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

Abstract

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 −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.

Swietenia mahagoni Leaves Extract: Antifungal, Insecticidal, and Phytochemical Analysis

“…In addition, the SMAL extract was distinguished by derivatives of quercetin, in which it attained a good affinity on the active site of acetylcholinesterase but with a lower binding energy compared to chlorpyrifos against insect pests of the Hemiptera, Diptera, and Lepidoptera. On the contrary, quercetin was almost safe for natural enemies of Coleoptera and pollinators of Hymenoptera [54,55]. Moreover, the SMAL extract in this study featured derivatives of caffeic acid.…”

“…Sequential binding of multiple molecules of caffeic acid was shown to possess a potent inhibitor of Helicoverpa armigera Hubner gut proteases' activity and gene expression [56]. Ultimately, some of the moieties of the SMAL extract might share only a synergistic action, for instance, the synergistic effects of the derivatives of chlorogenic acid on quercetin [55], vanillin mixtures with imidacloprid or α-cypermethrin [57], and daidzein on the baculovirus biopesticide [58]. Moreover, the hesperidin-Mg complex was found to be a trigger for the insecticide's potential against the adults of Bemisia tabaci Gennadius and Spodoptera frugiperda (J.E.…”

Activity of Methanolic and Hydrolyzed Methanolic Extracts of Ricinus communis (Euphorbiaceae) and Kaempferol against Spodoptera frugiperda (Lepidoptera: Noctuidae)

“…It must be remembered that, despite being of the same genus, the species are different, which could explain the greater activity observed in this study. In the same sense, Herrera-Mayorga et al [47] evaluated the insecticidal activity of some flavonoids (e.g., quercetin), as well as some phenolic acids (e.g., chlorogenic acid), against S. frugiperda larvae, and they found that quercetin had a mean lethal concentration (LC 50 ) of 157 ppm, lower than that presented in this study (525 ppm). Likewise, Herrera-Mayorga et al [47] evaluated a 1:1 mixture of quercetin with chlorogenic acid, which presented an LC 50 of 729 ppm-higher than that obtained in this research.…”

Onygenaleosides A–F, 6/5 Bicyclic Ring Skeleton Triterpene Glycosides with Insecticidal Activity from Onygenales sp. YX1425

“…The insecticidal activity against Spodoptera frugiperda was evaluated according to a previous method. − The compounds (10 mg/mL) in DMSO were prepared and further diluted with distilled water containing 1‰ Tween-80 to the concentrations of 62.5, 125, 250, and 500 μg/mL. The fresh corn leaf disks (5 mm × 5 mm) were soaked in the solution of the test reagent 3–5 times.…”