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Title: | Chemistry of the sternal gland secretion of the Mediterranean centipede Himantarium gabrielis (Linnaeus, 1767) (Chilopoda: Geophilomorpha: Himantariidae) | Authors: | Vujisić, Ljubodrag Vučković, Ivan Makarov, Slobodan Ilić, Bojan Antić, Dragan Jadranin, Milka Todorović, Nina Mrkić, Ivan Vajs, Vlatka Lučić, Luka Ćurčić, Božidar Mitić, Bojan. |
Keywords: | Chemical deterrents;;Geophilomorphs;;Viscid proteinaceous secretion;;Himantarine;;Farnesyl 2,3-dihydrofarnesoate;;Montenegro. | Issue Date: | 2013 | Rank: | M21 | Publisher: | Springer, New York | Journal: | Science of Nature - Naturwissenschaften | Volume: | 100 | Start page: | 861 | End page: | 870 | 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. |
URI: | https://biore.bio.bg.ac.rs/handle/123456789/5970 | DOI: | 10.1007/s00114-013-1086-6 |
Appears in Collections: | Journal Article |
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