Polymorphic scent gland secretions in Nelima harvestmen: “Sclerosomatid compounds” but different chemical lineages
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 ac...
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Frontiers Media S.A.
2022-10-01
|
| Series: | Frontiers in Ecology and Evolution |
| Subjects: | |
| Online Access: | https://www.frontiersin.org/articles/10.3389/fevo.2022.993368/full |
| _version_ | 1811239371863490560 |
|---|---|
| author | Günther Raspotnig Antje Hüfner Michaela Bodner Julia Blesl Julia Blesl Miriam Schaider Ignacio Escalante Olaf Kunert |
| author_facet | Günther Raspotnig Antje Hüfner Michaela Bodner Julia Blesl Julia Blesl Miriam Schaider Ignacio Escalante Olaf Kunert |
| author_sort | Günther Raspotnig |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-12T12:59:44Z |
| format | Article |
| id | doaj.art-01638403a4274ab3b0db9fb76131defa |
| institution | Directory Open Access Journal |
| issn | 2296-701X |
| language | English |
| last_indexed | 2024-04-12T12:59:44Z |
| publishDate | 2022-10-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Ecology and Evolution |
| spelling | doaj.art-01638403a4274ab3b0db9fb76131defa2022-12-22T03:32:13ZengFrontiers Media S.A.Frontiers in Ecology and Evolution2296-701X2022-10-011010.3389/fevo.2022.993368993368Polymorphic scent gland secretions in Nelima harvestmen: “Sclerosomatid compounds” but different chemical lineagesGünther Raspotnig0Antje Hüfner1Michaela Bodner2Julia Blesl3Julia Blesl4Miriam Schaider5Ignacio Escalante6Olaf Kunert7Institute of Biology, University of Graz, Graz, AustriaInstitute of Pharmaceutical Sciences, University of Graz, Graz, AustriaInstitute of Biology, University of Graz, Graz, AustriaInstitute of Biology, University of Graz, Graz, AustriaInstitute of Pharmaceutical Sciences, University of Graz, Graz, AustriaInstitute of Biology, University of Graz, Graz, AustriaDepartment of Biological Sciences, University of Wisconsin, Milwaukee, WI, United StatesInstitute of Pharmaceutical Sciences, University of Graz, Graz, AustriaThe 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.https://www.frontiersin.org/articles/10.3389/fevo.2022.993368/fullOpilionesSclerosomatidaeLeiobuninaeLeiobunumethyl-ketoneschemosystematics |
| spellingShingle | Günther Raspotnig Antje Hüfner Michaela Bodner Julia Blesl Julia Blesl Miriam Schaider Ignacio Escalante Olaf Kunert Polymorphic scent gland secretions in Nelima harvestmen: “Sclerosomatid compounds” but different chemical lineages Frontiers in Ecology and Evolution Opiliones Sclerosomatidae Leiobuninae Leiobunum ethyl-ketones chemosystematics |
| title | Polymorphic scent gland secretions in Nelima harvestmen: “Sclerosomatid compounds” but different chemical lineages |
| title_full | Polymorphic scent gland secretions in Nelima harvestmen: “Sclerosomatid compounds” but different chemical lineages |
| title_fullStr | Polymorphic scent gland secretions in Nelima harvestmen: “Sclerosomatid compounds” but different chemical lineages |
| title_full_unstemmed | Polymorphic scent gland secretions in Nelima harvestmen: “Sclerosomatid compounds” but different chemical lineages |
| title_short | Polymorphic scent gland secretions in Nelima harvestmen: “Sclerosomatid compounds” but different chemical lineages |
| title_sort | polymorphic scent gland secretions in nelima harvestmen sclerosomatid compounds but different chemical lineages |
| topic | Opiliones Sclerosomatidae Leiobuninae Leiobunum ethyl-ketones chemosystematics |
| url | https://www.frontiersin.org/articles/10.3389/fevo.2022.993368/full |
| work_keys_str_mv | AT guntherraspotnig polymorphicscentglandsecretionsinnelimaharvestmensclerosomatidcompoundsbutdifferentchemicallineages AT antjehufner polymorphicscentglandsecretionsinnelimaharvestmensclerosomatidcompoundsbutdifferentchemicallineages AT michaelabodner polymorphicscentglandsecretionsinnelimaharvestmensclerosomatidcompoundsbutdifferentchemicallineages AT juliablesl polymorphicscentglandsecretionsinnelimaharvestmensclerosomatidcompoundsbutdifferentchemicallineages AT juliablesl polymorphicscentglandsecretionsinnelimaharvestmensclerosomatidcompoundsbutdifferentchemicallineages AT miriamschaider polymorphicscentglandsecretionsinnelimaharvestmensclerosomatidcompoundsbutdifferentchemicallineages AT ignacioescalante polymorphicscentglandsecretionsinnelimaharvestmensclerosomatidcompoundsbutdifferentchemicallineages AT olafkunert polymorphicscentglandsecretionsinnelimaharvestmensclerosomatidcompoundsbutdifferentchemicallineages |