Naphthoquinones and Anthraquinones from Scent Glands of a Dyspnoid Harvestman, Paranemastoma quadripunctatum

Raspotnig, Günther; Leutgeb, Verena; Schaider, Miriam; Komposch, Christian

doi:10.1007/s10886-010-9745-y

Cited by 25 publications

(42 citation statements)

References 12 publications

(20 reference statements)

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“…Therefore, we propose that hydroquinones and their respective benzoquinones should be considered synonymous, if used for phylogenetic purposes. The identification of defensive compounds from the suborders Cyphophthalmi (Jones et al 2009;Raspotnig et al 2005Raspotnig et al , 2012 and Dyspnoi (Raspotnig et al 2010(Raspotnig et al , 2014bSchaider et al 2011) has allowed more precise inferences about the evolution of the defensive secretions in Opiliones (e.g., Raspotnig et al 2014a). As pointed out by these authors, knowing the biosynthetic routes of the defensive secretion is important because it allows a more realistic use of chemical data for phylogenetic purposes (e.g., proposing weight matrices).…”

Section: Discussionmentioning

confidence: 99%

“…Harvestmen defensive secretions may be composed of methyl ketones, naphtoquinones, benzoquinones, and phenols among other chemicals (e.g., Hara et al 2005;Jones et al 2009;Raspotnig et al 2005Raspotnig et al , 2010Raspotnig et al , 2014aWouters et al 2013). Although these chemicals can repel some predators (Eisner et al 2004;Machado et al 2005), defensive secretions are not always used against all predators (see Carvalho et al 2012;Dias and Willemart 2013;Dias et al 2014;Eisner et al 2004;Souza and Willemart 2011;Segovia et al 2015b).…”

Section: Introductionmentioning

confidence: 99%

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The Scent Glands of the Neotropical Harvestman Discocyrtus pectnifemur: Morphology, Behavior and Chemistry

et al. 2015

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Harvestmen have a pair of scent glands that open through ozopores. The literature suggests a link between the morphology of the ozopore area and the emission of a defensive secretion. A previous study on a species that aggregates in open areas, where individuals are probably more easily spotted by predators, showed that this defensive secretion causes conspecifics to flee. However, it is unknown whether this behavior occurs in species that aggregate in sheltered areas, where prey are harder to find. Herein, we describe the morphology of the ozopore area, the mode of emission of the defensive secretion, and its chemical composition in the harvestman Discocyrtus pectinifemur. We also tested if the defensive secretion is used as an alarm pheromone. We found that D. pectinifemur releases the defensive secretion in different ways, one of them being as a jet. Emission as a jet contrasts with that known for all congeners previously studied, and is in accord with the expected morphology of the ozopore. We found that the defensive secretion of D. pectinifemur does not function as an alarm pheromone. The composition of the defensive secretion, a mixture of quinones, is congruent with those already described for the clade that includes Discocyrtus. Our results support the link between the morphology of the scent glands area and the emission behavior of the defensive secretion, and they suggest that the alarm pheromone function in harvestmen may be dependent on ecological factors.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

The Scent Glands of the Neotropical Harvestman Discocyrtus pectnifemur: Morphology, Behavior and Chemistry

et al. 2015

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“…Gas chromatography (GC) (Raspotnig et al 2010;Zuo et al 2008), Raman microscopy (Beattie et al 2007), high-performance liquid chromatography (HPLC) (Sakunphueak and Panichayupakaranant 2010;Xue et al 2008), and mass spectrometry (MS) (Zhao et al 2010) Scheme 2 Illustration, using benzoquinone as an example, of the nucleophilic addition with formation of mono-,di-,tri, and tetra-susbtitution identification and quantification of quinones. An extensive literature search showed that among the methods, HPLC or HPLC/MS are the most often used methods.…”

Section: Analytical Methods For the Detection Of Quinonesmentioning

confidence: 99%

The chemical and biological activities of quinones: overview and implications in analytical detection

et al. 2011

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Quinones are a class of natural and synthetic compounds that have several beneficial effects. Quinones are electron carriers playing a role in photosynthesis. As vitamins, they represent a class of molecules preventing and treating several illnesses such as osteoporosis and cardiovascular diseases. Quinones, by their antioxidant activity, improve general health conditions. Many of the drugs clinically approved or still in clinical trials against cancer are quinone related compounds. Quinones have also toxicological effects through their presence as photoproducts from air pollutants. Quinones are fast redox cycling molecules and have the potential to bind to thiol, amine and hydroxyl groups. The aforementioned properties make the analytical detection of quinones problematic. However, recent advances of the available analytical techniques along with the possibility of using labeled compound facilitate their detection hence allowing a better understanding of their action. This review summarizes the current knowledge with respect to the oxido-reductive and electrophilic properties of quinones as well as to the analytical tools used for their analysis. It includes a general introduction about the physiological, and therapeutical functions of quinones. A number of studies are reported to cover the chemical reactivity in an attempt to understand quinones as biologically active compounds. Data ranging from normal analytical methods to study quinones derived from plant or biological matrices to the use of labeled compounds are presented. The examples illustrate how chemical, biological and analytical knowledge can be integrated to have a better understanding of the mode of action of the quinones.

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“…While best studied in insects, chemical defense is also well known from chelicerates (e.g., Eisner et al, 1961), with most of this work focused on opilionids (Roach et al, 1980;Raspotnig et al, 2010). Our experiments demonstrate, for the first time, that oil gland secretions of oribatid mites provide protection from predation by arthropod predators.…”

Section: Discussionmentioning

confidence: 70%

Tasty but Protected—First Evidence of Chemical Defense in Oribatid Mites

et al. 2011

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Oribatid mites (Acari, Oribatida) represent one of the most abundant and speciose groups of microarthropods in the decomposer food webs of soils, but little is known of their top-down regulation by predators. Oribatids are relatively long-lived and have numerous morphological defensive adaptations, and so have been proposed to live in 'enemy-free space'. Most also possess a pair of large exocrine oil glands that produce species-specific mixtures of hydrocarbons, terpenes, aromatics, and alkaloids with presumably allomonal functions, although their adaptive value has never been tested empirically. We developed a protocol that discharges the oil glands of the model oribatid species, Archegozetes longisetosus. and offered 'disarmed' individuals as prey to polyphagous Stenus beetles (Staphylinidae), using untreated mites as controls. Stenus juno fed on disarmed mites with behavioral sequences and success rates similar to those observed when they prey on springtails, a common prey. In contrast, mites from the control group with full glands were almost completely rejected; contact with the gland region elicited a strong reaction and cleaning behavior in the beetle. This is the first evidence of an adaptive value of oribatid mite oil gland secretions for chemical defense. The protocol of discharging oil glands should facilitate future studies on top-down control of oribatid mites that aim to differentiate between morphological and chemical aspects of defensive strategies.

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Naphthoquinones and Anthraquinones from Scent Glands of a Dyspnoid Harvestman, Paranemastoma quadripunctatum

Cited by 25 publications

References 12 publications

The Scent Glands of the Neotropical Harvestman Discocyrtus pectnifemur: Morphology, Behavior and Chemistry

The Scent Glands of the Neotropical Harvestman Discocyrtus pectnifemur: Morphology, Behavior and Chemistry

The chemical and biological activities of quinones: overview and implications in analytical detection

Tasty but Protected—First Evidence of Chemical Defense in Oribatid Mites

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