"Quinone Millipedes" Reconsidered: Evidence for a Mosaic-Like Taxonomic Distribution of Phenol-Based Secretions across the Julidae
2016
Autori
Bodner, MichaelaVagalinski, Boyan
Makarov, Slobodan E.
Antić, Dragan Ž.
Vujisić, Ljubodrag V.
Leis, Hans-Joerg
Raspotnig, Guenther
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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.
Ključne reči:
Chemical defense / Quinone millipedes / Phenols / Julida / Julidae / Cylindroiulini / Brachyiulini / Leptoiulini / DiplopodaIzvor:
Journal of Chemical Ecology, 2016, 42, 3, 249-258Izdavač:
- Springer, Dordrecht
Finansiranje / projekti:
- Ontogenetska karakterizacija filogenije bioraznovrsnosti (RS-MESTD-Basic Research (BR or ON)-173038)
- Bioaktivni prirodni proizvodi samoniklih, gajenih i jestivih biljaka: određivanje struktura i aktivnosti (RS-MESTD-Basic Research (BR or ON)-172053)
- Volkswagen Stiftung
- Austrian Academy of Sciences at the Institute of Zoology, University of Graz [23811]
- University of Graz
Napomena:
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3323
DOI: 10.1007/s10886-016-0680-4
ISSN: 0098-0331
PubMed: 26971956
WoS: 000374676200008
Scopus: 2-s2.0-84961171816
Kolekcije
Institucija/grupa
Hemijski fakultet / Faculty of ChemistryTY - 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 . .