Bio-guided isolation of a new sesquiterpene from Artemisia cina with anthelmintic activity against Haemonchus contortus L.sub.3 infective larvae
Haemonchus contortus 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. Artemisia cina (Asteraceae) is...
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creator | Arango-De la Pava, Luis David González-Cortázar, Manasés Zamilpa, Alejandro Cuéllar-Ordaz, Jorge Alfredo de la Cruz-Cruz, Héctor Alejandro Higuera-Piedrahita, Rosa Isabel López-Arellano, Raquel |
description | Haemonchus contortus 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. Artemisia cina (Asteraceae) is a plant whose n-hexane extract and ethyl acetate extract exhibit anthelmintic activity against H. contortus, the n-hexane more active. To discover additional bioactive metabolites, a chemical analysis was performed on ethyl acetate extract, which presented an LC.sub.90 of 3.30 mg/mL and allowed the isolation of 11-[(1R,5S,7R,8R,10S,)-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.sub.50 of 0.13 (0.11-0.14) mg/mL and LC.sub.90 of 0.40 (0.37-0.44) mg/mL, which, compared with ethyl acetate extract larvicidal activity, was 256-fold more active at LC.sub.50 and 15.71-fold at LC.sub.90 . In this study, a new sesquiterpene with larvicidal activity against H. contortus L.sub.3 infective larvae was isolated from the ethyl acetate extract of Artemisia cina. |
doi_str_mv | 10.1371/journal.pone.0305155 |
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Due to its anthelmintic resistance, alternative antiparasitic treatments like plant-based anthelmintics are necessary to explore. Artemisia cina (Asteraceae) is a plant whose n-hexane extract and ethyl acetate extract exhibit anthelmintic activity against H. contortus, the n-hexane more active. To discover additional bioactive metabolites, a chemical analysis was performed on ethyl acetate extract, which presented an LC.sub.90 of 3.30 mg/mL and allowed the isolation of 11-[(1R,5S,7R,8R,10S,)-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.sub.50 of 0.13 (0.11-0.14) mg/mL and LC.sub.90 of 0.40 (0.37-0.44) mg/mL, which, compared with ethyl acetate extract larvicidal activity, was 256-fold more active at LC.sub.50 and 15.71-fold at LC.sub.90 . In this study, a new sesquiterpene with larvicidal activity against H. contortus L.sub.3 infective larvae was isolated from the ethyl acetate extract of Artemisia cina.</description><identifier>ISSN: 1932-6203</identifier><identifier>EISSN: 1932-6203</identifier><identifier>DOI: 10.1371/journal.pone.0305155</identifier><language>eng</language><publisher>Public Library of Science</publisher><subject>Acetates ; Acrylic acid ; Esters ; Sheep</subject><ispartof>PloS one, 2024-06, Vol.19 (6), p.e0305155</ispartof><rights>COPYRIGHT 2024 Public Library of Science</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,860,27901,27902</link.rule.ids></links><search><creatorcontrib>Arango-De la Pava, Luis David</creatorcontrib><creatorcontrib>González-Cortázar, Manasés</creatorcontrib><creatorcontrib>Zamilpa, Alejandro</creatorcontrib><creatorcontrib>Cuéllar-Ordaz, Jorge Alfredo</creatorcontrib><creatorcontrib>de la Cruz-Cruz, Héctor Alejandro</creatorcontrib><creatorcontrib>Higuera-Piedrahita, Rosa Isabel</creatorcontrib><creatorcontrib>López-Arellano, Raquel</creatorcontrib><title>Bio-guided isolation of a new sesquiterpene from Artemisia cina with anthelmintic activity against Haemonchus contortus L.sub.3 infective larvae</title><title>PloS one</title><description>Haemonchus contortus 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. Artemisia cina (Asteraceae) is a plant whose n-hexane extract and ethyl acetate extract exhibit anthelmintic activity against H. contortus, the n-hexane more active. To discover additional bioactive metabolites, a chemical analysis was performed on ethyl acetate extract, which presented an LC.sub.90 of 3.30 mg/mL and allowed the isolation of 11-[(1R,5S,7R,8R,10S,)-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.sub.50 of 0.13 (0.11-0.14) mg/mL and LC.sub.90 of 0.40 (0.37-0.44) mg/mL, which, compared with ethyl acetate extract larvicidal activity, was 256-fold more active at LC.sub.50 and 15.71-fold at LC.sub.90 . In this study, a new sesquiterpene with larvicidal activity against H. contortus L.sub.3 infective larvae was isolated from the ethyl acetate extract of Artemisia cina.</description><subject>Acetates</subject><subject>Acrylic acid</subject><subject>Esters</subject><subject>Sheep</subject><issn>1932-6203</issn><issn>1932-6203</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqNkclKxEAQhoMouL6BhwZB8JDYy6Q7OY7iMjAguF2Hmk510kOmW9Mdl7fwkc2ghxnwIHWoovj-ov6qJDlmNGNCsfOF7zsHbfbiHWZU0Jzl-Vayx0rBU8mp2F6rd5P9EBaU5qKQci_5urA-rXtbYUVs8C1E6x3xhgBx-E4ChtfeRuxe0CExnV-ScRdxaYMFoq0D8m5jQ8DFBtulddFqAjraNxs_CdRgXYjkFnDpnW76QLR30XdxqKZZ6OeZINYZXAmQtNC9AR4mOwbagEe_-SB5ur56vLxNp3c3k8vxNK2ZlCod0ZLnWCBXVaUMo1wrpqQCpmBuCl4yIbUoDHAz5yUvQNJRTrUoWSEM0EKJg-TkZ24NLc6GLXzsQA_G9GysSjUqpZArKvuDGqIabjCYQWOH_obgbEOwMowfsYY-hNnk4f7_7N3zJnu6xjYIbWyGd_Wrd4V18BsNsKOX</recordid><startdate>20240612</startdate><enddate>20240612</enddate><creator>Arango-De la Pava, Luis David</creator><creator>González-Cortázar, Manasés</creator><creator>Zamilpa, Alejandro</creator><creator>Cuéllar-Ordaz, Jorge Alfredo</creator><creator>de la Cruz-Cruz, Héctor Alejandro</creator><creator>Higuera-Piedrahita, Rosa Isabel</creator><creator>López-Arellano, Raquel</creator><general>Public Library of Science</general><scope>IOV</scope><scope>ISR</scope></search><sort><creationdate>20240612</creationdate><title>Bio-guided isolation of a new sesquiterpene from Artemisia cina with anthelmintic activity against Haemonchus contortus L.sub.3 infective larvae</title><author>Arango-De la Pava, Luis David ; González-Cortázar, Manasés ; Zamilpa, Alejandro ; Cuéllar-Ordaz, Jorge Alfredo ; de la Cruz-Cruz, Héctor Alejandro ; Higuera-Piedrahita, Rosa Isabel ; López-Arellano, Raquel</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-g1667-40925e8e27dd7f102c71767a17abf829136c38fa2fb2928a60450c39183fa0873</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Acetates</topic><topic>Acrylic acid</topic><topic>Esters</topic><topic>Sheep</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Arango-De la Pava, Luis David</creatorcontrib><creatorcontrib>González-Cortázar, Manasés</creatorcontrib><creatorcontrib>Zamilpa, Alejandro</creatorcontrib><creatorcontrib>Cuéllar-Ordaz, Jorge Alfredo</creatorcontrib><creatorcontrib>de la Cruz-Cruz, Héctor Alejandro</creatorcontrib><creatorcontrib>Higuera-Piedrahita, Rosa Isabel</creatorcontrib><creatorcontrib>López-Arellano, Raquel</creatorcontrib><collection>Gale In Context: Opposing Viewpoints</collection><collection>Gale In Context: Science</collection><jtitle>PloS one</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Arango-De la Pava, Luis David</au><au>González-Cortázar, Manasés</au><au>Zamilpa, Alejandro</au><au>Cuéllar-Ordaz, Jorge Alfredo</au><au>de la Cruz-Cruz, Héctor Alejandro</au><au>Higuera-Piedrahita, Rosa Isabel</au><au>López-Arellano, Raquel</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Bio-guided isolation of a new sesquiterpene from Artemisia cina with anthelmintic activity against Haemonchus contortus L.sub.3 infective larvae</atitle><jtitle>PloS one</jtitle><date>2024-06-12</date><risdate>2024</risdate><volume>19</volume><issue>6</issue><spage>e0305155</spage><pages>e0305155-</pages><issn>1932-6203</issn><eissn>1932-6203</eissn><abstract>Haemonchus contortus 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. Artemisia cina (Asteraceae) is a plant whose n-hexane extract and ethyl acetate extract exhibit anthelmintic activity against H. contortus, the n-hexane more active. To discover additional bioactive metabolites, a chemical analysis was performed on ethyl acetate extract, which presented an LC.sub.90 of 3.30 mg/mL and allowed the isolation of 11-[(1R,5S,7R,8R,10S,)-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.sub.50 of 0.13 (0.11-0.14) mg/mL and LC.sub.90 of 0.40 (0.37-0.44) mg/mL, which, compared with ethyl acetate extract larvicidal activity, was 256-fold more active at LC.sub.50 and 15.71-fold at LC.sub.90 . In this study, a new sesquiterpene with larvicidal activity against H. contortus L.sub.3 infective larvae was isolated from the ethyl acetate extract of Artemisia cina.</abstract><pub>Public Library of Science</pub><doi>10.1371/journal.pone.0305155</doi><tpages>e0305155</tpages></addata></record> |
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subjects | Acetates Acrylic acid Esters Sheep |
title | Bio-guided isolation of a new sesquiterpene from Artemisia cina with anthelmintic activity against Haemonchus contortus L.sub.3 infective larvae |
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