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3′-Demethoxy-6-O-Demethylisoguaiacin and Norisoguaiacin Nematocidal Lignans from Artemisia cina against Haemonchus contortus Infective Larvae

Artemisia cina is a plant used in traditional Chinese medicine as a remedy for parasitic diseases. This study describes the isolation and chemical characterization of anthelmintic compounds of A. cina against Haemonchus contortus infective larvae (L(3)) through lethal testing. Previously, three extr...

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Autores principales: Higuera-Piedrahita, Rosa Isabel, Dolores-Hernández, Mariana, de la Cruz-Cruz, Héctor Alejandro, López-Arellano, Raquel, Gives, Pedro Mendoza-de, Olmedo-Juárez, Agustín, Cuéllar-Ordaz, Jorge Alfredo, González-Cortazar, Manasés, Ble-González, Ever A., López-Arellano, María Eugenia, Zamilpa, Alejandro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9962954/
https://www.ncbi.nlm.nih.gov/pubmed/36840168
http://dx.doi.org/10.3390/plants12040820
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author Higuera-Piedrahita, Rosa Isabel
Dolores-Hernández, Mariana
de la Cruz-Cruz, Héctor Alejandro
López-Arellano, Raquel
Gives, Pedro Mendoza-de
Olmedo-Juárez, Agustín
Cuéllar-Ordaz, Jorge Alfredo
González-Cortazar, Manasés
Ble-González, Ever A.
López-Arellano, María Eugenia
Zamilpa, Alejandro
author_facet Higuera-Piedrahita, Rosa Isabel
Dolores-Hernández, Mariana
de la Cruz-Cruz, Héctor Alejandro
López-Arellano, Raquel
Gives, Pedro Mendoza-de
Olmedo-Juárez, Agustín
Cuéllar-Ordaz, Jorge Alfredo
González-Cortazar, Manasés
Ble-González, Ever A.
López-Arellano, María Eugenia
Zamilpa, Alejandro
author_sort Higuera-Piedrahita, Rosa Isabel
collection PubMed
description Artemisia cina is a plant used in traditional Chinese medicine as a remedy for parasitic diseases. This study describes the isolation and chemical characterization of anthelmintic compounds of A. cina against Haemonchus contortus infective larvae (L(3)) through lethal testing. Previously, three extracts—n-hexane (HexAc), ethyl acetate (EtOAc) and methanol (MeOAc)—were evaluated at concentrations of 4 to 0.5 mg/mL, resulting in the HexAc extract with the greatest effect of 76.6% mortality of the larvae at 4 mg/mL. Then, this was chemically fractioned by polarity, obtaining seven fractions (C1F1–C1F7), and, when evaluated at concentrations from 2 to 0.25 mg/mL, the 2 mg/mL C1F5 fraction produced an effect against the nematode H. contortus of 100% mortality of the larvae. Thus, this fraction was fractionated again by column chromatography, obtaining twelve subfractions (C2F1–C2F12) which were evaluated from 1 to 0.125 mg/mL, with the C2F5 subfraction causing a nematicidal effect of 100% mortality. NMR analysis of one ((1)H, (13)C and DEPT) and two dimensions (COSY, HSQC and HMBC) and mass spectrometry of this fraction allowed us to identify the mixture of 3′-demethoxy-6-O-demethylisoguaiacin and norisoguaiacin. Therefore, it can be assumed that the mixture of these compounds is responsible for the anthelmintic effect. These results indicate that A. cina containing anthelmintic compounds and might be used as an antiparasitic drug against H. contortus.
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spelling pubmed-99629542023-02-26 3′-Demethoxy-6-O-Demethylisoguaiacin and Norisoguaiacin Nematocidal Lignans from Artemisia cina against Haemonchus contortus Infective Larvae Higuera-Piedrahita, Rosa Isabel Dolores-Hernández, Mariana de la Cruz-Cruz, Héctor Alejandro López-Arellano, Raquel Gives, Pedro Mendoza-de Olmedo-Juárez, Agustín Cuéllar-Ordaz, Jorge Alfredo González-Cortazar, Manasés Ble-González, Ever A. López-Arellano, María Eugenia Zamilpa, Alejandro Plants (Basel) Article Artemisia cina is a plant used in traditional Chinese medicine as a remedy for parasitic diseases. This study describes the isolation and chemical characterization of anthelmintic compounds of A. cina against Haemonchus contortus infective larvae (L(3)) through lethal testing. Previously, three extracts—n-hexane (HexAc), ethyl acetate (EtOAc) and methanol (MeOAc)—were evaluated at concentrations of 4 to 0.5 mg/mL, resulting in the HexAc extract with the greatest effect of 76.6% mortality of the larvae at 4 mg/mL. Then, this was chemically fractioned by polarity, obtaining seven fractions (C1F1–C1F7), and, when evaluated at concentrations from 2 to 0.25 mg/mL, the 2 mg/mL C1F5 fraction produced an effect against the nematode H. contortus of 100% mortality of the larvae. Thus, this fraction was fractionated again by column chromatography, obtaining twelve subfractions (C2F1–C2F12) which were evaluated from 1 to 0.125 mg/mL, with the C2F5 subfraction causing a nematicidal effect of 100% mortality. NMR analysis of one ((1)H, (13)C and DEPT) and two dimensions (COSY, HSQC and HMBC) and mass spectrometry of this fraction allowed us to identify the mixture of 3′-demethoxy-6-O-demethylisoguaiacin and norisoguaiacin. Therefore, it can be assumed that the mixture of these compounds is responsible for the anthelmintic effect. These results indicate that A. cina containing anthelmintic compounds and might be used as an antiparasitic drug against H. contortus. MDPI 2023-02-12 /pmc/articles/PMC9962954/ /pubmed/36840168 http://dx.doi.org/10.3390/plants12040820 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Higuera-Piedrahita, Rosa Isabel
Dolores-Hernández, Mariana
de la Cruz-Cruz, Héctor Alejandro
López-Arellano, Raquel
Gives, Pedro Mendoza-de
Olmedo-Juárez, Agustín
Cuéllar-Ordaz, Jorge Alfredo
González-Cortazar, Manasés
Ble-González, Ever A.
López-Arellano, María Eugenia
Zamilpa, Alejandro
3′-Demethoxy-6-O-Demethylisoguaiacin and Norisoguaiacin Nematocidal Lignans from Artemisia cina against Haemonchus contortus Infective Larvae
title 3′-Demethoxy-6-O-Demethylisoguaiacin and Norisoguaiacin Nematocidal Lignans from Artemisia cina against Haemonchus contortus Infective Larvae
title_full 3′-Demethoxy-6-O-Demethylisoguaiacin and Norisoguaiacin Nematocidal Lignans from Artemisia cina against Haemonchus contortus Infective Larvae
title_fullStr 3′-Demethoxy-6-O-Demethylisoguaiacin and Norisoguaiacin Nematocidal Lignans from Artemisia cina against Haemonchus contortus Infective Larvae
title_full_unstemmed 3′-Demethoxy-6-O-Demethylisoguaiacin and Norisoguaiacin Nematocidal Lignans from Artemisia cina against Haemonchus contortus Infective Larvae
title_short 3′-Demethoxy-6-O-Demethylisoguaiacin and Norisoguaiacin Nematocidal Lignans from Artemisia cina against Haemonchus contortus Infective Larvae
title_sort 3′-demethoxy-6-o-demethylisoguaiacin and norisoguaiacin nematocidal lignans from artemisia cina against haemonchus contortus infective larvae
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9962954/
https://www.ncbi.nlm.nih.gov/pubmed/36840168
http://dx.doi.org/10.3390/plants12040820
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