2-Nitroethenylbenzenes as natural products in millipede defense secretions.
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 microg 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 microg) demonstrated repellent activity against foraging wild ants, indicating that the compound functioned as a defense substance against potential predators. alpha,beta,2,3,4,5,6-d7-(1E)-2-Nitroethenylbenzene was detected by GC/MS analysis in the millipede secretion after feeding with alpha,beta,beta,2,3,4,5,6-d8-L-phenylalanine, indicating that L-phenylalanine is the precursor of these compounds.
Kuwahara
Yasumasa
Y
Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Japan. kuwa34@kais.kyoto-u.ac.jp
Omura
Hisashi
H
Tanabe
Tsutomu
T
D000818:Animals; D001688:Biological Products; D008401:Gas Chromatography-Mass Spectrometry; D006376:Helminths / Q000502:physiology*; D015394:Molecular Structure; D009578:Nitrobenzenes / Q000737:chemistry / Q000378:metabolism*
D001688:Biological Products; D009578:Nitrobenzenes