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Günther Raspotnig - One of the best experts on this subject based on the ideXlab platform.
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Methyl N-methylanthranilate: major compound in the defensive secretion of Typhloiulus orpheus (Diplopoda, Julida)
Chemoecology, 2017Co-Authors: Michaela Bodner, Boyan Vagalinski, Slobodan E. Makarov, Günther RaspotnigAbstract:The defensive secretion of the julid diplopod Typhloiulus orpheus contains methyl N -methylanthranilate (MNMA), an ester of N -methylanthranilic acid that comprises more than 99% of secretion of this species. MNMA is accompanied by small amounts of methyl anthranilate and two Benzoquinones (2-methyl-1,4-benzoquinone and 2-ethyl-1,4-benzoquinone, respectively). MNMA is a known intermediate in the biosynthesis of both Benzoquinones (as present in defensive secretions of juliformians) and glomerin-like quinazolines (chemical defense in Glomerida). The compound may have evolved independently in the pathway to glomeridan chemistry, or may even represent a pivotal branching point in the pathway to different chemical classes of diplopod defensive chemistry.
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A Model for Phylogenetic Chemosystematics: Evolutionary History of Quinones in the Scent Gland Secretions of Harvestmen
Frontiers Media S.A., 2017Co-Authors: Günther Raspotnig, Petra Föttinger, Miriam Schaider, Axel SchönhoferAbstract:By the possession of unique exocrine scent glands, Opiliones (harvestmen) arise as a perfect model for studies on the evolutionary history of secretion chemistry. Among gland compounds of harvestmen, it is the quinones that represent recurring elements across the secretions of all suborders. Reliable data on quinone-distribution, however, is only known for Laniatores (Benzoquinones) and Cyphophthalmi (naphthoquinones). We here unraveled the quinone-distribution across scent gland secretions of the third large harvestman suborder, the Palpatores (= Eu- and Dyspnoi): Naphthoquinones were found in phalangiid Eupnoi across all subfamilies as well as in nemastomatid (and at least one ischyropsalid) Dyspnoi. Benzoquinones (1,4-benzoquinone) were restricted to a small entity within Eupnoi, namely platybunine Phalangiidae, probably misplaced Gyantinae (currently Sclerosomatidae) and Amilenus (incertae sedis). Our findings, combined with data from Laniatores and Cyphophthalmi, allow evaluation of a comprehensive chemosystematic model for Opiliones for the first time. Evolutionary scenarios imply naphthoquinones as scent gland compounds of common ancestry, having evolved in an early harvestman ancestor and present in cyphophthalmids and palpatoreans, but lost in laniatoreans. Benzoquinones evolved later and independently at least twice: once in the secretions of gonyleptoid Laniatores (alkylated Benzoquinones), and a second time in a lineage of phalangiid Eupnoi (1,4-benzoquinone)
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“Quinone Millipedes” Reconsidered: Evidence for a Mosaic-Like Taxonomic Distribution of Phenol-Based Secretions across the Julidae
Journal of Chemical Ecology, 2016Co-Authors: Michaela Bodner, Boyan Vagalinski, Slobodan E. Makarov, Dragan Ž. Antić, Ljubodrag V. Vujisić, Hans-jörg Leis, Günther RaspotnigAbstract: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.
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Benzoquinones from scent glands of phalangiid harvestmen (Arachnida, Opiliones, Eupnoi): a lesson from Rilaena triangularis
Chemoecology, 2015Co-Authors: Günther Raspotnig, Petra Föttinger, Miriam Schaider, Verena Leutgeb, Christian KomposchAbstract:In case of disturbance, the phalangiine harvestman Rilaena triangularis (Eupnoi, Phalangiidae) emits a directed jet from large prosomal scent (“defensive”) glands. The pungent-smelling secretion was analyzed by gas chromatography–mass spectrometry and found to contain mainly 1,4-benzoquinone along with 1,4-naphthoquinone and caprylic (=octanoic) acid. While various alkylated Benzoquinones are characteristic for the scent gland secretions of many grassatorean Laniatores, this is the first incidence of benzoquinone-based chemical defense in palpatorean harvestmen.
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Benzoquinone-rich exudates from the harvestman Pachylus paessleri (Opiliones: Gonyleptidae: Pachylinae)
Journal of Arachnology, 2010Co-Authors: Petra Föttinger, Hans-jörg Leis, Luis E. Acosta, Günther RaspotnigAbstract:Abstract The chemical composition of the scent gland secretion of Pachylus paessleri Roewer 1913, a pachyline harvestman, was analysed by gas chromatography–mass spectrometry. The secretion is a six-component mixture of Benzoquinones, with 2,3-dimethyl-1,4-benzoquinone and 2,3,5-trimethyl-1,4-benzoquinone being the main components (together amounting for ¾ of the secretion). Minor components are 2,5-dimethyl-1,4-benzoquinone (about 12%), 2-ethyl-3-methyl-1,4-benzoquinone (about 8%), 2,5-dimethyl-3-ethyl-1,4-benzoquinone (5%), and 2-ethyl-5-methyl-1,4-benzoquinone (about 1%). No sex-dependent differences could be detected. While dimethyl- and trimethyl-Benzoquinones are widespread in scent gland secretions of Gonyleptoidea, 2,5-dimethyl-3-ethyl-1,4-benzoquinone and 2-ethyl-5-methyl-1,4-benzoquinone are reported for the first time in Opiliones. The phylogenetic implications of these compounds are briefly discussed in the scope of the present knowledge of Laniatores.
Slobodan E. Makarov - One of the best experts on this subject based on the ideXlab platform.
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Methyl N-methylanthranilate: major compound in the defensive secretion of Typhloiulus orpheus (Diplopoda, Julida)
Chemoecology, 2017Co-Authors: Michaela Bodner, Boyan Vagalinski, Slobodan E. Makarov, Günther RaspotnigAbstract:The defensive secretion of the julid diplopod Typhloiulus orpheus contains methyl N -methylanthranilate (MNMA), an ester of N -methylanthranilic acid that comprises more than 99% of secretion of this species. MNMA is accompanied by small amounts of methyl anthranilate and two Benzoquinones (2-methyl-1,4-benzoquinone and 2-ethyl-1,4-benzoquinone, respectively). MNMA is a known intermediate in the biosynthesis of both Benzoquinones (as present in defensive secretions of juliformians) and glomerin-like quinazolines (chemical defense in Glomerida). The compound may have evolved independently in the pathway to glomeridan chemistry, or may even represent a pivotal branching point in the pathway to different chemical classes of diplopod defensive chemistry.
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Chemical Ecology of Cave-Dwelling Millipedes: Defensive Secretions of the Typhloiulini (Diplopoda, Julida, Julidae)
Journal of Chemical Ecology, 2017Co-Authors: Slobodan E. Makarov, Michaela Bodner, Boyan Vagalinski, Dragan Ž. Antić, Ljubodrag V. Vujisić, Doris Reineke, Marina M. Todosijević, Luka R. Lučić, Bojan M. Mitić, Plamen MitovAbstract: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.
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“Quinone Millipedes” Reconsidered: Evidence for a Mosaic-Like Taxonomic Distribution of Phenol-Based Secretions across the Julidae
Journal of Chemical Ecology, 2016Co-Authors: Michaela Bodner, Boyan Vagalinski, Slobodan E. Makarov, Dragan Ž. Antić, Ljubodrag V. Vujisić, Hans-jörg Leis, Günther RaspotnigAbstract: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.
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chemical defense in millipedes myriapoda diplopoda do representatives of the family blaniulidae belong to the quinone clade
Chemistry & Biodiversity, 2014Co-Authors: Ljubodrag Vujisic, Dragan ž Antic, Ivan Vuckovic, Tatjana Lj Sekulic, V T Tomic, Boris Mandic, Vele Tesevic, Božidar P M Curcic, V Vajs, Slobodan E. MakarovAbstract: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.
Michaela Bodner - One of the best experts on this subject based on the ideXlab platform.
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Methyl N-methylanthranilate: major compound in the defensive secretion of Typhloiulus orpheus (Diplopoda, Julida)
Chemoecology, 2017Co-Authors: Michaela Bodner, Boyan Vagalinski, Slobodan E. Makarov, Günther RaspotnigAbstract:The defensive secretion of the julid diplopod Typhloiulus orpheus contains methyl N -methylanthranilate (MNMA), an ester of N -methylanthranilic acid that comprises more than 99% of secretion of this species. MNMA is accompanied by small amounts of methyl anthranilate and two Benzoquinones (2-methyl-1,4-benzoquinone and 2-ethyl-1,4-benzoquinone, respectively). MNMA is a known intermediate in the biosynthesis of both Benzoquinones (as present in defensive secretions of juliformians) and glomerin-like quinazolines (chemical defense in Glomerida). The compound may have evolved independently in the pathway to glomeridan chemistry, or may even represent a pivotal branching point in the pathway to different chemical classes of diplopod defensive chemistry.
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Chemical Ecology of Cave-Dwelling Millipedes: Defensive Secretions of the Typhloiulini (Diplopoda, Julida, Julidae)
Journal of Chemical Ecology, 2017Co-Authors: Slobodan E. Makarov, Michaela Bodner, Boyan Vagalinski, Dragan Ž. Antić, Ljubodrag V. Vujisić, Doris Reineke, Marina M. Todosijević, Luka R. Lučić, Bojan M. Mitić, Plamen MitovAbstract: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.
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“Quinone Millipedes” Reconsidered: Evidence for a Mosaic-Like Taxonomic Distribution of Phenol-Based Secretions across the Julidae
Journal of Chemical Ecology, 2016Co-Authors: Michaela Bodner, Boyan Vagalinski, Slobodan E. Makarov, Dragan Ž. Antić, Ljubodrag V. Vujisić, Hans-jörg Leis, Günther RaspotnigAbstract: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.
K. Peschke - One of the best experts on this subject based on the ideXlab platform.
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Chemical composition and pheromonal function of the defensive secretions in the subtribe Stizopina (Coleptera, Tenebrionidae, Opatrini)
Chemoecology, 2009Co-Authors: S. Geiselhardt, T. Schmitt, K. PeschkeAbstract:The chemical composition of the defensive secretions of 52 species from 15 genera of the tenebrionid subtribe Stizopina was analyzed. The secretions of all species contained 1,4-Benzoquinones, 1-alkenes, and monoterpene hydrocarbons, only one species was lacking the latter. Methyl- and ethyl-1,4-benzoquinone were ubiquitous, mostly accompanied by smaller amounts of 1,4-benzoquinone as well as isopropyl- and propyl-1,4-benzoquinone. 1-Alkenes were dominated by 1-undecene with varying admixtures of other 1-alkenes. The monoterpene hydrocarbons always consisted of a mixture of α-pinene, camphene, β-pinene and limonene, but also p -cymene, α-terpinene or α-phellandrene were found in some species. Furthermore, some species synthesized additional compounds such as phenols, ketones, 2,5-dihydroxy-6-methylbenzoate, 2-hydroxy-4-methoxyacetophenone and naphthoquinones. Bioassays showed that the defensive secretion co-functioned as an aggregation pheromone in the subtribe Stizopina. All nine tested species from six genera were attracted to defensive secretion of Stizopina species, but they did not distinguish between defensive secretions of different Stizopina species. This lack of discrimination might be the initial step for the formation of interspecific aggregations and the evolution of cleptoparasitism within the Stizopina.
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Defensive Secretion Components of the Host Parastizopus armaticeps as Kairomones for the Cleptoparasite Eremostibes opacus
Journal of Chemical Ecology, 2006Co-Authors: S. Geiselhardt, T Szepat, O A E Rasa, K. PeschkeAbstract:The subsocial tenebrionid Parastizopus armaticeps Pér. is parasitized by the closely related Eremostibes opacus Koch (Coleoptera: Tenebrionidae). We found that the pygidial defensive secretions of both species are similar and contain a mixture of 1,4-Benzoquinones, 1-alkenes, and monoterpene hydrocarbons. The 1-alkenes are dominated by 1-undecene, with admixtures of 1-tridecene in both species and 1-pentadecene in P. armaticeps only. Methyl- and ethyl-1,4-benzoquinone are the major quinones of the secretions of both species. The monoterpene fractions consist of (−)-α-pinene, (−)-camphene, sabinene, (−)-β-pinene, and (−)-limonene. Volatiles trapped with Porapak Q at the entrance to the breeding burrows of P. armaticeps were identified as components of the defensive secretion. However, in contrast to the secretion, the 1,4-Benzoquinones were almost completely absent in the volatiles. Bioassays investigating attraction showed that the cleptoparasite E. opacus was drawn to the monoterpene hydrocarbons, produced by P. armaticeps , and deterred by the 1,4-Benzoquinones. The 1-alkenes had no effect. Among the monoterpenes, only (−)-camphene was attractive to E. opacus . This is one of the rare cases of chemical exploitation of defensive allomones, and the first based on odor homology. We have drawn an evolutionary scenario including various functional changes in the defensive secretion compounds, leading to the kairomonal exploitation.
Boyan Vagalinski - One of the best experts on this subject based on the ideXlab platform.
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Methyl N-methylanthranilate: major compound in the defensive secretion of Typhloiulus orpheus (Diplopoda, Julida)
Chemoecology, 2017Co-Authors: Michaela Bodner, Boyan Vagalinski, Slobodan E. Makarov, Günther RaspotnigAbstract:The defensive secretion of the julid diplopod Typhloiulus orpheus contains methyl N -methylanthranilate (MNMA), an ester of N -methylanthranilic acid that comprises more than 99% of secretion of this species. MNMA is accompanied by small amounts of methyl anthranilate and two Benzoquinones (2-methyl-1,4-benzoquinone and 2-ethyl-1,4-benzoquinone, respectively). MNMA is a known intermediate in the biosynthesis of both Benzoquinones (as present in defensive secretions of juliformians) and glomerin-like quinazolines (chemical defense in Glomerida). The compound may have evolved independently in the pathway to glomeridan chemistry, or may even represent a pivotal branching point in the pathway to different chemical classes of diplopod defensive chemistry.
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Chemical Ecology of Cave-Dwelling Millipedes: Defensive Secretions of the Typhloiulini (Diplopoda, Julida, Julidae)
Journal of Chemical Ecology, 2017Co-Authors: Slobodan E. Makarov, Michaela Bodner, Boyan Vagalinski, Dragan Ž. Antić, Ljubodrag V. Vujisić, Doris Reineke, Marina M. Todosijević, Luka R. Lučić, Bojan M. Mitić, Plamen MitovAbstract: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.
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“Quinone Millipedes” Reconsidered: Evidence for a Mosaic-Like Taxonomic Distribution of Phenol-Based Secretions across the Julidae
Journal of Chemical Ecology, 2016Co-Authors: Michaela Bodner, Boyan Vagalinski, Slobodan E. Makarov, Dragan Ž. Antić, Ljubodrag V. Vujisić, Hans-jörg Leis, Günther RaspotnigAbstract: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.