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In this study, cubebin\ue5f8a dibenzylbutyrolactole lignan\ue5f8was isolated for the first time from Drimys andina (Winteraceae), a Chilean endemic plant, and evaluated for its antiparasitic activity. Chromatographic purification of fresh leaves yielded cubebin as a 3:2 epimeric mixture, with its structure confirmed by 500 MHz NMR and single-crystal X-ray diffraction. In vitro assays demonstrated potent anthelmintic activity against both first-stage (L1) and infective third-stage (L3) larvae of A. cantonensis, with EC50 values of 4.7 and 15.3 \u03bcM, respectively, making it approximately three times more potent than albendazole against L1 and comparably effective against L3. Cubebin exhibited no cytotoxicity toward monkey (Vero) or human (HaCaT) cell lines and no toxicity in Caenorhabditis elegans, indicating a favorable safety profile. In silico ADME analysis further revealed favorable pharmacokinetic and drug-likeness properties. These results highlight cubebin as a promising lead compound for the development of novel anthelmintic therapies targeting A. cantonensis and potentially other parasitic nematodes.<\/jats:p>","DOI":"10.1021\/acsomega.5c05451","type":"journal-article","created":{"date-parts":[[2025,7,11]],"date-time":"2025-07-11T20:05:32Z","timestamp":1752264332000},"page":"31161-31169","source":"Crossref","is-referenced-by-count":14,"title":["Cubebin, a Lignan\nIsolated from\n                    <i>Drimys\nandina<\/i>\n                    , Exhibits Potent and Selective Antiparasitic\nActivity against\n                    <i>Angiostrongylus cantonensis<\/i>"],"prefix":"10.1021","volume":"10","author":[{"given":"Thaina\u0301\nR.","family":"Teixeira","sequence":"first","affiliation":[{"name":"Guarulhos University , , , ,","place":["Guarulhos, SP, Brazil, 07023-070"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0224-6069","authenticated-orcid":true,"given":"Bernd","family":"Schmidt","sequence":"additional","affiliation":[{"name":"Universita\u0308t Potsdam , , Karl-Liebknecht-Str. 24-25 , ,","place":["Potsdam, Germany, D-14476"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Eric","family":"Sperlich","sequence":"additional","affiliation":[{"name":"Universita\u0308t Potsdam , , Karl-Liebknecht-Str. 24-25 , ,","place":["Potsdam, Germany, D-14476"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bruna L.","family":"Lemes","sequence":"additional","affiliation":[{"name":"Guarulhos University , , , ,","place":["Guarulhos, SP, Brazil, 07023-070"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Monique C.","family":"Amaro","sequence":"additional","affiliation":[{"name":"Guarulhos University , , , ,","place":["Guarulhos, SP, Brazil, 07023-070"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rebeca","family":"Pe\u0301rez","sequence":"additional","affiliation":[{"name":"Universidad Auto\u0301noma de Chile , , Avenida Alemania 01090 , ,","place":["Temuco, Chile, 4780000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Camilo","family":"Ce\u0301spedes-Me\u0301ndez","sequence":"additional","affiliation":[{"name":"Universidad Auto\u0301noma de Chile , , Avenida Alemania 01090 , ,","place":["Temuco, Chile, 4780000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Cecilia","family":"Villegas","sequence":"additional","affiliation":[{"name":"Universidad Cato\u0301lica de Temuco , , Rudecindo Ortega , ,","place":["Temuco, Chile, 4780000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Viviana","family":"Burgos","sequence":"additional","affiliation":[{"name":"Universidad Santo Toma\u0301s , , ,","place":["Temuco, Chile, 4780000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1766-7031","authenticated-orcid":true,"given":"Josue\u0301","family":"de Moraes","sequence":"additional","affiliation":[{"name":"Guarulhos University , , , ,","place":["Guarulhos, SP, Brazil, 07023-070"]},{"name":"Brazil University , , , ,","place":["Sa\u0303o Paulo, SP, Brazil, 08230-030"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4668-4984","authenticated-orcid":true,"given":"Cristian","family":"Paz","sequence":"additional","affiliation":[{"name":"Universidad de La Frontera , , ,","place":["Temuco, Chile, 4780000"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2025,7,11]]},"reference":[{"key":"2026081813103912300_cit1","doi-asserted-by":"publisher","first-page":"573","DOI":"10.1016\/j.pt.2020.04.005","article-title":"FDA-approved antiparasitic drugs\nin the 21st Century: a success for helminthiasis?","volume":"36","author":"de\nMoraes","year":"2020","journal-title":"Trends Parasitol."},{"key":"2026081813103912300_cit2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2023.115268","article-title":"Toward anthelmintic drug candidates\nfor toxocariasis:\nChallenges and recent developments","volume":"251","author":"Mengarda","year":"2023","journal-title":"Eur. J.\nMed. Chem."},{"key":"2026081813103912300_cit3","doi-asserted-by":"publisher","DOI":"10.3390\/pathogens12010023","article-title":"Management of rat lungworm\ndisease (neuroangiostrongyliasis) using anthelmintics: recent updates\nand recommendations","volume":"12","author":"Jacob","year":"2023","journal-title":"Pathogens"},{"key":"2026081813103912300_cit4","doi-asserted-by":"publisher","first-page":"397","DOI":"10.1016\/j.rvsc.2020.10.023","article-title":"Angiostrongylus spp.\n(Nematoda; Metastrongyloidea) of global public health importance","volume":"135","author":"da\nSilva","year":"2021","journal-title":"Res. Vet. Sci."},{"key":"2026081813103912300_cit5","doi-asserted-by":"publisher","DOI":"10.3390\/pathogens12040624","article-title":"International\nNetwork\non Angiostrongyliasis\ue5f8INA. Neuroangiostrongyliasis: Updated\nProvisional Guidelines for Diagnosis and Case Definitions","volume":"12","author":"Graeff-Teixeira","year":"2023","journal-title":"Pathogens"},{"key":"2026081813103912300_cit6","doi-asserted-by":"publisher","DOI":"10.3389\/fphar.2022.901459","article-title":"Susceptibility of Angiostrongylus cantonensis larvae to anthelmintic\ndrugs","volume":"13","author":"Roquini","year":"2022","journal-title":"Front. 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Virtual Quim."},{"key":"2026081813103912300_cit20","doi-asserted-by":"publisher","DOI":"10.3390\/molecules23081976","article-title":"An ethnopharmacological,\nphytochemical\nand pharmacological review on lignans from Mexican Bursera spp","volume":"23","author":"Marcotullio","year":"2018","journal-title":"Molecules"},{"key":"2026081813103912300_cit21","doi-asserted-by":"publisher","DOI":"10.1055\/s-0029-1234316","article-title":"Spectral aliasing\nin 2D-NMR. 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Ecol."},{"key":"2026081813103912300_cit23","doi-asserted-by":"publisher","first-page":"1865","DOI":"10.1016\/S0031-9422(00)82577-7","article-title":"Lignoids\nfrom the fruit of three Virola species","volume":"24","author":"Cavalcante","year":"1985","journal-title":"Phytochemistry"},{"key":"2026081813103912300_cit24","doi-asserted-by":"publisher","first-page":"303","DOI":"10.1016\/j.bmcl.2004.10.079","article-title":"Trypanocidal activity of (\u2212)-cubebin\nderivatives against free amastigote forms of Trypanosoma\ncruzi","volume":"15","author":"de\nSouza","year":"2005","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"2026081813103912300_cit25","doi-asserted-by":"publisher","first-page":"255","DOI":"10.4103\/ijmr.IJMR_156_14","article-title":"Neuroprotective\neffect of cubebin:\nA dibenzylbutyrolactone lignan on scopolamine-induced amnesia in mice","volume":"146","author":"Somani","year":"2017","journal-title":"Indian J. Med. Res."},{"key":"2026081813103912300_cit26","doi-asserted-by":"publisher","first-page":"142","DOI":"10.1055\/s-2008-1034290","article-title":"Piper cubeba demonstrates\nanti-estrogenic and anti-inflammatory properties","volume":"74","author":"Yam","year":"2008","journal-title":"Planta Med."},{"key":"2026081813103912300_cit27","doi-asserted-by":"publisher","first-page":"1784","DOI":"10.1002\/ptr.4932","article-title":"The lignan (\u2212)-cubebin inhibits\nvascular contraction and induces relaxation via nitric oxide activation\nin isolated rat aorta","volume":"27","author":"Carvalho","year":"2013","journal-title":"Phytother. Res."},{"key":"2026081813103912300_cit28","doi-asserted-by":"publisher","first-page":"2030","DOI":"10.21577\/0103-5053.20200103","article-title":"Martins dos\nSantos Junior F. 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Microbiol."},{"key":"2026081813103912300_cit37","doi-asserted-by":"publisher","DOI":"10.1016\/j.phrs.2019.104284","article-title":"Lignans and\nneolignans:\nPlant secondary metabolites as a reservoir of biologically active\nsubstances","volume":"146","author":"Za\u0301les\u030ca\u0301k","year":"2019","journal-title":"Pharmaco.l Res."},{"key":"2026081813103912300_cit38","doi-asserted-by":"publisher","first-page":"3744","DOI":"10.1021\/acs.jnatprod.0c01050","article-title":"15\u03b2-Senecioyl-oxy-ent-kaur-16-en-19-oic\nAcid,\na diterpene Isolated from Baccharis lateralis, as promising oral compound for the treatment of schistosomiasis","volume":"83","author":"Sessa","year":"2020","journal-title":"J. Nat. Prod."},{"key":"2026081813103912300_cit39","doi-asserted-by":"publisher","first-page":"71","DOI":"10.1093\/genetics\/77.1.71","article-title":"The genetics\nof Caenorhabditis elegans","volume":"77","author":"Brenner","year":"1974","journal-title":"Genetics"},{"key":"2026081813103912300_cit40","doi-asserted-by":"publisher","first-page":"5","DOI":"10.53393\/rial.1954.14.33246","article-title":"Nova te\u0301cnica para isolar larvas\nde nemato\u0301ides das fezes - modificac\u0327a\u0303o do me\u0301todo\nde Baermann","volume":"14","author":"Rugai","year":"1954","journal-title":"Rev. Inst. 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Nano Mater."},{"key":"2026081813103912300_cit43","doi-asserted-by":"publisher","DOI":"10.1016\/j.phymed.2024.156045","article-title":"In vivo antischistosomal efficacy of Porcelia ponderosa \u03b3-lactones","volume":"135","author":"Souza","year":"2024","journal-title":"Phytomedicine"},{"key":"2026081813103912300_cit44","doi-asserted-by":"publisher","DOI":"10.1038\/s41598-021-02792-0","article-title":"Pyrazoline\nderivatives as promising novel antischistosomal agents","volume":"11","author":"Morais","year":"2021","journal-title":"Sci. Rep."},{"key":"2026081813103912300_cit45","doi-asserted-by":"publisher","DOI":"10.1128\/spectrum.01807-22","article-title":"N-(4-methoxyphenyl)\u00adpentanamide,\na simplified derivative of albendazole, displays anthelmintic roperties\nagainst the nematode Toxocara canis","volume":"10","author":"Silva","year":"2022","journal-title":"Microbiol. Spectr."},{"key":"2026081813103912300_cit46","doi-asserted-by":"publisher","DOI":"10.1038\/srep42717","article-title":"SwissADME: a free web\ntool to evaluate\npharmacokinetics, drug-likeness and medicinal chemistry friendliness\nof small molecules","volume":"7","author":"Daina","year":"2017","journal-title":"Sci. Rep."},{"key":"2026081813103912300_cit47","doi-asserted-by":"publisher","DOI":"10.1186\/s13071-020-04140-z","article-title":"H1-antihistamines\nas antischistosomal drugs: in vitro and in\nvivo studies","volume":"13","author":"Xavier","year":"2020","journal-title":"Parasit. 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