Estudo quimiossistemático de espécies do gênero Polygala e avaliação das propriedades biológicas

Tese (doutorado) - Universidade Federal de Santa Catarina, Centro de Ciências Físicas e Matemáticas, Programa de Pós-Graduação em Química, Florianópolis, 2015.No presente trabalho realizou-se o estudo fitoquímico das espécies P. molluginifolia, P. campestris e P. longicaulis. A fração acetato de etila de P. molluginifolia foi submetida ao fracionamento cromatográfico levando ao isolamento de quatro isoflavonas (1-4) da coleta 1, e duas isoflavonas (7) e (8) da coleta 2, das quais a isoflavona (1) é inédita na literatura. A fração aquosa de P. molluginifolia da coleta 1 forneceu os compostos isolados rutina (5) e sacarose (6). As diidroestirilpironas (9) e (10) foram obtidas do fracionamento da fração acetato de etila de P. longicaulis e as xantonas (11) e (12) foram isoladas da fração aquosa de P. campestris. A análise de determinação dos componentes voláteis de P. molluginifolia mostrou o salicilato de metila como componente majoritário na raiz (37,7%), nas folhas o dodecanoato de etila (2,6%), nos caules o tetradecanoato de etila (9,4%) e nas flores dodecanoato de isoamila (28,1%). Na determinação de atividade antioxidante e inibição da AchE dos extratos, frações e compostos isolados (1-4), o extrato bruto de P. molluginifolia (PMEB), a fração acetato de etila (PMFA) e as isoflavonas (1) e (4) apresentaram os melhores resultados. A xantona (12) e as diidroestirilpironas (9) e (10) apresentaram as maiores permeabilidades no ensaio PAMPA. PMEB, PMFA e compostos (1) e (4) também apresentaram atividade frente a T. cruzi e Leishmania spp. As isoflavonas (1), (4) e PMEB exibiram atividade antifúngica frente a cepas de Pb18, C. neoformans, C. gattii. Os testes de atividade anti-inflamatória no modelo de pleurisia mostraram que PMEB, PMFA e compostos isolados (4) e (5) inibiram a migração de leucócitos, neutrófilos e a exsudação. PMEB e isoflavona (4) também mostraram efeitos antinociceptivos e não afetaram a atividade locomotora dos camundongos. Na determinação de atividade anti-hiperglicêmica observou-se que PMFA e isoflavonas (1) e (4) reduziram a glicemia de forma significativa.Abstract : In the present work, a phytochemical study of the species P. molluginifolia, P. campestris and P. longicaulis was done. The ethyl acetate fraction of P. molluginifolia was subjected to silica gel chromatographic column leading to isolation of isoflavones (1-4) (collection 1), and two isoflavones (7) and (8) (collection 2), of which the isoflavone (1) is an unpublished compound. The aqueous fraction of P. molluginifolia provided the isolated compounds rutin (5) and sucrose (6). The dihydrostyrylpyrones (9) and (10) were obtained from chromatographic fractionation of ethyl acetate fraction and the xanthones (11) e (12) were obtained from the aqueous fraction of P. campestris. The analyses of volatile components of P. molluginifolia showed methyl salicylate as the main constituent in the roots (37,7%), ethyl dodecanoate in the leaves (2,6%), ethyl tetradecanoate (9,4%) in the stems and isoamyl dodecanoate (28,1%) in the flowers. In the determination of antioxidant activity and AchE inhibition of extracts, fractions and isolated compounds (1-4), the crude extract of P. molluginifolia, ethyl acetate fraction (PMFA) and isoflavones (1) and (4) showed the best results. The xanthone (12) and dihydrostyrylpyrones (9) e (10) presented the highest permeabilities in the PAMPA assay. PMEB, PMFA and compounds (1) and (4) also showed activities agains T. cruzi e Leishmania spp. The isoflavones (1), (4) and PMEB exhibited antifungal activity against strains of Pb18, C. neoformans, C. gattii. The anti-inflamatory activity evaluation on the model of pleurisy showed that PMEB, PMFA and isolated compounds (4) and rutin (5) of P. molluginifolia inhibited the migration of leukocytes, neutrophils and exudation. PMEB and isoflavone (4) also showed antinociceptive effects and did not affect spontaneous locomotor activity of the mice. In the determination of antihyperglycemic activity, PMFA and isoflavones (1) and (4), significantly decreased the glycemia

Cultivation of algae in photobioreator and obtention of biodiesel

In this work we described the cultivation of Chlorella vulgaris in a photobioreactor to algal biomass production. The dried biomass was used as feedstock for biodiesel production, it presented 26% lipids and via sonocatalysis stage of the methodology resulted in 60% of fatty acid methyl esters (FAME). The FAME content was confirmed by Gas Chromatography (GC).CNPqFAPERGSCoordenacao de Aperfeicoamento de Pessoal de Nivel Superior (CAPES

Ultrasound promoted greener synthesis of 2-(3,5-diaryl-4,5-dihydro-1H-pyrazol-1-yl)-4-phenylthiazoles

This work describes a rapid and clean procedure for the synthesis of a series of 2-(3,5-diaryl-4,5-dihydro-1H-pyrazol-1-yl)-4-phenylthiazoles under ultrasonic irradiation, from the cyclization of 1-thiocarbamoyl-3,5-diaryl-4,5-dihydro-1H-pyrazoles and phenacyl bromide. These reactions were carried out in ethanol in periods of reduced time concerning to the methods described in the literature. Were isolated 11 compounds, with good yields (47-93 %) and excellent purities.Este trabalho descreve um procedimento rápido e limpo para a síntese de uma série de 2-(3,5-diaril-4,5-diidro-1H-pirazol-1-il)-4-feniltiazóis sob irradiação de ultrassom a partir da ciclização de 3,5-diaril-1-tiocarbamoil-4,5-diidro-1H-pirazóis com brometo de fenacila. Estas reações foram realizadas em etanol em períodos de tempo reduzidos em relação aos métodos descritos na literatura. Foram isolados 11 compostos com bons rendimentos (47-93 %) e excelente pureza

Síntese de heterociclos bioativos derivados do ferroceno

The discovery of ferrocene marked one of the points of departure for modern organometallic chemistry. In general, the compounds of ferrocene derivatives are widely applied in several areas. One of the most important applications of ferrocene is the development of more active drugs, especially in cases where there is resistance to current drugs. Bioactive agents containing ferrocene have proven effective in combating diseases such as cancer, malaria, HIV, Alzheimer and conditions caused by fungi and bacteria. In this context, the present paper aims to highlights the synthesis of heterocycles containing ferrocene moiety and their use in medicinal chemistry

Ultrasound promoted greener synthesis of 2-(3,5-diaryl-4,5-dihydro-1H-pyrazol-1-yl)-4-phenylthiazoles

A rapid and cleaner procedure for the synthesis of a series of 2-(3,5-diaryl-45-dihydro-1H-pyrazol-1-yl)-4-phenylthiazoles under ultrasonic irradiation in ethanol is described. (C) 2010 Elsevier B.V. All rights reserved.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)CAPESFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)FAPESP[06/56315-6]FAPESP[06/58124-3]Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)INCT de Estudos do Meio AmbienteINCT de Estudos do Meio Ambiente[573.667/2008-0]Universidade de São Paulo - CEPEMA-USP (Centro de Capacitacao e Pesquisa em Meio Ambiente)Universidade de São Paulo - CEPEMA-USP ( Centro de Capacitacao e Pesquisa em Meio Ambiente)CNPq[310472/2007-5]Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)CNPq[475575/2008-3]Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq

Sulfated β-glucan from Agaricus subrufescens inhibits flavivirus infection and nonstructural protein 1-mediated pathogenesis.

Despite substantial morbidity and mortality, no therapeutic agents exist for treatment of dengue or Zika, and the currently available dengue vaccine is only recommended for dengue virus (DENV)-immune individuals. Thus, development of therapeutic and/or preventive drugs is urgently needed. DENV and Zika virus (ZIKV) nonstructural protein 1 (NS1) can directly trigger endothelial barrier dysfunction and induce inflammatory responses, contributing to vascular leak in vivo. Here we evaluated the efficacy of the (1-6,1-3)-β-D-glucan isolated from Agaricus subrufescens fruiting bodies (FR) and its sulfated derivative (FR-S) against DENV-2 and ZIKV infection and NS1-mediated pathogenesis. FR-S, but not FR, significantly inhibited DENV-2 and ZIKV replication in human monocytic cells (EC50 = 36.5 and 188.7 μg/mL, respectively) when added simultaneously with viral infection. No inhibitory effect was observed when FR or FR-S were added post-infection, suggesting inhibition of viral entry as a mechanism of action. In an in vitro model of endothelial permeability using human pulmonary microvascular endothelial cells (HPMECs), FR and FR-S (0.12 μg/mL) inhibited DENV-2 NS1- and ZIKV NS1-induced hyperpermeability by 50% and 100%, respectively, as measured by Trans-Endothelial Electrical Resistance. Treatment with 0.25 μg/mL of FR and FR-S inhibited DENV-2 NS1 binding to HPMECs. Further, FR-S significantly reduced intradermal hyperpermeability induced by DENV-2 NS1 in C57BL/6 mice and protected against DENV-induced morbidity and mortality in a murine model of dengue vascular leak syndrome. Thus, we demonstrate efficacy of FR-S against DENV and ZIKV infection and NS1-induced endothelial permeability in vitro and in vivo. These findings encourage further exploration of FR-S and other glycan candidates for flavivirus treatment alone or in combination with compounds with different mechanisms of action

PAMPA Permeability, Acetylcholinesterase Inhibition and Antioxidant Activity of Pyranoisoflavones from Polygala molluginifolia

A phytochemical investigation of Polygala molluginifolia (root, stem, leaves and flowers) resulted in the isolation of four pyranoisoflavones, of which isoflavone 1 was previously unknown in the literature. Isoflavones 2-4: , although they are known synthetic compounds, are described in this work as new natural products. The isolated compounds were evaluated for their antioxidant effects and potential for inhibiting the acetylcholinesterase enzyme. Isoflavones 1 and 4 inhibited acetylcholinesterase, displaying IC50 values of 68 µmol L-1 and 84 µmol L-1, respectively. In the DPPH assay, the same compounds and rutin 5 exhibited EC50 values of 61 µmol L-1, 55 µmol L-1 and 16 µmol L-1, respectively. Moreover, the permeability of compounds 1-4: was evaluated using parallel artificial membrane permeability assay (PAMPA) with isoflavones 3 (9.25 × 10-6 cm s-1) and 4 (3.48 × 10-6 cm s-1) exhibiting the highest permeabilities

Ultrasound-assisted synthesis of aliphatic acid esters at room temperature

This work describes the ultrasound-assisted synthesis of saturated aliphatic esters from synthetic aliphatic acids and either methanol or ethanol. The products were isolated in good yields after short reaction times under mild conditions. (C) 2011 Elsevier BM. All rights reserved.INCT de Estudos do Meio AmbienteINCT de Estudos do Meio Ambiente [573.667/2008-0]CEPEMAUSP (Centro de Capacitacao e Pesquisa em Meio Ambiente)CEPEMA-USP (Centro de Capacitacao e Pesquisa em Meio Ambiente)CNPqCNPq [310472/2007-5, 475575/2008-3]FAPERGSFAPERGSCAPESCAPE