The scent gland chemistry of Gagrellinae (Opiliones, Sclerosomatidae): evidence for sequestration of myrmicacin in a species of Prionostemma

Raspotnig, Günther; Bodner, Michaela; Blesl, Julia; Víquez, Carlos

doi:10.1007/s00049-022-00373-9

Cited by 2 publications

(2 citation statements)

References 41 publications

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“…Rilaena triangularis Prionostemma sp. Raspotnig et al, 2015aRaspotnig et al, , 2020Raspotnig et al, , 2022 *"Sclerosomatid compounds sensu stricto" (Raspotnig, 2012) refer to 12 compounds, displaying motifs of SCs of subgroups 1 and 2, as detected in North American Leiobuninae of the genera Leiobunum and Hadrobunus (Blum and Edgar, 1971;Meinwald et al, 1971;Jones et al, 1976Jones et al, , 1977Ekpa et al, 1985). Some of these compounds, possibly as a result of convergence, have meanwhile also been detected in triaenonychid and gonyleptid Laniatores.…”

Section: Egaenus Convexusmentioning

confidence: 99%

“…Formally, the family Sclerosomatidae includes four subfamilies: Leiobuninae, Sclerosomatinae, Gagrellinae, and Gyantinae. We now know that gagrellines may rely on acid-rich secretions (Raspotnig et al, 2022) and gyantines are no sclerosomatids, but phalangiids (Hedin et al, 2012) and they produce benzoquinonic secretions (Raspotnig et al, 2017). Thus, SCs may occur in leiobunines and sclerosomatines or at least in a part of these: so far, SCs have been documented for North American Leiobunum and Hadrobunus species of the clade "US Leiobunines" (sensu Hedin et al, 2012) and for Nelima spp.…”

Section: Delineating the Distribution And Enlarging The Pool Of Scler...mentioning

confidence: 99%

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Polymorphic scent gland secretions in Nelima harvestmen: “Sclerosomatid compounds” but different chemical lineages

et al. 2022

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The scent glands of harvestmen (Opiliones) produce secretions of taxon-specific composition. One class of compounds, assumed to be a key group in opilionid chemosystematics and prevalent among sclerosomatid Eupnoi, was termed “sclerosomatid compounds” (SCs). Known compounds of this group comprise acyclic 4-methyl-branched ethyl-ketones and -alcohols as well as 2,4-dimethyl-branched primary alcohols and aldehydes, originally described from several species of North American Leiobuninae. We analyzed the scent gland secretions of Nelima ssp. (Sclerosomatidae, Leiobuninae) from two continents by gas chromatography-mass spectrometry, NMR, stereoselective synthesis, and chiral chromatography. We found a surprising chemical dichotomy: while North American N. paesserli produced typical acyclic SCs such as (E)-4-methyl-4-hexen-3-one, the secretions of European Nelima species exhibited a mixture of aromatic and aliphatic compounds, namely (R)-2-methyl-1-phenyl-pentan-3-one (MPP), 4-phenyl-2-butanone (PB), 2-phenylacetamide (PA), as well as (2R,4R)-2,4-dimethylhexanoic acid (DHA), all of which are new for the secretions of harvestmen. Remarkably, in N. sempronii, the secretions of juveniles (containing PB) differed from the secretions of adults (containing MPP and DHA). Though the chemistry of European Nelima species clearly diverged at first sight, all compounds detected either possess specific chemical motifs that allow an assignment to the class of SCs or appear to be biochemically/ontogenetically connected to SC-components. Thus, we here add novel compounds to the pool of SCs along with an extension of the definition of SCs to include aromatic compounds with SC-motifs. Furthermore, we describe a first case of juvenile-adult polymorphism for the exocrine secretions of harvestmen and provide a scheme of how secretions are regenerated.

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Section: Egaenus Convexusmentioning

confidence: 99%

Section: Delineating the Distribution And Enlarging The Pool Of Scler...mentioning

confidence: 99%

Polymorphic scent gland secretions in Nelima harvestmen: “Sclerosomatid compounds” but different chemical lineages

et al. 2022

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Chemical and evolutionary analysis of the scent gland secretions of two species of Gonyleptes Kirby, 1819 (Arachnida: Opiliones: Laniatores)

et al. 2023

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The subfamily Gonyleptinae is the second largest in Gonyleptidae, harboring over 100 species.Gonyleptinae is polyphyletic, nestled in the clade K92, and despite its richness, several species of that subfamily have not had their chemicals of the defensive secretions analyzed. Among these are Gonyleptes curticornis (Mello-Leitão, 1940) and G. horridus Kirby, 1819, the latter being particularly important because it is the type species of the genus, which in turn names the subfamily. Gonyleptes horridus is also used in many phylogenetic analyses, be it using morphological or molecular data. The chemical study of the secretions of these two species by GC-MS and NMR 1 H showed the presence of 1-(6-isopropyl-3,4-dihydro-2H-pyran-2-yl)-methylbutanone, 1-(6-isopropyl-3,4-dihydro-2H-pyran-2-yl) isobutanone and 4-methyl-1-hepten-3-one in both species. On the other hand, 4-methyl-1 hexen-3-one, benzaldehyde and 3-octanone were observed only in G. curticornis. Both species are Gonyleptinae and chemical mapping of the group corroborates that vinyl ketones are synapomorphy of K92 and that the compound 1-(6-isopropyl-3,4-dihydro-2H-pyran-2-yl) isobutanone is synapomorphic to G. curticornis and G. horridus, but homoplastic to the genus Sodreana Mello-Leitão, 1922. 1-(6-(1-methyl-propyl)3,4-dihydro-2H-pyran-2yl)2-methylbutanone and 4-methyl-1-hepten3-one is also synapomorphic to G. curticornis and G. horridus, but homoplastic in Moreiranula saprophila.

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The scent gland chemistry of Gagrellinae (Opiliones, Sclerosomatidae): evidence for sequestration of myrmicacin in a species of Prionostemma

Cited by 2 publications

References 41 publications

Polymorphic scent gland secretions in Nelima harvestmen: “Sclerosomatid compounds” but different chemical lineages

Polymorphic scent gland secretions in Nelima harvestmen: “Sclerosomatid compounds” but different chemical lineages

Chemical and evolutionary analysis of the scent gland secretions of two species of Gonyleptes Kirby, 1819 (Arachnida: Opiliones: Laniatores)

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