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Pesquisa do Estado de S?o Paulo","doi-asserted-by":"publisher","award":["2023\/08418-6"],"award-info":[{"award-number":["2023\/08418-6"]}],"id":[{"id":"10.13039\/501100001807","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002322","name":"Coordena??o de Aperfei?oamento de Pessoal de N?vel Superior","doi-asserted-by":"publisher","award":["001"],"award-info":[{"award-number":["001"]}],"id":[{"id":"10.13039\/501100002322","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002322","name":"Coordena??o de Aperfei?oamento de Pessoal de N?vel Superior","doi-asserted-by":"publisher","award":["00x0ma614"],"award-info":[{"award-number":["00x0ma614"]}],"id":[{"id":"10.13039\/501100002322","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2025,7,22]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Schistosomiasis, a neglected tropical disease (NTD) caused by flatworms of the genus Schistosoma, affects more than 250 million people globally. Praziquantel (PZQ) remains the sole therapeutic option, underscoring the need for novel treatments. This study investigates the antischistosomal activity of Eremanthus erythropappus DC. MacLeish (Asteraceae) extracts, and their isolated compounds are against Schistosoma mansoni. In vitro assays revealed that the rinsed extract (LEE) exhibited a significantly lower EC50 (18.1 \u03bcg\/mL) compared to that of the ethanolic extract (EEE) (191.5 \u03bcg\/mL), with no cytotoxicity observed at concentrations up to 500 \u03bcg\/mL. UHPLC-ESI-MS\/MS analysis annotated 16 metabolites, including sesquiterpene lactones (STLs) and pentacyclic triterpenoids. From LEE, friedelin (7), betulinic acid (8), and acacetin (14) were isolated, with the latter two being reported in E. erythropappus for the first time. Among them, only betulinic acid (8) demonstrated significant in vitro antischistosomal activity (EC50 = 36.8 \u03bcM, SI &amp;gt; 15.5), while friedelin (7) and acacetin (14) were inactive (EC50 &amp;gt; 50 \u03bcM). In S. mansoni-infected mice, the oral administration of betulinic acid (8) (400 mg\/kg) reduced the worm burden by 41.9%, whereas LEE (400 mg\/kg) achieved a substantial reduction in both the worm (\u223c86%) and egg burden (\u223c81%), also decreasing immature egg deposition by \u223c87%. These findings highlight the promising antischistosomal potential of E. erythropappus, particularly LEE, warranting further studies to optimize the isolation and characterization of bioactive compounds.<\/jats:p>","DOI":"10.1021\/acsomega.5c03005","type":"journal-article","created":{"date-parts":[[2025,7,9]],"date-time":"2025-07-09T17:02:56Z","timestamp":1752080576000},"page":"30773-30784","source":"Crossref","is-referenced-by-count":5,"title":["<i>Eremanthus erythropappus<\/i>\n                    as a Source of Antiparasitic\nAgents:\n                    <i>In Vitro<\/i>\n                    and\n                    <i>In Vivo<\/i>\n                    Efficacy\nagainst\n                    <i>Schistosoma mansoni<\/i>"],"prefix":"10.1021","volume":"10","author":[{"given":"Leonardo\nLuiz O.","family":"de Mello","sequence":"first","affiliation":[{"name":"Universidade Federal de Juiz de Fora , , R. Jose\u0301 Lourenc\u0327o Kelmer s\/n, Campus Universita\u0301rio , , ,","place":["Juiz de Fora, MG, Brazil, 36036-900"]},{"name":"Universidade Federal de Juiz de Fora , , R. Jose\u0301 Lourenc\u0327o Kelmer s\/n, Campus Universita\u0301rio , , ,","place":["Juiz de Fora, MG, Brazil, 36036-900"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Carla M.","family":"Leal","sequence":"additional","affiliation":[{"name":"Universidade Federal de Juiz de Fora , , R. Jose\u0301 Lourenc\u0327o Kelmer s\/n, Campus Universita\u0301rio , , ,","place":["Juiz de Fora, MG, Brazil, 36036-900"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Monique C.","family":"Amaro","sequence":"additional","affiliation":[{"name":"Universidade Guarulhos , , , ,","place":["Guarulhos, SP, Brazil, 07023-070"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Allan I.","family":"Andrade-de-Siqueira","sequence":"additional","affiliation":[{"name":"Universidade Guarulhos , , , ,","place":["Guarulhos, SP, Brazil, 07023-070"]}],"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":"Universidade Guarulhos , , , ,","place":["Guarulhos, SP, Brazil, 07023-070"]},{"name":"Universidade Brasil , , , ,","place":["Sa\u0303o Paulo, SP, Brazil, 08230-030"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9096-1336","authenticated-orcid":true,"given":"Ademar A.","family":"da Silva Filho","sequence":"additional","affiliation":[{"name":"Universidade Federal de Juiz de Fora , , R. Jose\u0301 Lourenc\u0327o Kelmer s\/n, Campus Universita\u0301rio , , ,","place":["Juiz de Fora, MG, Brazil, 36036-900"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1004-5395","authenticated-orcid":true,"given":"Giovanni W.","family":"Amarante","sequence":"additional","affiliation":[{"name":"Universidade Federal de Juiz de Fora , , R. Jose\u0301 Lourenc\u0327o Kelmer s\/n, Campus Universita\u0301rio , , ,","place":["Juiz de Fora, MG, Brazil, 36036-900"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2025,7,9]]},"reference":[{"issue":"10479","key":"2026081812222925100_cit1","doi-asserted-by":"publisher","first-page":"658","DOI":"10.1016\/S0140-6736(24)02814-9","article-title":"Human schistosomiasis","volume":"405","author":"Buonfrate","year":"2025","journal-title":"Lancet"},{"key":"2026081812222925100_cit2","unstructured":"WHO\n          . World Health Organization, 2024. https:\/\/www.who.int\/news-room\/fact-sheets\/detail\/schistosomiasis (accessed March 6, 2024)."},{"key":"2026081812222925100_cit3","doi-asserted-by":"publisher","first-page":"499","DOI":"10.1038\/nri843","article-title":"The immunobiology\nof schistosomiasis","volume":"2","author":"Pearce","year":"2002","journal-title":"Nat. Rev. Immunol."},{"issue":"4","key":"2026081812222925100_cit4","doi-asserted-by":"publisher","first-page":"383","DOI":"10.1080\/17425247.2022.2051477","article-title":"Recent trends\nin praziquantel nanoformulations for helminthiasis treatment","volume":"19","author":"Mengarda","year":"2022","journal-title":"Expert Opin. Drug Delivery"},{"key":"2026081812222925100_cit5","doi-asserted-by":"publisher","first-page":"1872","DOI":"10.3390\/molecules20021872","article-title":"Natural Products\nas Leads in Schistosome\nDrug Discovery","volume":"20","author":"Neves","year":"2015","journal-title":"Molecules"},{"key":"2026081812222925100_cit6","unstructured":"World Health Organization\n          . Ending the Neglect to Attain the\nSustainable Development Goals: A\nRoad Map for Neglected Tropical Diseases 2021\u20132030; World Health Organization: Geneva, Switzerland, 2021. https:\/\/www.who.int\/publications\/i\/item\/9789240010352."},{"key":"2026081812222925100_cit7","doi-asserted-by":"publisher","first-page":"646","DOI":"10.1002\/minf.201100078","article-title":"Rule-Based Classification of Chemical\nStructures by Scaffold","volume":"30","author":"Schuffenhauer","year":"2011","journal-title":"Mol. Inf."},{"key":"2026081812222925100_cit8","doi-asserted-by":"publisher","first-page":"9785","DOI":"10.3390\/molecules18089785","article-title":"Chemical\nComposition and Biological Activities of Essential Oils of Eremanthus erythropappus (DC) McLeisch (Asteraceae)","volume":"18","author":"Silve\u0301rio","year":"2013","journal-title":"Molecules"},{"key":"2026081812222925100_cit9","doi-asserted-by":"publisher","first-page":"2137","DOI":"10.1080\/14786419.2011.631135","article-title":"In vitro evaluation of the schistosomicidal\npotential of Eremanthus erythropappus (DC) McLeisch (Asteraceae) extracts","volume":"26","author":"Almeida","year":"2012","journal-title":"Nat.\nProd. Res."},{"key":"2026081812222925100_cit10","doi-asserted-by":"publisher","first-page":"6117","DOI":"10.1080\/14786419.2020.1827402","article-title":"Antileishmanial activity of the essential\noils of Myrcia ovata Cambess. and Eremanthus erythropappus (DC) McLeisch leads to parasite mitochondrial damage","volume":"35","author":"Amorim\nGomes","year":"2021","journal-title":"Nat. Prod. Res."},{"key":"2026081812222925100_cit11","doi-asserted-by":"publisher","first-page":"1321","DOI":"10.1007\/s00436-020-06963-2","article-title":"In vitro and in vivo evaluation of cnicin from blessed thistle (Centaurea\nbenedicta) and its inclusion complexes with cyclodextrins\nagainst Schistosoma mansoni","volume":"120","author":"Queiroz","year":"2021","journal-title":"Parasitol. Res."},{"issue":"1","key":"2026081812222925100_cit12","doi-asserted-by":"publisher","first-page":"278","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":"Parasites Vectors"},{"key":"2026081812222925100_cit13","doi-asserted-by":"publisher","DOI":"10.1016\/j.actatropica.2020.105741","article-title":"Antischistosomal\nproperties of aurone\nderivatives against juvenile and adult worms of Schistosoma\nmansoni","volume":"213","author":"Pereira","year":"2021","journal-title":"Acta Trop."},{"issue":"1","key":"2026081812222925100_cit14","doi-asserted-by":"publisher","DOI":"10.1038\/s41598-025-88484-5","article-title":"Anthelmintic\nactivity of 1,10-phenanthroline-5,6-dione-based\nmetallodrugs","volume":"15","author":"Cirino","year":"2025","journal-title":"Sci. Rep."},{"issue":"12","key":"2026081812222925100_cit15","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":"2026081812222925100_cit16","doi-asserted-by":"publisher","DOI":"10.1016\/j.jep.2020.113387","article-title":"Brazilian red propolis exhibits antiparasitic\nproperties in vitro and reduces worm burden and egg\nproduction in a mouse model harboring either early or chronic Schistosoma mansoni infection","volume":"264","author":"Silva","year":"2021","journal-title":"J. Ethnopharmacol."},{"issue":"1","key":"2026081812222925100_cit17","doi-asserted-by":"publisher","first-page":"89","DOI":"10.4155\/fmc-2017-0112","article-title":"Antischistosomal agents: state of\nart and perspectives","volume":"10","author":"Lago","year":"2018","journal-title":"Future Med. Chem."},{"issue":"9","key":"2026081812222925100_cit18","doi-asserted-by":"publisher","first-page":"5154","DOI":"10.1002\/ptr.7184","article-title":"Licarin A, a neolignan isolated from Nectandra oppositifolia Nees & Mart. (Lauraceae),\nexhibited moderate preclinical efficacy against Schistosoma\nmansoni infection","volume":"35","author":"Mengarda","year":"2021","journal-title":"Phytother.\nRes."},{"issue":"11","key":"2026081812222925100_cit19","doi-asserted-by":"publisher","DOI":"10.1002\/cbdv.202100604","article-title":"Cardamonin presents in vivo activity against Schistosoma mansoni and inhibits potato apyrase","volume":"18","author":"de\nCarvalho","year":"2021","journal-title":"Chem. Biodiversity"},{"issue":"5","key":"2026081812222925100_cit20","doi-asserted-by":"publisher","first-page":"1071","DOI":"10.3390\/pharmaceutics14051071","article-title":"Identification\nof asiaticoside from Centella erecta (Apiaceae) as potential apyrase inhibitor by UF-UHPLC-MS and its in vivo antischistosomal activity","volume":"14","author":"de\nCarvalho","year":"2022","journal-title":"Pharmaceutics"},{"key":"2026081812222925100_cit21","doi-asserted-by":"publisher","DOI":"10.1016\/j.jep.2023.116607","article-title":"Antiparasitic properties of 4-nerolidylcatechol\nfrom Pothomorphe umbellata (L.) Miq.\n(Piperaceae) in vitro and in mice models with either\nprepatent or patent Schistosoma mansoni infections","volume":"313","author":"Costa","year":"2023","journal-title":"J. Ethnopharmacol."},{"key":"2026081812222925100_cit22","doi-asserted-by":"crossref","first-page":"237","DOI":"10.1007\/978-1-61779-080-5_20","article-title":"Cell\nSensitivity Assays: the MTT Assay","volume-title":"Cancer\nCell Culture","author":"van Meerloo","year":"2011"},{"key":"2026081812222925100_cit23","doi-asserted-by":"publisher","DOI":"10.1038\/s41598-022-23110-2","article-title":"Neolignans\nisolated from Saururus cernuus L. (Saururaceae)\nexhibit efficacy against Schistosoma mansoni","volume":"12","author":"Brito","year":"2022","journal-title":"Sci. Rep."},{"issue":"1","key":"2026081812222925100_cit24","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."},{"issue":"10","key":"2026081812222925100_cit25","doi-asserted-by":"publisher","first-page":"3697","DOI":"10.1007\/s00436-014-4034-2","article-title":"Acaricide activity in vitro of Acmella oleracea against Rhipicephalus microplus","volume":"113","author":"Castro","year":"2014","journal-title":"Parasitol. Res."},{"key":"2026081812222925100_cit26","doi-asserted-by":"publisher","first-page":"321","DOI":"10.1017\/S0022149X13000205","article-title":"In vitro schistosomicidal effects\nof aqueous and dichloromethane\nfractions from leaves and stems of Piper species and the isolation\nof an active amide from P. amalago L.\n(Piperaceae)","volume":"88","author":"Carrara","year":"2014","journal-title":"J. Helminthol."},{"key":"2026081812222925100_cit27","doi-asserted-by":"publisher","DOI":"10.1002\/cbdv.202100503","article-title":"Evaluation of gibbilimbol B, isolated\nfrom Piper malacophyllum (piperaceae),\nas an antischistosomal agent","volume":"18","author":"Carnau\u0301ba","year":"2021","journal-title":"Chem. Biodiversity"},{"issue":"1","key":"2026081812222925100_cit28","doi-asserted-by":"publisher","DOI":"10.1016\/j.jep.2024.119028","article-title":"Efficacy\nof spilanthol and Acmella oleracea (L.)\nR. K. Jansen (Asteraceae) extract against Schistosoma\nmansoni infection","volume":"338","author":"Costa","year":"2025","journal-title":"J. Ethnopharmacol."},{"key":"2026081812222925100_cit29","first-page":"349","volume-title":"Structure-Activity\nand Activity-Activity Relationships of Sesquiterpene Lactones","author":"Schmidt","year":"2018"},{"key":"2026081812222925100_cit30","doi-asserted-by":"publisher","first-page":"1030","DOI":"10.1002\/jms.877","article-title":"Triple quadrupole tandem mass spectrometry\nof sesquiterpene lactones: a study of goyazensolide and its congeners","volume":"40","author":"Crotti","year":"2005","journal-title":"J. Mass Spectrom."},{"key":"2026081812222925100_cit31","doi-asserted-by":"publisher","first-page":"5","DOI":"10.1016\/j.bse.2018.03.002","article-title":"LC-UV-HRMS dereplication of secondary\nmetabolites from Brazilian Vernonieae (Asteraceae) species supported\nthrough in-house database","volume":"78","author":"Gallon","year":"2018","journal-title":"Biochem. Syst. Ecol."},{"key":"2026081812222925100_cit32","doi-asserted-by":"publisher","first-page":"927","DOI":"10.1016\/j.jasms.2007.01.012","article-title":"Analysis\nof Triterpenoids in Ganoderma lucidum Using Liquid Chromatography Coupled with Electrospray Ionization\nMass Spectrometry","volume":"18","author":"Yang","year":"2007","journal-title":"J. Am. Soc. Mass Spectrom."},{"key":"2026081812222925100_cit33","doi-asserted-by":"publisher","DOI":"10.1016\/j.talanta.2019.06.011","article-title":"High throughput\nidentification of pentacyclic triterpenes in Hippophae\nrhamnoides using multiple neutral loss markers scanning\ncombined with substructure recognition (MNLSR)","volume":"205","author":"Sun","year":"2019","journal-title":"Talanta"},{"issue":"4","key":"2026081812222925100_cit34","doi-asserted-by":"publisher","DOI":"10.1002\/rcm.9243","article-title":"Structure\u2013fragmentation\nstudy of pentacyclic triterpenoids using electrospray ionization quadrupole\ntime-of-flight tandem mass spectrometry (ESI-QTOFMS\/MS)","volume":"36","author":"Uddin","year":"2021","journal-title":"Rapid Commun. Mass Spectrom."},{"key":"2026081812222925100_cit35","doi-asserted-by":"publisher","first-page":"530","DOI":"10.1021\/jasms.1c00343","article-title":"Neutral Loss Mass Spectral Data Enhances\nMolecular Similarity Analysis in METLIN","volume":"33","author":"Aisporna","year":"2022","journal-title":"J.\nAm. Soc. Mass Spectrom."},{"issue":"11","key":"2026081812222925100_cit36","doi-asserted-by":"publisher","first-page":"1098","DOI":"10.3390\/ph14111098","article-title":"HPLC\/ESI-MS and NMR Analysis of Chemical\nConstitutes in Bioactive Extract from the Root Nodule of Vaccinium emarginatum","volume":"14","author":"Huang","year":"2021","journal-title":"Pharmaceuticals"},{"key":"2026081812222925100_cit37","doi-asserted-by":"crossref","DOI":"10.1002\/9780470742761","volume-title":"Medicinal Natural\nProducts: A Biosynthetic Approach","author":"Dewick","year":"2009","edition":"3"},{"key":"2026081812222925100_cit38","doi-asserted-by":"publisher","first-page":"6297","DOI":"10.1016\/j.bmc.2014.07.014","article-title":"Synthesis and activity of new triphenylphosphonium\nderivatives of betulin and betulinic acid against Schistosoma\nmansoniin vitro and in vivo","volume":"22","author":"Spivak","year":"2014","journal-title":"Bioorg. Med. Chem."},{"issue":"1","key":"2026081812222925100_cit39","doi-asserted-by":"publisher","first-page":"391","DOI":"10.3390\/nu6010391","article-title":"Recent Advances\nand Uses of Grape\nFlavonoids as Nutraceuticals","volume":"6","author":"Georgiev","year":"2014","journal-title":"Nutrients"},{"key":"2026081812222925100_cit40","doi-asserted-by":"publisher","first-page":"35","DOI":"10.1002\/jms.395","article-title":"Liquid chromatographic\/electrospray\nionization tandem mass spectrometric study of the phenolic composition\nof cocoa (Theobroma cacao)","volume":"38","author":"Sa\u0301nchez-Rabaneda","year":"2003","journal-title":"J. Mass Spectrom."},{"key":"2026081812222925100_cit41","doi-asserted-by":"publisher","first-page":"707","DOI":"10.1016\/S1044-0305(01)00226-4","article-title":"Determination\nof Flavone, Flavonol, and Flavanone Aglycones by Negative Ion Liquid\nChromatography Electrospray Ion Trap Mass Spectrometry","volume":"12","author":"Fabre","year":"2001","journal-title":"J. Am. Soc. Mass Spectrom."},{"key":"2026081812222925100_cit42","doi-asserted-by":"publisher","first-page":"5530","DOI":"10.1021\/acs.jafc.9b00330","article-title":"A systematic\nstudy of the metabolites of dietary acacetin in vivo and in vitro based on UHPLC-Q-TOF- MS\/MS Analysis","volume":"67","author":"Yin","year":"2019","journal-title":"J. Agric. Food Chem."},{"key":"2026081812222925100_cit43","doi-asserted-by":"publisher","first-page":"401","DOI":"10.1002\/pca.995","article-title":"Identification of antioxidant\nphenolic compounds in feverfew (Tanacetum parthenium) by HPLC-ESI-MS\/MS and NMR","volume":"18","author":"Wu","year":"2007","journal-title":"Phytochem. Anal."},{"key":"2026081812222925100_cit44","doi-asserted-by":"publisher","first-page":"31","DOI":"10.3390\/metabo8020031","article-title":"Software Tools and\nApproaches for Compound Identification of LC-MS\/MS Data in Metabolomics","volume":"8","author":"Blaz\u030cenovic\u0301","year":"2018","journal-title":"Metabolites"},{"key":"2026081812222925100_cit45","doi-asserted-by":"publisher","first-page":"7760","DOI":"10.3390\/molecules28237760","article-title":"Friedelin:\nStructure, Biosynthesis, Extraction, and\nIts Potential Health Impact","volume":"28","author":"Singh","year":"2023","journal-title":"Molecules"},{"key":"2026081812222925100_cit46","doi-asserted-by":"publisher","first-page":"853","DOI":"10.1111\/j.2042-7158.1972.tb08903.x","article-title":"Chemoprophylactic agents in schistosomiasis:\neremanthine, costunolide, \u03b1-cyclocostunolide and bisabolol","volume":"24","author":"Baker","year":"1972","journal-title":"J. Pharm. Pharmacol."},{"key":"2026081812222925100_cit47","doi-asserted-by":"publisher","DOI":"10.1016\/j.bse.2021.104379","article-title":"Allelopathic\npotential of the extracts of non-galled stems and globoid stem galls\nof Eremanthus erythropappus (DC) McLeish\n(Asteraceae)","volume":"100","author":"Jorge","year":"2022","journal-title":"Biochem. Syst. Ecol."},{"key":"2026081812222925100_cit48","doi-asserted-by":"publisher","first-page":"52","DOI":"10.1002\/mrc.2836","article-title":"1H and 13C NMR characterization of new cycloartane triterpenes from\nMangifera indica, Magnetic Resonance in Chemistry","volume":"50","author":"Escobedo-Marti\u0301nez","year":"2010","journal-title":"Magn. Reson. Chem."},{"key":"2026081812222925100_cit49","doi-asserted-by":"publisher","first-page":"1917","DOI":"10.1021\/np9003245","article-title":"Betulin- Derived Compounds\nas Inhibitors of Alphavirus\nReplication","volume":"72","author":"Pohjala","year":"2009","journal-title":"J. Nat. 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