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1.
J Oleo Sci ; 73(5): 761-772, 2024.
Artículo en Inglés | MEDLINE | ID: mdl-38692898

RESUMEN

Volatile secondary metabolites of plants interact with environments heavily. In this work, characteristic components of Michelia yunnanensis essential oils (EOs) were isolated, purified and identified by column chromatography, GC-MS and NMR. Leaves of M. yunnanensis were collected monthly and extracted for EOs to investigate chemical and insecticidal activity variations as well as potential influencing environments. Different organs were employed to reveal distribution strategies of characteristic components. Results of insecticidal activities showed that all EOs samples exerted stronger contact activity to Lasioderma serricorne, but repellent effect was more efficient on Tribolium castaneum. One oxygenated sesquiterpene was isolated from EOs, basically it could be confirmed as (+)-cyclocolorenone (1). It exerted contact toxicity to L. serricorne (LD 50 = 28.8 µg/adult). Chemical analysis showed that M. yunnanensis leaves in reproductive period would produce and accumulate more 1 than in vegetative period. Moreover, reproductive organs (flowers and fruits) contained more 1 than vegetative organs (leaves and twigs). Partial correlation analysis indicated that temperature-related elements positively correlated with the relative content of 1.


Asunto(s)
Insecticidas , Aceites Volátiles , Hojas de la Planta , Tribolium , Animales , Insecticidas/aislamiento & purificación , Insecticidas/análisis , Hojas de la Planta/química , Aceites Volátiles/farmacología , Aceites Volátiles/química , Aceites Volátiles/aislamiento & purificación , Tribolium/efectos de los fármacos , Sesquiterpenos/aislamiento & purificación , Sesquiterpenos/análisis , Repelentes de Insectos/análisis , Repelentes de Insectos/aislamiento & purificación , Repelentes de Insectos/farmacología , Temperatura
2.
Molecules ; 29(8)2024 Apr 13.
Artículo en Inglés | MEDLINE | ID: mdl-38675598

RESUMEN

Plant extracts and essential oils can be alternative environmentally friendly agents to combat pathogenic microbes and malaria vectors. Myrrh is an aromatic oligum resin that is extracted from the stem of Commiphora spp. It is used in medicine as an insecticide, cytotoxic, and aromatic. The current study assessed the effect of Commiphora myrrha resin extracts on the biological potency of the third larval stage of Aedes aegypti, as well as its antioxidant and cytotoxic properties against two types of tumor cells (HepG-2 and Hela cell lines). It also used GC-MS to determine the chemical composition of the C. myrrha resin extracts. Fifty components from the extracted plant were tentatively identified using the GC-MS method, with curzerene (33.57%) typically listed as the primary ingredient, but other compounds also make up a significant portion of the mixture, including 1-Methoxy-3,4,5,7-tetramethylnaphthalene (15.50%), ß-Elemene (5.80%), 2-Methoxyfuranodiene (5.42%), 2-Isopropyl-4,7-Dimethyl-1-Naphthol (4.71%), and germacrene B (4.35%). The resin extracts obtained from C. myrrha exhibited significant efficacy in DPPH antioxidant activity, as evidenced by an IC50 value of 26.86 mg/L and a radical scavenging activity percentage of 75.06%. The 50% methanol extract derived from C. myrrha resins exhibited heightened potential for anticancer activity. It demonstrated substantial cytotoxicity against HepG-2 and Hela cells, with IC50 values of 39.73 and 29.41 µg mL-1, respectively. Notably, the extract showed non-cytotoxic activity against WI-38 normal cells, with an IC50 value exceeding 100 µg mL-1. Moreover, the selectivity index for HepG-2 cancer cells (2.52) was lower compared to Hela cancer cells (3.40). Additionally, MeOH resin extracts were more efficient against the different growth stages of the mosquito A. aegypti, with lower LC50, LC90, and LC95 values of 251.83, 923.76, and 1293.35 mg/L, respectively. In comparison to untreated groups (1454 eggs/10 females), the average daily number of eggs deposited (424 eggs/L) decreases at higher doses (1000 mg/L). Finally, we advise continued study into the possible use of C. myrrha resins against additional pests that have medical and veterinary value, and novel chemicals from this extract should be isolated and purified for use in medicines.


Asunto(s)
Antioxidantes , Commiphora , Cromatografía de Gases y Espectrometría de Masas , Larva , Extractos Vegetales , Resinas de Plantas , Commiphora/química , Humanos , Cromatografía de Gases y Espectrometría de Masas/métodos , Antioxidantes/farmacología , Antioxidantes/química , Animales , Extractos Vegetales/farmacología , Extractos Vegetales/química , Células HeLa , Resinas de Plantas/química , Larva/efectos de los fármacos , Células Hep G2 , Insecticidas/farmacología , Insecticidas/química , Insecticidas/aislamiento & purificación , Aedes/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos
3.
Phytochemistry ; 222: 114075, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38570006

RESUMEN

Six undescribed bisindole alkaloids, namely taberdisines A-F (1-6), were isolated from the leaves of Tabernaemontana divaricata 'Dwaft'. Among them, alkaloids 1 and 2 were the first examples of strychnos-iboga type alkaloid with both C-C linkage patterns. Alkaloid 3, a new type of aspidosperma-iboga with a furan-ring, as well as other three undescribed ones was disclosed. Their structures were elucidated by comprehensive spectroscopic analyses. Alkaloids 1 and 5 showed insecticide activity on Sf9 cell and eggs of Spodoptera frugiperda in vivo, which might explain the potential of the plants for insect resistance.


Asunto(s)
Alcaloides Indólicos , Insecticidas , Hojas de la Planta , Spodoptera , Tabernaemontana , Tabernaemontana/química , Hojas de la Planta/química , Insecticidas/química , Insecticidas/farmacología , Insecticidas/aislamiento & purificación , Animales , Spodoptera/efectos de los fármacos , Alcaloides Indólicos/química , Alcaloides Indólicos/aislamiento & purificación , Alcaloides Indólicos/farmacología , Estructura Molecular , Células Sf9
4.
Phytochemistry ; 222: 114092, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38604323

RESUMEN

Phytochemical study of the fruits of Chisocheton erythrocarpus (Hiern) allowed the identification of eight undescribed limonoids, namely erythrocarpines O - V (1-6, 7a and 7b), along with seven known compounds. The structures of these compounds were elucidated based on spectroscopic and HRMS data, along with electronic circular dichroism to configure the absolute configuration. Erythrocarpines O and P are γ-hydroxybutenolide analogs of mexicanolide-type limonoids while erythrocarpine Q - V are phragmalin-type limonoids possessing a 1,29-oxymethylene bridge with either benzoyl or cinnamoyl moiety in their structures. Mosquito larvicidal activity revealed that crude DCM extract of C. erythrocarpus possessed a good larvicidal effect against Aedes aegypti larvae in 48 h (LC50 = 153.0 ppm). Subsequent larvicidal activity of isolated compounds indicated that erythrocarpine G (10) and 14-deoxyxyloccensin K (11) were responsible for the enhanced larvicidal effect of the extract, reporting LC50 values of 18.55 ppm and 41.16 ppm, respectively. Moreover, residual activity testing of the crude DCM extract revealed that the duration of its larvicidal effects is up to 14 days, where it maintained a 98 % larval mortality throughout the test period, under laboratory conditions.


Asunto(s)
Aedes , Frutas , Insecticidas , Larva , Limoninas , Meliaceae , Animales , Larva/efectos de los fármacos , Limoninas/farmacología , Limoninas/aislamiento & purificación , Limoninas/química , Insecticidas/farmacología , Insecticidas/química , Insecticidas/aislamiento & purificación , Frutas/química , Aedes/efectos de los fármacos , Meliaceae/química , Estructura Molecular , Relación Estructura-Actividad , Relación Dosis-Respuesta a Droga
5.
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
6.
J Nat Prod ; 85(9): 2159-2167, 2022 09 23.
Artículo en Inglés | MEDLINE | ID: mdl-36040034

RESUMEN

Cultures of a termite-associated and a free-living member of the fungal genus Podaxis, revived from spores maintained in century-old herbarium collections, were analyzed for their insecticidal and antimicrobial effects. Their secondary metabolomes were explored to uncover possible adaptive mechanisms of termite association, and dereplication of LC-HRMS/MS data sets led to the isolation of podaxisterols A-D (1-4), modified ergosterol derivatives that result from a Diels-Alder reaction with endogenous nitrosyl cyanide. Chemical structures were determined based on HRMS/MS and NMR analyses as well as X-ray crystallography. The putative origin of the endogenous fungal nitrosyl cyanide and ergosterol derivatives is discussed based on results obtained from stable isotope experiments and in silico analysis. Our "omics"-driven analysis of this underexplored yet worldwide distributed fungal genus builds a foundation for studies on a potential metabolic adaptations to diverse lifestyles.


Asunto(s)
Agaricales , Antiinfecciosos , Ergosterol , Insecticidas , Isópteros , Agaricales/química , Agaricales/metabolismo , Animales , Antiinfecciosos/química , Antiinfecciosos/aislamiento & purificación , Antiinfecciosos/farmacología , Ergosterol/análogos & derivados , Ergosterol/aislamiento & purificación , Ergosterol/farmacología , Insecticidas/química , Insecticidas/aislamiento & purificación , Insecticidas/farmacología , Isópteros/microbiología , Metabolómica , Óxidos de Nitrógeno/química
7.
J Biol Chem ; 298(10): 102413, 2022 10.
Artículo en Inglés | MEDLINE | ID: mdl-36007611

RESUMEN

Cyclotides and acyclic versions of cyclotides (acyclotides) are peptides involved in plant defense. These peptides contain a cystine knot motif formed by three interlocked disulfide bonds, with the main difference between the two classes being the presence or absence of a cyclic backbone, respectively. The insecticidal activity of cyclotides is well documented, but no study to date explores the insecticidal activity of acyclotides. Here, we present the first in vivo evaluation of the insecticidal activity of acyclotides from Rinorea bengalensis on the vinegar fly Drosophila melanogaster. Of a group of structurally comparable acyclotides, ribe 31 showed the most potent toxicity when fed to D. melanogaster. We screened a range of acyclotides and cyclotides and found their toxicity toward human red blood cells was substantially lower than toward insect cells, highlighting their selectivity and potential for use as bioinsecticides. Our confocal microscopy experiments indicated their cytotoxicity is likely mediated via membrane disruption. Furthermore, our surface plasmon resonance studies suggested ribe 31 preferentially binds to membranes containing phospholipids with phosphatidyl-ethanolamine headgroups. Despite having an acyclic backbone, we determined the three-dimensional NMR solution structure of ribe 31 is similar to that of cyclotides. In summary, our results suggest that, with further optimization, ribe 31 could have applications as an insecticide due to its potent in vivo activity against D. melanogaster. More broadly, this work advances the field by demonstrating that acyclotides are more common than previously thought, have potent insecticidal activity, and have the advantage of potentially being more easily manufactured than cyclotides.


Asunto(s)
Ciclotidas , Drosophila melanogaster , Insecticidas , Proteínas de Plantas , Violaceae , Animales , Humanos , Secuencia de Aminoácidos , Ciclotidas/química , Ciclotidas/aislamiento & purificación , Ciclotidas/farmacología , Drosophila melanogaster/efectos de los fármacos , Insecticidas/química , Insecticidas/aislamiento & purificación , Insecticidas/farmacología , Proteínas de Plantas/química , Proteínas de Plantas/aislamiento & purificación , Proteínas de Plantas/farmacología , Violaceae/química , Eritrocitos/efectos de los fármacos
8.
Molecules ; 27(4)2022 Feb 16.
Artículo en Inglés | MEDLINE | ID: mdl-35209137

RESUMEN

Vector-borne diseases, such as those transmitted by Aedes aegypti, are a constant threat to inhabitants of tropical regions of the planet. Synthetic chemicals are commonly used as a strategy to control them; however, these products are known to persist in ecosystems and drive the appearance of resistance genes in arthropod vectors. Thus, the use of natural products has emerged as an environmentally friendly alternative in integrated vector control strategies. The present bioguided study investigated the larvicidal potential of Ipomoea cairica extracts, fractionated using thin-layer and open-column chromatography, because this species has been shown to exert larvicidal effects on the genus Aedes. The objective of this study was to evaluate the nonvolatile components in ethanolic extract of I. cairica stems as a potential natural larvicidal, and coumarins, such as 7-hydroxy-6-methoxychromen-2-one (scopoletin) and 7-hydroxychromen-2-one (umbelliferone), were identified as major compounds; however, they were not shown to be responsible for the larvicidal activity. Based on the results of the larvicidal action tests, these coumarins are not directly responsible for the larvicidal activity, but this activity might be attributed to a synergistic effect of all the compounds present in the most active secondary fraction, called F.DCM, which had an LC50 value of 30.608 mg/L. This type of study has yet not been conducted in the region; therefore, it is an important contribution to recognizing a natural and easy-to-cultivate source of vector control, such I. cairica.


Asunto(s)
Aedes/efectos de los fármacos , Insecticidas/farmacología , Ipomoea/química , Fitoquímicos/farmacología , Extractos Vegetales/farmacología , Animales , Fraccionamiento Químico , Cromatografía Líquida de Alta Presión , Cromatografía en Capa Delgada , Relación Dosis-Respuesta a Droga , Insecticidas/química , Insecticidas/aislamiento & purificación , Larva/efectos de los fármacos , Espectrometría de Masas , Fitoquímicos/química , Fitoquímicos/aislamiento & purificación , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación
9.
Mar Drugs ; 20(2)2022 Jan 18.
Artículo en Inglés | MEDLINE | ID: mdl-35200612

RESUMEN

To enhance the biological activity of the natural product geodin (1), isolated from the marine-derived fungus Aspergillus sp., a series of new ether derivatives (2-37) was designed and semisynthesized using a high-yielding one-step reaction. In addition, the insecticidal and antibacterial activities of all geodin congeners were evaluated systematically. Most of these derivatives showed better insecticidal activities against Helicoverpa armigera Hübner than 1. In particular, 15 showed potent insecticidal activity with an IC50 value of 89 µM, comparable to the positive control azadirachtin (IC50 = 70 µM). Additionally, 5, 12, 13, 16, 30 and 33 showed strong antibacterial activity against Staphylococcus aureus and Aeromonas salmonicida with MIC values in the range of 1.15-4.93 µM. The preliminary structure-activity relationships indicated that the introduction of halogenated benzyl especially fluorobenzyl, into 1 and substitution of 4-OH could be key factors in increasing the insecticidal and antibacterial activities of geodin.


Asunto(s)
Antibacterianos/farmacología , Benzofuranos/farmacología , Insecticidas/farmacología , Animales , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Aspergillus/metabolismo , Benzofuranos/química , Benzofuranos/aislamiento & purificación , Concentración 50 Inhibidora , Insecticidas/química , Insecticidas/aislamiento & purificación , Pruebas de Sensibilidad Microbiana , Mariposas Nocturnas/efectos de los fármacos , Relación Estructura-Actividad
10.
Mar Drugs ; 20(2)2022 Feb 16.
Artículo en Inglés | MEDLINE | ID: mdl-35200673

RESUMEN

In this review, we summarized the distribution of the chemically investigated Oceanapia sponges, including the isolation and biological activities of their secondary metabolites, covering the literature from the first report in 1989 to July 2019. There have been 110 compounds reported during this period, including 59 alkaloids, 33 lipids, 14 sterols and 4 miscellaneous compounds. Besides their unique structures, they exhibited promising bioactivities ranging from insecticidal to antibacterial. Their complex structural characteristics and diverse biological properties have attracted a great deal of attention from chemists and pharmaceuticals seeking to perform their applications in the treatment of disease.


Asunto(s)
Productos Biológicos/aislamiento & purificación , Poríferos/metabolismo , Alcaloides/química , Alcaloides/aislamiento & purificación , Alcaloides/farmacología , Animales , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Antibacterianos/farmacología , Productos Biológicos/química , Productos Biológicos/farmacología , Humanos , Insecticidas/química , Insecticidas/aislamiento & purificación , Insecticidas/farmacología , Lípidos/química , Lípidos/aislamiento & purificación , Lípidos/farmacología , Metabolismo Secundario , Esteroles/aislamiento & purificación , Esteroles/farmacología
11.
Molecules ; 27(3)2022 Jan 25.
Artículo en Inglés | MEDLINE | ID: mdl-35164055

RESUMEN

Rice weevil, Sitophilus oryzae L. (Coleoptera: Curculionidae), is one of the most destructive stored-product pests that is resistant to a wide range of chemical insecticides. In the present study, we investigated whether a lectin extracted from Polygonum persicaria L. (PPA) can be used as a biorational agent to control such insect pests. Along with the lethal digestive assay, the sub-lethal insecticidal activities of PPA, including the effects on digestive, detoxifying, and antioxidant enzyme activities, were evaluated against S. oryzae adults. The effect of feeding a diet containing PPA and carob extract as a food attractant on the mortality of S. oryzae adults was also investigated. Feeding on the diet containing PPA resulted in a significant mortality of S. oryzae adults with a LC50 (Lethal Concentration to kill 50% of insects) of 3.68% (w/w). The activity of digestive enzymes, including α-amylase, α-glucosidase, TAG-lipase, trypsin, chymotrypsin, elastase, and carboxy- and aminopeptidase, were decreased by the sub-lethal concentration of PPA. Detoxifying and antioxidant enzymes, including esterase, superoxide dismutase, catalase, glutathione-S-transferase, ascorbate peroxidase, glucose 6-phosphate dehydrogenase, and malondialdehyde, were activated in adults affected by PPA. These findings indicated that PPA, in addition to causing digestive disorders, leads to oxidative stress in S. oryzae. The presence of carob extract had no effect on the PPA-induced mortality of the insect. According to the results of the present study, PPA has promising insecticidal efficiency against S. oryzae. In addition, the usage of PPA with a food attractant carob extract in bait traps can be recommended as a new biorational formulation in S. oryzae management.


Asunto(s)
Insecticidas/farmacología , Lectinas/farmacología , Extractos Vegetales/farmacología , Polygonum/química , Gorgojos/efectos de los fármacos , Animales , Activación Enzimática/efectos de los fármacos , Insecticidas/aislamiento & purificación , Lectinas/aislamiento & purificación , Estrés Oxidativo/efectos de los fármacos
12.
Bioorg Med Chem ; 54: 116560, 2022 01 15.
Artículo en Inglés | MEDLINE | ID: mdl-34923389
13.
Parasit Vectors ; 14(1): 595, 2021 Dec 04.
Artículo en Inglés | MEDLINE | ID: mdl-34863250

RESUMEN

BACKGROUND: Mosquitoes transmit a variety of diseases. Due to widespread insecticide resistance, new effective pesticides are urgently needed. Entomopathogenic fungi are widely utilized to control pest insects in agriculture. We hypothesized that certain fungal metabolites may be effective insecticides against mosquitoes. METHODS: A high-throughput cytotoxicity-based screening approach was developed to search for insecticidal compounds in our newly established global fungal extract library. We first determined cell survival rates after adding various fungal extracts. Candidate insecticides were further analyzed using traditional larval and adult survival bioassays. RESULTS: Twelve ethyl acetate extracts from a total of 192 fungal extracts displayed > 85% inhibition of cabbage looper ovary cell proliferation. Ten of these 12 candidates were confirmed to be toxic to Anopheles gambiae Sua5B cell line, and six showed > 85% inhibition of Anopheles mosquito cell growth. Further bioassays determined a LC50, the lethal concentration that kills 50% of larval or adult mosquitoes, of 122 µg/mL and 1.7 µg/mosquito, respectively, after 24 h for extract 76F6 from Penicillium toxicarium. CONCLUSIONS: We established a high-throughput MTT-based cytotoxicity screening approach for the discovery of new mosquitocides from fungal extracts. We discovered a candidate extract from P. toxicarium that exhibited high toxicity to mosquito larvae and adults, and thus were able to demonstrate the value of our recently developed approach. The active fungal extracts discovered here are ideal candidates for further development as mosquitocides.


Asunto(s)
Anopheles/efectos de los fármacos , Hongos/química , Insecticidas/farmacología , Mosquitos Vectores/efectos de los fármacos , Penicillium/química , Enfermedades Transmitidas por Vectores/prevención & control , Animales , Femenino , Resistencia a los Insecticidas , Insecticidas/aislamiento & purificación , Dosificación Letal Mediana , Control de Mosquitos
14.
PLoS One ; 16(11): e0260281, 2021.
Artículo en Inglés | MEDLINE | ID: mdl-34843539

RESUMEN

BACKGROUND: There is a growing need to use green alternative larvicidal control for Aedes larvae compared to chemical insecticides. Substantial reliance on chemical insecticides caused insecticide resistance in mosquito populations. Thus, research for alternate chemical compounds from natural products is necessary to control Aedes larvae. This study explores the analysis of chemical compositions from Areca catechu nut as a potential larvicide for Aedes (Diptera: Culicidae). METHODS: The Areca catechu nut collected from Ipoh, Perak, Malaysia was grounded into powder and used for Soxhlet extraction. The chemical analysis of the extracts and their structures were identified using the GCMS-QP2010 Ultra (Shimadzu) system. National Institute of Standards and Technology (NIST) Chemistry WebBook, Standard Reference Database 69 (https://webbook.nist.gov/chemistry/) and PubChem (https://pubchem.ncbi.nlm.nih.gov/), the two databases used to retrieve the synonyms, molecular formula, molecular weight, and 2-dimensional (2D) structure of chemical compounds. Next, following WHO procedures for larval bioassays, the extracts were used to asses larvicidal activity against early 4th instar larvae of Aedes aegypti and Aedes albopictus. RESULTS: The larvicidal activities were observed against early 4th stage larvae with different concentrations in the range from 200 mg/L to 1600 mg/L. The LC50 and LC95 of Aedes aegypti were 621 mg/L and 2264 mg/L respectively; whereas the LC50 and LC95 of Aedes albopictus were 636 mg/L and 2268 mg/L respectively. Mortality was not observed in the non-target organism test. The analysis using gas chromatography and mass spectrometer recovered several chemical compounds such as Arecaidine, Dodecanoic acid, Methyl tetradecanoate, Tetradecanoic acid , and n-Hexadecanoic acid bioactive components. These chemical constituents were used as additive formulations in pesticides, pest control, insect repellent, and insecticidal agents. CONCLUSIONS: Our study showed significant outcomes from the extract of Areca catechu nut and it deserves further investigation in relation to chemical components and larvicidal actions between different species of Aedes mosquitoes. Even though all these findings are fundamental, it may have some interesting potentials to be developed as natural bio-larvicidal products.


Asunto(s)
Aedes/efectos de los fármacos , Areca/química , Insecticidas/toxicidad , Nueces/química , Extractos Vegetales/toxicidad , Aedes/fisiología , Animales , Control de Insectos , Repelentes de Insectos/química , Repelentes de Insectos/aislamiento & purificación , Repelentes de Insectos/toxicidad , Insecticidas/química , Insecticidas/aislamiento & purificación , Larva/efectos de los fármacos , Larva/fisiología , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación
15.
Molecules ; 26(21)2021 Oct 22.
Artículo en Inglés | MEDLINE | ID: mdl-34770794

RESUMEN

The sustainability of agroecosystems are maintained with agro-chemicals. However, after more than 80 years of intensive use, many pests and pathogens have developed resistance to the currently used chemistries. Thus, we explored the isolation and bioactivity of a chemical compound, Precocene I, isolated from the perennial grass, Desmosstachya bipinnata (L.) Stapf. Fractions produced from chloroform extractions showed suppressive activity on larvae of Spodoptera litura (Lepidoptera: Noctuidae), the Oriental armyworm. Column chromatography analyses identified Precocene I confirmed using FTIR, HPLC and NMR techniques. The bioactivity of the plant-extracted Dp-Precocene I was compared to a commercially produced Precocene I standard. The percentage of mortality observed in insects fed on plant tissue treated with 60 ppm Db-Precocene I was 97, 87 and 81, respectively, for the second, third and fourth instar larvae. The LC50 value of third instars was 23.2 ppm. The percentages of survival, pupation, fecundity and egg hatch were altered at sub-lethal concentrations of Db-Precocene I (2, 4, 6 and 8 ppm, sprays on castor leaves). The observed effects were negatively correlated with concentration, with a decrease in effects as concentrations increased. Distinct changes in feeding activity and damage to gut tissues were observed upon histological examination of S. litura larvae after the ingestion of Db-Precocene I treatments. Comparative analyses of mortality on a non-target organism, the earthworm, Eisenia fetida, at equal concentrations of Precocene I and two chemical pesticides (cypermethrin and monocrotophos) produced mortality only with the chemical pesticide treatments. These results of Db-Precocene I as a highly active bioactive compound support further research to develop production from the grass D. bipinnata as an affordable resource for Precocene-I-based insecticides.


Asunto(s)
Anélidos/efectos de los fármacos , Benzopiranos/farmacología , Insecticidas/farmacología , Extractos Vegetales/farmacología , Poaceae/química , Spodoptera/efectos de los fármacos , Animales , Benzopiranos/química , Benzopiranos/aislamiento & purificación , Insecticidas/química , Insecticidas/aislamiento & purificación , Pruebas de Sensibilidad Parasitaria , Fitoquímicos/química , Fitoquímicos/farmacología , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Análisis Espectral
16.
Steroids ; 176: 108933, 2021 12.
Artículo en Inglés | MEDLINE | ID: mdl-34695457

RESUMEN

The steroidal glycoalkaloid α-tomatine (αTM) and its aglycone tomatidine (TD) are abundant in the skin of unripe green tomato and present in tomato leaves and flowers. They mainly serve as defensive agents to protect the plant against infections by insects, bacteria, parasites, viruses, and fungi. In addition, the two products display a range of pharmacological properties potentially useful to treat various human diseases. We have analyzed all known pharmacological activities of αTM and TD, and the corresponding molecular targets and pathways impacted by these two steroidal alkaloids. In experimental models, αTM displays anticancer effects, particularly strong against androgen-independent prostate cancer, as well as robust antifungal effects. αTM is a potent cholesterol binder, useful as a vaccine adjuvant to improve delivery of protein antigens or therapeutic oligonucleotides. TD is a much less cytotoxic compound, able to restrict the spread of certain viruses (such as dengue, chikungunya and porcine epidemic diarrhea viruses) and to provide cardio and neuro-protective effects toward human cells. Both αTM and TD exhibit marked anti-inflammatory activities. They proceed through multiple signaling pathways and protein targets, including the sterol C24 methyltransferase Erg6 and vitamin D receptor, both directly targeted by TD. αTM is a powerful regulator of the NFkB/ERK signaling pathway implicated in various diseases. Collectively, the analysis shed light on the multitargeted action of αTM/TD and their usefulness as chemo-preventive or chemotherapeutic agents. A novel medicinal application for αTM is proposed.


Asunto(s)
Antiinfecciosos/farmacología , Antiinflamatorios/farmacología , Antineoplásicos Fitogénicos/farmacología , Antiparasitarios/farmacología , Insecticidas/farmacología , Solanum lycopersicum/química , Antiinfecciosos/química , Antiinfecciosos/aislamiento & purificación , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Antiparasitarios/química , Antiparasitarios/aislamiento & purificación , Humanos , Insecticidas/química , Insecticidas/aislamiento & purificación , Conformación Molecular , Tomatina/análogos & derivados , Tomatina/química , Tomatina/aislamiento & purificación , Tomatina/farmacología
17.
Molecules ; 26(19)2021 Oct 02.
Artículo en Inglés | MEDLINE | ID: mdl-34641534

RESUMEN

Spodoptera litura Fab. is a polyphagous pest causing damage to many agriculture crops leading to yield loss. Recurrent usage of synthetic pesticides to control this pest has resulted in resistance development. Plant-derived diterpenoid compound andrographolide was isolated from the leaves of Andrographis paniculata. It was analysed by gas chromatography-mass spectroscopy and quantified by HPLC. Nutritional indices and digestive enzymatic profile were evaluated. Third, fourth and fifth instar larvae were treated with different concentrations of andrographolide. At 3, 6 and 9 ppm-treated concentrations the larvae showed decreased RGR, RCR, ECI, ECD values with adverse increase in AD. The digestive enzymes were significantly inhibited when compared with control. Conspicuously, andrographolide showed pronounced mortality of S. litura by inhibition of enzyme secretion and intake of food. The binding ability of andrographolide with CYTP450 showed high affinity with low binding energy. Andrographolide has the potential to be exploited as a biocontrol agent against S. litura as an eco-friendly pesticide.


Asunto(s)
Sistema Enzimático del Citocromo P-450/metabolismo , Diterpenos/farmacología , Proteínas de Insectos/metabolismo , Insecticidas/farmacología , Spodoptera/efectos de los fármacos , Amilasas/metabolismo , Andrographis/química , Animales , Diterpenos/aislamiento & purificación , Diterpenos/metabolismo , Diterpenos/toxicidad , Relación Dosis-Respuesta a Droga , Inactivación Metabólica/efectos de los fármacos , Insecticidas/aislamiento & purificación , Insecticidas/metabolismo , Insecticidas/toxicidad , Larva/efectos de los fármacos , Lipasa/metabolismo , Simulación del Acoplamiento Molecular , Péptido Hidrolasas/metabolismo
18.
Chem Biodivers ; 18(12): e2100594, 2021 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-34704347

RESUMEN

Terrein is a small-molecule polyketide compound with a simple structure mainly isolated from fungi. Since its discovery in 1935, many scholars have conducted a series of research on its structure identification, isolation source, production increase, synthesis and biological activity. Studies have shown that terrein has a variety of biological activities, not only can inhibit melanin production and epidermal hyperplasia, but also has anti-cancer, anti-inflammatory, anti-angiopoietic secretion, antibacterial, insecticidal activities, and so on. It has potential application prospects in beauty, medicine, agriculture and other fields. This article reviews the process of structural identification of terrein since 1935, and summarizes the latest advances in its isolation, source, production increase, synthesis, and biological activity evaluation, with a view to providing a reference and helping for the in-depth research of terrein.


Asunto(s)
Antibacterianos/farmacología , Antineoplásicos/farmacología , Ciclopentanos/farmacología , Fusarium/efectos de los fármacos , Insecticidas/farmacología , Schistosoma mansoni/efectos de los fármacos , Animales , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Aspergillus/química , Proliferación Celular/efectos de los fármacos , Ciclopentanos/química , Ciclopentanos/aislamiento & purificación , Humanos , Insecticidas/química , Insecticidas/aislamiento & purificación , Estructura Molecular
19.
PLoS One ; 16(8): e0255751, 2021.
Artículo en Inglés | MEDLINE | ID: mdl-34358278

RESUMEN

The changes in residual amounts of an insecticide (etofenprox) in processed rice cakes and cookies were investigated in this study. Test samples were sprayed with etofenprox during rice cultivation, and brown rice samples were dipped in a pesticide solution to investigate the effects of washing and processing. A multiresidue method for multiclass pesticides was employed for etofenprox analysis using a high-performance liquid chromatography-ultraviolet detector setup. Etofenprox was not detected in polished rice that was processed into rice cakes and cookies. The etofenprox residue levels were 2.13 mg/kg in each processing stage of brown rice products that were dipped in 400 mg/kg etofenprox solutions. The residual amounts of etofenprox in washed/polished rice and rice flour obtained by grinding were 1.25 and 0.77 mg/kg, respectively. The residual levels were 0.38 mg/kg in rice cakes prepared by cooking rice flour in a steamer for 20 min (a decrease of 82.1% compared to that in polished rice), 0.47 mg/kg in rice cookies baked in an oven for 20 min (a decrease of 78.0%), and 0.21 mg/kg in fried rice cookies (a decrease of 90.2%). Overall, the residual levels of etofenprox decreased in a range of 40-100% during the processing of rice cakes and cookies.


Asunto(s)
Insecticidas/aislamiento & purificación , Oryza/química , Residuos de Plaguicidas/aislamiento & purificación , Plaguicidas/aislamiento & purificación , Piretrinas/aislamiento & purificación , Cromatografía Líquida de Alta Presión , Culinaria , Harina/análisis , Análisis de los Alimentos , Manipulación de Alimentos , Humanos , Insecticidas/química , Oryza/efectos de los fármacos , Residuos de Plaguicidas/química , Plaguicidas/química , Piretrinas/química
20.
Chem Biodivers ; 18(11): e2100497, 2021 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-34453396

RESUMEN

Among the alternatives to environmentally toxic and socio-economically unacceptable chemical pesticides, essential oils from Ocimum gratissimum and Cymbopogon citratus were tested on the main pests and beneficial insects of the cotton plant in Côte d'Ivoire. After extraction and chemical analysis of the essential oils, field trials were carried out using a Fisher block system with three treatment repetitions where their effects compared with those of a registered synthetic insecticide (IBIS A 52 EC). Foliar applications of the products were carried out in accordance with the cotton plant protection extension programme in Côte d'Ivoire from the 45th to the 115th day after plant emergence, with one application every fortnight. Twenty-three and forty compounds representing about 96 and 99 % of the oil composition of O. gratissimum and C. citratus respectively were elucidated. The most abundant compounds were p-cymene and thymol (O. gratissimum) and myrcene, neral and geranial (C. citratus). The essential oil of O. gratissimum at concentrations of 2 and 5 % showed insecticidal activity on all pests (biting-sucking and carpophagous), except the phyllophagous Syllepte derogata. C. citratus, at a low concentration (1 %), was particularly toxic to whiteflies (Bemisia tabaci), however, it favoured the action of beneficial insects, specifically black ants and ladybirds in the cotton plots, unlike the chemical product. EO of O. gratissimum (1.60 and 4.62 mg GALAE/g, respectively) and C. citratus (2.26 and 2.78 mg GALAE, respectively) exhibited also significant acetyl and butyryl cholinesterase inhibitors. Insecticide formulations based on the essential oils of O. gratissimum and C. citratus offer favourable prospects for their use in cotton cultivation as an alternative to chemical pesticides.


Asunto(s)
Cymbopogon/química , Insectos/efectos de los fármacos , Insecticidas/farmacología , Ocimum/química , Aceites Volátiles/farmacología , Animales , Côte d'Ivoire , Insecticidas/química , Insecticidas/aislamiento & purificación , Aceites Volátiles/química , Aceites Volátiles/aislamiento & purificación
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