Design, Synthesis and Bioassays of 3-substituted-3-hydroxyoxindoles for cholinesterase inhibition

Based on the positive bioassay results of the known oxindole hit compound rac-1-benzyl-3-hydroxy-3-phenylindolin-2-one which showed significant inhibition of butyrylcholinesterase (BuChE) (IC50=7.41 μM), a library of 31 analogues of 3-substituted-3-hydroxyoxindoles was synthesized and screened for both acetylcholinesterase (AChE) and BuChE activity. Our bioassays revealed that some of the new compounds exhibited moderate inhibition of eel AChE (EeAChE) and very good inhibition of equine serum BuChE (EqBuChE) with a best IC50 of 1.02 μM. On the basis of these results, the lead compound 1-((1-benzylpiperidin-4-yl)methyl)-3-hydroxy-3-phenylindolin-2-one was designed, which was shown to interact well with the enzymes active sites by molecular docking, was synthesized and upon bioassay gave an IC50 of 6.61 μM for BuChE. Interestingly, when we separated rac-benzyl-3-hydroxy-3-phenylindolin-2-one into the individual enantiomers (R)- and (S)-benzyl-3-hydroxy-3-phenylindolin-2-one it was the latter enantiomer that gave the best IC50 of 6.19 μM for BuChE.

Susceptibility and Interactions of Drosophila suzukii and Zaprionus indianus (Diptera: Drosophilidae) in Damaging Strawberry.

Resumo: Drosophila suzukii (Matsumura) foi recentemente detectado causando danos idade para morangos no Brasil. Infestação na cultura de morango tem frequentemente foi observado conjuntamente com a presença de Zaprionus indianus Gupta. este estudo investigou a suscetibilidade de morangos em três amadurecimento estágios para infestação de D. suzukii e Z. indianus e sua interação. Abstracts: Drosophila suzukii (Matsumura) has been recently detected causing damage to strawberries in Brazil. Infestation in strawberry culture has often been observed jointly with the presence of Zaprionus indianus Gupta. This study investigated the susceptibility of strawberries at three ripening stages to infestation of D. suzukii and Z. indianus and their interaction. In the laboratory, strawberries cv. Albion at different ripening stages (green, semi-ripe and ripe) were exposed to D. suzukii and Z. indianus for 24 h in choice and no-choice bioassays. Additionally, we evaluated the effects of mechanical damage incurred artificially or by D. suzukii ovi-position on Z. indianus infestation. In no-choice bioassay, there were no significant differences in fruit susceptibility to D. suzukii infestation at different ripening stages. However, in choice bioassay, D. suzukii adults preferred to oviposit on R fruit. The presence of mechanical damage did not increase susceptibility of fruit to D. suzukii oviposition. For Z. indianus , there was greater susceptibility of R fruit in relation to SR and G fruit in both the choice and no-choice bioassays. There was a significant and positive interaction of mechanical damage and damage caused by D. suzukii to R fruit and infestation by Z. indianus , which was not observed in SR and G fruit. Although infestation of Z. indianus is related to attack damaged or decaying fruit, this work shows that this species has the ability to oviposit and develop in healthy strawberry fruit with and increased infestation level when the fruit has damage to its epidermis.

Bioaccumulation and elimination of Endosulfan in zebra fish (Brachydanio rerio).

The bioaccumulation and elimination of endosulfan in zebra fish (Brachydanio rerio) were investigated in a semi-static bioassay. The pesticide mean concentration in water was 03ug litre(-1) and the level of endosulfan residues (x(alfa)+B(beta)-isomers+endosulfan sulfate) in the exposed fish at day 21 was 0.81 (+-0.12)ug g(-1) body weight. The estimated value of the bioconcentration factor (BCF) was 2650 (+-441), the total endosulfan residues being eliminated with a biological half-life of four days. Histopathological studies showed predominantly lipid accumulation in the liver and necrotic focus in the gills of exposed fish.

Ação alelopática de sementes de Canavalia ensiformis contra Cyperus rotundus.

Ação alelopática da leguminosa Canavalia ensiformis (feijão de porco) já é praticada em campo semeado com essa leguminosa. Tentativa de esclarecer o modo de ação, levou a testar as partes, raízes, caules, folhas moídas misturadas a terra, plantando-se em seguida os tubérculos de Cyperus rotundus L. em ambiente de laboratório ou em casa de vegetação. Utilizando copos plásticos com capacidade de 160ml, terra argilosa misturada com quantidades diferentes das partes acima citadas, não revelaram qualquer ação sobre a capacidade de brotação dos tubérculos do Cyperus. Utilizando o mesmo método com vagens secas do feijão de porco, e separadamente com sementes, foi possível observar pequena ação da vagem seca, e pronunciada ação das sementes moídas, observou que quantidades menores que 10g pouco afetavam a brotação. Todavia a partir de 15 g de sementes moídas, misturadas em copo plástico contendo 160 de terra argilosa demonstraram a ação inibitória de brotação dos tubérculos de Cyperus. Foram conduzidos 7 ensaios nos quais procurou-se adicionar a terra argilosa diferentes quantidades da semente moída, encontrando-se os resultados: nas doses de 5 a 7,5g houve redução de 47% de brotação; de 10 a 15g a redução dos tubérculos; com a aplicação de maior dose houve total inibição da brotação dos tubérculos do C. rotundus. O trabalho visa esclarecer qual o elemento contido na planta do feijão de porco que provoca redução sensível da populacao da invasora.

Susceptibility and Interactions of Drosophila suzukii and Zaprionus indianus (Diptera: Drosophilidae) in Damaging Strawberry.

Resumo: Drosophila suzukii (Matsumura) foi recentemente detectado causando danos idade para morangos no Brasil. Infestação na cultura de morango tem frequentemente foi observado conjuntamente com a presença de Zaprionus indianus Gupta. este estudo investigou a suscetibilidade de morangos em três amadurecimento estágios para infestação de D. suzukii e Z. indianus e sua interação. Abstracts: Drosophila suzukii (Matsumura) has been recently detected causing damage to strawberries in Brazil. Infestation in strawberry culture has often been observed jointly with the presence of Zaprionus indianus Gupta. This study investigated the susceptibility of strawberries at three ripening stages to infestation of D. suzukii and Z. indianus and their interaction. In the laboratory, strawberries cv. Albion at different ripening stages (green, semi-ripe and ripe) were exposed to D. suzukii and Z. indianus for 24 h in choice and no-choice bioassays. Additionally, we evaluated the effects of mechanical damage incurred artificially or by D. suzukii ovi-position on Z. indianus infestation. In no-choice bioassay, there were no significant differences in fruit susceptibility to D. suzukii infestation at different ripening stages. However, in choice bioassay, D. suzukii adults preferred to oviposit on R fruit. The presence of mechanical damage did not increase susceptibility of fruit to D. suzukii oviposition. For Z. indianus , there was greater susceptibility of R fruit in relation to SR and G fruit in both the choice and no-choice bioassays. There was a significant and positive interaction of mechanical damage and damage caused by D. suzukii to R fruit and infestation by Z. indianus , which was not observed in SR and G fruit. Although infestation of Z. indianus is related to attack damaged or decaying fruit, this work shows that this species has the ability to oviposit and develop in healthy strawberry fruit with and increased infestation level when the fruit has damage to its epidermis.