Chemistry of the sternal gland secretion of the Mediterranean centipede Himantarium gabrielis (Linnaeus, 1767) (Chilopoda: Geophilomorpha: Himantariidae)
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2013
Authors
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.
Article (Published version)

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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 / MontenegroSource:
Naturwissenschaften, 2013, 100, 9, 861-870Publisher:
- Springer, New York
Funding / projects:
- Natural products of wild, cultivated and edible plants: structure and bioactivity determination (RS-172053)
- Ontogenetic characterization of phylogenetic biodiversity (RS-173038)
DOI: 10.1007/s00114-013-1086-6
ISSN: 0028-1042
PubMed: 23907296
WoS: 000323670800006
Scopus: 2-s2.0-84883453390
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Hemijski fakultet / Faculty of ChemistryTY - 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 . .