TY  - JOUR
AU  - Makarov, Slobodan E.
AU  - Bodner, Michaela
AU  - Reineke, Doris
AU  - Vujisić, Ljubodrag V.
AU  - Todosijević, Marina
AU  - Antić, Dragan Ž.
AU  - Vagalinski, Boyan
AU  - Lučić, Luka
AU  - Mitić, Bojan M.
AU  - Mitov, Plamen
AU  - Anđelković, Boban D.
AU  - Lucić, Sofija Pavković
AU  - Vajs, Vlatka
AU  - Tomić, Vladimir T.
AU  - Raspotnig, Guenther
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2450
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 Antić, Dragan Ž. and Vagalinski, Boyan and Lučić, Luka and Mitić, Bojan M. and Mitov, Plamen and Anđelković, Boban D. and Lucić, Sofija Pavković 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., Antić, D. Ž., Vagalinski, B., Lučić, L., Mitić, B. M., Mitov, P., Anđelković, B. D., Lucić, 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, Antić DŽ, Vagalinski B, Lučić L, Mitić BM, Mitov P, Anđelković BD, Lucić 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, Antić, Dragan Ž., Vagalinski, Boyan, Lučić, Luka, Mitić, Bojan M., Mitov, Plamen, Anđelković, Boban D., Lucić, Sofija Pavković, 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  - Bodner, Michaela
AU  - Vagalinski, Boyan
AU  - Makarov, Slobodan E.
AU  - Antić, Dragan Ž.
AU  - Vujisić, Ljubodrag V.
AU  - Leis, Hans-Joerg
AU  - Raspotnig, Guenther
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1924
AB  - The defensive chemistry of juliformian millipedes is characterized mainly by benzoquinones ("quinone millipedes"), whereas the secretions of the putative close outgroup Callipodida are considered to be exclusively phenolic. We conducted a chemical screening of julid secretions for phenolic content. Most species from tribes Cylindroiulini (15 species examined), Brachyiulini (5 species examined), Leptoiulini (15 species examined), Uncigerini (2 species examined), Pachyiulini (3 species examined), and Ommatoiulini (2 species examined) had non-phenolic, in most cases exclusively benzoquinonic secretions. In contrast, tribes Cylindroiulini, Brachyiulini, and Leptoiulini also contained representatives with predominantly phenol-based exudates. In detail, p-cresol was a major compound in the secretions of the cylindroiulines Styrioiulus pelidnus and S. styricus (p-cresol content 93 %) and an undetermined Cylindroiulus species (p-cresol content 51 %), in the brachyiulines Brachyiulus lusitanus (p-cresol content 21 %) and Megaphyllum fagorum (p-cresol content 92 %), as well as in an undescribed Typhloiulus species (p-cresol content 32 %, Leptoiulini). In all species, p-cresol was accompanied by small amounts of phenol. The secretion of M. fagorum was exclusively phenolic, whereas phenols were accompanied by benzoquinones in all other species. This is the first incidence of clearly phenol-dominated secretions in the Julidae. We hypothesize a shared biosynthetic route to phenols and benzoquinones, with benzoquinones being produced from phenolic precursors. The patchy taxonomic distribution of phenols documented herein supports multiple independent regression events in a common pathway of benzoquinone synthesis rather than multiple independent incidences of phenol biosynthesis.
PB  - Springer, Dordrecht
T2  - Journal of Chemical Ecology
T1  - "Quinone Millipedes" Reconsidered: Evidence for a Mosaic-Like Taxonomic Distribution of Phenol-Based Secretions across the Julidae
VL  - 42
IS  - 3
SP  - 249
EP  - 258
DO  - 10.1007/s10886-016-0680-4
ER  - 

@article{
author = "Bodner, Michaela and Vagalinski, Boyan and Makarov, Slobodan E. and Antić, Dragan Ž. and Vujisić, Ljubodrag V. and Leis, Hans-Joerg and Raspotnig, Guenther",
year = "2016",
abstract = "The defensive chemistry of juliformian millipedes is characterized mainly by benzoquinones ("quinone millipedes"), whereas the secretions of the putative close outgroup Callipodida are considered to be exclusively phenolic. We conducted a chemical screening of julid secretions for phenolic content. Most species from tribes Cylindroiulini (15 species examined), Brachyiulini (5 species examined), Leptoiulini (15 species examined), Uncigerini (2 species examined), Pachyiulini (3 species examined), and Ommatoiulini (2 species examined) had non-phenolic, in most cases exclusively benzoquinonic secretions. In contrast, tribes Cylindroiulini, Brachyiulini, and Leptoiulini also contained representatives with predominantly phenol-based exudates. In detail, p-cresol was a major compound in the secretions of the cylindroiulines Styrioiulus pelidnus and S. styricus (p-cresol content 93 %) and an undetermined Cylindroiulus species (p-cresol content 51 %), in the brachyiulines Brachyiulus lusitanus (p-cresol content 21 %) and Megaphyllum fagorum (p-cresol content 92 %), as well as in an undescribed Typhloiulus species (p-cresol content 32 %, Leptoiulini). In all species, p-cresol was accompanied by small amounts of phenol. The secretion of M. fagorum was exclusively phenolic, whereas phenols were accompanied by benzoquinones in all other species. This is the first incidence of clearly phenol-dominated secretions in the Julidae. We hypothesize a shared biosynthetic route to phenols and benzoquinones, with benzoquinones being produced from phenolic precursors. The patchy taxonomic distribution of phenols documented herein supports multiple independent regression events in a common pathway of benzoquinone synthesis rather than multiple independent incidences of phenol biosynthesis.",
publisher = "Springer, Dordrecht",
journal = "Journal of Chemical Ecology",
title = ""Quinone Millipedes" Reconsidered: Evidence for a Mosaic-Like Taxonomic Distribution of Phenol-Based Secretions across the Julidae",
volume = "42",
number = "3",
pages = "249-258",
doi = "10.1007/s10886-016-0680-4"
}

Bodner, M., Vagalinski, B., Makarov, S. E., Antić, D. Ž., Vujisić, L. V., Leis, H.,& Raspotnig, G.. (2016). "Quinone Millipedes" Reconsidered: Evidence for a Mosaic-Like Taxonomic Distribution of Phenol-Based Secretions across the Julidae. in Journal of Chemical Ecology
Springer, Dordrecht., 42(3), 249-258.
https://doi.org/10.1007/s10886-016-0680-4

Bodner M, Vagalinski B, Makarov SE, Antić DŽ, Vujisić LV, Leis H, Raspotnig G. "Quinone Millipedes" Reconsidered: Evidence for a Mosaic-Like Taxonomic Distribution of Phenol-Based Secretions across the Julidae. in Journal of Chemical Ecology. 2016;42(3):249-258.
doi:10.1007/s10886-016-0680-4 .

Bodner, Michaela, Vagalinski, Boyan, Makarov, Slobodan E., Antić, Dragan Ž., Vujisić, Ljubodrag V., Leis, Hans-Joerg, Raspotnig, Guenther, ""Quinone Millipedes" Reconsidered: Evidence for a Mosaic-Like Taxonomic Distribution of Phenol-Based Secretions across the Julidae" in Journal of Chemical Ecology, 42, no. 3 (2016):249-258,
https://doi.org/10.1007/s10886-016-0680-4 . .

TY  - JOUR
AU  - Vujisić, Ljubodrag V.
AU  - Antić, Dragan Ž.
AU  - Vučković, Ivan M.
AU  - Sekulić, Tatjana Lj.
AU  - Tomić, Vladimir T.
AU  - Mandić, Boris
AU  - Tešević, Vele
AU  - Curčić, Božidar P. M.
AU  - Vajs, Vlatka
AU  - Makarov, Slobodan E.
PY  - 2014
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1515
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 Antić, Dragan Ž. and Vučković, Ivan M. and Sekulić, Tatjana Lj. and Tomić, Vladimir T. and Mandić, Boris and Tešević, Vele and Curčić, Božidar 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., Antić, D. Ž., Vučković, I. M., Sekulić, T. Lj., Tomić, V. T., Mandić, B., Tešević, V., Curčić, 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, Antić DŽ, Vučković IM, Sekulić TL, Tomić VT, Mandić B, Tešević V, Curčić 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., Antić, Dragan Ž., Vučković, Ivan M., Sekulić, Tatjana Lj., Tomić, Vladimir T., Mandić, Boris, Tešević, Vele, Curčić, Božidar 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 . .