TY  - JOUR
AU  - Makarov, Slobodan E.
AU  - Bodner, Michaela
AU  - Reineke, Doris
AU  - Vujisić, Ljubodrag V.
AU  - Todosijević, Marina
AU  - Antic, Dragan Z.
AU  - Vagalinski, Boyan
AU  - Lučić, Luka
AU  - Mitic, Bojan M.
AU  - Mitov, Plamen
AU  - Anđelković, Boban D.
AU  - Lucic, Sofija Pavkovic
AU  - Vajs, Vlatka
AU  - Tomić, Vladimir T.
AU  - Raspotnig, Guenther
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2735
AB  - Cave animals live under highly constant ecological conditions and in permanent darkness, and many evolutionary adaptations of cave-dwellers have been triggered by their specific environment. A similar "cave effect" leading to pronounced chemical interactions under such conditions may be assumed, but the chemoecology of troglobionts is mostly unknown. We investigated the defensive chemistry of a largely cave-dwelling julid group, the controversial tribe "Typhloiulini", and we included some cave-dwelling and some endogean representatives. While chemical defense in juliform diplopods is known to be highly uniform, and mainly based on methyl- and methoxy-substituted benzoquinones, the defensive secretions of typhloiulines contained ethyl-benzoquinones and related compounds. Interestingly, ethyl-benzoquinones were found in some, but not all cave-dwelling typhloiulines, and some non-cave dwellers also contained these compounds. On the other hand, ethyl-benzoquinones were not detected in troglobiont nor in endogean typhloiuline outgroups. In order to explain the taxonomic pattern of ethyl-benzoquinone occurrence, and to unravel whether a cave-effect triggered ethyl-benzoquinone evolution, we classed the "Typhloiulini" investigated here within a phylogenetic framework of julid taxa, and traced the evolutionary history of ethyl-benzoquinones in typhloiulines in relation to cave-dwelling. The results indicated a cave-independent evolution of ethyl-substituted benzoquinones, indicating the absence of a "cave effect" on the secretions of troglobiont Typhloiulini. Ethyl-benzoquinones probably evolved early in an epi- or endogean ancestor of a clade including several, but not all Typhloiulus (basically comprising a taxonomic entity known as "Typhloiulus sensu stricto") and Serboiulus. Ethyl-benzoquinones are proposed as novel and valuable chemical characters for julid systematics.
PB  - Springer, Dordrecht
T2  - Journal of Chemical Ecology
T1  - Chemical Ecology of Cave-Dwelling Millipedes: Defensive Secretions of the Typhloiulini (Diplopoda, Julida, Julidae)
VL  - 43
IS  - 4
SP  - 317
EP  - 326
DO  - 10.1007/s10886-017-0832-1
ER  - 

@article{
author = "Makarov, Slobodan E. and Bodner, Michaela and Reineke, Doris and Vujisić, Ljubodrag V. and Todosijević, Marina and Antic, Dragan Z. and Vagalinski, Boyan and Lučić, Luka and Mitic, Bojan M. and Mitov, Plamen and Anđelković, Boban D. and Lucic, Sofija Pavkovic and Vajs, Vlatka and Tomić, Vladimir T. and Raspotnig, Guenther",
year = "2017",
abstract = "Cave animals live under highly constant ecological conditions and in permanent darkness, and many evolutionary adaptations of cave-dwellers have been triggered by their specific environment. A similar "cave effect" leading to pronounced chemical interactions under such conditions may be assumed, but the chemoecology of troglobionts is mostly unknown. We investigated the defensive chemistry of a largely cave-dwelling julid group, the controversial tribe "Typhloiulini", and we included some cave-dwelling and some endogean representatives. While chemical defense in juliform diplopods is known to be highly uniform, and mainly based on methyl- and methoxy-substituted benzoquinones, the defensive secretions of typhloiulines contained ethyl-benzoquinones and related compounds. Interestingly, ethyl-benzoquinones were found in some, but not all cave-dwelling typhloiulines, and some non-cave dwellers also contained these compounds. On the other hand, ethyl-benzoquinones were not detected in troglobiont nor in endogean typhloiuline outgroups. In order to explain the taxonomic pattern of ethyl-benzoquinone occurrence, and to unravel whether a cave-effect triggered ethyl-benzoquinone evolution, we classed the "Typhloiulini" investigated here within a phylogenetic framework of julid taxa, and traced the evolutionary history of ethyl-benzoquinones in typhloiulines in relation to cave-dwelling. The results indicated a cave-independent evolution of ethyl-substituted benzoquinones, indicating the absence of a "cave effect" on the secretions of troglobiont Typhloiulini. Ethyl-benzoquinones probably evolved early in an epi- or endogean ancestor of a clade including several, but not all Typhloiulus (basically comprising a taxonomic entity known as "Typhloiulus sensu stricto") and Serboiulus. Ethyl-benzoquinones are proposed as novel and valuable chemical characters for julid systematics.",
publisher = "Springer, Dordrecht",
journal = "Journal of Chemical Ecology",
title = "Chemical Ecology of Cave-Dwelling Millipedes: Defensive Secretions of the Typhloiulini (Diplopoda, Julida, Julidae)",
volume = "43",
number = "4",
pages = "317-326",
doi = "10.1007/s10886-017-0832-1"
}

Makarov, S. E., Bodner, M., Reineke, D., Vujisić, L. V., Todosijević, M., Antic, D. Z., Vagalinski, B., Lučić, L., Mitic, B. M., Mitov, P., Anđelković, B. D., Lucic, S. P., Vajs, V., Tomić, V. T.,& Raspotnig, G.. (2017). Chemical Ecology of Cave-Dwelling Millipedes: Defensive Secretions of the Typhloiulini (Diplopoda, Julida, Julidae). in Journal of Chemical Ecology
Springer, Dordrecht., 43(4), 317-326.
https://doi.org/10.1007/s10886-017-0832-1

Makarov SE, Bodner M, Reineke D, Vujisić LV, Todosijević M, Antic DZ, Vagalinski B, Lučić L, Mitic BM, Mitov P, Anđelković BD, Lucic SP, Vajs V, Tomić VT, Raspotnig G. Chemical Ecology of Cave-Dwelling Millipedes: Defensive Secretions of the Typhloiulini (Diplopoda, Julida, Julidae). in Journal of Chemical Ecology. 2017;43(4):317-326.
doi:10.1007/s10886-017-0832-1 .

Makarov, Slobodan E., Bodner, Michaela, Reineke, Doris, Vujisić, Ljubodrag V., Todosijević, Marina, Antic, Dragan Z., Vagalinski, Boyan, Lučić, Luka, Mitic, Bojan M., Mitov, Plamen, Anđelković, Boban D., Lucic, Sofija Pavkovic, Vajs, Vlatka, Tomić, Vladimir T., Raspotnig, Guenther, "Chemical Ecology of Cave-Dwelling Millipedes: Defensive Secretions of the Typhloiulini (Diplopoda, Julida, Julidae)" in Journal of Chemical Ecology, 43, no. 4 (2017):317-326,
https://doi.org/10.1007/s10886-017-0832-1 . .

TY  - JOUR
AU  - Vujisić, Ljubodrag V.
AU  - Antic, Dragan Z.
AU  - Vučković, Ivan
AU  - Sekulic, Tatjana Lj.
AU  - Tomić, Vladimir T.
AU  - Mandić, Boris
AU  - Tešević, Vele
AU  - Curcic, Bozidar P. M.
AU  - Vajs, Vlatka
AU  - Makarov, Slobodan E.
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2733
AB  - The defensive secretions of two blaniulid millipedes, Nopoiulus kochii and Cibiniulus phlepsii, were characterized by GC-FID and GC/MS analyses, which showed the presence of a complex mixture of benzoquinones, hydroquinones, and oleates. Altogether, 13 compounds were identified. The major compound in the secretions of both analyzed species was 2-methyl-1,4-benzoquinone (toluquinone). The second major constituent in the N. kochii secretion was 2-methyl-3,4-(methylenedioxy)phenol, while in that of C. phlepsii, it was 2-methoxy-3-methyl-1,4-benzoquinone. The defensive secretion of N. kochii also showed a high content of hydroquinones (13.5%) in comparison to that of C. phlepsii (0.8%). Hexyl oleate and octyl oleate were detected for the first time in defensive millipede fluids. The chemical composition of the defensive secretions supports the chemotaxonomic position of the family Blaniulidae in the 'quinone' millipede clade.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Chemistry and Biodiversity
T1  - Chemical Defense in Millipedes (Myriapoda, Diplopoda): Do Representatives of the Family Blaniulidae Belong to the 'Quinone' Clade?
VL  - 11
IS  - 3
SP  - 483
EP  - 490
DO  - 10.1002/cbdv.201300355
ER  - 

@article{
author = "Vujisić, Ljubodrag V. and Antic, Dragan Z. and Vučković, Ivan and Sekulic, Tatjana Lj. and Tomić, Vladimir T. and Mandić, Boris and Tešević, Vele and Curcic, Bozidar P. M. and Vajs, Vlatka and Makarov, Slobodan E.",
year = "2014",
abstract = "The defensive secretions of two blaniulid millipedes, Nopoiulus kochii and Cibiniulus phlepsii, were characterized by GC-FID and GC/MS analyses, which showed the presence of a complex mixture of benzoquinones, hydroquinones, and oleates. Altogether, 13 compounds were identified. The major compound in the secretions of both analyzed species was 2-methyl-1,4-benzoquinone (toluquinone). The second major constituent in the N. kochii secretion was 2-methyl-3,4-(methylenedioxy)phenol, while in that of C. phlepsii, it was 2-methoxy-3-methyl-1,4-benzoquinone. The defensive secretion of N. kochii also showed a high content of hydroquinones (13.5%) in comparison to that of C. phlepsii (0.8%). Hexyl oleate and octyl oleate were detected for the first time in defensive millipede fluids. The chemical composition of the defensive secretions supports the chemotaxonomic position of the family Blaniulidae in the 'quinone' millipede clade.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Chemistry and Biodiversity",
title = "Chemical Defense in Millipedes (Myriapoda, Diplopoda): Do Representatives of the Family Blaniulidae Belong to the 'Quinone' Clade?",
volume = "11",
number = "3",
pages = "483-490",
doi = "10.1002/cbdv.201300355"
}

Vujisić, L. V., Antic, D. Z., Vučković, I., Sekulic, T. Lj., Tomić, V. T., Mandić, B., Tešević, V., Curcic, B. P. M., Vajs, V.,& Makarov, S. E.. (2014). Chemical Defense in Millipedes (Myriapoda, Diplopoda): Do Representatives of the Family Blaniulidae Belong to the 'Quinone' Clade?. in Chemistry and Biodiversity
Wiley-V C H Verlag Gmbh, Weinheim., 11(3), 483-490.
https://doi.org/10.1002/cbdv.201300355

Vujisić LV, Antic DZ, Vučković I, Sekulic TL, Tomić VT, Mandić B, Tešević V, Curcic BPM, Vajs V, Makarov SE. Chemical Defense in Millipedes (Myriapoda, Diplopoda): Do Representatives of the Family Blaniulidae Belong to the 'Quinone' Clade?. in Chemistry and Biodiversity. 2014;11(3):483-490.
doi:10.1002/cbdv.201300355 .

Vujisić, Ljubodrag V., Antic, Dragan Z., Vučković, Ivan, Sekulic, Tatjana Lj., Tomić, Vladimir T., Mandić, Boris, Tešević, Vele, Curcic, Bozidar P. M., Vajs, Vlatka, Makarov, Slobodan E., "Chemical Defense in Millipedes (Myriapoda, Diplopoda): Do Representatives of the Family Blaniulidae Belong to the 'Quinone' Clade?" in Chemistry and Biodiversity, 11, no. 3 (2014):483-490,
https://doi.org/10.1002/cbdv.201300355 . .

TY  - JOUR
AU  - Vujisić, Ljubodrag V.
AU  - Vučković, Ivan
AU  - Makarov, Slobodan E.
AU  - Ilic, Bojan S.
AU  - Antic, Dragan Z.
AU  - Jadranin, Milka
AU  - Todorović, Nina
AU  - Mrkić, Ivan
AU  - Vajs, Vlatka
AU  - Lučić, Luka
AU  - Curcic, Bozidar P. M.
AU  - Mitic, Bojan M.
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1177
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 and Makarov, Slobodan E. and Ilic, Bojan S. and Antic, Dragan Z. and Jadranin, Milka and Todorović, Nina and Mrkić, Ivan and Vajs, Vlatka and Lučić, Luka and Curcic, Bozidar P. M. and Mitic, 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., Makarov, S. E., Ilic, B. S., Antic, D. Z., Jadranin, M., Todorović, N., Mrkić, I., Vajs, V., Lučić, L., Curcic, B. P. M.,& Mitic, 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 I, Makarov SE, Ilic BS, Antic DZ, Jadranin M, Todorović N, Mrkić I, Vajs V, Lučić L, Curcic BPM, Mitic 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, Makarov, Slobodan E., Ilic, Bojan S., Antic, Dragan Z., Jadranin, Milka, Todorović, Nina, Mrkić, Ivan, Vajs, Vlatka, Lučić, Luka, Curcic, Bozidar P. M., Mitic, 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 . .