Chemistry of the sternal gland secretion of the Mediterranean centipede Himantarium gabrielis (Linnaeus, 1767) (Chilopoda: Geophilomorpha: Himantariidae)

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 spectromet...

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Bibliographic Details
Published in:Die Naturwissenschaften 2013-09, Vol.100 (9), p.861-870
Main Authors: Vujisić, Ljubodrag V, Vučković, Ivan M, Makarov, Slobodan E, Ilić, Bojan S, Antić, Dragan Ž, Jadranin, Milka B, Todorović, Nina M, Mrkić, Ivan V, Vajs, Vlatka E, Lučić, Luka R, Ćurčić, Božidar P. M, Mitić, Bojan M
Format: Article
Language:English
Subjects:
Animals
Arthropods - chemistry
benzaldehyde
Biomedical and Life Sciences
Bodily Secretions - chemistry
Chromatography, Liquid
electrophoresis
Environment
gas chromatography
Gas Chromatography-Mass Spectrometry
Geophilomorpha
hydrogen cyanide
Life Sciences
Magnetic Resonance Spectroscopy
mass spectrometry
Nitriles - chemistry
nuclear magnetic resonance spectroscopy
Original Paper
Proteins - chemistry
Proteins - secretion
secretion
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Summary: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.
ISSN:0028-1042
1432-1904
DOI:10.1007/s00114-013-1086-6