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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)
Metadata
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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 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
Source:
Naturwissenschaften, 2013, 100, 9, 861-870
Publisher:
  • 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
[ Google Scholar ]
9
9
URI
https://cherry.chem.bg.ac.rs/handle/123456789/1394
Collections
  • Publikacije
  • Publikacije
Institution/Community
Hemijski fakultet
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
UR  - Kon_2514
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",
url = "Kon_2514"
}
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
Kon_2514
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
Kon_2514 .
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 .,
Kon_2514 .

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