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Naturwissenschaften

, Volume 89, Issue 7, pp 308–310 | Cite as

2-Nitroethenylbenzenes as natural products in millipede defense secretions

  • Yasumasa Kuwahara
  • Hisashi Ômura
  • Tsutomu Tanabe
Short Communication

Abstract.

The white millipede Eucondylodesmus elegans Miyosi (Polydesmida: Doratodesmidae) secretes odoriferous droplets from the glands on both lateral surfaces of its body segments. The secretion was shown to be composed of a mixture of (1E)- and (1Z)-2-nitroethenylbenzenes (2–3 µg per millipede), identified by GC/MS analyses and synthesis. This is the first identification of these compounds as natural products. A granulated sugar block baited with the synthetic compound (more than 0.71 µg) demonstrated repellent activity against foraging wild ants, indicating that the compound functioned as a defense substance against potential predators. α,β,2,3,4,5,6-d 7-(1E)-2-Nitroethenylbenzene was detected by GC/MS analysis in the millipede secretion after feeding with α,β,β,2,3,4,5,6-d 8-L-phenylalanine, indicating that L-phenylalanine is the precursor of these compounds.

Keywords

Sugar Natural Product Lateral Surface Body Segment Synthetic Compound 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Springer-Verlag 2002

Authors and Affiliations

  • Yasumasa Kuwahara
    • 1
  • Hisashi Ômura
    • 1
  • Tsutomu Tanabe
    • 2
  1. 1.Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan
  2. 2.Tokushima Prefectural Museum, Hachiman-cho, Tokushima 770-8070, Japan

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