H.E., Hurst, J.J., Kafatos, F.C., andMeinwald, J. 1963b. Cyanogenic glandular apparatus of a millipede.Science 139:1218–1220.

    Google Scholar 

  • Guldensteeden-Egeling, C. 1882. Uber Bildung von Cyanwasserstoffsäure bei einem Myriapoden.Arch. Ges. Physiol. 28:576–577.

    Google Scholar 

  • Huffman, R.L. 1976. Personal communication.

  • Holm, T. 1965. Thermal rearrangement of esters of cyanohydrins of α,β-unsaturated aldehydes.Acta Chem. Scand. 19:242–245.

    Google Scholar 

  • Monteiro, H.J. 1961. Constituents of the secretion ofOrthomorpha coarctata Schubert.Anais Assoc. Brasil Quim. 20:29–31.

    Google Scholar 

  • Pallares, E.S. 1946. Note on the poison produced by thePolydesmus (fontaria) vicinus Lin-Arch.Biochem. 9:105–108.

    Google Scholar 

  • Rivers, J.J. 1886. Contributions to the larval history of Pacific coast Coleoptera.Bull. Calif. Acad. Sci. 2:64–72.

    Google Scholar 

  • Roth, L.M., andEisner, T. 1962. Chemical defenses of arthropods.Annu. Rev. Entomol. 7:107–136.

    Google Scholar 

  • Tiemann, D.L. 1967. Observations on the natural history of the western banded glowwormZarhipis integripennis (Le Conte) (Coleoptera: Phengodidae).Proc. Calif. Acad. Sci. 35:235–264.

    Google Scholar 

  • Towers, G.H.N., Duffey, S.S., andSiegel, S.M. 1972. Defensive secretion: Biosynthesis of hydrogen cyanide and benzaldehyde from phenylalanine by a millipede.Can. J. Zool. 50:1047–1050.

    Google Scholar 

  • Weatherston, J., andPercy, J.E. 1970. Arthropod defensive secretions,in Chemicals Controlling Insect Behavior, M. Beroza (ed.), Academic Press, New York.

    Google Scholar 

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Duffey, S.S., Blum, M.S., Fales, H.M. et al. Benzoyl cyanide and mandelonitrile benzoate in the defensive secretions of millipedes. J Chem Ecol 3, 101–113 (1977). https://doi.org/10.1007/BF00988137

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  • DOI: https://doi.org/10.1007/BF00988137

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