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

Rosa Isabel Higuera-Piedrahita; Mariana Dolores-Hernández; Héctor Alejandro de la Cruz-Cruz; Raquel López-Arellano; Pedro Mendoza-de Gives; Agustín Olmedo-Juárez; Jorge Alfredo Cuéllar-Ordaz; Manasés González-Cortazar; Ever A Ble-González; María Eugenia López-Arellano; Alejandro Zamilpa

doi:10.3390/plants12040820

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

Plants (Basel). 2023 Feb 12;12(4):820. doi: 10.3390/plants12040820.

Affiliations

¹ Facultad de Estudios Superiores Cuautitlán, Universidad Nacional Autónoma de México, Cuautitlán 54714, Mexico.
² Centro Nacional de Investigación Disciplinaria en Salud Animal e Inocuidad, Instituto Nacional de Investigaciones Forestales, Agrícolas y Pecuarias, Jiutepec 62574, Mexico.
³ Centro de Investigación Biomédica del Sur, Instituto Mexicano del Seguro Social, Argentina No. 1, Centro, Xochitepec 62790, Mexico.
⁴ División Académica de Ciencias Básicas, Universidad Juárez Autónoma de Tabasco, Carretera Cunduacán-Jalpa Km. 0.5, Cunduacán 86690, Mexico.

Abstract

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 (L₃) 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 (¹H, ¹³C 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.

Keywords: Artemisia cina; Haemonchus contortus; isoguaiacin; lignans; norisoguaiacin.

Grants and funding

This research received financial support from two projects: (1) Fondo para la Investigación Científica y Desarrollo Tecnológico del Estado de México from Consejo Mexiquense de Ciencia y Tecnología (COMECYT), Proyect titled: Evaluación del efecto antihelmíntico de los metabolitos obtenidos a partir del extracto n-hexánico de Artemisia cina sobre fases de vida libre de Haemonchus contortus (FICDTEM-2021-063). (2) Support Program for Research and Technological Innovation Projects (PAPIIT-UNAM), titled: Evaluación del efecto tóxico del extracto n-hexánico de Artemisia cina y cinaguaiacina sobre los parámetros bioquímicos en sangre y alteraciones anatomopatológicas en ratas Wistar después de su administración por vía oral (IA204822). Some materials were covered with resources from CIBIS-IMSS.