Activity of chalcones derived from 2,4,5-trimethoxybenzaldehyde against Meloidogyne exigua and in silico interaction of one chalcone with a putative caffeic acid 3-O-methyltransferase from Meloidogyne incognita

Nunes, Alexandro da Silva; Campos, Vicente Paulo; Mascarello, Alessandra; Stumpf, Taisa Regina; Chiaradia-Delatorre, Louise Domenghini; Machado, Alan Rodrigues Teixeira; Júnior, Helvécio M. Santos; Yunes, Rosendo A.; Nunes, Ricardo José; Oliveira, Denilson F.

doi:10.1016/j.exppara.2013.10.003

Cited by 15 publications

(16 citation statements)

References 55 publications

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“…The 110 assayed synthetic compounds (Table S1, Supplementary information), were prepared as described in our previous reports [19][20][21][22][23][24][25][26][27][28][29] . Reagents were obtained from Sigma-Aldrich Õ (St. Louis, MO) and solvents from Vetec (Duque de Caxias, RJ, Brazil).…”

Section: Synthesis and Purification Of The Compoundsmentioning

confidence: 99%

“…The (E)-N 0 -benzylidene-benzohydrazides 83-99 were synthesized by condensation of the benzohydrazide (2 mmol) or 3,4,5-trimethoxy-benzohydrazide (2 mmol), with the appropriate aldehyde (2 mmol) in methanol (15 mL) and refluxed for 2 h. After cooling, the crude product was collected by filtration, washed and recrystallized from hot ethanol to give white solids [20][21][22][23][24][25][26][27][28][29] .…”

Section: Synthesis and Purification Of The Compoundsmentioning

confidence: 99%

“…The (E)-chalcones 1-82 were prepared by aldol condensation using methanol as solvent under basic conditions (KOH 50% w/v) at room temperature for 24 h. Distilled water and 10% hydrochloric acid were added to the reaction for total precipitation of the compounds, which were then obtained by vacuum filtration and later recrystallized in dichloromethane and hexane [20][21][22][23][24][25][26][27][28][29] . The (E)-N 0 -benzylidene-benzohydrazides 83-99 were synthesized by condensation of the benzohydrazide (2 mmol) or 3,4,5-trimethoxy-benzohydrazide (2 mmol), with the appropriate aldehyde (2 mmol) in methanol (15 mL) and refluxed for 2 h. After cooling, the crude product was collected by filtration, washed and recrystallized from hot ethanol to give white solids [20][21][22][23][24][25][26][27][28][29] .…”

Section: Synthesis and Purification Of The Compoundsmentioning

confidence: 99%

See 2 more Smart Citations

Synthetic compounds from an in house library as inhibitors of falcipain-2 from Plasmodium falciparum

Bertoldo¹,

Chiaradia-Delatorre²,

Mascarello³

et al. 2014

Journal of Enzyme Inhibition and Medicinal Chemistry

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Falcipain-2 (FP-2) is a key cysteine protease from the malaria parasite Plasmodium falciparum. Many previous studies have identified FP-2 inhibitors; however, none has yet met the criteria for an antimalarial drug candidate. In this work, we assayed an in-house library of non-peptidic organic compounds, including (E)-chalcones, (E)-N'-benzylidene-benzohydrazides and alkylesters of gallic acid, and assessed the activity toward FP-2 and their mechanisms of inhibition. The (E)-chalcones 48, 54 and 66 showed the lowest IC 50 values (8.5 ± 0.8 mM, 9.5 ± 0.2 mM and 4.9 ± 1.3 mM, respectively). The best inhibitor (compound 66) demonstrated non-competitive inhibition, and using mass spectrometry and fluorescence spectroscopy assays, we suggest a potential allosteric site for the interaction of this compound, located between the catalytic site and the hemoglobin binding arm in FP-2. We combined structural biology tools and mass spectrometry to characterize the inhibition mechanisms of novel compounds targeting FP-2.

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Section: Synthesis and Purification Of The Compoundsmentioning

confidence: 99%

Section: Synthesis and Purification Of The Compoundsmentioning

confidence: 99%

Section: Synthesis and Purification Of The Compoundsmentioning

confidence: 99%

See 1 more Smart Citation

Synthetic compounds from an in house library as inhibitors of falcipain-2 from Plasmodium falciparum

Bertoldo¹,

Chiaradia-Delatorre²,

Mascarello³

et al. 2014

Journal of Enzyme Inhibition and Medicinal Chemistry

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show abstract

“…Many synthetic chalcones are highly active against Meloidogyne exigua that causes important coffee crop losses (Nunes et al, 2013). The chalcone (2E)-1-(4´-nitrophenyl)-3-(2,4,5-trimethoxyphenyl) prop-2-en-1-one showed stronger nematicide activity than the commercial nematicide carbofuran.…”

Section: Nematicides Insect Deterrents and Antifeedantsmentioning

confidence: 99%

“…Fungicidal (Jayasinghe et al, 2004) 2',3',4',4-tetrahydroxy-chalcone Antiviral (Onyilagha et al, 1997) (2E)-1-(4´-nitrophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one Nematicide (Nunes et al, 2013) Derricin:…”

Section: Nematicides Insect Deterrents and Antifeedantsmentioning

confidence: 99%

Biological Activities and Novel Applications of Chalcones

et al. 2016

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-This review provides information on the biological activities of chalcones (whether natural or synthetic derivatives) on different organisms, as well as an overview of the functions and possible new applications of these plant secondary metabolites on crop protection, as eco-friendly pesticides and weed control agents. Naturally occurring chalcones have been used in traditional medicine for many years; however, recent scientific advances have shown that these molecules have a broad range of biological activities in a variety of organisms. A review on the major sources of chalcones and the main molecular events involved in the modes of action of these natural products is achieved. Chalcones are molecules with a broad spectrum of biological activities, which are of great interest in agriculture to control weeds and unwanted pests.Keywords: mode of action, secondary metabolites, crop protection, pesticide, fungicide, antiviral, phytotoxicity. RESUMO -Esta avaliação fornece informações sobre as atividades biológicas de chalconas (quer derivados naturais ou sintéticos) em diferentes organismos, bem como uma visão geral das funções e eventuais novas aplicações desses metabólitos secundários de plantas em proteção de cultivos e pesticidas orgânicos e para controlar as plantas daninhas. Durante muitos anos têm sido utilizadas na medicina tradicional chalconas de ocorrência natural; no entanto, os recentes avanços científicos têm mostrado que essas moléculas têm vasta gama de atividades biológicas em uma variedade de organismos. Este estudo permite ter uma ideia das principais fontes de chalconas e dos eventos moleculares envolvidos nos principais mecanismos de ação desses produtos naturais. As chalconas são moléculas com um largo espectro de atividade biológica, de grande interesse na agricultura para controlar plantas daninhas e pragas indesejadas.Palavras-chave: modo de ação, metabólitos secundários, proteção de cultivos, pesticida, fungicida, antiviral, fitotoxicidade.

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Nematicidal activity of acetophenones and chalcones against Meloidogyne incognita and structure–activity considerations

Caboni

Aissani

Demurtas

et al. 2015

Pest Management Science

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Activity of chalcones derived from 2,4,5-trimethoxybenzaldehyde against Meloidogyne exigua and in silico interaction of one chalcone with a putative caffeic acid 3-O-methyltransferase from Meloidogyne incognita

Cited by 15 publications

References 55 publications

Synthetic compounds from an in house library as inhibitors of falcipain-2 from Plasmodium falciparum

Synthetic compounds from an in house library as inhibitors of falcipain-2 from Plasmodium falciparum

Biological Activities and Novel Applications of Chalcones

Nematicidal activity of acetophenones and chalcones against Meloidogyne incognita and structure–activity considerations

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