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Journal of Chemical Ecology

, Volume 3, Issue 1, pp 101–113 | Cite as

Benzoyl cyanide and mandelonitrile benzoate in the defensive secretions of millipedes

  • S. S. Duffey
  • M. S. Blum
  • H. M. Fales
  • S. L. Evans
  • R. W. Roncadori
  • D. L. Tiemann
  • Y. Nakagawa
Article

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.

Key words

cyanogenesis polydesmoid millipedes phenol guaiacol benzoyl cyanide mandelonitrile benzoate ethyl benzoate defense antibiosis 

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Copyright information

© Plenum Publishing Corporation 1977

Authors and Affiliations

  • S. S. Duffey
    • 1
  • M. S. Blum
    • 1
    • 2
  • H. M. Fales
    • 1
    • 2
  • S. L. Evans
    • 1
    • 2
  • R. W. Roncadori
    • 1
    • 3
  • D. L. Tiemann
    • 1
    • 4
  • Y. Nakagawa
    • 1
    • 5
  1. 1.Department of EntomologyUniversity of GeorgiaAthens
  2. 2.Chemistry LaboratoryNational Heart and Lung InstituteBethesda
  3. 3.Department of Plant PathologyUniversity of GeorgiaAthens
  4. 4.Goleta
  5. 5.Shiongi & Co. Ltd.OsakaJapan

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