Studies of physiologically active arthropod secretions. III. Chemical, morphological, and histological studies of the defence mechanism of <i>Uroblaniulus canadensis</i> (Say) (Diplopoda:Julida)

Weatherston, J.; Percy, Jean

doi:10.1139/z69-214

Cited by 14 publications

(12 citation statements)

References 18 publications

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“…In addition, one hitherto undescribed compound, 2-methoxy-6-methyl-1,4-benzoquinone (compound F), was characterized from the defensive secretion. Julid species reportedly produce various 1,4-benzoquinones (Behal and Phisalix, 1900;Weatherston and Percy, 1969;Röper and Heyns, 1977;Eisner et al, 1978). Among them, the defensive secretion of a millipede, Uroblaniulus canadensis (Say), was shown to consist of a mixture of benzoquinones and unidentified aliphatic compounds (Weatherston and Percy, 1969).…”

Section: Discussionmentioning

confidence: 99%

“…Julid species reportedly produce various 1,4-benzoquinones (Behal and Phisalix, 1900;Weatherston and Percy, 1969;Röper and Heyns, 1977;Eisner et al, 1978). Among them, the defensive secretion of a millipede, Uroblaniulus canadensis (Say), was shown to consist of a mixture of benzoquinones and unidentified aliphatic compounds (Weatherston and Percy, 1969). In quinone-producing spirobolid species, an aliphatic compound from Rhinocricus insulatus has been characterized as trans-2-dodecenal (Wheeler et al, 1964), while uncharacterized components have been reported for two species, Narceus annularis and Floridobolus penneri (Monro et al, 1962).…”

Section: Discussionmentioning

confidence: 99%

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n-Hexyl Laurate and Fourteen Related Fatty Acid Esters: New Secretory Compounds from the Julid Millipede, Anaulaciulus sp.

et al. 2012

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A total of fifteen saturated fatty acid esters were newly identified from the secretions of an unidentified Anaulaciulus sp. (Julida: Julidae). The fatty acid components of the esters were composed of normal chain acids (from C(10) to C(14)) and of branched chain acids (from iso-C(12) to iso-C(15) and anteiso-C(15)). The alcohol moieties were all composed of normal chain alcohols varying from n-butanol to n-octanol. The most abundant component found in the total esters was n-hexyl laurate (64.7%). Novel compounds identified from the millipede secretion extracts include six branched iso- and anteiso-fatty esters, an odd-numbered C(11)-fatty acid ester, a C(13)-fatty acid ester, and a C(7)-alcohol ester, all of which were previously undescribed natural products. In addition, a characteristic mixture of benzoquinones, such as 2-methyl-1,4-benzoquinone, 2-methoxy-3-methyl-1,4-benzoquinone, 2,3-dimethoxy-1,4-benzoquinone, 2-methoxy-6-methyl-1,4-benzoquinone, and 2,3-dimethoxy-5-methyl-1,4-benzoquinone were identified from the secretions, together with trace amounts of 1,4-benzoquinone.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

n-Hexyl Laurate and Fourteen Related Fatty Acid Esters: New Secretory Compounds from the Julid Millipede, Anaulaciulus sp.

et al. 2012

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“…The histology of the glands has not been studied very thoroughly; the most detailed work to date using light microscopy being that of Weatherston and Percy (1969). Woodring and Blum (1963) and Eisner et al (1963aEisner et al ( , 1963bEisner et al ( , 1993c examined Type 3 glands at a gross histological level.…”

Section: Histology Of the Glandsmentioning

confidence: 99%

“…What histological work has been done focuses on Type 2 glands. Weatherston and Percy (1969) found that the gland cells of Uroblaniulus canadensis (Julida, Parajulidae) were not continuous in lining the gland, but were interspersed among the hypodermal cells that secrete the procuticular lining of the gland. There appeared to be two types of gland cells arrayed in not more than about 20 pairs.…”

Section: Histology Of the Glandsmentioning

confidence: 99%

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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“…Along with (E)-2-dodecenal from Rhinocricus insulatus (Wheeler et al, 1964), this is the second record of the occurrence of (E)-2-alkenals in the secretions of juliform Diplopoda, and the first incidence of alkenals in the secretions of Julida. For other Juliformia, sporadic reports on nonbenzoquinone compounds are available, but these either deal with probably cuticle-derived components (e.g., Monro et al, 1962;Weatherston and Percy, 1969), or the identification of these components is only tentative and/or might need reconsideration. For example, analytical data for the identification of a putative alkaloid, 3,3a,4,5-tetrahydro-1H-pyrrolo-[2,3-b] pyridine-2,6-dione, from the secretion of R. padbergi are largely missing (Arab et al, 2003).…”

Section: Discussionmentioning

confidence: 99%

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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Studies of physiologically active arthropod secretions. III. Chemical, morphological, and histological studies of the defence mechanism of Uroblaniulus canadensis (Say) (Diplopoda:Julida)

Cited by 14 publications

References 18 publications

n-Hexyl Laurate and Fourteen Related Fatty Acid Esters: New Secretory Compounds from the Julid Millipede, Anaulaciulus sp.

n-Hexyl Laurate and Fourteen Related Fatty Acid Esters: New Secretory Compounds from the Julid Millipede, Anaulaciulus sp.

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

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

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