Journal of Chemical Ecology

, Volume 28, Issue 12, pp 2601–2612 | Cite as

1-Octen-3-ol Together with Geosmin: New Secretion Compounds from a Polydesmid Millipede, Niponia nodulosa

  • Hisashi Ômura
  • Yasumasa Kuwahara
  • Tsutomu Tanabe


The small millipede Niponia nodulosa (Polydesmida: Cryptodesmidae) emits an earthy smell when disturbed. This smell was obtained from hexane extracts from both sexes at the sixth and seventh instars and adult stages, and was found by GC/MS analyses to be composed of two compounds, 1-octen-3-ol as the major component and geosmin as the minor component. This is the first report of these compounds in secreted substances from millipedes. As they showed little repellent activity against foraging ants in bioassays, their biological function as defensive allomones was not clearly elucidated. However, both compounds provoked negative chemotaxis of conspecific millipedes in a Y-tube olfactometer, especially 1-octen-3-ol, which was active at a dose equivalent to the content of a single millipede. Such biological activity suggests that this compound is involved in intraspecific communication in this millipede and may play a role as an alarm pheromone.

Polydesmid millipede Niponia nodulosa secretion substances 1-octen-3-ol geosmin Y-tube olfactometer repellency alarm pheromone 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. Assaf, S., Hadar, Y., and Dosoretz, C. G. 1995. Biosynthesis of 13-hydroperoxylinoleate, 10-oxo-8-decenoic acid, and 1-octen-3-ol from linoleic acid by a mycelial pellet homogenate of Pleurotus pulmonarius. J. Agric. Food Chem. 43:2173–2178.CrossRefGoogle Scholar
  2. Beltran-Garcia, M. J., Estarron-Espinosa, M., and OGURA, T. 1997.Volatile compounds secreted by the oyster mushroom (Pleurotus ostreatus) and their antibacterial activities. J. Agric. Food Chem. 45:4049–4052.CrossRefGoogle Scholar
  3. Bentley, R. and Meganathan, R. 1981. Geosmin and methylisoborneol biosynthesis in Streptomycetes. FEBS Lett. 125:220–222.CrossRefGoogle Scholar
  4. Blum, M. S. and Woodring, J. P. 1962. Secretion of benzaldehyde and hydrogen cyanide by the millipede Pachydesmus crassicutis (Wood). Science 138:512–513.CrossRefGoogle Scholar
  5. Blum, M. S., MacConnell, J. G., Brand, J. M., Duffield, R. M., and Fales, H. M. 1973. Phenol and benzaldehyde in the defensive secretion of a strongylosomid millipede. Ann. Entomol. Soc. Am. 66:234–235.CrossRefGoogle Scholar
  6. Breheret, S., Talou, T., Rapior, S., and BessiÈre, J. M. 1999. Geosmin, as sesquiterpenoid compound responsible for the musty-earthy odor of Cortinarius herculeus, Cystoderma amianthinum, and Cy. carcharias. Mycologia 91:117–120.CrossRefGoogle Scholar
  7. Duffey, S. S. and Towers, G. H. N. 1978. On the biochemical basis of HCN production in the millipede Harpaphe haydeniana (Xystodesmidae: Polydesmida). Can. J. Zool. 56:7–16.CrossRefGoogle Scholar
  8. Duffey, S. S., Underhill, E. W., and Towers, G. H. N. 1974. Intermediates in the biosynthesis of HCN and benzaldehyde by a polydesmid millipede, Harpaphe haydeniana (Wood). Comp. Biochem. Physiol. 47B:753–766.Google Scholar
  9. Duffey, S. S., Blum, M. S., Fales, H. M., Evans, S. L., Roncadori, R. W., Tiemann, D. L., and Nakagawa, Y. 1977. Benzoyl cyanide and mandelonitrile benzoate in the defensive secretions of millipedes. J. Chem. Ecol. 3:101–113.CrossRefGoogle Scholar
  10. Eisner, T. and Meinwald, J. 1966. Defensive secretions of arthropods. Science 153:1341–1350.CrossRefGoogle Scholar
  11. Eisner, T., Alsop, D., Hicks, K., and Meinwald, J. 1978. Defensive secretions of millipedes, pp. 41–72, inS. Bettini (ed.). Arthropod Venoms. Handbook of Experimental Pharmacology, Vol. 48. Springer-Verlag, Berlin.CrossRefGoogle Scholar
  12. Fischer, G., Schwalbe, R., MÖller, M., Ostrowski, R., and Dott, W. 1999. Species-specific production of microbial volatile organic compounds (MVOC) by airborne fungi from a compost facility. Chemoshere 39:795–810.CrossRefGoogle Scholar
  13. Gerber, N. N. and Lechevalier, H. A. 1965. Geosmin, an earthy-smelling substance isolated from actinomycetes. Appl. Microbiol. 13:935–938.PubMedPubMedCentralGoogle Scholar
  14. Jelen, H. and Wasowicz, E. 1998. Volatile fungal metabolites and their relation to the spoilage of agricultural commodities. Food Rev. Int. 14:391–426.CrossRefGoogle Scholar
  15. Korpi, A., Kasanen, J. P., Alarie, Y., Kosma, V. M., and Pasanen, A. L. 1999. Sensory irritating potency of some microbial volatile organic compound (MVOCs) and a mixture of five MVOCs. Arch. Environ. Health 54:347–352.CrossRefGoogle Scholar
  16. Kuwahara, Y., Ômura, H., and Tanabe, T. 2002. 2-Nitroethenylbenzenes as natural products in millipede defense secretions. Naturwissenschaften. 89:308–310.CrossRefGoogle Scholar
  17. Medsker, L. L., Jenkins, D., and Thomas, J. F. 1968. An earthy-smelling compound associated with blue-green algae and actinomycetes. Environ. Sci. Technol. 2:461–464.CrossRefGoogle Scholar
  18. Meinwald, Y. C., Meinwald, J., and Eisner, T. 1966. 1,2-Dialkyl-4(3H)-quinazolinones in the defensive secretion of a millipede (Glomeris marginata). Science 154:390–391.CrossRefGoogle Scholar
  19. Monro, A., Chadha, M., Meinwald, J., and Eisner, T. 1962. Defensive mechanisms of arthropods VI. Para-benzoquinones in the secretion of five species of millipedes. Ann. Entomol. Soc. Am. 55:261–262.CrossRefGoogle Scholar
  20. Mori, N., Kuwahara, Y., Yoshida, T., and Nishida, R. 1994. Identification of benzaldehyde, phenol and mandelonitrile from Epanerchodus japonicus Carl (Polydesmida: Polydesmidae) as possible defense substances. Appl. Entomol. Zool. 29:517–552.CrossRefGoogle Scholar
  21. Mori, N., Kuwahara, Y., Yoshida, T., and Nishida, R. 1995. Major defensive cyanogen from Parafontaria laminata armigera Verhoeff (Xystodesmidae: Polydesmida). Appl. Entomol. Zool. 30:197–202.CrossRefGoogle Scholar
  22. Murahashi, S. 1936. Über die Riechstoffe des Matsutake. I Mitteil. Sci. Pap. Inst. Phys. Chem. Res. Tokyo 30:263–271.Google Scholar
  23. Murahashi, S. 1938. Über die Riechstoffe des Matsutake (Armillaria Matsutake Ito et Imai Agaricaceae). II Mitt. Sci. Pap. Inst. Phys. Chem. Res. Tokyo 34:155–172.Google Scholar
  24. Noguchi, S., Mori, N., Higa, Y., and Kuwahara, Y. 1997a. Identification of Nedyopus patrioticus patrioticus (Attems, 1898) (Polydesmida: Paradoxosomatidae) secretions as possible defense substances. Appl. Entomol. Zool. 32:447–452.CrossRefGoogle Scholar
  25. Noguchi, S., Mori, N., Higa, Y., and Kuwahara, Y. 1997b. Identification of mandelonitrile as a major secretory compound from Chamberlinius hualienensisWang (Polydesmida: Paradoxosomatidae). Jpn. J. Environ. Entomol. Zool. 8:208–214.Google Scholar
  26. Ômura, H., Kuwahara, Y., and Tanabe, T. 2002. Species-specific chemical compositions of defense secretions from Parafontaria tonominea Attems and Riukiaria semicircularis semicircularis Takakuwa (Polydesmida: Xystodesmidae).Appl. Entomol. Zool. 37:73–78.CrossRefGoogle Scholar
  27. Pasteels, J. M., GrÉgoire, J.-C., and Rowell-Rahier, M. 1983. The chemical ecology of defense in arthropods. Annu. Rev. Entomol. 28:263–289.CrossRefGoogle Scholar
  28. Pyysalo, H. 1976. Identification of volatile compounds in seven edible fresh mushrooms. Acta Chem. Scand. B 30:235–244.CrossRefGoogle Scholar
  29. Rapior, S., CavaliÉ, S., Andary, C., PÉlissier, Y., Marion, C., and BessiÈre, J.-M. 1996a. Investigation of some volatile components of seven fresh wild mushrooms (Basidiomycetes). J. Essent. Oil Res. 8:199–201.CrossRefGoogle Scholar
  30. Rapior, S., CavaliÉ, S., Croze, P., Andary, C., PÉlissier, Y., and BessiÈre, J.-M. 1996b. Volatile components of ten frozen mushrooms (Basidiomycetes). J. Essent. Oil Res. 8: 63–66.CrossRefGoogle Scholar
  31. Rapior, S., CavaliÉ, S., PÉlissier, Y., and BessiÉre, J.-M. 1997. Volatile composition of fourteen species of fresh wild mushrooms (Boletales). J. Essent. Oil Res. 9:231–234.CrossRefGoogle Scholar
  32. Roncadori, R. W., Duffey, S. S., and Blum, M. S. 1985. Antifungal activity of defensive secretions of certain millipedes. Mycologia 77:185–191.CrossRefGoogle Scholar
  33. SchnÜrer, J., Olsson, J., and BÖrjesson, T. 1999. Fungal volatiles as indicators of food and feed spoilage. Fungal Genet. Biol. 27:209–217.CrossRefGoogle Scholar
  34. Shinohara, K. and Tanabe, T. 1999. Arthropoda—Myriapoda—Diplopoda, pp. 680, in J. Aoki (ed.). Pictorial Keys to Soil Animals of Japan. Tokai University Press, Tokyo (in Japanese).Google Scholar
  35. Smolanoff, J., Kluge, A. F., Meinwald, J., McPhail, A., Miller, R.W., Hicks, K., and Eisner, T. 1975. Polyzonimine: a novel terpenoid insect repellent produced by a millipede. Science 188:734–736.CrossRefGoogle Scholar
  36. Towers, G. H. N., Duffey, S. S., and Siegel, S. M. 1972. Defensive secretions: biosynthesis of hydrogen cyanide and benzaldehyde from phenylalanine by a millipede. Can. J. Zool. 50:1047–1050.CrossRefGoogle Scholar
  37. Wood, W. F., Hanke, F. J., Kubo, I., Carroll, J. A., and Crews, P. 2000. Buzonamine, a new alkaloid from the defensive secretion of the millipede, Buzonium crassipes. Biochem. Syst. Ecol. 28:305–312.CrossRefGoogle Scholar
  38. Wood, W. F., Archer, C. L., and Largent, D. L. 2001. 1-Octen-3-ol, a banana slug antifeedant from mushrooms. Biochem. Syst. Ecol. 29:531–533.CrossRefGoogle Scholar
  39. Wurzenberger, M. and Werner, G. 1982. The enzymic oxidative breakdown of linoleic acid in mushrooms (Psalliota bispora). Z. Lebensm. Unters Forsch. 175:186–190.CrossRefGoogle Scholar

Copyright information

© Plenum Publishing Corporation 2002

Authors and Affiliations

  • Hisashi Ômura
    • 1
  • Yasumasa Kuwahara
    • 1
  • Tsutomu Tanabe
    • 2
  1. 1.Laboratory of Chemical Ecology, Division of Applied Life Sciences, Graduate School of AgricultureKyoto UniversitySakyo-ku, KyotoJapan
  2. 2.Tokushima Prefectural MuseumTokushimaJapan

Personalised recommendations