N,N-dimethyl-β-phenylethylamine and bornyl esters from the harvestman (arachnida: Opiliones)

Ekpa, Okon D.; Wheeler, J. W.; Cokendolpher, James C.; Duffield, R. M.

doi:10.1016/s0040-4039(01)80145-3

Cited by 24 publications

(22 citation statements)

References 16 publications

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“… * Ekpa et al (1984), Hara et al (2005), Raspotnig et al (2005, 2011, 2012), Gnaspini and Hara (2007), Jones et al (2009), Shear et al (2010, 2014), Rocha et al (2013). ** The naphthalenedione in the undetermined stylocellid was identified as 6-methyl-1,4-naphthalendione (Jones et al, 2009). NQ, (1,4-naphthoquinone); MNQ, (6-methyl-1,4-naphthoquinone); MOQ, (2-methoxy-1,4-naphthoquinone); MMOQ, (methoxy-methyl-1,4-naphthoquinone); ND, (1,4-naphththalendione derivative); CNQ, (chloro-naphthoquinones); MAQ, (2-methyl-9,10-anthraquinone); DMAQ, (1,2-dimethyl-9,10-anthraquinone); BQ, (1,4-benzoquinone); ABQ, (alkyl-substituted benzoquinones).…”

Section: Figurementioning

confidence: 99%

“…From previous studies we know that the composition of secretions clearly characterizes different opilionid lineages. For instance, and very roughly, alkaloids and terpenes appear characteristic for travunioid Insidiatores, phenolics for lower Grassatores, and a number of acyclic compounds (mainly ketones) as well as quinones have been reported from Cyphophthalmi, Eupnoi, Dyspnoi, and Laniatores (e.g., Eisner et al, 1977; Roach et al, 1980; Duffield et al, 1981; Ekpa et al, 1984; Raspotnig et al, 2011, 2014, 2015a,b; Raspotnig, 2012; Wouters et al, 2013).…”

Section: Introductionmentioning

confidence: 99%

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A Model for Phylogenetic Chemosystematics: Evolutionary History of Quinones in the Scent Gland Secretions of Harvestmen

et al. 2017

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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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Section: Figurementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A Model for Phylogenetic Chemosystematics: Evolutionary History of Quinones in the Scent Gland Secretions of Harvestmen

et al. 2017

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“…The defensive secretion of Sclerobunus robustus contains, in admixture with terpenic compounds, N,N-dimethyl-J3-phenylethylamine as a major constituent and nicotine as a minor one (Ekpa et al, 1984).…”

Section: Opiliones (Harvestmen)mentioning

confidence: 99%

Alkaloids in Animals

1998

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“…Thus, according to current knowledge, opilionid scent glands are comparable to defensive glands of many other arthropods. They generally consist of large hollow sacs provided with glandular tissue and they are known to produce different classes of rather volatile, in some species highly scented compounds (e.g., Ekpa et al, 1984, 1985; Shear et al, 2010; Pomini et al, 2010; Raspotnig et al, 2005, 2010; Föttinger et al, 2010). Beyond these common features, scent gland organization and chemistry greatly differs among the phyletic lineages of Opiliones, rendering the gland systems well suited to study evolutionary traits of opilionid groups on different taxonomic levels: Typical defensive glands obviously only occur in cyphophthalmids and laniatoreans (Gnaspini and Hara, 2007), whereas scent glands in the Eupnoi and even more in the Dyspnoi are frequently modified, rather inconspicuous or even hidden (e.g., Schaider and Raspotnig, 2009).…”

Section: Introductionmentioning

confidence: 99%

Functional anatomy of scent glands in Paranemastoma quadripunctatum (Opiliones, Dyspnoi, Nemastomatidae)

Schaider

Komposch²,

Stabentheiner

et al. 2011

Journal of Morphology

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The morphological organization and functional anatomy of prosomal defensive (scent) glands in Paranemastoma quadripunctatum, a representative of the dyspnoid harvestmen, was investigated by means of histological semithin sections, software-based 3D-reconstruction and scanning electron microscopy. Scent glands comprise large, hollow sacs on either side of the prosoma, each of these opening to the outside via one orifice (ozopore) immediately above coxa I. In contrast to the situation known from laniatorean, cyphophthalmid and some eupnoid Opiliones, ozopores are not exposed but hidden in a depression (atrium), formed by a dorsal integumental fold of the carapace and the dorsal parts of coxae I. Glandular sacs are connected to ozopores via a short duct which is equipped with a specific closing mechanism in its distal part: A layer of modified epidermal cells forms a kind of pad-like tissue, surrounding the duct like a valve. Several muscles attached to the anterior parts of the glandular reservoir and to the epithelial pad may be associated with ozopore-opening. The actual mechanism of secretion discharge seems to be highly unusual and may be hypothesized on the basis of corroborating data from behavioral observations, scent gland anatomy and secretion chemistry as follows: Enteric fluid is considered to be directed towards the ozopores via cuticular grooves in the surface of the coxapophyses of legs I. Then, the fluid is sucked into the anterior part of the scent gland reservoirs by the action of dorsal dilator muscles that widen the reservoir and produce a short-term negative pressure. After dilution/solution of the naphthoquinone-rich scent gland contents, a secretion-loaded fluid is thought to be discharged with the help of transversal compressor muscles. This is the first detailed study on the functional anatomy of scent glands and the mechanisms of secretion discharge in the Dyspnoi.

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N,N-dimethyl-β-phenylethylamine and bornyl esters from the harvestman (arachnida: Opiliones)

Cited by 24 publications

References 16 publications

A Model for Phylogenetic Chemosystematics: Evolutionary History of Quinones in the Scent Gland Secretions of Harvestmen

A Model for Phylogenetic Chemosystematics: Evolutionary History of Quinones in the Scent Gland Secretions of Harvestmen

Alkaloids in Animals

Functional anatomy of scent glands in Paranemastoma quadripunctatum (Opiliones, Dyspnoi, Nemastomatidae)

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