In the present work, we have investigated the effect of essential oils obtained from Origanum vulgare L. (oregano) and Thymus vulgaris L. (thyme) on growth and ultrastructure of diverse evolutive forms of Trypanosoma cruzi. Culture epimastigotes and bloodstream trypomastigotes were incubated for 24 h with different concentrations of oregano or thyme essential oils and with thymol (the main constituent of thyme), and the inhibitory concentration (IC)(50) was determined by cell counting. Crude extract of oregano essential oil inhibited epimastigote growth (IC(50)/24 h = 175 microg/ml) and also induced trypomastigote lysis (IC(50)/24 h = 115 microg/ml). Thyme essential oil presented IC(50)/24 h values of 77 microg/ml for epimastigotes and 38 mug/ml for trypomastigotes, while treatment with thymol resulted in an IC(50)/24 h of 62 microg/ml for epimastigotes and 53 microg/ml for trypomastigotes. Scanning electron microscopy of treated cells showed few morphological alterations at the plasma membrane. Observation by transmission electron microscopy showed cytoplasmic swelling with occasional morphological alterations in plasma and flagellar membrane. Our data indicate that oregano and thyme essential oils are effective against T. cruzi, with higher activity of thyme, and that thymol may be the main component responsible for the trypanocidal activity.

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This study analyses the anti-proliferative effect of lemongrass essential oil and its main constituent (citral) on all 3 evolutive forms of Trypanosoma cruzi. Steam distillation was used to obtain lemongrass essential oil, with chemical composition determined by gas chromatography (GC) and GC coupled to mass spectrometry (GC-MS). The IC50/24 h (concentration that reduced the parasite population by 50%) of the oil and of citral upon T. cruzi was determined by cell counting in a Neubauer chamber, while morphological alterations were visualized by scanning and transmission electron microscopy. Treatment with the essential oil resulted in epimastigote growth inhibition with IC50=126.5 microg/ml, while the IC50 for trypomastigote lysis was 15.5 microg/ml. The IC50/48 h for the Association Index (% macrophage infection x number of amastigotes per cell) was 5.1 microg/ml, with a strong inhibition of intracellular amastigote proliferation. Ultrastructural analysis demonstrated cytoplasmic and nuclear extraction, while the plasma membrane remained morphologically preserved. Our data show that lemongrass essential oil is effective against T. cruzi trypomastigotes and amastigotes, and that its main component, citral, is responsible for the trypanocidal activity. These results indicate that essential oils can be promising anti-parasitic agents, opening perspectives to the discovery of more effective drugs of vegetal origin for treatment of parasitic diseases. However, additional cytotoxicity experiments on different cell lines and tests in a T. cruzi-mouse model are needed to support these data.

The free energy profile of the piperidine catalyzed Knoevenagel condensation reaction of acetylacetone with benzaldehyde has been obtained by theoretical calculations. The carbinolamine formation step involves catalysis by methanol solvent, and its decomposition takes place via hydroxide ion elimination without a classical transition state, leading to the iminium ion. Hydroxide ion deprotonates the acetylacetone, forming an enolate that attacks the iminium ion and leads to an addition intermediate. The final step involves elimination of piperidine catalyst. Our analysis suggests the iminium ion formation has the highest barrier and the catalytic effect of piperidine is facilitating the elimination step rather than activation of the benzaldehyde electrophile. Experimental measures of the kinetics lead to an observed free energy barrier of 20.0 kcal mol, in good agreement with the theoretical value of 21.8 kcal mol based on the free energy profile.

RESUMO:Objetivou-se determinar o rendimento, a composição química e avaliar a atividade antilisterial dos óleos essenciais de Cymbopogon citratus (DC.) Stapf. (capim-limão) e Cymbopogon nardus (L.) Rendle (capim-citronela), puros e em combinação. A obtenção dos óleos essenciais foi realizada a partir de folhas frescas, empregando-se a técnica de hidrodestilação e utilizandose aparelho de Clevenger modificado. Os rendimentos foram calculados a partir da massa obtida na extração e da umidade do material vegetal. A análise qualitativa foi realizada por cromatografia em fase gasosa acoplada à espectrometria de massas e a avaliação dos teores dos constituintes químicos por cromatografia em fase gasosa com detector de ionização de chamas. O efeito bacteriostático de diferentes concentrações dos óleos essenciais, puros e em combinação, foi determinado pela técnica de difusão em ágar. As concentrações mínimas inibitórias (CMIs) foram utilizadas na determinação do tempo de ação bactericida. O rendimento, em base seca, foi de 1,39% (v/p) para o óleo essencial de C. citratus e de 2,27% (v/p) para o óleo essencial de C. nardus. Geranial e neral foram os constituintes majoritários do óleo essencial de C. citratus, enquanto, para C. nardus, foram citronelal, geraniol e citronelol. A maioria das concentrações utilizadas mostrou-se efetiva contra Listeria monocytogenes e observaram-se efeitos bactericidas nas CMIs. Óleos essenciais de C. citratus e C. nardus, puros e em combinação, constituem novas alternativas de antibacterianos naturais a serem utilizados no controle de L. monocytogenes na indústria de alimentos. Palavras-chave: Cymbopogon citratus, Cymbopogon nardus, óleos essenciais, atividade antibacteriana, Listeria monocytogenes ABSTRACT: Yield, chemical composition and antilisterial activity of essential oils fromCymbopogon species. The aim of this study was to determine the yield and the chemical composition of essential oils from Cymbopogon citratus (DC.) Stapf. (lemongrass) and Cymbopogon nardus (L.) Rendle (citronella), and to evaluate their antilisterial activity when pure and combined. The essential oils were obtained from fresh leaves through hydrodistillation by using a modified Clevenger-type device. Yield was calculated based on the extracted mass and the plant humidity. The qualitative analysis was done by gas chromatography-mass spectrometry and the levels of the chemical components were detected by gas chromatography with flame ionization detector. The bacteriostatic effect of different concentrations of pure and combined essential oils was determined by the agar diffusion technique. Minimum inhibitory concentrations (MICs) were used to determine the time of bactericidal action. The yield was 1.39% (v w -1 dry basis) for C. citratus essential oil and 2.27% (v w -1 ) for C. nardus essential oil. Geranial and neral were the major components of C. citratus essential oil, while citronellal, geraniol and citronellol were predominant in C. nardus oil. Most of the used concentrations were efficient against Listeri...