Insecticidal Activity of Organic Extracts of <i>Solidago graminifolia</i> and Its Main Metabolites (Quercetin and Chlorogenic Acid) against <i>Spodoptera frugiperda</i>: An In Vitro and In Silico Approach
<i>Spodoptera frugiperda</i> (<i>S. frugiperda</i>) remains a global primary pest of maize. Therefore, new options to combat this pest are necessary. In this study, the insecticidal activity of three crude foliar extracts (ethanol, dichloromethane, and hexane) and their main...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-05-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/10/3325 |
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| author | Verónica Herrera-Mayorga José Alfredo Guerrero-Sánchez Domingo Méndez-Álvarez Francisco A. Paredes-Sánchez Luis Víctor Rodríguez-Duran Nohemí Niño-García Alma D. Paz-González Gildardo Rivera |
| author_facet | Verónica Herrera-Mayorga José Alfredo Guerrero-Sánchez Domingo Méndez-Álvarez Francisco A. Paredes-Sánchez Luis Víctor Rodríguez-Duran Nohemí Niño-García Alma D. Paz-González Gildardo Rivera |
| author_sort | Verónica Herrera-Mayorga |
| collection | DOAJ |
| description | <i>Spodoptera frugiperda</i> (<i>S. frugiperda</i>) remains a global primary pest of maize. Therefore, new options to combat this pest are necessary. In this study, the insecticidal activity of three crude foliar extracts (ethanol, dichloromethane, and hexane) and their main secondary metabolites (quercetin and chlorogenic acid) of the species <i>Solidago graminifolia</i> (<i>S. graminifolia</i>) by ingestion bioassays against <i>S. frugiperda</i> larvae was analyzed. Additionally, the extracts were phytochemically elucidated by ultra-performance liquid chromatography-mass spectrometry (UPLC-MS) analysis. Finally, an in silico study of the potential interaction of quercetin on <i>S. frugiperda</i> acetylcholinesterase was performed. Organic extracts were obtained in the range from 5 to 33%. The ethanolic extract caused higher mortality (81%) with a half-maximal lethal concentration (LC<sub>50</sub>) of 0.496 mg/mL. Flavonoid secondary metabolites such as hyperoside, quercetin, isoquercetin, kaempferol, and avicularin and some phenolic acids such as chlorogenic acid, solidagoic acid, gallic acid, hexoside, and rosmarinic acid were identified. In particular, quercetin had an LC<sub>50</sub> of 0.157 mg/mL, and chlorogenic acid did not have insecticidal activity but showed an antagonistic effect on quercetin. The molecular docking analysis of quercetin on the active site of <i>S. frugiperda</i> acetylcholinesterase showed a −5.4 kcal/mol binding energy value, lower than acetylcholine and chlorpyrifos (−4.45 and −4.46 kcal/mol, respectively). Additionally, the interactions profile showed that quercetin had π–π interactions with amino acids W198, Y235, and H553 on the active site. |
| first_indexed | 2024-03-10T03:18:41Z |
| format | Article |
| id | doaj.art-e72cc78f7a03407db144c0df8d7b7a53 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T03:18:41Z |
| publishDate | 2022-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-e72cc78f7a03407db144c0df8d7b7a532023-11-23T12:24:39ZengMDPI AGMolecules1420-30492022-05-012710332510.3390/molecules27103325Insecticidal Activity of Organic Extracts of <i>Solidago graminifolia</i> and Its Main Metabolites (Quercetin and Chlorogenic Acid) against <i>Spodoptera frugiperda</i>: An In Vitro and In Silico ApproachVerónica Herrera-Mayorga0José Alfredo Guerrero-Sánchez1Domingo Méndez-Álvarez2Francisco A. Paredes-Sánchez3Luis Víctor Rodríguez-Duran4Nohemí Niño-García5Alma D. Paz-González6Gildardo Rivera7Laboratorio de Botánica, Unidad Académica Multidisciplinaria Mante, Universidad Autónoma de Tamaulipas, El Mante 89840, MexicoLaboratorio de Botánica, Unidad Académica Multidisciplinaria Mante, Universidad Autónoma de Tamaulipas, El Mante 89840, MexicoLaboratorio de Biotecnología Farmacéutica, Centro de Biotecnología Genómica, Instituto Politécnico Nacional, Reynosa 88710, MexicoLaboratorio de Botánica, Unidad Académica Multidisciplinaria Mante, Universidad Autónoma de Tamaulipas, El Mante 89840, MexicoLaboratorio de Botánica, Unidad Académica Multidisciplinaria Mante, Universidad Autónoma de Tamaulipas, El Mante 89840, MexicoLaboratorio de Botánica, Unidad Académica Multidisciplinaria Mante, Universidad Autónoma de Tamaulipas, El Mante 89840, MexicoLaboratorio de Biotecnología Farmacéutica, Centro de Biotecnología Genómica, Instituto Politécnico Nacional, Reynosa 88710, MexicoLaboratorio de Biotecnología Farmacéutica, Centro de Biotecnología Genómica, Instituto Politécnico Nacional, Reynosa 88710, Mexico<i>Spodoptera frugiperda</i> (<i>S. frugiperda</i>) remains a global primary pest of maize. Therefore, new options to combat this pest are necessary. In this study, the insecticidal activity of three crude foliar extracts (ethanol, dichloromethane, and hexane) and their main secondary metabolites (quercetin and chlorogenic acid) of the species <i>Solidago graminifolia</i> (<i>S. graminifolia</i>) by ingestion bioassays against <i>S. frugiperda</i> larvae was analyzed. Additionally, the extracts were phytochemically elucidated by ultra-performance liquid chromatography-mass spectrometry (UPLC-MS) analysis. Finally, an in silico study of the potential interaction of quercetin on <i>S. frugiperda</i> acetylcholinesterase was performed. Organic extracts were obtained in the range from 5 to 33%. The ethanolic extract caused higher mortality (81%) with a half-maximal lethal concentration (LC<sub>50</sub>) of 0.496 mg/mL. Flavonoid secondary metabolites such as hyperoside, quercetin, isoquercetin, kaempferol, and avicularin and some phenolic acids such as chlorogenic acid, solidagoic acid, gallic acid, hexoside, and rosmarinic acid were identified. In particular, quercetin had an LC<sub>50</sub> of 0.157 mg/mL, and chlorogenic acid did not have insecticidal activity but showed an antagonistic effect on quercetin. The molecular docking analysis of quercetin on the active site of <i>S. frugiperda</i> acetylcholinesterase showed a −5.4 kcal/mol binding energy value, lower than acetylcholine and chlorpyrifos (−4.45 and −4.46 kcal/mol, respectively). Additionally, the interactions profile showed that quercetin had π–π interactions with amino acids W198, Y235, and H553 on the active site.https://www.mdpi.com/1420-3049/27/10/3325chlorogenic acidinsecticidequercetin<i>Spodoptera frugiperda</i><i>Solidago graminifolia</i> |
| spellingShingle | Verónica Herrera-Mayorga José Alfredo Guerrero-Sánchez Domingo Méndez-Álvarez Francisco A. Paredes-Sánchez Luis Víctor Rodríguez-Duran Nohemí Niño-García Alma D. Paz-González Gildardo Rivera Insecticidal Activity of Organic Extracts of <i>Solidago graminifolia</i> and Its Main Metabolites (Quercetin and Chlorogenic Acid) against <i>Spodoptera frugiperda</i>: An In Vitro and In Silico Approach Molecules chlorogenic acid insecticide quercetin <i>Spodoptera frugiperda</i> <i>Solidago graminifolia</i> |
| title | Insecticidal Activity of Organic Extracts of <i>Solidago graminifolia</i> and Its Main Metabolites (Quercetin and Chlorogenic Acid) against <i>Spodoptera frugiperda</i>: An In Vitro and In Silico Approach |
| title_full | Insecticidal Activity of Organic Extracts of <i>Solidago graminifolia</i> and Its Main Metabolites (Quercetin and Chlorogenic Acid) against <i>Spodoptera frugiperda</i>: An In Vitro and In Silico Approach |
| title_fullStr | Insecticidal Activity of Organic Extracts of <i>Solidago graminifolia</i> and Its Main Metabolites (Quercetin and Chlorogenic Acid) against <i>Spodoptera frugiperda</i>: An In Vitro and In Silico Approach |
| title_full_unstemmed | Insecticidal Activity of Organic Extracts of <i>Solidago graminifolia</i> and Its Main Metabolites (Quercetin and Chlorogenic Acid) against <i>Spodoptera frugiperda</i>: An In Vitro and In Silico Approach |
| title_short | Insecticidal Activity of Organic Extracts of <i>Solidago graminifolia</i> and Its Main Metabolites (Quercetin and Chlorogenic Acid) against <i>Spodoptera frugiperda</i>: An In Vitro and In Silico Approach |
| title_sort | insecticidal activity of organic extracts of i solidago graminifolia i and its main metabolites quercetin and chlorogenic acid against i spodoptera frugiperda i an in vitro and in silico approach |
| topic | chlorogenic acid insecticide quercetin <i>Spodoptera frugiperda</i> <i>Solidago graminifolia</i> |
| url | https://www.mdpi.com/1420-3049/27/10/3325 |
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