title: Chemistry of the sternal gland secretion of the Mediterranean centipede Himantarium gabrielis (Linnaeus, 1767) (Chilopoda: Geophilomorpha: Himantariidae).
abstract: The geophilomorph centipede, Himantarium gabrielis, when disturbed, discharges a viscous and proteinaceous secretion from the sternal glands. This exudate was found by gas chromatography-mass spectrometry, liquid chromatography-high resolution mass spectrometry, liquid chromatography-mass spectrometry-mass spectrometry and NMR analyses to be composed of hydrogen cyanide, benzaldehyde, benzoyl nitrile, benzyl nitrile, mandelonitrile, mandelonitrile benzoate, 3,7,6O-trimethylguanine (himantarine), farnesyl 2,3-dihydrofarnesoate and farnesyl farnesoate. This is the first report on the presence of benzyl nitrile and mandelonitrile benzoate in secreted substances from centipedes. Farnesyl 2,3-dihydrofarnesoate is a new compound, while himantarine and farnesyl farnesoate were not known as natural products. A post-secretion release of hydrogen cyanide by reaction of mandelonitrile and benzoyl nitrile was observed by NMR, and hydrogen cyanide signals were completely assigned. In addition, a protein component of the secretion was analysed by electrophoresis which revealed the presence of a major 55 kDa protein. Analyses of the defensive exudates of other geophilomorph families should produce further chemical surprises.
authors.affiliation: Faculty of Chemistry, University of Belgrade, Studentski Trg 12-16, 11000 Belgrade, Serbia.
authors.forename: Ljubodrag V
authors.initials: LV
authors.lastname: Vujisić
authors.forename: Ivan M
authors.initials: IM
authors.lastname: Vučković
authors.forename: Slobodan E
authors.initials: SE
authors.lastname: Makarov
authors.forename: Bojan S
authors.initials: BS
authors.lastname: Ilić
authors.forename: Dragan Z
authors.initials: DZ
authors.lastname: Antić
authors.forename: Milka B
authors.initials: MB
authors.lastname: Jadranin
authors.forename: Nina M
authors.initials: NM
authors.lastname: Todorović
authors.forename: Ivan V
authors.initials: IV
authors.lastname: Mrkić
authors.forename: Vlatka E
authors.initials: VE
authors.lastname: Vajs
authors.forename: Luka R
authors.initials: LR
authors.lastname: Lučić
authors.forename: Božidar P M
authors.initials: BP
authors.lastname: Curčić
authors.forename: Bojan M
authors.initials: BM
authors.lastname: Mitić
mesh_terms: D000818:Animals; D001181:Arthropods / Q000737:chemistry*; D012634:Bodily Secretions / Q000737:chemistry*; D002853:Chromatography, Liquid; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D009570:Nitriles / Q000737:chemistry; D011506:Proteins / Q000737:chemistry / Q000378:metabolism
chemical_list: D009570:Nitriles; D011506:Proteins; C011206:cyanogen
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