{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,16]],"date-time":"2026-10-16T17:42:50Z","timestamp":1792172570426,"version":"4.4.0"},"reference-count":37,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2022,5,22]],"date-time":"2022-05-22T00:00:00Z","timestamp":1653177600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Spodoptera frugiperda (S. frugiperda) 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 Solidago graminifolia (S. graminifolia) by ingestion bioassays against S. frugiperda 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 S. frugiperda 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 (LC50) 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 LC50 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 S. frugiperda acetylcholinesterase showed a \u22125.4 kcal\/mol binding energy value, lower than acetylcholine and chlorpyrifos (\u22124.45 and \u22124.46 kcal\/mol, respectively). Additionally, the interactions profile showed that quercetin had \u03c0\u2013\u03c0 interactions with amino acids W198, Y235, and H553 on the active site.<\/jats:p>","DOI":"10.3390\/molecules27103325","type":"journal-article","created":{"date-parts":[[2022,5,22]],"date-time":"2022-05-22T07:13:57Z","timestamp":1653203637000},"page":"3325","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":43,"title":["Insecticidal Activity of Organic Extracts of Solidago graminifolia and Its Main Metabolites (Quercetin and Chlorogenic Acid) against Spodoptera frugiperda: An In Vitro and In Silico Approach"],"prefix":"10.3390","volume":"27","author":[{"given":"Ver\u00f3nica","family":"Herrera-Mayorga","sequence":"first","affiliation":[{"name":"Laboratorio de Bot\u00e1nica, Unidad Acad\u00e9mica Multidisciplinaria Mante, Universidad Aut\u00f3noma de Tamaulipas, El Mante 89840, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jos\u00e9 Alfredo","family":"Guerrero-S\u00e1nchez","sequence":"additional","affiliation":[{"name":"Laboratorio de Bot\u00e1nica, Unidad Acad\u00e9mica Multidisciplinaria Mante, Universidad Aut\u00f3noma de Tamaulipas, El Mante 89840, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Domingo","family":"M\u00e9ndez-\u00c1lvarez","sequence":"additional","affiliation":[{"name":"Laboratorio de Biotecnolog\u00eda Farmac\u00e9utica, Centro de Biotecnolog\u00eda Gen\u00f3mica, Instituto Polit\u00e9cnico Nacional, Reynosa 88710, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Francisco A.","family":"Paredes-S\u00e1nchez","sequence":"additional","affiliation":[{"name":"Laboratorio de Bot\u00e1nica, Unidad Acad\u00e9mica Multidisciplinaria Mante, Universidad Aut\u00f3noma de Tamaulipas, El Mante 89840, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6148-6097","authenticated-orcid":false,"given":"Luis V\u00edctor","family":"Rodr\u00edguez-Duran","sequence":"additional","affiliation":[{"name":"Laboratorio de Bot\u00e1nica, Unidad Acad\u00e9mica Multidisciplinaria Mante, Universidad Aut\u00f3noma de Tamaulipas, El Mante 89840, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nohem\u00ed","family":"Ni\u00f1o-Garc\u00eda","sequence":"additional","affiliation":[{"name":"Laboratorio de Bot\u00e1nica, Unidad Acad\u00e9mica Multidisciplinaria Mante, Universidad Aut\u00f3noma de Tamaulipas, El Mante 89840, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alma D.","family":"Paz-Gonz\u00e1lez","sequence":"additional","affiliation":[{"name":"Laboratorio de Biotecnolog\u00eda Farmac\u00e9utica, Centro de Biotecnolog\u00eda Gen\u00f3mica, Instituto Polit\u00e9cnico Nacional, Reynosa 88710, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9842-4167","authenticated-orcid":false,"given":"Gildardo","family":"Rivera","sequence":"additional","affiliation":[{"name":"Laboratorio de Biotecnolog\u00eda Farmac\u00e9utica, Centro de Biotecnolog\u00eda Gen\u00f3mica, Instituto Polit\u00e9cnico Nacional, Reynosa 88710, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,5,22]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"14275","DOI":"10.3390\/molecules171214275","article-title":"In Vitro Antimicrobial, Antioxidant, Cytotoxicity and GC-MS Analysis of Mazus goodenifolius","volume":"17","author":"Riaz","year":"2012","journal-title":"Molecules"},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Toiu, A., Vlase, L., Vodnar, D.C., Gheldiu, A.-M., and Oniga, I. (2019). Solidago graminifolia L. Salisb. (Asteraceae) as a Valuable Source of Bioactive Polyphenols: HPLC Profile, In Vitro Antioxidant and Antimicrobial Potential. Molecules, 24.","DOI":"10.3390\/molecules24142666"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"12686","DOI":"10.1021\/acs.jafc.1c03676","article-title":"Goldenrod Root Compounds Active against Crop Pathogenic Fungi","volume":"69","author":"Bakonyi","year":"2021","journal-title":"J. Agric. Food Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"460602","DOI":"10.1016\/j.chroma.2019.460602","article-title":"Distinction and valorization of 30 root extracts of five goldenrod (Solidago) species","volume":"1611","author":"Darcsi","year":"2020","journal-title":"J. Chromatogr. A"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"51","DOI":"10.1016\/j.flora.2015.11.009","article-title":"Interactions between alien goldenrods (Solidago and Euthamia species) and comparison with native species in Central Europe","volume":"218","author":"Szymura","year":"2016","journal-title":"Flora Morphol. Distrib. Funct. Ecol. Plants"},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Fursenco, C., Calalb, T., Uncu, L., Dinu, M., and Ancuceanu, R. (2020). Solidago virgaurea L.: A Review of Its Ethnomedicinal Uses, Phytochemistry, and Pharmacological Activities. Biomolecules, 10.","DOI":"10.20944\/preprints202010.0277.v1"},{"key":"ref_7","first-page":"9210","article-title":"Synthesis, Biological Evaluation and In Silico Computational Studies of 7-Chloro-4-(1H-1,2,3-triazol-1-yl) quinoline Derivatives: Search for New Controlling Agents against Spodoptera frugiperda (Lepidoptera: Noctuidae) Larvae","volume":"33","year":"2019","journal-title":"J. Agric. Food Chem."},{"key":"ref_8","first-page":"382","article-title":"Acetylcho-linesterase and Insect Growth Inhibitory Activities of Gutierrezia microcephala on Fall Army worm Spodoptera frugiperda JE Smith","volume":"6","author":"Rosas","year":"2001","journal-title":"Z. Nat. C"},{"key":"ref_9","first-page":"1613","article-title":"Bioactivity of semisynthetic eugenol derivatives against Spodoptera frugiperda (Lepidoptera: Noctuidae) larvae infesting maize in Colombia","volume":"26","author":"Kouznetsov","year":"2018","journal-title":"Saudi J. Biol. Sci."},{"key":"ref_10","first-page":"76","article-title":"Developmental Parameters of Spodoptera frugiperda (Lepidoptera: Noctuidae) Immature Stages Under Controlled and Standardized Conditions","volume":"11","author":"Montezano","year":"2019","journal-title":"J. Agric. Sci."},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"Guo, J.-M., Liu, X.-L., Liu, S.-R., Wei, Z.-Q., Han, W.-K., Guo, Y., and Dong, S.-L. (2020). Functional Characterization of Sex Pheromone Receptors in the Fall Armyworm (Spodoptera frugiperda). Insects, 11.","DOI":"10.3390\/insects11030193"},{"key":"ref_12","first-page":"10","article-title":"Observation on law of diffusion damage of Spodoptera frugiperda in China in 2019","volume":"45","author":"Jiang","year":"2019","journal-title":"Int. J. Plant Prot."},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Huang, Y., Dong, Y., Huang, W., Ren, B., Deng, Q., Shi, Y., Bai, J., Ren, Y., Geng, Y., and Ma, H. (2020). Overwintering Distribution of Fall Armyworm (Spodoptera frugiperda) in Yunnan, China, and Influencing Environmental Factors. Insects, 11.","DOI":"10.3390\/insects11110805"},{"key":"ref_14","first-page":"277","article-title":"Phenolic compounds in two Solidago L. species from in vitro culture","volume":"58","author":"Thiem","year":"2001","journal-title":"Acta Pol. Pharm. Drug Res."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"104","DOI":"10.1016\/j.phytochem.2009.09.032","article-title":"Antibacterial clerodane diterpenes from Goldenrod (Solidago virgaurea)","volume":"71","author":"Starks","year":"2010","journal-title":"Phytochemistry"},{"key":"ref_16","first-page":"111","article-title":"Gastroprotective activity of the diterpene solidagenone and its de-rivatives on experimentally induced gastric lesions in mice","volume":"1","author":"Rodriguez","year":"2002","journal-title":"J. Ethnopharmacol."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1","DOI":"10.4081\/mr.2017.6877","article-title":"Antibacterial properties of quercetin","volume":"8","author":"Jaisinghani","year":"2017","journal-title":"Microbiol. Res."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"434","DOI":"10.1089\/jmf.2010.0053","article-title":"Anti-Acetylcholinesterase and Antioxidant Assets of the Major Components (Salicin, Amentoflavone, and Chlorogenic Acid) and the Extracts of Viburnum opulus and Viburnum lantana and Their Total Phenol and Flavonoid Contents","volume":"14","author":"Altun","year":"2011","journal-title":"J. Med. Food"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"210","DOI":"10.1016\/j.ejphar.2010.09.001","article-title":"Neuroprotective effects of chlorogenic acid on scopolamine-induced amnesia via anti-acetylcholinesterase and anti-oxidative activities in mice","volume":"649","author":"Kwon","year":"2010","journal-title":"Eur. J. Pharmacol."},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"Xu, D., Hu, M.-J., Wang, Y.-Q., and Cui, Y.-L. (2019). Antioxidant Activities of Quercetin and Its Complexes for Medicinal Application. Molecules, 24.","DOI":"10.3390\/molecules24061123"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"6806","DOI":"10.1038\/s41598-020-63746-6","article-title":"Biopesticide synergy when combining plant flavonoids and entomopathogenic baculovirus","volume":"10","author":"Hay","year":"2020","journal-title":"Sci. Rep."},{"key":"ref_22","doi-asserted-by":"crossref","unstructured":"Olennikov, D.N., Kashchenko, N.I., Chirikova, N.K., Akobirshoeva, A., Zilfikarov, I.N., and Vennos, C. (2017). Isorhamnetin and Quercetin Derivatives as Anti-Acetylcholinesterase Principles of Marigold (Calendula officinalis) Flowers and Preparations. Int. J. Mol. Sci., 18.","DOI":"10.3390\/ijms18081685"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"34","DOI":"10.1016\/j.phytol.2016.10.024","article-title":"Flavonol triglycosides of leaves from Maytenus robusta with acetylcholinesterase inhibition","volume":"19","author":"Takahashi","year":"2017","journal-title":"Phytochem. Lett."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1590\/2175-7860202071046","article-title":"Determination of the metabolic profile of Solidago canadensis using UFLC-PDA-ESI-TOF","volume":"71","author":"Kelly","year":"2020","journal-title":"Rodrigu\u00e9sia"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"16240","DOI":"10.3390\/molecules191016240","article-title":"Flavonoids as Important Molecules of Plant Interactions with the Environment","volume":"19","author":"Mierziak","year":"2014","journal-title":"Molecules"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"178","DOI":"10.1016\/j.biotechadv.2016.12.005","article-title":"Natural products against Alzheimer\u2019s disease: Pharma-co-therapeutics and biotechnological interventions","volume":"2","author":"Dey","year":"2017","journal-title":"Biotechnol. Adv."},{"key":"ref_27","doi-asserted-by":"crossref","unstructured":"Riddick, E. (2021). Potential of Quercetin to Reduce Herbivory without Disrupting Natural Enemies and Pollinators. Agriculture, 11.","DOI":"10.3390\/agriculture11060476"},{"key":"ref_28","first-page":"445","article-title":"Joint action of quercetin with four insecticides on the cotton leaf-worm larvae, Spodoptera littoralis Boisd. (Lep.: Noctuidae) in Egypt","volume":"72","author":"Mesbah","year":"2007","journal-title":"Commun. Agric. Appl. Biol. Sci."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"103216","DOI":"10.1016\/j.bioorg.2019.103216","article-title":"Synthesis, In-Vitro Cholines-terase Inhibition, In-Vivo Anticonvulsant Activity and In-Silico Exploration of N-(4-Methylpyridin-2-yl) thio-phene-2-carboxamide Analogs","volume":"92","author":"Ahmad","year":"2019","journal-title":"Bioorg. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"283","DOI":"10.1107\/S0021889892009944","article-title":"PROCHECK: A program to check the stereochemical quality of protein structures","volume":"26","author":"Laskowski","year":"1993","journal-title":"J. Appl. Crystallogr."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"4574","DOI":"10.1038\/s41467-018-07072-6","article-title":"Structural insights into the \u03c0-\u03c0-\u03c0 stacking mechanism and DNA-binding ac-tivity of the YEATS domain","volume":"9","author":"Klein","year":"2018","journal-title":"Nat. Commun."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"13","DOI":"10.1016\/j.molstruc.2016.08.040","article-title":"Characterization of \u03c0-stacking interactions between aromatic amino acids and quercetagetin","volume":"1128","author":"Akher","year":"2017","journal-title":"J. Mol. Struct."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"539","DOI":"10.2307\/2666695","article-title":"Phylogeny of the Coneflowers and Relatives (Heliantheae: Asteraceae) Based on Nuclear rDNA Internal Transcribed Spacer (ITS) Sequences and Chlorplast DNA Restriction Site Data","volume":"25","author":"Urbatsch","year":"2000","journal-title":"Syst. Bot."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1792","DOI":"10.1093\/nar\/gkh340","article-title":"MUSCLE: Multiple sequence alignment with high accuracy and high throughput","volume":"5","author":"Egar","year":"2004","journal-title":"Nucleic Acid Res."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"W296","DOI":"10.1093\/nar\/gky427","article-title":"SWISS-MODEL: Homology modelling of protein structures and complexes","volume":"46","author":"Waterhouse","year":"2018","journal-title":"Nucleic Acids Res."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"1605","DOI":"10.1002\/jcc.20084","article-title":"UCSF Chimera? A visualization system for exploratory research and analysis","volume":"25","author":"Pettersen","year":"2004","journal-title":"J. Comput. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"2785","DOI":"10.1002\/jcc.21256","article-title":"Autodock4 and Auto-DockTools4: Automated docking with selective receptor flexiblity","volume":"16","author":"Morris","year":"2009","journal-title":"J. Comput. Chem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/10\/3325\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T23:16:25Z","timestamp":1760138185000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/10\/3325"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,5,22]]},"references-count":37,"journal-issue":{"issue":"10","published-online":{"date-parts":[[2022,5]]}},"alternative-id":["molecules27103325"],"URL":"https:\/\/doi.org\/10.3390\/molecules27103325","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,5,22]]}}}