Browsing by Author "Takahashi, Jacqueline Aparecida"

Now showing 1 - 13 of 13
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    Anti-inflammatory, antimicrobial and acetylcholinesterase inhibitory activities of friedelanes from Maytenus robusta branches and isolation of further triterpenoids.
    (2017) Sousa, Grasiely Faria de; Aguilar, Mariana Guerra de; Dias, Danielle Ferreira; Takahashi, Jacqueline Aparecida; Moreira, Maria Eliza de Castro; Vieira Filho, Sidney Augusto; Silva, Grácia Divina de Fátima; Rodrigues, Salomão Bento Vasconcelos; Messias, Maria Cristina Teixeira Braga; Duarte, Lucienir Pains
    The new pentacyclic triterpenoids friedel-1-en-3,16-dione (1), 1α,29-dihydroxyfriedelan-3-one (2) and 16β,28,29-trihydroxyfriedelan-3-one (3) were isolated from Maytenus robusta branches in addition to the known, but new for this species, triterpenoid 12α,29-dihydroxyfriedelan-3-one (4). The structures and stereochemistry of the novel triterpenoids were established by IR, 1D/2D NMR and HR-APCIMS spectral data. In addition, the biological activity of compound 2 and the previously isolated friedelanes 5–8 (friedelan-3,16-dione, 29-hydroxyfriedelan- 3-one, 29-hydroxyfriedelan-3,16-dione and 16β,29-dihydroxyfriedelan-3-one) was investigated. Compounds 2 and 8 were tested for their acetylcholinesterase properties and antimicrobial activity against the bacteria Staphylococcus aureus, Pseudomonas aeruginosa, Listeria monocytogenes, Citrobacter freundii, and the fungus Candida albicans. Compound 2 was the most active compound for both assays, with values of 32.3% acetylcholinesterase inhibition, 42% activity against the fungus Candida albicans and 34% against the bacterium Pseudomonas aeruginosa. Compounds 5–8 were assayed for their antiedematogenic activity using the carrageenan- induced paw edema assay. At maximum inflammation after three hours, compounds 6 and 8 showed 42% and 57% activity, respectively. After four hours, compounds 5 and 7 showed activity of 71% and 75% compared to 79% of the control indomethacin.
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    Biodegradation studies on fatty amines used for reverse flotation of iron ore.
    (2010) Araujo, Danielle Marques de; Yoshida, Maria Irene; Takahashi, Jacqueline Aparecida; Carvalho, Cornélio de Freitas; Stapelfeldt, Frank
    Bacteria present in effluents from the process of iron ore flotation were isolated and identified in an attempt to identify the microorganisms responsible for fatty amine degradation.Water samples collected at the tailings dam led to the identification of the bacterial species Serratia marcescens as the microorganism responsible for degradation, while in laboratory flotation conditions, a strain of Enterobacter cloacae was shown to be the biodegrading agent. Both S. marcescens and E. cloacae are Gram-negative, non-sporulated, mobile and facultative anaerobic bacteria. Monitoring of the effluent had shown that after 5 days, around 34% of amine was already consumed, increasing to 75% after 10 days; these data are important for testing the reuse of the fatty amines contained in effluents. Biodegradation experiments carried out with S. marcescens revealed the significant role of temperature and concentration on the biodegradation rate of the etheramine EDA 3B. For the concentration of 10 mg L_1, amine biodegradation rates are very close at all temperatures. However, as amine concentration increases, the influence of temperature can be better observed, mainly for concentrations of 40 and 60 mg L_1. This isolate will be potentially useful in biotreatment of wastewaters and bioremediation of contaminated soils.
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    Bioprospecção do potencial farmacêutico de duas espécies de fungos do solo do cerrado mineiro.
    (Programa de Pós-Graduação em Ciências Farmacêuticas. CIPHARMA, Escola de Farmácia, Universidade Federal de Ouro Preto., 2009) Moreira, Betânia Teixeira; Takahashi, Jacqueline Aparecida
    Produtos naturais são definidos como metabólitos secundários ou derivados produzidos por organismos em resposta a um estímulo externo como mudanças nutricionais, infecções e competições. Os fungos são conhecidos como produtores de uma grande variedade de metabólitos secundários e, apesar de muitas vezes ser desconhecido o papel dessas substâncias nesses organismos, esses compostos apresentam grande importância na medicina, na indústria e na agricultura. Muitas substâncias produzidas por fungos, ou seus derivados químicos, são utilizadas no tratamento de doenças pelo homem. Como exemplo pode-se citar os antibióticos – lactâmicos penicilinas e cefalosporinas, os antifúngicos da classe das equinocandinas, as estatinas, substâncias redutoras do colesterol sanguíneo e o imunossupressor ciclosporina A. Nesse trabalho, foi realizado o estudo de bioprospecção de metabólitos secundários dos fungos filamentosos Clonostachys rosea f catenulata e Penicillium brasilianum, isolados de solo do cerrado mineiro. Do extrato do fungo Clonostachys rosea f catenulata foram isolados uma mistura de triacilgliceróis, o ergosterol e uma mistura de ácidos graxos livres. Já do extrato do fungo Penicillium brasilianum foram isolados o poliol manitol, os meroterpenos austina e dehidroaustina e o ácido penicílico. Os extratos obtidos e as substâncias isoladas foram submetidos aos testes de atividade antibacteriana e anticolinesterásica. Apesar de os extratos terem apresentado atividade antibacteriana, das substâncias puras isoladas, somente o ácido penicílico foi ativo contra os microrganismos testados. Em relação ao teste de atividade anticolinesterásica, o ácido penicílico foi também a única substância ativa. Com o objetivo de avaliar a melhor condição de obtenção de substâncias com atividade antibacteriana, foi realizado para o fungo Penicillium brasilianum, um estudo de variação nutricional e das condições de fermentação. O fungo foi cultivado em três diferentes meios de cultura (meio de cultura líquido complexo, caldo batata dextrosado e arroz) e em duas condições diferentes de cultivo (com e sem agitação). Os extratos obtidos foram submetidos ao teste de atividade antibacteriana, sendo que, entre todas as condições testadas, o cultivo em caldo de batata dextrosado mostrou-se o mais promissor.
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    Chemical constituents from branches of Maytenus gonoclada (Celastraceae) and evaluation of antimicrobial activity.
    (2011) Silva, Fernando César; Duarte, Lucienir Pains; Silva, Grácia Divina de Fátima; Vieira Filho, Sidney Augusto; Lula, Ivana Silva; Takahashi, Jacqueline Aparecida; Sallum, William S. T.
    Seis triterpenos pentacíclicos isolados dos galhos de Maytenus gonoclada (Celastraceae), incluindo todos os dados de RMN do novo composto 3-oxo-12α,29-diidroxifriedelano são aqui relatados. A estereoquímica do novo friedelano foi estabelecida por dados de RMN bidimensional (HSQC, HMBC e NOESY), e sua massa molecular confirmada por espectrometria de massas (ESI). Testes de atividade antimicrobiana usando método de difusão em disco e de macrodiluição foram realizados contra as bactérias Escherichia coli, Citrobacter freundii e Bacillus cereus, e contra o fungo Candida albicans. O triterpeno 3-oxo-12a-hidroxifriedelano mostrou resultado positivo contra C. albicans.
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    Estudo químico e avaliação das atividades antimicrobiana e anticolinesterásica de extratos brutos acetato de etila e metabólitos secundários do fungo Paecilomyces.
    (2012) Teles, Ana Paula Campos; Takahashi, Jacqueline Aparecida; Miranda, Roqueline Rodrigues Silva de; Vieira Filho, Sidney Augusto
    A utilização de produtos naturais pela humanidade, em busca por alívio e cura de doenças é prática antiga, principalmente devido à vasta riqueza de espécies vegetais e de micro-organismos pertencentes ao país. Os fungos são importantes organismos utilizados nesta prática, devido aos avanços no campo da biotecnologia e à capacidade destes de produzirem uma variedade de metabólitos secundários. Utilizando-se técnicas como OSMAC (one strain-many active compounds), são obtidos diversos protótipos bioativos, que podem ser utilizados na prevenção e no tratamento de uma gama de enfermidades, entre elas encontram-se as doenças infecciosas e a doença de Alzheimer. Este trabalho teve como objetivo avaliar os diferentes extratos obtidos do cultivo de Paecilomyces lilacinus quanto às ações antibacteriana, antifúngica e inibidores da acetilcolinesterase, enzima representativa no Mal de Alzheimer, além de isolar e identificar os metabólitos secundários. Os resultados dos ensaios biológicos realizados com os extratos brutos e os cromatogramas, estes últimos obtidos por CLAE, mostraram que, variando-se as condições de cultivo, houve variação do perfil químico dos extratos de P. lilacinus. No teste antimicrobiano utilizando o método de difusão em placa, a maioria dos extratos testados mostrou satisfatória atividade para as bactérias Staphylococcus aureus, Listeria monocytogenes e para a levedura Candida albicans. Utilizando a metodologia de microdiluição em caldo, os extratos mostraram inibição de até 100% do crescimento microbiano. Para a avaliação qualitativa de inibição da enzima AchE, dos vinte e oito extratos brutos testados, utilizando o método de Ellmann, dezesseis apresentaram tal atividade; no método quantitativo, o percentual de inibição variou entre 78 e 97%. Três substâncias foram isoladas, por métodos cromatográficos, das quais uma foi identificada como sendo uma δ-lactama. Duas substâncias isoladas foram bioensaiadas para as atividades acima citadas, apresentando resultados significativos para o teste de inibição da enzima AchE. Em ambos os testes antimicrobianos, uma substância mostrou atividade antibacteriana, contra as bactérias Gram-positivas S. aureus e L. monocytogenes.
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    Evaluation of antimicrobial activity and toxic potential of extracts and triterpenes isolated from Maytenus imbricata.
    (2012) Rodrigues, Vanessa Gregório; Duarte, Lucienir Pains; Silva, Grácia Divina de Fátima; Silva, Fernando César; Góes, Jefferson Vieira de; Takahashi, Jacqueline Aparecida; Pimenta, Lúcia Pinheiro Santos; Vieira Filho, Sidney Augusto
    The phytochemical study of hexane/ethyl ether (1:1) extract of the roots of M. imbricata, Celastraceae, resulted in the isolation and characterization of six known triterpenes: 11α-hydroxylup-20(29)-en-3-one, previously isolated from this species besides, 3β,11α- di-hydroxylup-20(29)-ene, 3,7-dioxofriedelane, 3-oxo-29-hydroxyfriedelane, tingenone and 6-oxo-tingenol. The chemical structures of these triterpenes were established by spectrometric data (IR, 1H and 13C NMR) and through comparison with literature data. The hexane/ethyl ether (1:1), ethyl acetate and methanol extracts, and 11α-hydroxylup-20(29)-en-3-one, tingenone and 6-oxo-tingenol, showed antimicrobial properties on in vitro assays. All extracts and triterpenes, except 3β,11α-di-hydroxylup-20(29)-ene, presented toxicity demonstrated by the larvicidal effect test using Artemia salina.
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    Flavonol triglycosides of leaves from Maytenus robusta with acetylcholinesterase inhibition.
    (2017) Sousa, Grasiely Faria de; Aguiar, Mariana Guerra de; Takahashi, Jacqueline Aparecida; Alves, Tânia Maria de Almeida; Kohlhoff, Markus; Vieira Filho, Sidney Augusto; Silva, Grácia Divina de Fátima; Duarte, Lucienir Pains
    Although Maytenus robusta aqueous infusions of leaves are used in Brazilian traditional medicine for stomach disease treatment, only a few chemical studies of this species are found in literature. The phytochemical investigation of methanol extract from M. robusta leaves yielded the known compound kaempferol (3) and two new flavonol glycosides: kaempferol-3-O-b-D-glucopyranosyl-(1 !3)-a-Lrhamnopyranosyl-( 1 ! 2)-b-D-glucopyranoside (1) and quercetin-3-O-b-D-glucopyranosyl-(1 !3)-a-Lrhamnopyranosyl-( 1 ! 2)-b-D-glucopyranoside (2). The chemical structures of 1 and 2 were elucidated by 1D/2D NMR, ESI–MS and ESI–MS2 spectral data. It is the first time flavonoids have been reported from M. robusta. Flavonols 1 and 2 showed 66% and 80% acetylcholinesterase (AChE) inhibition, compared to 93% of the standard eserine, by the Ellman’s method. These substances are one of the few active flavonols linked to a trisaccharide chain in the literature presenting this activity, and contribute to the screening for new types of natural AChE inhibitors.
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    Maytenus salicifolia Reissek (Celastraceae) : evaluation of the activity of extracts and constituents against Helicobacter pylori and oral pathogenic microorganisms.
    (2016) Magalhães, Cássia Gonçalves; Silva, Grácia Divina de Fátima; Duarte, Lucienir Pains; Takahashi, Jacqueline Aparecida; Santos, Vagner Rodrigues; Figueiredo, Rute Cunha; Vieira Filho, Sidney Augusto
    Maytenus salicifolia Reissek é conhecida como "cafezinho" em Minas Gerais, Brasil. Suas folhas são utilizadas na medicina popular no tratamento de úlceras estomacais. Neste trabalho é reportado o isolamento de 4´-Ometilepigalocatequina (1) e proantocianidina A (2) dos extratos polares da raiz (1; 4,36%; 2, 2,17%) e tronco (1, 4,16%; 2, 0,26%) de M. salicifolia. Pela primeira vez, esses compostos foram encontrados na raiz dessa espécie. Esses constituintes foram encontrados em quantidades expressivas, o que torna M. salicifolia uma fonte alternativa desses compostos. Além disto, a atividade antimicrobiana de extratos polares (etanólico das raízes, etanólico e acetato-etílico dos galhos) e apolares (hexânico das raízes) dessa planta foi avaliada in vitro contra os patógenos da cavidade oral: Candida albicans, Streptococcus mutans, Streptococcus sanguinis e Staphylococcus aureus. Todos os extratos exibiram atividade antimicrobiana e C. albicans foi o micro-organismo mais sensível. Os triterpenos nepeticina, rigidenol, gloquidona, 11- hidroxigloquidona e 16- -hidroxipristimerina, previamente isolados desta espécie, também foram testados contra Helicobacter pylori. Rigidenol e 16- -hidroxipristimerina foram ativos contra essa bactéria. Os resultados contribuem para confirmar o uso na medicina popular de M. salicifolia no tratamento de úlceras e outros problemas estomacais e indicam que extratos dessa planta apresentam grande potencial para o uso no tratamento de doenças infecciosas da cavidade oral.
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    New triterpenes from Maytenus robusta : structural elucidation based on NMR experimental data and theoretical calculations.
    (2012) Sousa, Grasiely Faria de; Duarte, Lucienir Pains; Alcântara, Antônio Flávio de Carvalho; Silva, Grácia Divina de Fátima; Vieira Filho, Sidney Augusto; Miranda, Roqueline Rodrigues Silva de; Oliveira, Djalma Menezes de; Takahashi, Jacqueline Aparecida
    Leaves of Maytenus robusta (Celastraceae) were subjected to phytochemical investigation mainly directed at the isolation of pentacyclic triterpenes. The compounds friedelin (1), β-friedelinol (2), 3-oxo-21β-H-hop-22(29)-ene (7), 3,4-seco-friedelan-3,11β- olide (8), 3β-hydroxy-21β-H-hop-22(29)-ene (9), 3,4-seco-21β-H-hop-22(29)-en-3-oic acid (10), 3,4-seco-friedelan-3-oic acid (11), and sitosterol were identified in the hexane extract of M. robusta leaves. Compounds 8 and 9 are described herein for the first time. The structure and stereochemistry of both compounds were experimentally established by IR, HRLC-MS, and 1D (1H, 13C, and DEPT 135) and 2D (HSQC, HMBC and COSY) NMR data and supported by correlations with carbon chemical shifts calculated using the DFT method (BLYP/6-31G* level). Compounds 7 and 10 are also described for the first time, and their chemical structures were established by comparison with NMR data of similar structures described in the literature and correlations with BLYP/6-31G* calculated carbon chemical shifts. Compound 9, a mixture of 11 and sitosterol, and 3β,11β-dihydroxyfriedelane (4) were evaluated by the Ellman’s method and all these compounds showed acethylcholinesterase inhibitory properties.
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    Pentacyclic triterpenes from Maytenus genus as acetylcholinesterase inhibitors.
    (2014) Rodrigues, Vanessa Gregório; Silva, Fernando César; Duarte, Lucienir Pains; Takahashi, Jacqueline Aparecida; Matildes, Bibiane Lindsay Guimarães; Silva, Grácia Divina de Fátima; Miranda, Roqueline Rodrigues Silva de; Vieira Filho, Sidney Augusto
    Objective: Species of the Maytenus genus have been used in traditional medicine to treat a wide variety of human diseases. These species represent a promising source of bioactive substances of pharmacological interest. As part of a research project on phytochemical and biological activity studies of the low polarity extracts of the Maytenus genus, the extracts and eleven known pentacyclic triterpenes isolated from roots of Maytenus imbricata, and branches of Maytenus gonoclada were investigated for acetylcholinesterase inhibitory property. Methods: The acetylcholinesterase inhibition was evaluated by direct thin layer chromatography bioautography and microplate assays. Results: The crude extracts did not exhibit acetylcholinesterase inhibitory activity, but pentacyclic triterpenes, 3-oxo-11α-hydroxylup-20(29)-ene, 3-oxo-29-hydroxyfriedelane and 3,7-dioxofriedelane were active when compared to the standard compound physostigmine (eserine). Conclusion: The in vitro acetylcholinesterase inhibition property of these three pentacyclic triterpenes from Maytenus genus gives them the potential compounds to be applied in the treatment of Alzheimer’s disease.
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    Preparation of magnetoliposomes with a green, low-cost, fast and scalable methodology and activity study against S. aureus and C. freundii bacterial strains.
    (2018) Silva, Rosangela Maria Ferreira da Costa e; Lara, Luciano Roni Silva; López Aguilar, Jorge Luis; Andrade, Ângela Leão; Oliveira, Junnia A. C.; Takahashi, Jacqueline Aparecida; Vieira, Henriete da Silva; Matencio, Tulio; Stumpf, Humberto Osório; Domingues, Rosana Zacarias
    A novel, fast, low-cost and scalable methodology to prepare stable magnetoliposomes (MGLs), without the use of organic solvents, is described. The concept of the work is based on the dual use of soy lecithin associated to a new liposome preparation methodology. Soy lecithin was used to coat the nanoparticles of magnetite (Fe3 O4 @lecithin) and for encapsulation of Fe3 O4 @lecithin (Lip-Fe3 O4 @lecithin). Liposomes with size less than 160 nm, polydispersity index of 0.25 and zeta potential of -41 mV, were prepared with the use of autoclave and sonication. The liposomal formulations containing magnetite and stigmasterol (Lip-Fe3 O4 @lecithin, Lip-Stigma and Lip-Stigma-Fe3 O4 @lecithin) were shown to be promising for the application as antibacterial. The liposomal formulation and magnetite were characterized by the following techniques: conventional and high-resolution transmission electron microscopy (TEM/HRTEM), energy-filtered transmission electron microscopy (EFTEM), proton nuclear magnetic resonance (1H NMR), Fourier transform infrared spectroscopy (FTIR), X-ray powder diffraction (XRPD), dynamic light scattering (DLS) and zeta potential. The Lip-Fe3 O4 @lecithin had a minimum inhibitory concentration (MIC) of 8.4 µg mL-1 in the presence of 200 Oe magnetic field against S. aureus.
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    Psychotria viridis : chemical constituents from leaves and biological properties.
    (2017) Soares, Débora Barbosa da Silva; Duarte, Lucienir Pains; Cavalcanti, André D.; Silva, Fernando César; Braga, Ariadne Duarte; Lopes, Miriam Teresa Paz; Takahashi, Jacqueline Aparecida; Vieira Filho, Sidney Augusto
    The phytochemical study of hexane, chloroform and methanol extracts from leaves of Psychotria viridis resulted in the identification of: the pentacyclic triterpenes, ursolic and oleanolic acid; the steroids, 24-methylene-cycloartanol, stigmasterol and β-sitosterol; the glycosylated steroids 3-O-β-D-glucosyl-β- sitosterol and 3-O-β-D-glucosyl-stigmasterol; a polyunsaturated triterpene, squalene; the esters of glycerol, 1-palmitoylglycerol and triacylglycerol; a mixture of long chain hydrocarbons; the aldehyde nonacosanal; the long chain fat acids hentriacontanoic, hexadecanoic and heptadenoic acid; the ester methyl heptadecanoate; the 4-methyl-epi-quinate and two indole alkaloids, N,N-dimethyltryptamine (DMT) and N-methyltryptamine. The chemical structures were determined by means of spectroscopic (IR, 1H and 13C NMR, HSQC, HMBC and NOESY) and spectrometric (CG-MS and LCMS-ESI-ITTOF) methods. The study of biologic properties of P. viridis consisted in the evaluation of the acetylcholinesterase inhibition and cytotoxic activities. The hexane, chloroform, ethyl acetate and methanol extracts, the substances 24-methylene-cycloartanol, DMT and a mixture of 3-O-β-D-glucosyl-β-sitosterol and 3-O-β-D-glucosyl-stigmasterol showed cholinesterase inhibiting activity. This activity induced by chloroform and ethyl acetate extracts was higher than 90%. The methanol and ethyl acetate extracts inhibit the growth and/or induce the death of the tumor cells strains B16F10 and 4T1, without damaging the integrity of the normal cells BHK and CHO. DMT also demonstrated a marked activity against tumor cell strains B16F10 and 4T1.
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    Salacia crassifolia (Celastraceae) : chemical constituents and antimicrobial activity.
    (2015) Rodrigues, Vanessa Gregório; Duarte, Lucienir Pains; Silva, Roqueline Rodrigues; Silva, Grácia Divina de Fátima; Simões, Maria O. Mercadante; Takahashi, Jacqueline Aparecida; Matildes, Bibiane Lindsay Guimarães; Fonseca, Thaisa Helena Silva; Gomes, Maria Aparecida; Vieira Filho, Sidney Augusto
    The phytochemical study of hexane extract from leaves of Salacia crassifolia resulted in the isolation of 3β-palmitoxy-urs-12-ene, 3-oxofriedelane, 3β-hydroxyfriedelane, 3-oxo-28-hydroxyfriedelane, 3-oxo-29-hydroxyfriedelane, 28,29-dihydroxyfriedelan-3-one, 3,4-seco-friedelan-3-oic acid, 3β-hydroxy-olean-9(11):12-diene and the mixture of α-amirin and β-amirin. β-sitosterol, the polymer gutta-percha, squalene and eicosanoic acid were also isolated. The chemical structures of these constituents were established by IR, 1H and 13C NMR spectral data. Crude extracts and the triterpenes were tested against Entamoeba histolytica, Giardia lamblia and Trichomonas vaginalis and no activity was observed under the in vitro assay conditions. The hexane, chloroform, ethyl acetate and ethanol crude extracts, and the constituent 3,4-seco-friedelan-3-oic acid and 28,29-dihydroxyfriedelan-3-one showed in vitro antimicrobial activity against Salmonella typhimurium, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Bacillus cereus, Listeria monocytogenes, Streptococcus sanguinis and Candida albicans.