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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 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 pr...otein 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.
Keywords:
Chemical deterrents / Geophilomorphs / Viscid proteinaceous secretion / Himantarine / Farnesyl 2,3-dihydrofarnesoate / Montenegro
TY - JOUR
AU - Vujisić, Ljubodrag V.
AU - Vučković, Ivan M.
AU - Makarov, Slobodan E.
AU - Ilić, Bojan S.
AU - Antić, Dragan Ž.
AU - Jadranin, Milka
AU - Todorović, Nina
AU - Mrkić, Ivan
AU - Vajs, Vlatka
AU - Lučić, Luka
AU - Ćurčić, Božidar P. M.
AU - Mitić, Bojan M.
PY - 2013
UR - https://cherry.chem.bg.ac.rs/handle/123456789/1394
AB - 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.
PB - Springer, New York
T2 - Naturwissenschaften
T1 - Chemistry of the sternal gland secretion of the Mediterranean centipede Himantarium gabrielis (Linnaeus, 1767) (Chilopoda: Geophilomorpha: Himantariidae)
VL - 100
IS - 9
SP - 861
EP - 870
DO - 10.1007/s00114-013-1086-6
ER -
@article{
author = "Vujisić, Ljubodrag V. and Vučković, Ivan M. and Makarov, Slobodan E. and Ilić, Bojan S. and Antić, Dragan Ž. and Jadranin, Milka and Todorović, Nina and Mrkić, Ivan and Vajs, Vlatka and Lučić, Luka and Ćurčić, Božidar P. M. and Mitić, Bojan M.",
year = "2013",
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.",
publisher = "Springer, New York",
journal = "Naturwissenschaften",
title = "Chemistry of the sternal gland secretion of the Mediterranean centipede Himantarium gabrielis (Linnaeus, 1767) (Chilopoda: Geophilomorpha: Himantariidae)",
volume = "100",
number = "9",
pages = "861-870",
doi = "10.1007/s00114-013-1086-6"
}
Vujisić, L. V., Vučković, I. M., Makarov, S. E., Ilić, B. S., Antić, D. Ž., Jadranin, M., Todorović, N., Mrkić, I., Vajs, V., Lučić, L., Ćurčić, B. P. M.,& Mitić, B. M.. (2013). Chemistry of the sternal gland secretion of the Mediterranean centipede Himantarium gabrielis (Linnaeus, 1767) (Chilopoda: Geophilomorpha: Himantariidae). in Naturwissenschaften
Springer, New York., 100(9), 861-870.
https://doi.org/10.1007/s00114-013-1086-6
Vujisić LV, Vučković IM, Makarov SE, Ilić BS, Antić DŽ, Jadranin M, Todorović N, Mrkić I, Vajs V, Lučić L, Ćurčić BPM, Mitić BM. Chemistry of the sternal gland secretion of the Mediterranean centipede Himantarium gabrielis (Linnaeus, 1767) (Chilopoda: Geophilomorpha: Himantariidae). in Naturwissenschaften. 2013;100(9):861-870.
doi:10.1007/s00114-013-1086-6 .
Vujisić, Ljubodrag V., Vučković, Ivan M., Makarov, Slobodan E., Ilić, Bojan S., Antić, Dragan Ž., Jadranin, Milka, Todorović, Nina, Mrkić, Ivan, Vajs, Vlatka, Lučić, Luka, Ćurčić, Božidar P. M., Mitić, Bojan M., "Chemistry of the sternal gland secretion of the Mediterranean centipede Himantarium gabrielis (Linnaeus, 1767) (Chilopoda: Geophilomorpha: Himantariidae)" in Naturwissenschaften, 100, no. 9 (2013):861-870,
https://doi.org/10.1007/s00114-013-1086-6 . .
