The Chemistry of the Defensive Secretions of Three Species of Millipedes in the Genus Brachycybe

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dc.contributor.authorBanks, Paigeen
dc.contributor.authorFunkhouser, Emma M.en
dc.contributor.authorMacias, Angie M.en
dc.contributor.authorLovett, Brianen
dc.contributor.authorMeador, Shelbyen
dc.contributor.authorHatch, Ardenen
dc.contributor.authorGarraffo, H. Martinen
dc.contributor.authorCartwright, Kaitie C.en
dc.contributor.authorKasson, Matt T.en
dc.contributor.authorMarek, Paul E.en
dc.contributor.authorJones, Tappey H.en
dc.contributor.authorMevers, Emilyen
dc.date.accessioned2024-12-19T18:01:27Zen
dc.date.available2024-12-19T18:01:27Zen
dc.date.issued2024-06-10en
dc.description.abstractMillipedes have long been known to produce a diverse array of chemical defense agents that deter predation. These compounds, or their precursors, are stored in high concentration within glands (ozadenes) and are released upon disturbance. The subterclass Colobognatha contains four orders of millipedes, all of which are known to produce terpenoid alkaloids—spare the Siphonophorida that produce terpenes. Although these compounds represent some of the most structurally-intriguing millipede-derived natural products, they are the least studied class of millipede defensive secretions. Here, we describe the chemistry of millipede defensive secretions from three species of Brachycybe: Brachycybe producta, Brachycybe petasata, and Brachycybe rosea. Chemical investigations using mass spectrometry-based metabolomics, chemical synthesis, and 2D NMR led to the identification of five alkaloids, three of which are new to the literature. All identified compounds are monoterpene alkaloids with the new compounds representing indolizidine (i.e. hydrogosodesmine) and quinolizidine alkaloids (i.e. homogosodesmine and homo-hydrogosodesmine). The chemical diversity of these compounds tracks the known species phylogeny of this genus, rather than the geographical proximity of the species. The indolizidines and quinolizidines are produced by non-sympatric sister species, B. producta and B. petasata, while deoxybuzonamine is produced by another set of non-sympatric sister species, B. rosea and Brachycybe lecontii. The fidelity between the chemical diversity and phylogeny strongly suggests that millipedes generate these complex defensive agents de novo and begins to provide insights into the evolution of their biochemical pathways.en
dc.description.versionPublished versionen
dc.format.extentPages 478-488en
dc.format.extent11 page(s)en
dc.format.mimetypeapplication/pdfen
dc.identifier.doihttps://doi.org/10.1007/s10886-024-01518-6en
dc.identifier.eissn1573-1561en
dc.identifier.issn0098-0331en
dc.identifier.issue9-10en
dc.identifier.orcidMarek, Paul [0000-0002-7048-2514]en
dc.identifier.orcidMevers, Emily [0000-0001-7986-5610]en
dc.identifier.other10.1007/s10886-024-01518-6 (PII)en
dc.identifier.pmid38853234en
dc.identifier.urihttps://hdl.handle.net/10919/123844en
dc.identifier.volume50en
dc.language.isoenen
dc.publisherSpringeren
dc.relation.urihttps://www.ncbi.nlm.nih.gov/pubmed/38853234en
dc.rightsCreative Commons Attribution 4.0 Internationalen
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/en
dc.subjectMillipedesen
dc.subjectDefensive secretionsen
dc.subjectAlkaloidsen
dc.subjectStructure elucidationen
dc.subject.meshAnimalsen
dc.subject.meshArthropodsen
dc.subject.meshAlkaloidsen
dc.subject.meshSpecies Specificityen
dc.titleThe Chemistry of the Defensive Secretions of Three Species of Millipedes in the Genus <i>Brachycybe</i>en
dc.title.serialJournal of Chemical Ecologyen
dc.typeArticle - Refereeden
dc.type.dcmitypeTexten
dc.type.otherArticleen
dc.type.otherJournalen
dcterms.dateAccepted2024-05-22en
pubs.organisational-groupVirginia Techen
pubs.organisational-groupVirginia Tech/Agriculture & Life Sciencesen
pubs.organisational-groupVirginia Tech/Agriculture & Life Sciences/Entomologyen
pubs.organisational-groupVirginia Tech/Scienceen
pubs.organisational-groupVirginia Tech/Science/Chemistryen
pubs.organisational-groupVirginia Tech/Faculty of Health Sciencesen
pubs.organisational-groupVirginia Tech/All T&R Facultyen
pubs.organisational-groupVirginia Tech/Science/COS T&R Facultyen
pubs.organisational-groupVirginia Tech/Agriculture & Life Sciences/CALS T&R Facultyen

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