title: 2-Nitroethenylbenzenes as natural products in millipede defense secretions.
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 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.
authors.affiliation: Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Japan. kuwa34@kais.kyoto-u.ac.jp
authors.forename: Yasumasa
authors.initials: Y
authors.lastname: Kuwahara
authors.forename: Hisashi
authors.initials: H
authors.lastname: Omura
authors.forename: Tsutomu
authors.initials: T
authors.lastname: Tanabe
mesh_terms: D000818:Animals; D001688:Biological Products; D008401:Gas Chromatography-Mass Spectrometry; D006376:Helminths / Q000502:physiology*; D015394:Molecular Structure; D009578:Nitrobenzenes / Q000737:chemistry / Q000378:metabolism*
chemical_list: D001688:Biological Products; D009578:Nitrobenzenes