Leishmaniasis and trypanosomiasis are globally widespread parasitic diseases which have been responsible for high mortality rates. Since drugs available for their treatment are highly hepatotoxic, nephrotoxic and cardiotoxic, adherence to therapy has been affected. Thus, the search for new, more effective and safer drugs for the treatment of these diseases is necessary. Natural products have stood out as an alternative to searching for new bioactive molecules with therapeutic potential. In this study, the chemical composition and antiparasitic activity of the essential oil from Protium ovatum leaves against trypomastigote forms of Trypanosoma cruzi and the promastigote forms of Leishmania amazonensis were evaluated. The essential oil was promising against trypomastigote forms of T. cruzi (IC 50 = 28.55 μg.mL -1 ) and L.amazonensis promastigotes (IC 50 = 2.28 μg.mL -1 ). Eighteen chemical constituents were identified by GasChromatography coupled to Mass Spectrometry (GC-MS) in the essential oil, whose major constituents were spathulenol (17.6 %), caryophyllene oxide (16.4 %), β-caryophyllene (14.0 %) and myrcene (8.4 %).In addition, the essential oil from P. ovatum leaves had moderate cytotoxicity against LLCMK 2 adherent epithelial cell at the concentration range under analysis (CC 50 = 150.9 μg.mL -1 ). It should be highlighted that this is the first report of the chemical composition and anti-Trypanosoma cruzi and anti-Leishmania amazonensis activities of the essential oil from Protium ovatum leaves.
Artigo Composição Química e Atividades Biológicas dos Óleos Essenciais das Folhas Frescas de Citrus limonia Osbeck e Citrus latifolia Tanaka (Rutaceae)
-Chagas disease is a major neglected tropical disease caused by Trypanosoma cruzi. It has been treated with the antiparasitic drugs nifurtimox and benzonidazole, which cause several side effects. The market for natural products has considerably grown lately and the use of plants has become an alternative to the development of novel drugs to cure the disease. Therefore, this study aimed at describing the chemical analysis of the essential oil from green fruits of Protium ovatum and evaluating their trypanocidal and cytotoxic potential. The essential oil was obtained by Clevenger hydrodistillation whereas its chemical composition was determined by gas chromatography coupled to mass spectrometry (GC-MS). The major compounds found in the essential oil from green fruits of P. ovatum were β-myrcene (62.0 %), α-pinene (11.3 %) and limonene (7.3 %). To the best of our knowledge, this was the first time that the chemical composition of the essential oil from green fruits of P. ovatum was described. Results showed that the essential oil had strong trypanocidal activity against trypomastigote forms of theY strain of Trypanosoma cruzi (IC 50 = 1.2 µg/mL). In addition, the essential oil from green fruits of P. ovatum did not display cytotoxicity against LLCMK 2 adherent epithelial cell at the concentration range under analysis (CC 50 = 550.3 μg/mL). As a result, it is an excellent option for the development of novel antiparasitic drugs. Index terms: Protium ovatum, β-myrcene, fruits, essential oil, Trypanosoma cruzi, cytotoxic analysis. Composição química, atividades anti-Trypanosoma cruzi e citotóxica do óleo essencial dos frutos verdes de Protium ovatum (BURSERACEAE)Resumo -A doença de Chagas é uma das principais doenças tropicais negligenciadas causadas pelo Trypanosoma cruzi, e em seu tratamento utilizam-se medicamentos como o nifurtimox e o benzonidazol, que causam vários efeitos colaterais. O mercado de produtos naturais tem aumentado consideravelmente nos últimos anos, e o uso das plantas continua sendo uma alternativa para o desenvolvimento de novos medicamentos para cura de doenças. Portanto, este estudo aborda a composição química do óleo essencial dos frutos verdes de Protium ovatum e a avaliação de seus potenciais tripanocida e citotóxico. O óleo essencial foi obtido por hidrodestilação, utilizando o aparato do tipo Clevenger. A composição química foi determinada por cromatografia gasosa acoplada à espectrometria de massas (CG-EM). Os principais compostos encontrados no óleo essencial dos frutos verdes de P. ovatum foram: β-mirceno (62,0 %), α-pineno (11,3 %) e limoneno (7,3 %).
Recebido em 29/6/11; aceito em 28/2/12; publicado na web em 15/6/12 CHEMICAL CONSTITUENTS OF LEAVES FROM Riedeliella graciliflora HARMS (LEGUMINOSAE). A new salicylic acid derivative, pentacosanyl salicylate, was isolated from the leaves of the plant toxic to cattle, Riedeliella graciliflora, in addition to a digalactosyldiacylglycerol (DGDG), 1,2+)-catechin and the dimer (+)-catechin-(4β-8)-catechin, glutinol, squalene, β-sitosterol, stigmasterol, phytol, β-carotene, α-tocopherol and ficaprenol-12. Their structures were determined using spectral techniques (MS, IR, and NMR-1D and 2D) and based on literature data.Keywords: Riedeliella graciliflora; alkyl salicylate; toxic plant. INTRODUÇÃOA intoxicação de ruminantes por plantas tóxicas causa a morte de aproximadamente 1 milhão de animais anualmente no Brasil. [1][2][3] Entre estas plantas tóxicas encontra-se Riedeliella graciliflora Harms Leguminosae, conhecida como falsa-ciganinha, a qual possui porte arbustivo e com ocorrência em cerrados, campos e matas ciliares da região sudeste da América do Sul.4 A intoxicação experimental de gado e animais de laboratório por folhas desta planta resultou em danos histológicos severos em diversos órgãos.5 Outros experimentos demonstraram que 10 g de folhas por kg de peso de animal são suficientes para causar edema e hemorragia no gado. 6 Uma investigação preliminar da composição química desta espécie revelou a presença de proantocianidinas na fração tóxica, 7 sem, contudo, terem sido efetuados o isolamento e a caracterização das mesmas.O impacto econômico resultante das intoxicações de ruminantes por plantas tóxicas confere relevância ao estudo destas espécies, principalmente no intuito de se conhecer os princípios ativos e, assim, possibilitar a racionalização da terapia apropriada.Dando continuidade à nossa linha de pesquisa que visa conhecer a composição química de plantas tóxicas para o gado ocorrentes em Mato Grosso do Sul, 8 o presente trabalho refere-se ao estudo químico das folhas de R. graciliflora. PARTE EXPERIMENTAL Instrumentação e procedimentos geraisForam utilizadas placas de gel de sílica das marcas Whatman e Merck, com indicador de fluorescência UV 254 , empregando-se como revelador solução saturada de sulfato de cério IV em ácido sulfúrico 36%. As separações cromatográficas em coluna foram realizadas utilizando-se gel de sílica 70-230 e 230-400 mesh, marca Acros Organics, e Sephadex LH-20, Sigma-Aldrich. Os experimentos de RMN 1 H e 13 C (uni-e bidimensionais) foram obtidos em espectrômetro Bruker DPX-300 (300/75 MHz), utilizando-se CDCl 3 e CD 3 OD como solventes e o sinal do CHCl 3 ou do hidrogênio residual do CHD 2 OD como referência. Os espectros de IV foram registrados em espectrômetro Bomem-Hartmann & Braun FT, tendo sido as amostras preparadas sob a forma de pastilha de KBr. As medidas de rotação óptica foram determinadas em polarímetro Perkin-Elmer 341 e os espectros de massas obtidos em espectrômetro GCMS-QP2010 Plus, Shimadzu. Material vegetalAs folhas de R. graciliflora foram coletadas em março d...
D (4), 7-O-E-p-coumaroyljiofuranaldehyde (5), three known iridoids, including one iridoid glucoside, jioglutin D (1), rehmaglutin D (6), 6-O-E-p-coumaroylcatalpol (7). From the flowers were obtained six triterpenes, betulinic acid (8), olean-12-en-3-one (9), β-amyrin (10), oleanolic acid (11), ursolic acid (12), 3-O-E-p-coumaroylursolic acid (13), 2α-hydroxyursolic acid (14), 6β,19α-dihydroxyursolic acid (15), and one phenylethanoid, tyrosol (16), in addition to β-sitosterol, β-sitosterol-3-O-β-D-glucopyranoside and β-sitosterol-3-O-β-D-(6´-O-acyl)-glucopyranoside and E-p-coumaric acid. The structures of the isolated compounds were established on the basis of 1D and 2D NMR spectroscopic techniques. The chemical profile of the trunk bark of the plant was determined by HPLC/DAD/HRESIMS and did not present a good correlation with the phytochemical study. It did not detect most of the isolated substances and allowed to propose the presence of some non-isolated compounds.
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