{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,28]],"date-time":"2026-09-28T17:18:56Z","timestamp":1790615936905,"version":"4.1.0"},"reference-count":40,"publisher":"American Chemical Society (ACS)","issue":"8","license":[{"start":{"date-parts":[[2026,7,21]],"date-time":"2026-07-21T00:00:00Z","timestamp":1784592000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100000165","name":"Division of Chemistry","doi-asserted-by":"publisher","award":["CHE0821552"],"award-info":[{"award-number":["CHE0821552"]}],"id":[{"id":"10.13039\/100000165","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000165","name":"Division of Chemistry","doi-asserted-by":"publisher","award":["CHE2116395"],"award-info":[{"award-number":["CHE2116395"]}],"id":[{"id":"10.13039\/100000165","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100007263","name":"Virginia Polytechnic Institute and State University","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100007263","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000057","name":"National Institute of General Medical Sciences","doi-asserted-by":"publisher","award":["R35 GM146740"],"award-info":[{"award-number":["R35 GM146740"]}],"id":[{"id":"10.13039\/100000057","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,8,28]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Brachycybe is a genus of the millipede subterclass Colobognatha, a group that exhibits rare social characteristics, including species aggregations and male brood care. Although it has been hypothesized that alkaloid-based defensive secretions may also function as pheromones, no studies have examined these traits. Here, we evaluated the chemical secretions of six species, two of which had not been previously studied, and conducted Y-tube pheromone assays. Chemical investigations elucidated the structures of three new metabolites: hydrogosodesmine acid (6), homo-hydrogosodesmine acid (7), and buzonamine acid (8). Y-tube pheromone assays revealed that Brachycybe producta is significantly attracted to conspecifics (p = 0.0428) and is deterred by a different species of alkaloid-producing millipede (p = 0.0161). The former assay was repeated using a mixture of the crude (p = 0.0428) and purified (p = 0.0433) chemical defense secretion fromB. producta. This study provides the first evidence that colobognath millipede chemical secretions serve both defensive and pheromone roles.<\/jats:p>","DOI":"10.1021\/acs.jnatprod.6c00556","type":"journal-article","created":{"date-parts":[[2026,7,21]],"date-time":"2026-07-21T19:50:26Z","timestamp":1784663426000},"page":"2322-2331","source":"Crossref","is-referenced-by-count":0,"title":["Evaluation\nof the Alkaloid Secretions within the Millipede\n                    <i>Brachycybe<\/i>\n                    and Their Pheromone Properties"],"prefix":"10.1021","volume":"89","author":[{"ORCID":"https:\/\/orcid.org\/0009-0004-1454-2553","authenticated-orcid":true,"given":"Arden","family":"Hatch","sequence":"first","affiliation":[{"name":"Virginia Tech , , , ,","place":["Blacksburg, Virginia, United States, 24061"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anne C.","family":"Jones","sequence":"additional","affiliation":[{"name":"Virginia Tech , , , ,","place":["Blacksburg, Virginia, United States, 24061"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Luisa F.","family":"Vasquez-Valverde","sequence":"additional","affiliation":[{"name":"Virginia Tech , , , ,","place":["Blacksburg, Virginia, United States, 24061"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Paige","family":"Banks","sequence":"additional","affiliation":[{"name":"Virginia Tech , , , ,","place":["Blacksburg, Virginia, United States, 24061"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Isabel","family":"Gooding","sequence":"additional","affiliation":[{"name":"Virginia Tech , , , ,","place":["Blacksburg, Virginia, United States, 24061"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lisa","family":"Markoff","sequence":"additional","affiliation":[{"name":"Virginia Tech , , , ,","place":["Blacksburg, Virginia, United States, 24061"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7048-2514","authenticated-orcid":true,"given":"Paul E.","family":"Marek","sequence":"additional","affiliation":[{"name":"Virginia Tech , , , ,","place":["Blacksburg, Virginia, United States, 24061"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7986-5610","authenticated-orcid":true,"given":"Emily","family":"Mevers","sequence":"additional","affiliation":[{"name":"Virginia Tech , , , ,","place":["Blacksburg, Virginia, United States, 24061"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,7,21]]},"reference":[{"issue":"1","key":"2026092812303808000_cit1","doi-asserted-by":"publisher","first-page":"353","DOI":"10.1146\/annurev.en.41.010196.002033","article-title":"Semiochemical\nParsimony in the Arthropoda","volume":"41","author":"Blum","year":"1996","journal-title":"Annu. Rev. Entomol."},{"key":"2026092812303808000_cit2","doi-asserted-by":"publisher","first-page":"36","DOI":"10.1016\/j.cois.2017.09.004","article-title":"Evolutionary Origin of Insect Pheromones","volume":"24","author":"Sto\u0308kl","year":"2017","journal-title":"Curr. Opin. Insect Sci."},{"issue":"1","key":"2026092812303808000_cit3","doi-asserted-by":"publisher","first-page":"321","DOI":"10.1146\/annurev.ento.49.061802.123329","article-title":"Pheromone-Mediated\nAggregation in Nonsocial Arthropods: An Evolutionary Ecological Perspective","volume":"50","author":"Wertheim","year":"2005","journal-title":"Annu. Rev. Entomol."},{"key":"2026092812303808000_cit4","doi-asserted-by":"publisher","DOI":"10.1093\/oso\/9780195134520.001.0001","volume-title":"Signalers\nand Receivers","author":"Greenfield","year":"2002"},{"issue":"6","key":"2026092812303808000_cit5","doi-asserted-by":"publisher","first-page":"650","DOI":"10.1590\/0037-8682-0242-2015","article-title":"Venomous and Poisonous Arthropods: Identification,\nClinical Manifestations of Envenomation, and Treatments Used in Human\nInjuries","volume":"48","author":"Haddad Junior","year":"2015","journal-title":"Rev. Soc. Bras. Med. Trop."},{"key":"2026092812303808000_cit6","doi-asserted-by":"publisher","first-page":"167","DOI":"10.1007\/b98317","article-title":"Insect Chemical\nDefense","volume-title":"The Chemistry of Pheromones and\nOther Semiochemicals II","author":"Laurent","year":"2004"},{"issue":"9","key":"2026092812303808000_cit7","doi-asserted-by":"publisher","first-page":"1663","DOI":"10.1007\/s10886-007-9343-9","article-title":"One Hundred Million\nYears of Chemical Warfare by Insects","volume":"33","author":"Poinar","year":"2007","journal-title":"J. Chem.\nEcol."},{"key":"2026092812303808000_cit8","doi-asserted-by":"publisher","first-page":"78","DOI":"10.1016\/j.bse.2015.04.033","article-title":"The Chemical\nDefenses of Millipedes (Diplopoda): Biochemistry, Physiology and Ecology","volume":"61","author":"Shear","year":"2015","journal-title":"Biochem. Syst. Ecol."},{"issue":"4","key":"2026092812303808000_cit9","doi-asserted-by":"publisher","first-page":"512","DOI":"10.1016\/j.toxicon.2011.01.004","article-title":"On the Venom System of Centipedes\n(Chilopoda), a Neglected\nGroup of Venomous Animals","volume":"57","author":"Undheim","year":"2011","journal-title":"Toxicon"},{"key":"2026092812303808000_cit10","doi-asserted-by":"publisher","DOI":"10.1016\/j.jinsphys.2024.104649","article-title":"Chemical\nDefence of a Centipede (Clinopodes Flavidus)","volume":"155","author":"Mitic\u0301","year":"2024","journal-title":"J. Insect Physiol."},{"issue":"1","key":"2026092812303808000_cit11","doi-asserted-by":"publisher","first-page":"29","DOI":"10.1021\/acs.jnatprod.5c01363","article-title":"The Terpenoid\nAlkaloids of Colobognath\nMillipedes: Insights into Structural Diversity and Function","volume":"89","author":"Hatch","year":"2026","journal-title":"J. Nat. Prod."},{"issue":"10","key":"2026092812303808000_cit12","doi-asserted-by":"publisher","DOI":"10.3390\/toxins11100611","article-title":"Spider Venom:\nComponents, Modes of\nAction, and Novel Strategies in Transcriptomic and Proteomic Analyses","volume":"11","author":"Langenegger","year":"2019","journal-title":"Toxins"},{"key":"2026092812303808000_cit13","doi-asserted-by":"publisher","DOI":"10.1590\/1678-9199-JVATITD-2021-0002","article-title":"Armed Stem to Stinger: A Review of the Ecological Roles\nof Scorpion Weapons","volume":"27","author":"Simone","year":"2021","journal-title":"J. Venomous Anim. Toxins\nIncl. Trop. Dis."},{"issue":"5","key":"2026092812303808000_cit14","doi-asserted-by":"publisher","DOI":"10.3390\/insects13050470","article-title":"Olfactory Strategies in the Defensive\nBehaviour of Insects","volume":"13","author":"Kannan","year":"2022","journal-title":"Insects"},{"issue":"1","key":"2026092812303808000_cit15","doi-asserted-by":"publisher","first-page":"349","DOI":"10.1146\/annurev.en.18.010173.002025","article-title":"Behavioral\nResponses to Insect Pheromones","volume":"18","author":"Shorey","year":"1973","journal-title":"Annu. Rev. Entomol."},{"issue":"3","key":"2026092812303808000_cit16","doi-asserted-by":"publisher","first-page":"275","DOI":"10.1007\/s00040-013-0306-6","article-title":"Intracolony Chemical Communication in Social Insects","volume":"60","author":"Richard","year":"2013","journal-title":"Insectes Soc."},{"issue":"1","key":"2026092812303808000_cit17","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1007\/s10886-012-0231-6","article-title":"Spider Pheromones\n- a Structural Perspective","volume":"39","author":"Schulz","year":"2013","journal-title":"J. Chem. Ecol."},{"issue":"9","key":"2026092812303808000_cit18","doi-asserted-by":"publisher","first-page":"1503","DOI":"10.1016\/j.peptides.2003.10.024","article-title":"Crustacean Peptide and Peptide-like Pheromones and\nKairomones","volume":"25","author":"Rittschof","year":"2004","journal-title":"Peptides"},{"issue":"4","key":"2026092812303808000_cit19","doi-asserted-by":"publisher","first-page":"372","DOI":"10.1002\/jemt.1070220406","article-title":"Fine Structure of\nOlfactory Sensilla in Myriapods and\nArachnids","volume":"22","author":"Tichy","year":"1992","journal-title":"Microsc. Res. Technol."},{"key":"2026092812303808000_cit20","volume-title":"Biologically Active Natural Products","author":"Cutler","year":"1999"},{"issue":"1","key":"2026092812303808000_cit21","doi-asserted-by":"publisher","first-page":"353","DOI":"10.1146\/annurev.en.41.010196.002033","article-title":"Semiochemical\nParsimony in the Arthropoda","volume":"41","author":"Blum","year":"1996","journal-title":"Annu. Rev. Entomol."},{"issue":"4","key":"2026092812303808000_cit22","doi-asserted-by":"publisher","first-page":"773","DOI":"10.1007\/BF00988318","article-title":"Defensive and Pheromonal Secretion of the Tergal Gland\nof Aleochara Curtula: I. The Chemical Composition","volume":"8","author":"Peschke","year":"1982","journal-title":"J. Chem. Ecol."},{"issue":"1","key":"2026092812303808000_cit23","doi-asserted-by":"publisher","first-page":"232","DOI":"10.1016\/j.ympev.2012.04.003","article-title":"Phylogenetics of\nthe Millipede Genus Brachycybe Wood, 1864 (Diplopoda: Platydesmida:\nAndrognathidae): Patterns of Deep Evolutionary History and Recent\nSpeciation","volume":"64","author":"Brewer","year":"2012","journal-title":"Mol. Phylogenet. Evol."},{"issue":"2","key":"2026092812303808000_cit24","doi-asserted-by":"publisher","first-page":"137","DOI":"10.3161\/00159301FF2005.48.2.137","article-title":"A Synopsis of the Milliped Genus\nBrachycybe Wood, 1864 (Platydesmida: Andrognathidae)","volume":"48","author":"Shelley","year":"2005","journal-title":"Fragm. Faun."},{"key":"2026092812303808000_cit25","doi-asserted-by":"publisher","first-page":"187","DOI":"10.1016\/j.funeco.2019.06.006","article-title":"Diversity and Function\nof Fungi Associated with the Fungivorous Millipede, Brachycybe Lecontii","volume":"41","author":"Macias","year":"2019","journal-title":"Fungal Ecol."},{"key":"2026092812303808000_cit26","doi-asserted-by":"publisher","DOI":"10.3897\/BDJ.8.e50770","article-title":"Natural History of the\nSocial Millipede Brachycybe\nLecontii Wood, 1864","volume":"8","author":"Wong","year":"2020","journal-title":"Biodiversity Data J."},{"issue":"1","key":"2026092812303808000_cit27","doi-asserted-by":"publisher","first-page":"19","DOI":"10.1111\/j.1439-0310.2010.01851.x","article-title":"Exclusive\nMale Egg Care and Determinants of Brooding Success in a Millipede","volume":"117","author":"Kudo","year":"2011","journal-title":"Ethology"},{"issue":"30","key":"2026092812303808000_cit28","doi-asserted-by":"publisher","first-page":"26813","DOI":"10.1021\/jacs.5c08079","article-title":"The Discovery\nof Complex Heterocycles from Millipede Secretions","volume":"147","author":"Banks","year":"2025","journal-title":"J. Am. Chem. Soc."},{"issue":"1","key":"2026092812303808000_cit29","doi-asserted-by":"publisher","first-page":"110","DOI":"10.1021\/acs.jnatprod.4c01162","article-title":"Neuromodulating Alkaloids\nfrom Millipede Defensive Secretions","volume":"88","author":"Menegatti","year":"2025","journal-title":"J. Nat.\nProd."},{"issue":"4","key":"2026092812303808000_cit30","doi-asserted-by":"publisher","first-page":"305","DOI":"10.1016\/s0305-1978(99)00068-x","article-title":"Buzonamine,\na New Alkaloid from the Defensive Secretion of the Millipede, Buzonium\nCrassipes","volume":"28","author":"Wood","year":"2000","journal-title":"Biochem. Syst. Ecol."},{"issue":"34","key":"2026092812303808000_cit31","doi-asserted-by":"publisher","first-page":"6623","DOI":"10.1016\/S0040-4039(00)01133-3","article-title":"Enantioselective Synthesis\nof Polyzonimine and Nitropolyzonamine,\nSpirocyclic Compounds from the Defensive Glands of a Millipede, Polyzonium\nRosalbum","volume":"41","author":"Mori","year":"2000","journal-title":"Tetrahedron Lett."},{"key":"2026092812303808000_cit32","doi-asserted-by":"publisher","DOI":"10.3389\/fevo.2023.1212452","article-title":"Alkaloids from Millipedes:\nA Re-Evaluation of Defensive\nExudates from Polyzonium Germanicum","volume":"11","author":"Kunert","year":"2023","journal-title":"Front.\nEcol. Evol."},{"key":"2026092812303808000_cit33","doi-asserted-by":"publisher","first-page":"478","DOI":"10.1007\/s10886-024-01518-6","article-title":"The Chemistry\nof the Defensive Secretions of Three Species of Millipedes in the\nGenus Brachycybe","volume":"50","author":"Banks","year":"2024","journal-title":"J. Chem. Ecol."},{"issue":"28","key":"2026092812303808000_cit34","doi-asserted-by":"publisher","first-page":"2367","DOI":"10.1016\/0040-4039(75)80013-X","article-title":"Nitropolyzonamine:\nA Spirocyclic Nitro Compound from the Defensive\nGlands of a Milliped","volume":"16","author":"Meinwald","year":"1975","journal-title":"Tetrahedron Lett."},{"issue":"4","key":"2026092812303808000_cit35","doi-asserted-by":"publisher","first-page":"1134","DOI":"10.1021\/acs.jnatprod.2c00077","article-title":"Deoxybuzonamine Isomers from the\nMillipede Brachycybe Lecontii (Platydesmida: Andrognathidae)","volume":"85","author":"Jones","year":"2022","journal-title":"J. Nat. Prod."},{"issue":"15","key":"2026092812303808000_cit36","doi-asserted-by":"publisher","first-page":"2114","DOI":"10.1093\/bioinformatics\/btu170","article-title":"Trimmomatic:\nA Flexible Trimmer for\nIllumina Sequence Data","volume":"30","author":"Bolger","year":"2014","journal-title":"Bioinformatics"},{"key":"2026092812303808000_cit37","doi-asserted-by":"publisher","DOI":"10.1177\/1176934318774546","article-title":"aTRAM 2.0:\nAn Improved, Flexible Locus Assembler for NGS Data","volume":"14","author":"Allen","year":"2018","journal-title":"Evol. Bioinf."},{"issue":"1","key":"2026092812303808000_cit38","doi-asserted-by":"publisher","DOI":"10.1038\/s41598-021-02447-0","article-title":"The First\nTrue Millipede-1306 Legs\nLong","volume":"11","author":"Marek","year":"2021","journal-title":"Sci. Rep."},{"issue":"4","key":"2026092812303808000_cit39","doi-asserted-by":"publisher","first-page":"772","DOI":"10.1093\/molbev\/mst010","article-title":"MAFFT Multiple Sequence\nAlignment Software Version\n7: Improvements in Performance and Usability","volume":"30","author":"Katoh","year":"2013","journal-title":"Mol. Biol. Evol."},{"issue":"5","key":"2026092812303808000_cit40","doi-asserted-by":"publisher","first-page":"1530","DOI":"10.1093\/molbev\/msaa015","article-title":"IQ-TREE 2: New Models and Efficient\nMethods for Phylogenetic Inference in the Genomic Era","volume":"37","author":"Minh","year":"2020","journal-title":"Mol. Biol. Evol."}],"container-title":["Journal of\nNatural Products"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.jnatprod.6c00556","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jnprdf\/article-pdf\/89\/8\/2322\/68681775\/acs.jnatprod.6c00556.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jnprdf\/article-pdf\/89\/8\/2322\/68681775\/acs.jnatprod.6c00556.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,28]],"date-time":"2026-09-28T16:49:08Z","timestamp":1790614148000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jnprdf\/article\/89\/8\/2322\/5225099\/Evaluation-of-the-Alkaloid-Secretions-within-the"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,7,21]]},"references-count":40,"journal-issue":{"issue":"8","published-online":{"date-parts":[[2026,7,21]]},"published-print":{"date-parts":[[2026,8,28]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.jnatprod.6c00556","relation":{},"ISSN":["0163-3864","1520-6025"],"issn-type":[{"value":"0163-3864","type":"print"},{"value":"1520-6025","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,7,21]]}}}