Neuromodulating Alkaloids from Millipede Defensive Secretions

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dc.contributor.authorMenegatti, Carlaen
dc.contributor.authorWood, Jared S.en
dc.contributor.authorBanks, Paigeen
dc.contributor.authorKnott, Kennethen
dc.contributor.authorBriganti, Jonathan S.en
dc.contributor.authorBriganti, Anthony J.en
dc.contributor.authorMcNally, Samuel V. G.en
dc.contributor.authorMarek, Paul E.en
dc.contributor.authorBrown, Anne M.en
dc.contributor.authorJones, Tappey H.en
dc.contributor.authorWilliamson, R. Thomasen
dc.contributor.authorMevers, Emilyen
dc.date.accessioned2024-12-19T15:59:16Zen
dc.date.available2024-12-19T15:59:16Zen
dc.date.issued2024en
dc.description.abstractMillipedes have long been known to produce structurally diverse chemical defenses, including hydrogen cyanide, terpenoid alkaloids, and oxidized aromatics. Although the hydrogen cyanide and oxidized aromatic producing millipedes have been well studied, less than 10% of the terpenoid alkaloid producers have been chemically investigated. Several previous studies have shown that alkaloids disorient predators, but their biochemical target is currently unknown. Herein, we investigated the defensive secretions of a colobognath millipede, Ischnocybe plicata, and elucidated the constitution, absolute configuration, and conformation of four new highly oxidized terpenoid alkaloids, termed ischnocybines, using a range of analytical techniques. The ischnocybines are actively secreted from the defensive glands and were shown to disorient ants, a likely common predator. Evaluation of the ischnocybines in a panel of neuroreceptors revealed that ischnocybine A possesses potent (Ki 13.6 nM) and selective (100-fold) binding affinity for sigma-1, an orphan neuroreceptor, over sigma-2. These molecules represent the most complex alkaloids to be discovered from millipedes and provide the first potential insights into a biochemical target responsible for their defensive properties.en
dc.description.versionAccepted versionen
dc.identifier.orcidMevers, Emily [0000-0001-7986-5610]en
dc.identifier.urihttps://hdl.handle.net/10919/123841en
dc.language.isoenen
dc.publisherAmerican Chemical Societyen
dc.rightsIn Copyrighten
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/en
dc.titleNeuromodulating Alkaloids from Millipede Defensive Secretionsen
dc.title.serialJournal of Natural Productsen
dc.typeArticle - Refereeden
dc.type.dcmitypeTexten
dc.type.otherArticleen
dcterms.dateAccepted2024-12-09en
pubs.organisational-groupVirginia Techen
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

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