{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,16]],"date-time":"2026-10-16T06:16:43Z","timestamp":1792131403901,"version":"4.4.0"},"reference-count":23,"publisher":"Public Library of Science (PLoS)","issue":"6","license":[{"start":{"date-parts":[[2024,6,12]],"date-time":"2024-06-12T00:00:00Z","timestamp":1718150400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100005739","name":"Universidad Nacional Aut\u00f3noma de M\u00e9xico","doi-asserted-by":"publisher","award":["TA200324"],"award-info":[{"award-number":["TA200324"]}],"id":[{"id":"10.13039\/501100005739","id-type":"DOI","asserted-by":"publisher"}]},{"name":"DGAPA-UNAM","award":["Posdoctoral Grant"],"award-info":[{"award-number":["Posdoctoral Grant"]}]}],"content-domain":{"domain":["www.plosone.org"],"crossmark-restriction":false},"short-container-title":["PLoS ONE"],"abstract":"<jats:p><jats:italic>Haemonchus contortus<\/jats:italic> is a blood-feeding gastrointestinal parasite that impacts grazing sheep, causing economic losses in animal production. Due to its anthelmintic resistance, alternative antiparasitic treatments like plant-based anthelmintics are necessary to explore. <jats:italic>Artemisia cina<\/jats:italic> (Asteraceae) is a plant whose <jats:italic>n<\/jats:italic>-hexane extract and ethyl acetate extract exhibit anthelmintic activity against <jats:italic>H<\/jats:italic>. <jats:italic>contortus<\/jats:italic>, the <jats:italic>n<\/jats:italic>-hexane more active. To discover additional bioactive metabolites, a chemical analysis was performed on ethyl acetate extract, which presented an LC<jats:sub>90<\/jats:sub> of 3.30 mg\/mL and allowed the isolation of 11-[(1<jats:italic>R<\/jats:italic>,5<jats:italic>S<\/jats:italic>,7<jats:italic>R<\/jats:italic>,8<jats:italic>R<\/jats:italic>,10<jats:italic>S<\/jats:italic>,)-1,8-dihydroxy-5,10-dimethyl-4-oxodecahydroazulen-7-yl] acrylic acid. This new sesquiterpene was identified through one and two-dimensional NMR. The compound was named cinic acid and displayed an LC<jats:sub>50<\/jats:sub> of 0.13 (0.11\u20130.14) mg\/mL and LC<jats:sub>90<\/jats:sub> of 0.40 (0.37\u20130.44) mg\/mL, which, compared with ethyl acetate extract larvicidal activity, was 256-fold more active at LC<jats:sub>50<\/jats:sub> and 15.71-fold at LC<jats:sub>90<\/jats:sub>. In this study, a new sesquiterpene with larvicidal activity against <jats:italic>H<\/jats:italic>. <jats:italic>contortus<\/jats:italic> L<jats:sub>3<\/jats:sub> infective larvae was isolated from the ethyl acetate extract of <jats:italic>Artemisia cina<\/jats:italic>.<\/jats:p>","DOI":"10.1371\/journal.pone.0305155","type":"journal-article","created":{"date-parts":[[2024,6,12]],"date-time":"2024-06-12T17:35:46Z","timestamp":1718213746000},"page":"e0305155","update-policy":"https:\/\/doi.org\/10.1371\/journal.pone.corrections_policy","source":"Crossref","is-referenced-by-count":7,"title":["Bio-guided isolation of a new sesquiterpene from Artemisia cina with anthelmintic activity against Haemonchus contortus L3 infective larvae"],"prefix":"10.1371","volume":"19","author":[{"given":"Luis David","family":"Arango-De la Pava","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Manas\u00e9s","family":"Gonz\u00e1lez-Cort\u00e1zar","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alejandro","family":"Zamilpa","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jorge Alfredo","family":"Cu\u00e9llar-Ordaz","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9262-3111","authenticated-orcid":true,"given":"H\u00e9ctor Alejandro","family":"de la Cruz-Cruz","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9231-1556","authenticated-orcid":true,"given":"Rosa Isabel","family":"Higuera-Piedrahita","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Raquel","family":"L\u00f3pez-Arellano","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"340","published-online":{"date-parts":[[2024,6,12]]},"reference":[{"key":"pone.0305155.ref001","doi-asserted-by":"crossref","first-page":"181","DOI":"10.1016\/bs.apar.2016.02.024","article-title":"Diagnosis, treatment, and management of Haemonchus contortus in small ruminants","volume":"93","author":"RB Besier","year":"2016","journal-title":"Adv Parasitol"},{"key":"pone.0305155.ref002","doi-asserted-by":"crossref","DOI":"10.1038\/s41598-023-29096-9","article-title":"Metagenome reveals caprine abomasal microbiota diversity at early and late stages of Haemonchus contortus infection","volume":"13","author":"HM Aboshady","year":"2023","journal-title":"Sci Rep"},{"key":"pone.0305155.ref003","doi-asserted-by":"crossref","DOI":"10.1007\/s11250-022-03103-z","article-title":"An Artemisia cina n-hexane extract reduces the Haemonchus contortus and Teladorsagia circumcincta fecal egg count in naturally infected periparturient goats","volume":"54","author":"RI Higuera-Piedrahita","year":"2022","journal-title":"Trop Anim Health Prod"},{"key":"pone.0305155.ref004","doi-asserted-by":"crossref","first-page":"938","DOI":"10.1007\/s11686-021-00364-w","article-title":"In Vitro Nematocidal effect and anthelmintic activity of Artemisia cina against Haemonchus contortus in gerbils and relative expression of Hc29 gene in transitional larvae (L3\u2013L4)","volume":"66","author":"RI Higuera-Piedrahita","year":"2021","journal-title":"Acta Parasitol"},{"key":"pone.0305155.ref005","article-title":"Anthelmintic resistance status of gastrointestinal nematodes of sheep to the single or combined administration of benzimidazoles and closantel in three localities in Mexico","volume":"3","author":"Y Alcal\u00e1-Canto","year":"2016","journal-title":"Veterinaria Mexico"},{"key":"pone.0305155.ref006","doi-asserted-by":"crossref","DOI":"10.3390\/plants11212874","article-title":"Exploring the Artemisia genus: An insight into the phytochemical and multi-biological potential of A. campestris subsp. lednicensis (Spreng.) 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