Long chain alcohol acetates in the defensive secretion of the millipede Blaniulus guttulatus

Weatherston, J.; Tyrrell, D. Lorne; Percy, Jean

doi:10.1016/0009-3084(71)90023-5

Cited by 15 publications

(11 citation statements)

References 6 publications

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“…In insects, aliphatics are often present in defensive secretions along with benzoquinones and serve as solvents for the latter, and Shimizu et al (2012) suggested this was the case with millipedes as well. Weatherston et al (1971) had previously published this idea.…”

Section: Benzoquinone Liquifactionmentioning

confidence: 85%

“…Apfelbeckia insculpata p-cresol Curcic et al, 2009Callipodella fasciata p-cresol, phenol, p-ethylphenol Makarov et al, 2010 Glomeridae Glomeris marginata glomerin, homoglomerin Schildknecht et al, 1966aSchildknecht et al, , 1966bMeinwald et al, 1966 Onomeris sinuata glomerin, homoglomerin Shear et al, 2011 ulida Blaniulidae Blaniulus guttulatus 2-methyl, 1-4-benzoquinone, 2-methyl-3-methoxy-1,4-benzoquinone, hexadecyl acetate, D9-hexadecenyl acetate, D9-octadecenyl acetate Weatherston et al, 1971 Cibiulus phlepsii 2-methyl-1,4-benzoquinone, 2-hydroxy-3-methyl-1,4-benzoquinone, 2-methoxy-3-methyl-1,4-benzoquinone, 2-methyl hydroquinone, 2,3-dimethoxyhydroquinone, 2-methyl-3,4-methylenedioxyphenol, 2,3-dimethoxy-3-methyl-1,4-benzoquiinone, hexyl oleate, octyl oleate Vujisic et al, 2014 Nopoiulus kochii 2-methyl-1,4-benzoquinone, 2-hydroxy-3-methyl-1,4-benzoquinone, 2-methoxy-3-methyl-1,4-benzoquinone, 2,3-dimethoxyhydroquinone, 2-methyl-3,4-methylenedioxyphenol, 2,3-dimethoxy-5-methyl-1,4-benzoquinone, hexyl oleate, octyl oleate Vujisic et al, 2014 Julidae Allajulus dicentrus 2-hydroxy-3-methyl-1,4-benzoquinone, 2-methoxy-3-methyl-1,4-benzoquinone, 2,3-dimethoxy-1,4-benzoquinone, 2,3-dimethoxy-5-methyl-1,4-benzoquinone, (E)-2-octenal, 3 other aliphatic (E)-alkenals and their corresponding alcohols Bodner and Raspotnig, 2012 Anaulaciulus okinawaensis 2-methyl-1,4-hydroquinone, 2-methoxy-3-methyl-1,4-benzoquinone, 2,3-dimethoxy-5-methyl-1,4-benzoquinone Kikunaga et al, 1993 Anaulaciulus sp. 2-methyl-1,4-benzoquinone, 2-methoxy-3-methl-1,4-benzoquinone, 2-methoxy-6-methyl-1,4-benzoquinone, n-hexyl laurate, 14 additional C 16-21 fatty acid esters.…”

Section: Ordermentioning

confidence: 98%

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The chemical defenses of millipedes (diplopoda): Biochemistry, physiology and ecology

Shear

2015

Biochemical Systematics and Ecology

121

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a b s t r a c tMillipedes are some of the earliest examples of terrestrial animals, and fossils from the early Carboniferous Period indicate they were also some of the earliest prey. These fossils record ozopores, the openings of chemical defense glands, occurring along the length of the body. The secretions of these glands may consist of topical irritants, repellents, antifeedants, or, in the case of the large and widespread Order Polydesmida, hydrogen cyanide (HCN) gas that can be fatal to other arthropods or even small vertebrates in a confined environment. Müllerian mimicry rings may develop in which unrelated species of millipedes that co-occur closely resemble one another, while participating in a completely differently patterned ring in another part of their geographic range. Chemistry is not the only defense of millipedes. Polyxenids carry tufts of entangling setae, many species rely on crypsis and the ability to roll into a smooth, resistant sphere or coil, and still others have spikey projections that may deter soft-mouthed predators. Nevertheless, chemical defense has been of significance in helminthomorph millipedes at least since the Lower Carboniferous. The distribution of classes of chemical defense compounds follows major phylogenetic groupings. Evidence suggests that the defensive glands of Glomerida arose independently of those of the Helminthomorpha.

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Section: Benzoquinone Liquifactionmentioning

confidence: 85%

Section: Ordermentioning

confidence: 98%

The chemical defenses of millipedes (diplopoda): Biochemistry, physiology and ecology

Shear

2015

Biochemical Systematics and Ecology

121

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“…The defensive secretion of B. guttulatus was studied by Weatherston et al (1971) and was found to contain lipoid esters (palmityl acetate, a monounsaturated C16-alcohol acetate and a monounsaturated C18-alcohol acetate). Quite different chemical spectra were found in two other blaniulids: Nopoiulus kochii (Gervais, 1847) and Cibiniulus phelpsii (Verhoeff, 1897) by Vujisić et al (2014).…”

Section: Role Of Defensive Secretions?mentioning

confidence: 99%

Infectious intimacy and contaminated caves—three new species of ectoparasitic fungi (Ascomycota: Laboulbeniales) from blaniulid millipedes (Diplopoda: Julida) and inferences about their transmittal mechanisms

Enghoff

Santamaria

2015

Org Divers Evol

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Laboulbeniales is an order of more than 2000 species of small ascomycete fungi which are ectoparasites of insects, millipedes and mites. They are often highly hostspecific and often are also highly specific with regard to which body parts they infect. Laboulbeniales from millipedes are particularly poorly known-only 12 species have been described until now, mostly from Europe. Here, we describe the first laboulbeniaceous parasites from blaniulid millipedes: Troglomyces bilabiatus from Acipes spp., Troglomyces pusillus from Iberoiulus cavernicola Ceuca, 1967 and Troglomyces triandrus from Archiboreoiulus palidus (BradeBirks, 1920). The generic description of Troglomyces is emended. Different types of site specificity of the three new parasites, as well as of previously described species, are explained in terms of aspects of host biology: mating behaviour and habitat. Species from epigean hosts tend to show a high degree of site specificity suggesting transfer during host copulation, whereas most species from cave hosts show no pronounced site specificity and are probably transferred via the substrate. Possible roles of host defensive secretions and parthenogenesis in relation to infection with Laboulbeniales are briefly discussed.

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“…This order of Juliformia is chemically less studied than the Spirobolida and Spirostreptida. However, at least some early reports on the defensive chemistry of European Julida (e.g., Schildkecht and Weis, 1961;Röper and Heyns, 1977) as well as more recent publications (e.g., Huth, 2000) are available, referring to 16 thus far analyzed species of the Julidae (Vujisic et al, 2011) and at least one species of Blaniulidae (Weatherston et al, 1971). In addition, one report deals with julids from South East Asia (Shimizu et al, 2012).…”

Section: Introductionmentioning

confidence: 96%

“…Additionally, from Julida, examples of chemically unusual secretions have been published. Weatherston et al (1971) found long chain acetates in filter papers loaded with defensive exudates of the blaniulid Blaniulus guttatus, again together with a benzoquinonic compound. Recently, Shimizu et al (2012) identified a series of fatty acid esters together with benzoquinones from a species of the East Asian julid Anaulaciulus.…”

Section: Introductionmentioning

confidence: 98%

Millipedes That Smell Like Bugs: (E)-Alkenals in the Defensive Secretion of the Julid Diplopod Allajulus Dicentrus

Bodner

Raspotnig

2012

J Chem Ecol

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The secretions from serial defensive glands of the Austrian diplopod Allajulus dicentrus (Julidae, Cylindroiulini) were extracted and analyzed by means of gas chromatography - mass spectrometry. In adults, 13 components from two chemical classes were detected: 1) The common juliform benzoquinones were represented by four compounds (2-hydroxy-3-methyl-1,4-benzoquinone, 2-methoxy-3-methyl-1,4-benzoquinone, 2,3-dimethoxy-1,4-benzoquinone, and 2,3-dimethoxy-5-methyl-1,4-benzoquinone). From this series, 2-methoxy-3-methyl-1,4-benzoquinone was most abundant, comprising about 40 % of the whole secretion. 2) All remaining compounds were identified as aliphatic (E)-alkenals [(E)-2-heptenal, (E)-2-octenal, (E)-2-nonenal, (E)-2-decenal)] along with their corresponding alcohols. (E)-2-Octenal was most abundant, roughly accounting for another 35 % of the secretion. In juveniles, different stages in the ontogenetic development of the secretion were observed, with early instars (stadium III and IV) exclusively containing the benzoquinone fraction. Alkenols and alkenals were added in later instars (stadium V and VI), with secretions of stadium VI-juveniles being already similar to those of adults. Representatives of Spirostreptida, Spirobolida, and Julida traditionally have been considered to produce benzoquinonic secretions only ("quinone millipedes"), and information on secretion components from other chemical classes is still scarce. We here provide evidence for the participation of non-quinonic compounds in the defensive exudates of the Cylindroiulini. The occurrence of additional, non-quinonic compounds in certain species within a chemically homogenous, benzoquinone-producing taxon indicates the rapid adoption of novel exocrine compounds, possibly in order to meet the demands in a changed ecological environment.

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Long chain alcohol acetates in the defensive secretion of the millipede Blaniulus guttulatus

Cited by 15 publications

References 6 publications

The chemical defenses of millipedes (diplopoda): Biochemistry, physiology and ecology

The chemical defenses of millipedes (diplopoda): Biochemistry, physiology and ecology

Infectious intimacy and contaminated caves—three new species of ectoparasitic fungi (Ascomycota: Laboulbeniales) from blaniulid millipedes (Diplopoda: Julida) and inferences about their transmittal mechanisms

Millipedes That Smell Like Bugs: (E)-Alkenals in the Defensive Secretion of the Julid Diplopod Allajulus Dicentrus

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