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1.
Molecules ; 29(17)2024 Sep 08.
Artículo en Inglés | MEDLINE | ID: mdl-39275103

RESUMEN

Tribolium castaneum is a challenging pest of stored products, causing significant economic losses. The present study explored the efficacy of Coridothymus capitatus essential oil and its primary constituent, carvacrol, as eco-friendly alternatives for managing this pest. To evaluate their insecticidal potential, repellency, fumigant toxicity, and antifeedant properties, progeny inhibition assays were performed. Carvacrol exhibited superior repellency compared to the essential oil, achieving a 92% repellency rate at 2 mg/cm2. Both compounds demonstrated significant fumigant toxicity against T. castaneum, with LC50 values of 168.47 and 106.5 µL/L for the essential oil and carvacrol, respectively, after 24 h. Carvacrol also outperformed the essential oil in antifeedant activity, inducing an 80.7% feeding deterrence at 1.17 mg/g. Moreover, both treatments effectively suppressed the development of the pest's progeny. These results collectively underscore the potent insecticidal properties of C. capitatus essential oil and carvacrol, particularly carvacrol, as promising candidates for the sustainable management of T. castaneum in stored product protection.


Asunto(s)
Cimenos , Repelentes de Insectos , Insecticidas , Aceites Volátiles , Tribolium , Animales , Cimenos/farmacología , Repelentes de Insectos/farmacología , Repelentes de Insectos/química , Aceites Volátiles/farmacología , Aceites Volátiles/química , Insecticidas/farmacología , Insecticidas/química , Tribolium/efectos de los fármacos , Fumigación , Escarabajos/efectos de los fármacos
2.
J Agric Food Chem ; 72(40): 22035-22044, 2024 Oct 09.
Artículo en Inglés | MEDLINE | ID: mdl-39316709

RESUMEN

ß-Ionone, sustainably derived from Petunia hybrida as a natural bioresource, was identified as a lead compound for integrated aphid management. A series of ß-ionone derivatives containing ester groups were designed and synthesized for the purpose of discovering renewable botanical-based products. The odorant-binding protein (OBP) binding test indicated that ß-ionone and its derivatives displayed binding affinities with Acyrthosiphon pisum OBP9 (ApisOBP9) and Harmonia axyridis OBP15 (HaxyOBP15). Bioactivity assays revealed that most ß-ionone derivatives exhibited a higher repellent activity than that of ß-ionone. ß-Ionone and derivatives 4g and 4l displayed attractiveness to H. axyridis. Specifically, 4g was a highly promising derivative, possessing good repellent activity against A. pisum and attractiveness to H. axyridis. Molecular dynamics simulations revealed that integrating the hydrophobic ester group into the ß-ionone framework strengthened the van der Waals interactions of 4g with ApisOBP9/HaxyOBP15, improving the binding affinity with OBPs and producing higher push-pull activity than ß-ionone; 4g also had low toxicity toward nontarget organisms. Thus, 4g is a potential ecofriendly, botanical-based option for aphid management.


Asunto(s)
Áfidos , Proteínas de Insectos , Repelentes de Insectos , Norisoprenoides , Receptores Odorantes , Áfidos/efectos de los fármacos , Animales , Norisoprenoides/química , Norisoprenoides/farmacología , Repelentes de Insectos/química , Repelentes de Insectos/farmacología , Proteínas de Insectos/química , Proteínas de Insectos/metabolismo , Receptores Odorantes/metabolismo , Receptores Odorantes/química , Receptores Odorantes/genética , Extractos Vegetales/química , Extractos Vegetales/farmacología , Control de Insectos , Escarabajos/efectos de los fármacos , Escarabajos/química
3.
Sci Rep ; 14(1): 21599, 2024 09 16.
Artículo en Inglés | MEDLINE | ID: mdl-39284902

RESUMEN

Mentha arvensis is an herbaceous plant commonly known as peppermint or Japanese mint. This study investigated the toxic potential and repellent efficacy of M. arvensis essential oil (MaEO) at varying concentrations (15.625-250 mg/mL) in Nauphoeta cinerea, along with its impact on biochemical parameters in N. cinerea. The potential of the major compounds as a new analgesic target was investigated using molecular docking. The essential oil was analyzed by gas Chromatography-mass spectrometry (GC-MS) and the toxic potential, repellent property, and changes in lipid peroxidation (LPO) levels were evaluated as markers of oxidative stress. GC-MS results revealed that the main components were oxygenated monoterpenes such as menthol (71.31%), mentone (13.34%) and isomentone (5.35%). MaEO significantly reduced lipid peroxidation (LPO), the levels of non-protein thiols and iron(II) at the concentration of 125 mg/mL in N. cinerea. Furthermore, the major components, L-(-)-Menthol and menthone demonstrated high gastrointestinal absorption and high affinity with the target protein, suggesting possible links that contribute to the analgesic effect of MaEO.


Asunto(s)
Antioxidantes , Peroxidación de Lípido , Mentha , Aceites Volátiles , Mentha/química , Antioxidantes/farmacología , Antioxidantes/química , Aceites Volátiles/farmacología , Aceites Volátiles/química , Peroxidación de Lípido/efectos de los fármacos , Animales , Simulación del Acoplamiento Molecular , Estrés Oxidativo/efectos de los fármacos , Cromatografía de Gases y Espectrometría de Masas , Repelentes de Insectos/farmacología , Repelentes de Insectos/química , Aceites de Plantas/farmacología , Aceites de Plantas/química
4.
J Mater Chem B ; 12(37): 9249-9257, 2024 Sep 25.
Artículo en Inglés | MEDLINE | ID: mdl-39176566

RESUMEN

Mosquito-borne diseases are responsible for 700 000 deaths annually. Current outdoor protective strategies primarily focus on direct skin application of commercial repellents (i.e., aerosol sprays or topical lotions) which are typically limited to efficacy times of ≤10 hours due to rapid evaporation and dermal absorption. Consequently, frequent reapplication for continuous protection can increase associated health hazards and cause noncompliance. This study utilizes Hansen solubility parameter modeling to design physical gels composed of insect-repelling N,N-diethyl-meta-toluamide (DEET) and modacrylic copolymer poly(acrylonitrile-co-vinyl chloride) (P(AN-VC)). The P(AN-VC)/DEET composites exhibit tunable and reversible sol-gel transition temperatures that can meet the thermomechanical stability demands of the intended application and permit facile transition to commercial melt processing techniques such as injection molding, filament spinning, or film casting. P(AN-VC)/DEET gel films demonstrate mosquito repellency for more than half a year-performing longer than any other known material to date-due to the high reservoir of repellent and its desorption hindrance from the polymer matrix. Therefore, P(AN-VC)/DEET gels hold significant potential for extended protection against mosquitos and other biting arthropods.


Asunto(s)
Geles , Repelentes de Insectos , Repelentes de Insectos/química , Repelentes de Insectos/farmacología , Geles/química , Animales , DEET/química , DEET/farmacología , Culicidae/efectos de los fármacos , Temperatura
5.
SAR QSAR Environ Res ; 35(7): 591-610, 2024 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-39101323

RESUMEN

Essential oils (EOs) are natural products currently used to control arthropods, and their interaction with insect odorant-binding proteins (OBPs) is fundamental for the discovery of new repellents. This in silico study aimed to predict the potential of EO components to interact with odorant proteins. A total of 684 EO components from PubChem were docked against 23 odorant binding proteins from Protein Data Bank using AutoDock Vina. The ligands and proteins were optimized using Gaussian 09 and Sybyl-X 2.0, respectively. The nature of the protein-ligand interactions was characterized using LigandScout 4.0, and visualization of the binding mode in selected complexes was carried out by Pymol. Additionally, complexes with the best binding energy in molecular docking were subjected to 500 ns molecular dynamics simulations using Gromacs. The best binding affinity values were obtained for the 1DQE-ferutidine (-11 kcal/mol) and 2WCH-kaurene (-11.2 kcal/mol) complexes. Both are natural ligands that dock onto those proteins at the same binding site as DEET, a well-known insect repellent. This study identifies kaurene and ferutidine as possible candidates for natural insect repellents, offering a potential alternative to synthetic chemicals like DEET.


Asunto(s)
Simulación del Acoplamiento Molecular , Aceites Volátiles , Receptores Odorantes , Receptores Odorantes/química , Receptores Odorantes/metabolismo , Aceites Volátiles/química , Animales , Proteínas de Insectos/química , Proteínas de Insectos/metabolismo , Simulación de Dinámica Molecular , Repelentes de Insectos/química , Ligandos , Relación Estructura-Actividad Cuantitativa
6.
Acta Parasitol ; 69(3): 1426-1438, 2024 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-39147955

RESUMEN

PURPOSE: The flea Ctenocephalides felis (Siphonaptera: Pulicidae), parasitizes dogs and cats globally, acting as a vector for various pathogens affecting both animals and humans. Growing interest in environmentally friendly, plant-based products prompted this study. The aim of the study was to determine the chemical composition of essential oils (EOs) from Copaifera reticulata, Citrus paradisi, Lavandula hybrida and Salvia sclarea, assessing their insecticidal and repellent properties, determining lethal concentrations (LC50 and LC90), and evaluating residual efficacy in vitro against Ctenocephalides felis felis. METHODS: Gas Chromatography with Flame Ionization Detector analyzed EO composition. In vitro tests involved preparing EO solutions at various concentrations. Ten specimens from each life stage (egg, larva, pupa, adult) were used for insecticidal activity assessment. Adulticidal activity was assessed using 10 cm2 filter paper strip, each treated with 0.200 mL of the test solution. Immature stages activities were evaluated using 23.76 cm2 discs of the same filter paper, each treated with 0.470 mL of the test solution. Mortality percentage was calculated using (number of dead insects × 100) / number of incubated insects. Probit analysis calculated LC50 values with a 95% confidence interval. RESULTS: Major EO constituents were ß-caryophyllene (EOCR), linalool (EOLH), linalyl acetate (EOSS), and limonene (EOCP). LC50 values were obtained for all stages except for the essential oil of C. paradisi. All oils showed repellent activity at 800 µg/cm2. OECR exhibited greater residual efficacy. CONCLUSION: Each EO demonstrated superior insecticidal activity against specific C. felis felis stages.


Asunto(s)
Ctenocephalides , Repelentes de Insectos , Insecticidas , Aceites Volátiles , Salvia , Animales , Aceites Volátiles/farmacología , Aceites Volátiles/química , Salvia/química , Repelentes de Insectos/farmacología , Repelentes de Insectos/química , Insecticidas/farmacología , Insecticidas/química , Ctenocephalides/efectos de los fármacos , Fabaceae/química , Lavandula/química , Larva/efectos de los fármacos , Pupa/efectos de los fármacos , Citrus/química , Monoterpenos Acíclicos/farmacología , Monoterpenos/farmacología , Monoterpenos/química , Aceites de Plantas/farmacología , Aceites de Plantas/química , Dosificación Letal Mediana
7.
Acta Trop ; 258: 107359, 2024 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-39142548

RESUMEN

With growing interest in natural compounds as alternative mosquito repellents, assessing the toxicity and structure of potential repellent naturals like thymol (monoterpene phenol) and geraniol (monoterpene alcohol) is vital for understanding their stability and human impact. This study aimed to determine the structural, toxicity, and binding profiles of thymol and geraniol using computational predictions, xTB metadynamics, quantum mechanics, and principal component analysis. Toxicity studies using Protox-II, T.E.S.T, and SwissADME indicated that thymol and geraniol belong to toxicity class 4 and 5, respectively, with low toxicity predictions in other endpoints. Overall pharmacokinetic profile was generated via pkCSM. Off-target predictions via SwissTarget Predictions, LigTMap, Pharmapper, and SuperPred showed that these molecules can bind to 614 human proteins. The degradation of thymol and geraniol were performed using xTB metadynamics and the outcomes showed that the degradants for both compounds were stable and had lower toxicity profile. Nine tautomers were generated via quantum mechanics for thymol and four for geraniol, with RMSD ranging from 3.8 to 6.3 Å for thymol and 3.6 to 4 Å for geraniol after superimpositions. DFT studies found that HOMO-LUMO values and electronegativity parameters of thymol and geraniol did not differ significantly from their isomers. Binding affinity studies against 614 proteins, analysed via PCA and violin plots, highlighted the probable range of binding. These multifaceted in-silico findings corroborate the stability and potential utility of thymol and geraniol as safer alternatives in repellent applications.


Asunto(s)
Monoterpenos Acíclicos , Repelentes de Insectos , Proteoma , Timol , Timol/química , Timol/farmacología , Humanos , Monoterpenos Acíclicos/química , Repelentes de Insectos/química , Repelentes de Insectos/farmacología , Teoría Cuántica , Terpenos/química
8.
Int J Biol Macromol ; 279(Pt 1): 135140, 2024 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-39216571

RESUMEN

Genome wide analysis identified 14 OBPs in B. tabaci Asia II-1, of which six are new to science. Phylogenetic analysis traced their diversity and evolutionary lineage among Hemipteran insects. Comparative analysis reclassified the OBP gene families among B. tabaci cryptic species: Asia I, II-1, MEAM1, and MED. The 14 OBPs were clustered on four chromosomes of B. tabaci. RT-qPCR showed high expression of OBP3 and 8 across all body tissues and OBP10 in the abdomen. Molecular docking showed that OBP 3 and 10 had high affinity bonding with different candidate ligands, with binding energies ranging from -5.0 to -7.7 kcal/mol. Competitive fluorescence binding assays revealed that ß-caryophyllene and limonene had high binding affinities for OBP3 and 10, with their IC50 values ranging from 9.16 to 14 µmol·L-1 and KD values around 7 to 9 µmol·L-1. Behavioural assays revealed that ß-caryophyllene and carvacrol were attractants, ß-ocimene and limonene were repellents, and γ-terpinene and ß-ocimene were oviposition deterrents to B. tabaci. Functional validation by RNAi demonstrated that OBP3 and OBP10 modulated host recognition of B. tabaci. This study expands our understanding of the genomic landscape of OBPs in B. tabaci, offering scope for developing novel pest control strategies.


Asunto(s)
Hemípteros , Proteínas de Insectos , Filogenia , Receptores Odorantes , Sesquiterpenos , Animales , Hemípteros/genética , Receptores Odorantes/genética , Receptores Odorantes/metabolismo , Receptores Odorantes/química , Proteínas de Insectos/genética , Proteínas de Insectos/química , Proteínas de Insectos/metabolismo , Sesquiterpenos/farmacología , Sesquiterpenos/metabolismo , Sesquiterpenos/química , Sesquiterpenos Policíclicos/farmacología , Sesquiterpenos Policíclicos/química , Cimenos/farmacología , Cimenos/química , Simulación del Acoplamiento Molecular , Monoterpenos/farmacología , Monoterpenos/metabolismo , Monoterpenos/química , Limoneno/farmacología , Limoneno/química , Limoneno/metabolismo , Monoterpenos Acíclicos/metabolismo , Monoterpenos Acíclicos/farmacología , Monoterpenos Acíclicos/química , Ciclohexenos/metabolismo , Ciclohexenos/farmacología , Ciclohexenos/química , Terpenos/metabolismo , Terpenos/química , Terpenos/farmacología , Genoma de los Insectos , Repelentes de Insectos/farmacología , Repelentes de Insectos/química , Genómica/métodos , Monoterpenos Ciclohexánicos , Alquenos
9.
J Nat Prod ; 87(9): 2302-2309, 2024 Sep 27.
Artículo en Inglés | MEDLINE | ID: mdl-39196851

RESUMEN

Imported fire ants are significant agricultural pests. Repellents can be used to prevent foraging fire ants from entering sensitive areas, including electrical equipment, nursing homes, and hospitals. Bioassay-guided fractionation of the essential oil extracted from gurjun balsam (Dipterocarpus turbinatus) resulted in the identification of (-)-α-copaene (1) as the repellent constituent with a minimum repellent effective dose (MRED) of 15.6 µg/g against both red imported fire ants (Solenopsis invicta) and hybrid imported fire ants (Solenopsis invicta × Solenopsis richteri). Stereoselective oxidation of 1 via autoxidation and chemical methods produced (-)-5R-hydroperoxy-α-copaene (2), (+)-3S-hydroperoxycopa-4-ene (3), (-)-α-copaene oxide (4), (+)-ß-copaen-4α-ol (5), copaenediol (6), and copaene ketol (7). Reduction of 2 and 3 with triphenylphosphine afforded (-)-5R-hydroxy-α-copaene (2a) and (+)-3S-hydroxycopa-4-ene (3a), respectively, which led to the structural revision of copa-3-en-2α-ol and copa-2-en-4-ol as 2a and 3, respectively. The configurational assignment of compound 4 in the literature was also clarified by the detailed analysis of 2D NMR spectroscopic data. Compounds 2-7 showed repellency with MREDs ranging from 3.9 to 15.6 µg/g against hybrid and red imported fire ants, indicating that chemical modification can enhance the repellent effect of (-)-α-copaene.


Asunto(s)
Hormigas , Repelentes de Insectos , Aceites Volátiles , Oxidación-Reducción , Sesquiterpenos , Hormigas/efectos de los fármacos , Repelentes de Insectos/farmacología , Repelentes de Insectos/química , Animales , Sesquiterpenos/química , Sesquiterpenos/farmacología , Estereoisomerismo , Aceites Volátiles/química , Aceites Volátiles/farmacología , Estructura Molecular , Hormigas de Fuego
10.
Sci Rep ; 14(1): 18567, 2024 08 10.
Artículo en Inglés | MEDLINE | ID: mdl-39127742

RESUMEN

Encapsulation of essential oils (EOs) is an important strategy that can be applied to intensify the stability and efficiency of these compounds in integrated pest management. The present study aimed to investigate the sub-lethal activity of polymer-based EOs nanoparticles against red flour beetle, Tribolium castaneum adults as an important critical pest of stored products. Chitosan nanoparticles (CSNPs) containing garlic and cinnamon essential oils (GEO and CEO) prepared using the ionic cross-link technique. Stability of nano-formulations evaluated over temperature and storage time. The fumigant effect (LC10, LC20, LC30) and contact toxicity (LC10, LC15, LC25) determined. In addition, the contact toxicities of EOs and their nanoparticles on nutritional indices evaluated. An olfactometer used to assess the repellent activity of EOs and EOs loaded in CSNPs (EOs@CSNPs) in sub-lethal fumigant concentrations. Characterization results showed GEO loaded in CSNPs has particle size of 231.14 ± 7.55 nm, polydispersity index (PDI) value of 0.15 ± 0.02, encapsulation efficiency (EE) percentage of 76.77 ± 0.20 and zeta potential of - 18.82 ± 0.90 mV, in which these values for the CEO loaded in CSNPs (CEO@CSNPs) changed to 303.46 ± 0.00 nm, 0.20 ± 0.05, 86.81 ± 0.00% and - 20.16 ± 0.35 mV, respectively. A lower PDI value for both CSNPs showed an appropriate NPs size distribution. Furthermore, NPs size and encapsulation efficiency did not change in various temperatures and during four months which confirm good stability of the EOs@CSNPs. In LC30 of GEO@CSNPs, the maximum repellency was determined as 66.66 ± 3.33. Among nutritional indices, in LC25 of GEO@CSNPs, the relative growth rate (RGR) (0.011 ± 0.003 mg.mg-1.day-1), relative consumption rate (RCR) (0.075 ± 0.004 mg.mg-1.day-1) and feeding deterrence index (FDI) (54.662 ± 1.616%) were more affected, so GEO@CSNPs was more effective than CEO@CSNPs. The results of repellent and anti-dietary activities of EOs and EOs@CSNPs confirmed the higher repellency and adverse effectivity on nutritional indices of Tribolium castaneum pest treated with EOs@CSNPs compared to free EOs. In conclusion, the NPs form of GEO and CEO can be a novel and efficient carrier for improving the repellent and anti-nutritional activities of EOs.


Asunto(s)
Repelentes de Insectos , Nanopartículas , Aceites Volátiles , Tribolium , Animales , Aceites Volátiles/farmacología , Aceites Volátiles/química , Nanopartículas/química , Tribolium/efectos de los fármacos , Repelentes de Insectos/farmacología , Repelentes de Insectos/química , Quitosano/química , Quitosano/farmacología , Cinnamomum zeylanicum/química , Polímeros/química , Tamaño de la Partícula , Ajo/química , Insecticidas/farmacología , Insecticidas/química
11.
J Agric Food Chem ; 72(31): 17317-17327, 2024 Aug 07.
Artículo en Inglés | MEDLINE | ID: mdl-39067067

RESUMEN

With high aphid-repellent activity but low stability, (E)-ß-farnesene (EßF), the major component of the aphid alarm pheromone, can be used as a synergist to insecticides. Some EßF analogues possess both good aphid-repellent activity and stability, but the synergistic effect and related mechanism are still unclear. Therefore, this study investigated the synergistic effect and underlying mechanism of the EßF and its analogue against the aphid Myzus persicae. The results indicated that EßF and the analogue showed significantly synergistic effects to different insecticides, with synergism ratios from 1.524 to 3.446. Mechanistic studies revealed that EßF and the analogue exhibited effective repellent activity, significantly upregulated target OBP genes by 161 to 731%, increased aphid mobility, and thereby enhanced contact with insecticides. This research suggests that the EßF analogue represents a novel synergist for insecticides, with the potential for further application in aphid control owing to its enhanced bioactivity and the possibility of reducing insecticide doses.


Asunto(s)
Áfidos , Sinergismo Farmacológico , Insecticidas , Sesquiterpenos , Áfidos/efectos de los fármacos , Animales , Insecticidas/química , Insecticidas/farmacología , Sesquiterpenos/farmacología , Sesquiterpenos/química , Proteínas de Insectos/química , Proteínas de Insectos/genética , Proteínas de Insectos/metabolismo , Prunus persica/química , Prunus persica/parasitología , Repelentes de Insectos/química , Repelentes de Insectos/farmacología
12.
Molecules ; 29(14)2024 Jul 18.
Artículo en Inglés | MEDLINE | ID: mdl-39064968

RESUMEN

Diaphorina citri Kuwayama (D. citri) is one of the major pests in the citrus industry, which spreads Citrus Huanglongbing disease. It has developed resistance to chemical insecticides. Therefore, searching for greener solutions for pest management is critically important. The main aim of this study was to evaluate the repellent and insecticidal efficacy of essential oils (EOs) from four species of Myrtaceae plants: Psidium guajava (PG), Eucalyptus robusta (ER), Eucalyptus tereticornis (ET), and Baeckea frutescens (BF) against D. citri and to analyze their chemical compositions. GC-MS analysis was performed, and the results indicated that the EOs of PG, ER, ET, and BF were rich in terpenoids, ketones, esters, and alcohol compounds. The repellent rate of all four EOs showed that it decreased with exposure time but increased with the concentration of EOs from 80.50% to 100.00% after treating D. citri for 6 h with four EOs at 100% concentration and decreased to 67.71% to 85.49% after 24 h of exposure. Among the compounds from the EOs tested, eucalyptol had the strongest repellent activity, with a 24 h repellency rate of 100%. The contact toxicity bioassay results showed that all EOs have insecticidal toxicity to D. citri; the LC50 for nymphs was 36.47-93.15 mL/L, and for adults, it was 60.72-111.00 mL/L. These results show that when PG is used as the reference material, the ER, ET, and BF EOs have strong biological activity against D. citri, which provides a scientific basis for the further development of plant-derived agrochemicals.


Asunto(s)
Hemípteros , Repelentes de Insectos , Insecticidas , Myrtaceae , Aceites Volátiles , Animales , Aceites Volátiles/química , Aceites Volátiles/farmacología , Hemípteros/efectos de los fármacos , Repelentes de Insectos/farmacología , Repelentes de Insectos/química , Myrtaceae/química , Insecticidas/química , Insecticidas/farmacología , Citrus/química , Cromatografía de Gases y Espectrometría de Masas , Aceites de Plantas/química , Aceites de Plantas/farmacología
13.
Molecules ; 29(11)2024 Jun 04.
Artículo en Inglés | MEDLINE | ID: mdl-38893531

RESUMEN

In this study, the chemical composition, repellent, and oviposition deterrent effects of five plant essential oils (EOs) extracted from Lantana camara (Verbenaceae), Schinus terebinthifolia (Anacardiaceae), Callistemon viminalis (Myrtaceae), Helichrysum odoratissimum (Asteraceae), and Hyptis suaveolens (Lamiaceae) were evaluated against Aedes aegypti, Anopheles gambiae, and Culex quinquefasciatus. When tested at 33.3 µg/cm2, L. camara, S. terebinthifolia, C. viminalis, and H. odoratissimum were effective repellents against Ae. aegypti (89%, 91%, 90%, and 51% repellency, respectively), but they were less repellent against An. gambiae (66%, 86%, 59%, and 49% repellency, respectively). Interestingly, L. camara, S. terebinthifolia, C. viminalis, and H. odoratissimum exhibited 100% repellency against Cx. quinquefasciatus at 33.3 µg/cm2. In time-span bioassays performed at 333 µg/cm2, the EO of L. camara exhibited 100% repellence against Ae. aegypti and An. gambiae for up to 15 min and against Cx. quinquefasciatus for 75 min. The oviposition bioassays revealed that L. camara exhibited the highest activity, showing 85%, 59%, and 89% oviposition deterrence against Ae. aegypti, An. gambiae, and Cx. quinquefasciatus, respectively. The major compounds of L. camara, S. terebinthifolia, and C. viminalis were trans-ß-caryophyllene (16.7%), α-pinene (15.5%), and 1,8-cineole (38.1%), respectively. In conclusion, the L. camara and S. terebinthifolia EOs have the potential to be natural mosquito repellents.


Asunto(s)
Aedes , Repelentes de Insectos , Aceites Volátiles , Oviposición , Animales , Aceites Volátiles/farmacología , Aceites Volátiles/química , Repelentes de Insectos/farmacología , Repelentes de Insectos/química , Oviposición/efectos de los fármacos , Aedes/efectos de los fármacos , Culex/efectos de los fármacos , Anopheles/efectos de los fármacos , Anopheles/fisiología , Culicidae/efectos de los fármacos , Aceites de Plantas/farmacología , Aceites de Plantas/química , Lantana/química , Anacardiaceae/química , Extractos Vegetales/farmacología , Extractos Vegetales/química , Femenino
14.
Pest Manag Sci ; 80(9): 4523-4532, 2024 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-38747159

RESUMEN

BACKGROUND: Whiteflies are major pests in agriculture, causing damage to crops and transmitting plant viruses. Using Volatile Organic Compounds (VOCs) as semiochemicals offers a sustainable approach for combating whiteflies. One such group of compounds, represented by ß-ionone, has been found to possess repellent/attractant properties. To further explore the behavioral effects of these compounds on whiteflies, we selected five natural ionone compounds and synthesized six novel analogues to examine the impact of structural variations on whitefly behavior. RESULTS: Our results demonstrated that ß-ionone and its analogues have a significant impact on the behavior of whiteflies. Among them, 0.01% pseudo ionone solution exhibited an attractant effect on whiteflies. Notably, the application of 1% ß-ionone and 0.1% ß-ionol solution demonstrated a notable repellent effect and oviposition deterrent effect on whitefly. We also found that the novel ionone analogue (±)1A exhibited a strong repellent effect. Both ß-ionol and compound (±)1A possess high logP values and low saturation vapor pressures, which contribute to enhanced lipophilicity, making them more likely to penetrate insect antennae and prolong their presence in the air. CONCLUSION: The newly discovered ionone analogue (±)1A and ß-ionol exhibit improved repellent effects, while pseudo ionone shows an attractant effect. These three compounds hold promising potential for development as novel biological control agents. Our work highlights the efficacy of VOCs as a protection method against whiteflies. These findings indicate that our new technology for a 'push-pull' control method of B. tabaci can offer a novel tool for integrated pest management (IPM). © 2024 Society of Chemical Industry.


Asunto(s)
Hemípteros , Norisoprenoides , Animales , Hemípteros/efectos de los fármacos , Hemípteros/fisiología , Norisoprenoides/farmacología , Norisoprenoides/química , Repelentes de Insectos/farmacología , Repelentes de Insectos/química , Femenino , Control de Insectos/métodos , Conducta Animal/efectos de los fármacos , Oviposición/efectos de los fármacos , Compuestos Orgánicos Volátiles/farmacología , Compuestos Orgánicos Volátiles/química
15.
Molecules ; 29(9)2024 Apr 23.
Artículo en Inglés | MEDLINE | ID: mdl-38731415

RESUMEN

Investigations have shown that storage bugs seriously harm grains during storage. In the interim, essential oils (EOs) have been proven to be a good botanical pesticide. The anti-Lasioderma serricorne properties of Elsholtzia ciliata essential oil, which was obtained by steam distillation, were evaluated using DL-limonene, carvone, and their two optical isomer components using contact, repelling, and fumigation techniques. Simultaneously, the fumigation, contact, and repellent activities of carvone and its two optical isomers mixed with DL-limonene against L. serruricorne were evaluated. The results showed that E. ciliata, its main components (R-carvone, DL-limonene), and S-carvone exhibited both fumigations (LC50 = 14.47, 4.42, 20.9 and 3.78 mg/L) and contact (LD50 = 7.31, 4.03, 28.62 and 5.63 µg/adult) activity against L.serricorne. A binary mixture (1:1) of R-carvone and DL-limonene displayed an obvious synergistic effect. A binary mixture (1:1) of carvone and its two optical isomers exhibited an obvious synergistic effect, too. Furthermore, the repellent activity of the EO, carvone, and its two optical isomers, DL-limonene, and a combination of them varied. To stop insect damage during storage, E. ciliata and its components can be utilized as bio-insecticides.


Asunto(s)
Insecticidas , Lamiaceae , Aceites Volátiles , Aceites Volátiles/química , Aceites Volátiles/farmacología , Lamiaceae/química , Animales , Insecticidas/química , Insecticidas/farmacología , Limoneno/química , Limoneno/farmacología , Repelentes de Insectos/química , Repelentes de Insectos/farmacología , Monoterpenos Ciclohexánicos/química , Monoterpenos Ciclohexánicos/farmacología , Sinergismo Farmacológico , Fumigación
16.
Molecules ; 29(8)2024 Apr 12.
Artículo en Inglés | MEDLINE | ID: mdl-38675573

RESUMEN

The repellent capacity against Sitophilus zeamais and the in vitro inhibition on AChE of 11 essential oils, isolated from six plants of the northern region of Colombia, were assessed using a modified tunnel-type device and the Ellman colorimetric method, respectively. The results were as follows: (i) the degree of repellency (DR) of the EOs against S. zeamais was 20-68% (2 h) and 28-74% (4 h); (ii) the IC50 values on AChE were 5-36 µg/mL; likewise, the %inh. on AChE (1 µg/cm3 per EO) did not show any effect in 91% of the EO tested; (iii) six EOs (Bursera graveolens-bark, B. graveolens-leaves, B. simaruba-bark, Peperomia pellucida-leaves, Piper holtonii (1b*)-leaves, and P. reticulatum-leaves) exhibited a DR (53-74%) ≥ C+ (chlorpyrifos-61%), while all EOs were less active (8-60-fold) on AChE compared to chlorpyrifos (IC50 of 0.59 µg/mL). Based on the ANOVA/linear regression and multivariate analysis of data, some differences/similarities could be established, as well as identifying the most active EOs (five: B. simaruba-bark, Pep. Pellucida-leaves, P. holtonii (1b*)-leaves, B. graveolens-bark, and B. graveolens-leaves). Finally, these EOs were constituted by spathulenol (24%)/ß-selinene (18%)/caryophyllene oxide (10%)-B. simaruba; carotol (44%)/dillapiole (21%)-Pep. pellucida; dillapiole (81% confirmed by 1H-/13C-NMR)-P. holtonii; mint furanone derivative (14%)/mint furanone (14%)-B. graveolens-bark; limonene (17%)/carvone (10%)-B. graveolens-leaves.


Asunto(s)
Inhibidores de la Colinesterasa , Repelentes de Insectos , Aceites Volátiles , Sesquiterpenos Policíclicos , Animales , Acetilcolinesterasa/metabolismo , Inhibidores de la Colinesterasa/farmacología , Inhibidores de la Colinesterasa/química , Colombia , Repelentes de Insectos/farmacología , Repelentes de Insectos/química , Aceites Volátiles/farmacología , Aceites Volátiles/química , Piper/química , Aceites de Plantas/farmacología , Aceites de Plantas/química , Sesquiterpenos Policíclicos/química , Sesquiterpenos Policíclicos/farmacología , Gorgojos/enzimología , Gorgojos/efectos de los fármacos , Sesquiterpenos de Eudesmano/química , Sesquiterpenos de Eudesmano/farmacología , Sesquiterpenos/química , Sesquiterpenos/farmacología
17.
J Vector Borne Dis ; 61(1): 107-116, 2024 Jan 01.
Artículo en Inglés | MEDLINE | ID: mdl-38648412

RESUMEN

BACKGROUND OBJECTIVES: Mosquitoes alone transmit diseases to around 700 million individuals annually, killing approximately 0.7 million people every year worldwide. Considering the potential health risks linked with synthetic repellents, it has become vital to identify eco-friendly, natural repellents for mosquito control as well as to understand the underlying mechanism for mosquito repellent activity. To address this, objectives were set to extract essential oils from Citrus macroptera peel and Homalomena aromatica (Spreng.) Schott. rhizomes, evaluate their mosquito repellent activity against Aedes aegypti, and further explore their mosquito odorant receptor inhibition potential. METHODS: The oils were extracted using Clevenger's apparatus, and properties like specific gravity, refractive index, and boiling point were evaluated and characterised using Fourier transform infrared spectroscopy (FTIR) and gas chromatography-mass spectroscopy (GC-MS). Aedes aegypti mosquito eggs collected from the Indian Council of Medical Research (ICMR), Dibrugarh, were reared in the Department of Pharmaceutical Sciences, Research Laboratory, to obtain adult Aedes aegypti mosquitoes for the mosquito repellent activity evaluation of the essential oils using the Human Bait technique'. Molecular docking studies were performed for the oil components against mosquito odorant binding proteins. Further, toxicity studies of these two oils were evaluated against human dermal fibroblast adult (HDFa) cells. RESULTS: The results revealed the presence of limonene (86.76%) and linalool (52.35%), respectively, in Citrus macroptera and Homalomena aromatica oils. It was found that the combination of the oils in a ratio of 1:1 showed mosquito repellent activity for up to 6.33 ± 0.23 h. Molecular docking studies showed the presence of major oil components having mosquito odorant receptor blocking potential comparable to N, N-diethyl-meta-toluamide (DEET), indicating a rationale for extended mosquito repellent action. Further, both of these oils were found to be non-cytotoxic against HDFa cells after 24 h. INTERPRETATION CONCLUSION: The encouraging mosquito repellent activity of these two oils as compared to synthetic mosquito repellent DEET might pave the way for the development of novel herbal mosquito repellent formulations containing these essential oils.


Asunto(s)
Aedes , Citrus , Repelentes de Insectos , Simulación del Acoplamiento Molecular , Aceites Volátiles , Repelentes de Insectos/farmacología , Repelentes de Insectos/química , Repelentes de Insectos/aislamiento & purificación , Animales , Aedes/efectos de los fármacos , Aceites Volátiles/farmacología , Aceites Volátiles/química , Citrus/química , Humanos , Cromatografía de Gases y Espectrometría de Masas , Espectroscopía Infrarroja por Transformada de Fourier , Receptores Odorantes/metabolismo , Receptores Odorantes/química , Femenino , Rizoma/química
18.
Pestic Biochem Physiol ; 201: 105907, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38685228

RESUMEN

The use of essential oils (EOs) in the development of alternative management methods for bruchid control under storage conditions aroused great interest because they have proven to be effective, less toxic, and less persistent in the ecosystem than synthetic pesticides. In this sense, leaves of Lippia turbinata (Griseb.) Moldenke EO were studied in the present work. The monoterpene limonene and the monoterpenoid eucalyptol were its main constituents. EO showed a potent insecticidal activity, both in contact and fumigant conditions, against Rhipibruchus picturatus (F.) which is one of the main pests of Prosopis alba pods in stored conditions. Moreover, the EO produces repellency in these insects. Additionally, the toxicity mechanism of action was studied. In this regard, the EO inhibits the acetylcholinesterase enzyme in in vitro assays, alters the activity of the antioxidant enzymes superoxide dismutase and catalase, and produces an increase in the lipid peroxidation reactions. This is the first report of the use of the L. turbinata EO against R. picturatus insect pest. The data obtained demonstrate its potential for developing more efficient and natural storage pest control strategies.


Asunto(s)
Repelentes de Insectos , Insecticidas , Lippia , Aceites Volátiles , Animales , Aceites Volátiles/farmacología , Aceites Volátiles/química , Lippia/química , Insecticidas/farmacología , Insecticidas/química , Insecticidas/toxicidad , Repelentes de Insectos/farmacología , Repelentes de Insectos/química , Escarabajos/efectos de los fármacos , Peroxidación de Lípido/efectos de los fármacos , Superóxido Dismutasa/metabolismo , Acetilcolinesterasa/metabolismo , Catalasa/metabolismo , Hojas de la Planta/química
19.
Chem Biodivers ; 21(5): e202400185, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38513004

RESUMEN

The resin essential oil (REO) of the Tunisian Araucaria heterophylla trunk bark was investigated for its chemical composition. Then, it was evaluated for its insecticidal and allelopathic activities. The REO was obtained by hydrodistillation for 9 h (yield of 4.2 % w/w). Moreover, fractional hydrodistillation was carried out at 3-hour intervals, resulting in 3 fractions (R1-R3), to facilitate chemical identification and localization of the aforementioned biological activities. GC/MS analysis of the obtained samples allowed the identification of 25 compounds, representing between 91.2 and 96.3 % of their total constituents, which consisted predominantly of sesquiterpene hydrocarbons, oxygenated sesquiterpenes and diterpene hydrocarbons. α-Copaene (10.8 %), γ-muurolene (5.8 %), α-copaen-11-ol (7.8 %), spathulenol (10.5 %), 15-copaenol (8.2 %), ylangenal (10.3 %), dehydrosaussurea lactone (7.7 %), and sandaracopimaradiene (11.4 %) were identified as major compounds. The second part aimed to assess the impact of the A. heterophylla EO and its three fractions for their insecticidal and repellent activity against Tribolium castaneum (Herbst), a stored grain pest, of which a strong repellent activity was noted. In addition, the studied samples showed high phytotoxic effects against Lactuca sativa. The third fraction (R3) performed a total inhibitory potential on seed germination and seedling growth of the target plant. Furthermore, alongside this discovery, an estimation was conducted through molecular docking analysis. Wherein the main compounds of the studied samples were docked into the active pocket of protoporphyrinogen IX oxidase (PDB: 1SEZ), a key enzyme in chlorophyll biosynthesis. Thus, it is recommended to use the REO of A. heterophylla as a natural herbicide.


Asunto(s)
Araucaria , Insecticidas , Aceites Volátiles , Aceites Volátiles/farmacología , Aceites Volátiles/química , Aceites Volátiles/aislamiento & purificación , Túnez , Animales , Insecticidas/farmacología , Insecticidas/química , Insecticidas/aislamiento & purificación , Araucaria/efectos de los fármacos , Araucaria/química , Araucaria/metabolismo , Repelentes de Insectos/farmacología , Repelentes de Insectos/química , Repelentes de Insectos/aislamiento & purificación , Resinas de Plantas/química , Simulación del Acoplamiento Molecular , Cromatografía de Gases y Espectrometría de Masas
20.
Molecules ; 29(6)2024 Mar 19.
Artículo en Inglés | MEDLINE | ID: mdl-38542997

RESUMEN

The current study aimed to evaluate the presence of chemical variations in essential oils (EOs) extracted from Artemisia scoparia growing at different altitudes and to reveal their antibacterial, mosquito larvicidal, and repellent activity. The gas chromatographic-mass spectrometric analysis of A. scoparia EOs revealed that the major compounds were capillene (9.6-31.8%), methyleugenol (0.2-26.6%), ß-myrcene (1.9-21.4%), γ-terpinene (1.5-19.4%), trans-ß-caryophyllene (0.8-12.4%), and eugenol (0.1-9.1%). The EO of A. scoparia collected from the city of Attock at low elevation was the most active against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa bacteria (minimum inhibitory concentration of 156-1250 µg/mL) and showed the best mosquito larvicidal activity (LC50, 55.3 mg/L). The EOs of A. scoparia collected from the high-altitude areas of Abbottabad and Swat were the most repellent for females of Ae. aegypti and exhibited repellency for 120 min and 165 min, respectively. The results of the study reveal that different climatic conditions and altitudes have significant effects on the chemical compositions and the biological activity of essential oils extracted from the same species.


Asunto(s)
Aedes , Artemisia , Repelentes de Insectos , Insecticidas , Aceites Volátiles , Sesquiterpenos Policíclicos , Scoparia , Femenino , Animales , Aceites Volátiles/farmacología , Aceites Volátiles/química , Repelentes de Insectos/farmacología , Repelentes de Insectos/química , Altitud , Insecticidas/química , Antibacterianos/farmacología , Larva , Aceites de Plantas/química
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