Skip to main content
Log in

Benzoyl cyanide and mandelonitrile in the cyanogenetic secretion of a centipede

  • Published:
Journal of Chemical Ecology Aims and scope Submit manuscript

Abstract

Centipedes of the order Geophilomorpha produce a viscid odorous secretion that is effectively defensive against ants (Formica exsectoides). The secretion is proteinaceous and cyanogenetic. InGeophilus vittatus, the secretion contains two cyanogenetic compounds, mandelonitrile (I) and benzoyl cyanide (II), as well as two products derived from these compounds as a result of hydrogen cyanide production [benzaldehyde (III) and benzoic acid (IV)]. Benzoyl cyanide has not been reported previously from any natural source.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Attems, C.G. 1926. Chilopoda. Pages 239–402,in W. V. Kükenthal and T. Krumbach (eds.),Handbuch der Zoologie, Vol. 4, Walter de Gruyter and Co., Berlin.

    Google Scholar 

  • Barbetta, M., Casnati, G., andPavan, M. 1966. Sulla presenza di D-(+)-mandelonitrile nella secrezione difensiva del miriapodeGomphodesmus pavani Dem.Mem. Soc. Entomol. Ital. 45:169–176.

    Google Scholar 

  • Brade-Birks, H.K., andBrade-Birks, S.G. 1920. Note on Myriapoda. XX. Luminous Chilopoda, with special reference toGeophilus carpophagus, Leach.Ann. Mag. Nat. Hist. Ser. 9(5):1–30.

    Google Scholar 

  • Crabill, R.E. 1952.The centipedes of northeastern North America. Ph.D. thesis, Cornell University, Ithaca, New York. 450 pp.

    Google Scholar 

  • Eisner, H.E., Alsop, D.W., andEisner, T. 1967. Defense mechanisms of arthropods. XX. Quantitative assessment of hydrogen cyanide production in two species of millipedes.Psyche 74:107–117.

    Google Scholar 

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

    Google Scholar 

  • Feigl, F. 1966.Spot tests in organic analysis. Elsevier, New York. 772 pp.

    Google Scholar 

  • Koch, A. 1927. Studien an leuchtenden Tieren. I. Das Leuchten der Myriapoden.Z. Morphol. Ökol. Tiere 8:241–270.

    Google Scholar 

  • Moore, B.P. 1967. Hydrogen cyanide in the defensive secretions of larval Paropsini (Coleptera: Chrysomelidae).J. Aust. Entomol. Soc. 6:36–38.

    Google Scholar 

  • Murthy, M.R.V., andLeroux, T. 1975. Determination of protein in extracts containing interfering substances and in radioactive samples following scintillation counting.Anal. Biochem. 64:18–29.

    PubMed  Google Scholar 

  • Oakwood, T.S., andWeisgerber, C.A. 1965. Pages 112–114,in Organic syntheses, collected, Vol. 3, E.C. Horning, (ed.), John Wiley, New York.

    Google Scholar 

  • Schildknecht, H., Maschwitz, U., andKrauss, D. 1968. Blausäure im Wehrsekret des ErdläufersPachymerium ferrugineum.Naturwissenschaftern 55:230.

    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 

Download references

Author information

Authors and Affiliations

Authors

Additional information

This is Paper No. 48 in the seriesDefense Mechanisms of Arthropods.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Jones, T.H., Conner, W.E., Meinwald, J. et al. Benzoyl cyanide and mandelonitrile in the cyanogenetic secretion of a centipede. J Chem Ecol 2, 421–429 (1976). https://doi.org/10.1007/BF00988807

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00988807

Key words

Navigation