Atividade alelopática de chalcona sintética, de seus precursores e de cetonas e aldeídos relacionados

Bitencourt, Heriberto Rodrigues; Santos, Lourivaldo S.; Filho, A.P.S. Souza

doi:10.1590/s0100-83582007000400011

Cited by 16 publications

(8 citation statements)

References 13 publications

(8 reference statements)

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“…Although no previous in‐depth research regarding chalcone effects on plant metabolism has been done, some studies have shown the potential of this secondary metabolite to inhibit the germination of different plant species (Chen et al . 2004; Bitencourt, Santos & Souza 2007). Recently, Chen et al .…”

Section: Introductionmentioning

confidence: 99%

The natural compound trans‐chalcone induces programmed cell death in Arabidopsis thaliana roots

Díaz‐Tielas

Graña

Sotelo

et al. 2012

Plant Cell & Environment

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Chalcone (1,3-diphenyl-2-propen-1-one) is an aromatic ketone precursor of important molecules in plants such as flavonoids or anthocyanins. Its phytotoxicity has been demonstrated on different plant species, but to date little is known about the mechanisms of action of this secondary metabolite at plant cellular level. Detailed analysis by light and transmission electron microscopy (TEM) was conducted to examine the root meristems' ultrastructure of control and chalcone-treated Arabidopsis seedlings. Mitochondrial dysfunction was analysed by measuring mitochondrial membrane potential with JC-1 fluorochrome. Finally, acridine orange/ethidium bromide staining was used for the detection of programmed cell death. Microscopy revealed tissue alterations, inhibition of root hair formation and important changes after 7 and 14 d at the chalcone IC50 value. Chalcone-treated cells showed signs of programmed cell death such as mitochondrial condensation, disruption of organelles and chromatin fragmentation. Acridine orange/ethidium bromide staining confirmed the programmed cell death, which could be induced by the reduction of mitochondrial transmembrane potential (DYm) that was detected after chalcone treatment. These results confirm the phytotoxic activity of chalcone on Arabidopsis seedlings, the alteration of mitochondrial membrane potential and the induction of programmed cell death.

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Section: Introductionmentioning

confidence: 99%

The natural compound trans‐chalcone induces programmed cell death in Arabidopsis thaliana roots

Díaz‐Tielas

Graña

Sotelo

et al. 2012

Plant Cell & Environment

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“…Alguns fatores podem determinar maior competitividade das plantas daninhas sobre as espécies cultivadas, destacando-se o porte e a arquitetura; a velocidade de germinação e estabelecimento da plântula; a velocidade do crescimento e extensão do sistema de raízes; a suscetibilidade às intempéries climáticas, como veranicos e geadas; e a capacidade de produção e liberação de substâncias químicas com propriedades alelopáticas (Bitencourt et al, 2007;Rizzardi et al, 2008). Destacam-se também algumas espécies daninhas que podem alocar maior quantidade de assimilados às folhas; assim, elas desenvolvem maior área foliar e, consequentemente, maior interceptação luminosa e taxa fotossintética, aumentando a capacidade competitiva (Larcher, 2006).…”

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Habilidade competitiva de plantas de arroz com biótipos de capim-arroz resistente ou suscetível ao quinclorac

Tironi

Galon²,

Concenço³

et al. 2009

Planta daninha

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RESUMO -Objetivou-se com este trabalho avaliar a habilidade competitiva de plantas de arroz cultivar BRS Pelota com biótipos de capim-arroz resistente ou suscetível ao herbicida quinclorac. Para isso, foi instalado experimento em casa de vegetação, em delineamento completamente casualizado com quatro repetições, sendo os tratamentos dispostos em esquema fatorial 2 x 6. As unidades experimentais constaram de vasos plásticos contendo 10 dm 3 de solo, cujo pH e nível de nutrientes foram previamente corrigidos. Os tratamentos consistiram na competição entre uma planta de arroz, cultivar BRS Pelota, com populações (0, 1, 2, 3, 4 ou 5 plantas por vaso) dos biótipos de capim-arroz resistente (ECH-13) ou suscetível (ECH-12) ao herbicida quinclorac. As avaliações foram realizadas aos 40 dias após emergência, sendo avaliados; massa seca da parte aérea (MSPA), taxa de crescimento (TC), área foliar específica (AFE), razão de massa foliar (RMF), razão de área foliar (RAF) e índice de área foliar (IAF). A interferência no desenvolvimento do cultivar de arroz BRS Pelota foi proporcionalmente maior com o aumento da população de ambos os biótipos de capim-arroz. Os biótipos apresentaram, em geral, habilidade competitiva similar.Palavras-chave: Echinochloa spp., Oryza sativa, interferência, índices relativos.ABSTRACT -The objective of this study was to evaluate the competitive ability of the rice cultivar BRS Pelota with biotypes resistant or susceptible to the herbicide Quinclorac. The experiment was conducted under greenhouse conditions in a completely randomized design with four replications, with the treatments arranged in a 2 x 6 factorial. The experimental units consisted of plastic pots containing 10 dm 3 of soil, with pH and nutrient level being previously corrected. The treatments consisted of a competition between a rice plant, BRS Pelota cultivar, with populations (0, 1, 2, 3, 4 or 5 plants per pot) of the barnyardgrass biotypes resistant (ECH-13) or susceptible (ECH -12) to the herbicide Quinclorac. The evaluations were performed at 40 DAE,including shoot dry weight (MSPA), growth rate (TC), specific leaf area (SLA), leaf mass ratio (LWR), leaf area ratio (LAR) and leaf area index (LAI). The interference in the development of the BRS Pelota rice cultivar was proportionally higher with population increase of both barnyardgrass biotypes. The biotypes showed, in general, similar competitive ability.

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“…The chalcones 1 (68.5% yield), 27 2 (75.0% yield) 28 and 3 (60.0% yield) 29 were synthesized using methodology described in the literature 18 and their structures were determined by the analysis of 1D-and 2D-NMR, mass spectral information and comparison with reported physical and spectroscopic data. These chalcones were bioreduced by Aspergillus flavus producing the dihydrochalcones 4 (74.5% yield), 5 (36.3% yield) and 6 (15.6% yield), respectively, after 10 days of reaction ( Figure 1).…”

Section: Resultsmentioning

confidence: 99%

“…[10][11][12][13] Chalcones are precursors of the flavonoids and are defined as α,ß-unsaturated ketones in which both the carbonyl and the olefinic fragment are linked to an aromatic ring. They possess a large spectrum of action, such as antiviral activity, 14 inhibition of NS3 protease of dengue virus, 15 activity against herpes simplex virus, 16 HIV-1 replication inhibition in lymphocytes-H9 in mice, 17 allelopathic activity, 18 anti-inflammatory and antibacterial properties. 19 These activities have been raising the interest in synthesizing and characterizing different chalcones, in order to obtain the corresponding dihydrochalcones to correlate structure versus biological activity.…”

Section: Introductionmentioning

confidence: 99%

Biotransformation of chalcones by the endophytic fungus Aspergillus flavus isolated from Paspalum maritimum trin

Corrêa¹,

Nunes²,

Bitencourt³

et al. 2011

J. Braz. Chem. Soc.

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O fungo Aspergillus flavus isolado como endofítico da planta Paspalum maritimum Trin. foi avaliado quanto ao seu potencial de aplicação em reações de biotransformações. Os compostos chalcona (1), 3,4,5-trimetoxichalcona (2) e 2,3,4,4'-tetrametoxichalcona (3) foram biotransformados, respectivamente, na diidrochalcona (4), 3,4,5-trimetoxidiidrochalcona (5) e 2,3,4,4'-tetrametoxidiidrochalcona (6). As estruturas destes compostos foram determinadas por análises de RMN uni e bidimensionais e por espectrometria de massas. As diidrochalconas 5 e 6 são substâncias inéditas. The fungus Aspergillus flavus isolated as endophytic of the plant Paspalum maritimumTrin. was evaluated for its potential application in biotransformation reactions. The compounds chalcone (1), 3,4,5-trimethoxychalcone (2) and 2,3,4,4'-tetramethoxychalcone (3) were biotransformed, respectively, in dihydrochalcone (4), 3,4,5-trimethoxydihydrochalcone (5) and 2,3,4,4'-tetramethoxydihydrochalcone (6). The structures were elucidated by spectroscopic methods including 1D and 2D NMR techniques, and MS analysis. The dihydrochalcones 5 and 6 are new compounds.

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Atividade alelopática de chalcona sintética, de seus precursores e de cetonas e aldeídos relacionados

Cited by 16 publications

References 13 publications

The natural compound trans‐chalcone induces programmed cell death in Arabidopsis thaliana roots

The natural compound trans‐chalcone induces programmed cell death in Arabidopsis thaliana roots

Habilidade competitiva de plantas de arroz com biótipos de capim-arroz resistente ou suscetível ao quinclorac

Biotransformation of chalcones by the endophytic fungus Aspergillus flavus isolated from Paspalum maritimum trin

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