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Pinto, Luciano da Silva [UNESP]. « Fenilpropanoides da Paspalum atratum ». Universidade Estadual Paulista (UNESP), 2015. http://hdl.handle.net/11449/124482.
Texte intégralEste trabalho descreve o estudo fitoquímico do extrato etanólico de Paspalum atratum Swalen (Poaceae). O gênero Paspalum é o mais importante das gramíneas no Brasil e possui características compatíveis com a utilização no pastejo. Fenilpropanoides foram isolados por métodos cromatográficos (CC, CLAE) pela primeira vez neste gênero. Estes fenilpropanoides foram identificados como: (R)-ácido rosmarínico, (AR, 1), ácido 3-O-cafeoilquínico (2), fenilalanina (3), ácidos cis- e trans-coumaroilquínico (4 e 5), ácido 5-O-cafeoilquínico (6), ácido 4-O-cafeoilquínico (7) e ácido cafeico (8) pela análise de seus dados de EM, RMN de 1H e de 13C, incluindo COSY, HMBC, HSQC, TOCSY-1D e DOSY, e pela comparação destes dados com aqueles descritos na literatura para estas substâncias. A substância majoritária no extrato etanólico foi o AR (4,4%). Esta foi usada como padrão em análises qualitativas e quantitativas do extrato. Um método eficiente em CLAE-DAD para determinação de AR no extrato foi estabelecido (r2 = 0,9979). O limite de detecção (LD) e limite de quantificação (LQ) foram 4,00 e 12,13 μg/mL respectivamente, e a faixa de linearidade foi 12,1-100,0 μg/mL. As precisões intradia e interdia do método foram avaliadas pela análise das soluções de padrão AR. O desvio padrão da área do pico do analito foi utilizado como parâmetro de avaliação da precisão intradia, compreendendo o intervalo de 1,57-2,06%. A precisão interdia (7 dias) do método compreendeu o intervalo de 0,54-1,69%. A recuperação, avaliada pela adição do padrão AR, foi satisfatória (75-78%.
This work describes the phytochemical study on ethanol extract from aerial parts of Paspalum atratum Swalen (Poaceae). The Paspalum genus is one of the most important grasses in Brazil and has characteristics compatible with its utilization in pastures for cattle. Phenylpropanoids were isolated by chromatographic methods (CC and HPLC) for the first time in this genus. These phenylpropanoids were identified as (R)-rosmarinic acid (RA, 1), 3-O-caffeoylquinic acid (2), phenylalanine (3), cis- and trans-3-O-coumaroylquinic acids (4 and 5), 5-O-caffeoylquinic acid (6, chlorogenic acid), 4-O-caffeoylquinic acid (7), and caffeic acid (8) by analyses of their MS, 1H and 13C NMR data, including COSY, HMBC, HSQC and DOSY, and comparison of these data with those reported in the literature for these type of compounds. The major compound isolated from the ethanol extract was RA (4.4%). It was used as standard for qualitative and quantitative analyses of extract. An efficient HPLC-DAD method for determination of RA in extract was established (r2 = 0.9979). The limit of detection (LOD) and limit of quantification (LOQ) were 4.00 and 12.13 μg/mL, respectively, and the validated range was 12.1-100.0 μg/mL. The intra-day and inter-day precisions of the method were evaluated by analyzing the blank solution spiked by RA. The standard deviation (SD) as evaluation parameter for the intra-day precision of peak area of target analyte was in the range of 1.57-2.06%. The inter-day precision (7 days) of the method was in the range of 0.54-1.69%. Satisfactory recovery (75-78%), evaluated by standard additions method, was achieved.
Pinto, Luciano da Silva. « Fenilpropanoides da Paspalum atratum / ». Araraquara, 2015. http://hdl.handle.net/11449/124482.
Texte intégralCo-orientador: Isabele Rodrigues Nascimento
Banca: Lourdes Campaner dos Santos
Banca: Antonio Laverde Junior
Resumo: Este trabalho descreve o estudo fitoquímico do extrato etanólico de Paspalum atratum Swalen (Poaceae). O gênero Paspalum é o mais importante das gramíneas no Brasil e possui características compatíveis com a utilização no pastejo. Fenilpropanoides foram isolados por métodos cromatográficos (CC, CLAE) pela primeira vez neste gênero. Estes fenilpropanoides foram identificados como: (R)-ácido rosmarínico, (AR, 1), ácido 3-O-cafeoilquínico (2), fenilalanina (3), ácidos cis- e trans-coumaroilquínico (4 e 5), ácido 5-O-cafeoilquínico (6), ácido 4-O-cafeoilquínico (7) e ácido cafeico (8) pela análise de seus dados de EM, RMN de 1H e de 13C, incluindo COSY, HMBC, HSQC, TOCSY-1D e DOSY, e pela comparação destes dados com aqueles descritos na literatura para estas substâncias. A substância majoritária no extrato etanólico foi o AR (4,4%). Esta foi usada como padrão em análises qualitativas e quantitativas do extrato. Um método eficiente em CLAE-DAD para determinação de AR no extrato foi estabelecido (r2 = 0,9979). O limite de detecção (LD) e limite de quantificação (LQ) foram 4,00 e 12,13 μg/mL respectivamente, e a faixa de linearidade foi 12,1-100,0 μg/mL. As precisões intradia e interdia do método foram avaliadas pela análise das soluções de padrão AR. O desvio padrão da área do pico do analito foi utilizado como parâmetro de avaliação da precisão intradia, compreendendo o intervalo de 1,57-2,06%. A precisão interdia (7 dias) do método compreendeu o intervalo de 0,54-1,69%. A recuperação, avaliada pela adição do padrão AR, foi satisfatória (75-78%.
Abstract: This work describes the phytochemical study on ethanol extract from aerial parts of Paspalum atratum Swalen (Poaceae). The Paspalum genus is one of the most important grasses in Brazil and has characteristics compatible with its utilization in pastures for cattle. Phenylpropanoids were isolated by chromatographic methods (CC and HPLC) for the first time in this genus. These phenylpropanoids were identified as (R)-rosmarinic acid (RA, 1), 3-O-caffeoylquinic acid (2), phenylalanine (3), cis- and trans-3-O-coumaroylquinic acids (4 and 5), 5-O-caffeoylquinic acid (6, chlorogenic acid), 4-O-caffeoylquinic acid (7), and caffeic acid (8) by analyses of their MS, 1H and 13C NMR data, including COSY, HMBC, HSQC and DOSY, and comparison of these data with those reported in the literature for these type of compounds. The major compound isolated from the ethanol extract was RA (4.4%). It was used as standard for qualitative and quantitative analyses of extract. An efficient HPLC-DAD method for determination of RA in extract was established (r2 = 0.9979). The limit of detection (LOD) and limit of quantification (LOQ) were 4.00 and 12.13 μg/mL, respectively, and the validated range was 12.1-100.0 μg/mL. The intra-day and inter-day precisions of the method were evaluated by analyzing the blank solution spiked by RA. The standard deviation (SD) as evaluation parameter for the intra-day precision of peak area of target analyte was in the range of 1.57-2.06%. The inter-day precision (7 days) of the method was in the range of 0.54-1.69%. Satisfactory recovery (75-78%), evaluated by standard additions method, was achieved.
Mestre
Mažeikaitė, Ingrida. « Fenolinių rūgščių ir fenilpropanoidų nustatymas propolyje ». Master's thesis, Lithuanian Academic Libraries Network (LABT), 2008. http://vddb.library.lt/obj/LT-eLABa-0001:E.02~2008~D_20080616_100330-71888.
Texte intégralThe phenolic acids and phenylpropanoids have an important biological activity and are therapeutic agents of crude drugs. Development of validated analysis techniques of these phytotherapeutic agents (fingerprinting and assay procedures) is an important practice for efficacy, safety and quality control of herbal drug preparations. 18 samples of propolis were collected from different districts of Lithuania. The aim of the present work was to study chemical composition of collected samples and estimate analytical capabilities of the evaluation of selected phenolic acids and phenylpropanoids: caffeic acid, chlorogenic acid, cinnamic acid, coumaric acid, ferulic acid, gallic acid, protocatechuic (3,4-dihydroxybenzoic) acid, rosmarinic acid, vanillic acid and vanillin. Optimization and validation procedures of rapid and simple method of reversed phase high performance liquid chromatography were carried out. The mobile phase of the optimized chromatographic method consisted of methanol and 0.5 per cent acetic acid solvent in water. Under the optimal separation conditions (described in Methods), analysis was done in 27 min, with the retention times 4.04 min (gallic acid), 6.93 min (protocatechuic acid), 11.30 min (chlorogenic acid), 12.26 min (vanillic acid), 12.93 min (caffeic acid), 13.80 min (vanillin), 16.97 min (coumaric acid), 17.95 min (ferulic acid), 22.29 min (rosmarinic acid) and 26.30 min (cinnamic acid). The limits of detection and the limits of quantitation were between... [to full text]
Fehlberg, Isley. « Terpenos e fenilpropanoides de Myrcia guianesis (Myrtaceae) ». reponame:Repositório Institucional da UFBA, 2013. http://www.repositorio.ufba.br/ri/handle/ri/9749.
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CAPES
Os extratos etanólicos obtidos a partir das folhas e do caule de Myrcia guianensis foram particionados sequencialmente com hexano, diclorometano ou clorofórmio e acetato de etila. As fases em diclorometano e acetato de etila das folhas, bem como, as fases clorofórmica e hexânica do caule foram submetidas a vários procedimentos cromatográficos em coluna e em camada delgada preparativa. A partir da fase diclorometânica das folhas foram obtidos os sesquiterpenos 5-(6-metilheptan-2-ona)-biciclo-[3.1.0]-hexan-3-ona, 6-metil-5-(2-hidroxi-3-cloro-5-metilfenil)heptan-2-ona, 6-metil-5-(2-hidroxi-5-metilfenil)heptan-2-ona (sesquichamaenol) e oplopanona, sendo os dois primeiros inéditos. O estudo da fase acetato de etila resultou no isolamento do ácido gálico e dos flavonóides quercetina, quercitrina e guaijaverina. Da fase hexânica do caule foram isolados um sesquiterpeno aromático inédito do tipo cadinano, 7-hidroxi-5-isopropil-3,8-dimetil-2-metóxi-1,4-naftoquinona, e os esteróides β–sitosterol e seu derivado glicosilado, o daucosterol. A partir da fase clorofórmica foi isolada a lignana (-)-(8R,8’R)-9,9’-di-O-(E)-feruloil-secoisolariciresinol e sete triterpenos, sendo eles, ácido maslínico, ácido estáclico A e seu novo derivado p-cumárico, ácido 3β-trans-p-oxicumaroil-2α,23,29-triidroxi-olean-12-en-28-oico, ácido arjunólico e os derivados, ácido 3β-trans-p-oxicumaroil-2α,23-diidroxi-olean-12-en-28-oico, ácido 23-trans-p-oxicumaroil-2α,3β-diidroxi-olean-12-en-28-oico e o novo ácido 3β-trans-feruloil-2α,23-diidroxi-olean-12-en-28-oico. As estruturas destas substâncias foram determinadas e/ou identificadas por análises de Espectrometria no Infravermelho, Espectrometria de massas, RMN de 1H e 13C, DEPT 135º, HMBC, HMQC, COSY e NOESY.
Salvador
Marques, Sany Delany Gomes. « Síntese de lignanas por Acoplamento Oxidativo de Fenilpropanoides ». Universidade Federal da Paraíba, 2014. http://tede.biblioteca.ufpb.br:8080/handle/tede/6804.
Texte intégralCoordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPES
By means of oxidative coupling of phenylpropanoids, it was possible to develop a synthesis enantioselective method some natural lignans found in various plants that possess important biological activities. Through this method we obtained the novel synthesis of dihidrocarinatidina composed to be assigned valuable pharmacological activities. Thus, in patent (PI 1101946-8) submitted by our research group, describe the preparation of some natural process lignans, using this, peroxidase contained in coconut water (Cocos nucifera) that acts as a biocatalyst, and hydrogen peroxide as an agent oxidant in the oxidative coupling of acid p-(OH)-phenylpropanoids. Thus, dimeric forms of isoeugenol (Licarina A) and dihidrocarinatidina heterodimer production by oxidative cross-coupling between eugenol and isoeugenol were obtained. This technique was also carried out the synthesis of seringaresinol by dimerization sinapílico alcohol, once methylated provided in yangambin. Moreover, were made by this method, attempts to synthesize the conocarpan. It is noteworthy that all these substances have great pharmacological importance. Using an aqueous mixture of potassium ferrocyanide and ammonium hydroxide, promote oxidative coupling of eugenol, which provided the dehidrodieugenol, its methylation with methyl iodide and potassium carbonate provided mainly in the form monomethyl ether and minority, the dimethyl derivative. The products of the reactions were characterized by 13C-NMR and 1H-NMR spectra, which were then faced with spectral data of natural counterparts in the literature. Tests for leishmania activity licarina A, dehidrodieugenol and its mono and dimethyl ether derivatives were developed. Through these trials there were activities against Leishmania promastigotes and amastigotes of Leishmania major (licarina A) and promastigotes of Leishmania amazonensis (dehidrodieugenol), with more efficient results than the reference drug. The highlighted dehidrodieugenol monometilado showed antiparasitic activity against Leishmania amazonensis.
Por meio do acoplamento oxidativo de fenilpropanóides, foi possível desenvolver um método de síntese enantiosseletivo de algumas lignanas naturais encontradas em diversas plantas e que possuem importantes atividades biológicas. Através deste método obteve-se a síntese inédita da dihidrocarinatidina, composto ao qual se atribui importantes atividades farmacológicas. Destarte, em patente (PI 1101946-8) submetida por nosso grupo de pesquisa, descrevemos processo de preparo de algumas lignanas naturais, utilizando para isso, peroxidase contida na água de coco (Cocos nucifera) que atua como biocatalizador, e água oxigenada como agente oxidante nos acoplamentos oxidativos de ácidos p-(OH)-fenilpropanoides. Deste modo, foram obtidas formas diméricas do isoeugenol (Licarina A) e a produção do heterodímero dihidrocarinatidina por meio do acoplamento oxidativo cruzado entre eugenol e isoeugenol. Através desta técnica, foi também realizada a síntese do seringaresinol, pela dimerização do álcool sinapílico, que uma vez metilado nos forneceu iangambina. Além disso, foram realizadas por este método, tentativas de síntese do conocarpan. Vale ressaltar, que todas estas substâncias apresentam grande importância farmacológica. Utilizando uma mistura aquosa de ferrocianeto de potássio e hidróxido de amônia, promovemos o acoplamento oxidativo do eugenol, que nos forneceu o dehidrodieugenol, sua metilação com iodeto de metila e carbonato de potássio forneceu majoritariamente, a forma monometil éter e minoritariamente, o derivado dimetiléter. Os produtos das reações foram caracterizados pelos espectros de 13C-RMN e 1H-RMN, que depois foram confrontados com dados espectrais dos homólogos naturais encontrados na literatura. Foram desenvolvidos ensaios de atividade antileishmania para a licarina A, dehidrodieugenol e seus derivados mono e dimetil éteres. Por meio destes ensaios verificaram-se atividades antileishmania contra formas promastigotas e amastigotas de Leishmania major (licarina A) e formas promastigotas de Leishmania amazonensis (dehidrodieugenol), apresentando resultados mais eficientes que a droga de referência. O dehidrodieugenol monometilado mostrou destacada atividade antiparasitária contra Leishmania amazonensis.
Yoshida, Nídia Cristiane. « Análises filogenéticas e estudo do metabolismo fenilpropanoidico em espécies de Piper ». Universidade de São Paulo, 2013. http://www.teses.usp.br/teses/disponiveis/46/46136/tde-16012014-080943/.
Texte intégralThe phylogenetic analysis and reconstruction of chemical characters in Piper species distinguished clades specialized in the production of benzoic acids/chromenes, amides and lignoids. The chemical profiles of these species were determined by analysis of crude extracts by 1H NMR combined with principal component analysis (PCA). It is remarkable that lignans of dibenzylbutyrolactone and furofurans type occur in Macrostachys while Schilleria contains dimers of propenylphenols such as tetrahydrofurans lignans and benzofuran neolignans. Piper solmsianum specimens collected from distinct sites showed differences in their morphology and chemical profiles. The assessment of chemical and genetic variability by PCA and microsatellites, respectively, indicated the segregation of populations according to the sampling site and pointed out to the potential use for the combined approaches to distinguish P. solmsianum specimens. The sequences of the genes acetyltransferase, propenylphenol synthase and dirigent protein provided the first information about the genes involved in the biosynthesis of lignans/phenylpropanoids in P. solmsianum.
Ballester, Frutos Ana Rosa. « Resistencia frente a la infección por Penicillium digitatum durante la postcosecha de los frutos cítricos. Bases moleculares y metabolismo de fenilpropanoides ». Doctoral thesis, Universitat de València, 2007. http://hdl.handle.net/10803/10075.
Texte intégralPenicillium digitatum is the causal agent of green mould and constitutes the major postharvest pathogen of citrus fruit, accounting for up to 80 % of losses due to fungal decay. Although control of this pathogen is achieved by chemical fungicides, there is a trend to adopt new and safer control alternatives. Induction of natural resistance in fruit constitutes one of these alternatives. The aim of this work was to gain an insight into the biological and molecular bases of the induction of resistance in citrus fruit against P. digitatum.Different methods to induce resistance against P. digitatum have been evaluated in order to optimize and to select one of them for further studies. Various chemical (methyl jasmonate, β-aminobutyric acid and Brotomax®), biological (non pathogenic fungi of citrus and cellular walls of P. digitatum) treatments, as well as the possible resistance induced by a previous infection with P. digitatum followed by its inactivation by a heat treatment were compared. The latter system was selected because of the high resistance achieved (the incidence was reduced more than 70 % and the severity more than 85 %) and its reproducibility.Global changes in gene expression induced by the selected treatment were analyzed in the flavedo and albedo of citrus fruit. To that end, two cDNA microarrays developed by the Citrus Functional Genomics Project, named 7k and 12k, which contain about 7.000 and 12.000 genes, respectively, were used. The highest inductions were detected in genes that code for enzymes involved in phenylpropanoid metabolism, mainly methyltransferases (OMTs), ethylene biosynthesis, among which there are several ACO genes (1-aminocyclopropane 1-carboxylic acid oxidase), pathogenesis-related proteins (PR) and oxidoreductases. An important reduction in the expression of genes regulated by either cold or light, together with others of unknown function, was also observed. Gene ontology comparisons showed that processes related to amino acids and phenylpropanoid metabolism were upregulated in treated fruits, being these changes more marked in the internal tissue.An increase in ethylene production was observed after the heat treatment, coincident with the resistance acquisition, reaching a concentration similar to that observed in fruits infected by P. digitatum. Nevertheless, in the treated fruits the fungus does not progress, so the rise in ethylene must be due to the fruit. Northern blot analysis showed that this increase in ethylene paralleled a high induction on CsACO expression, as it occurs in infected fruits, and that the highest induction takes place into the albedo.In order to get a deeper insight into the role of the phenylpropanoid metabolism in the induction of resistance, the expression of genes encoding PAL, 4CL, F3H, IRL1, CADs, SAD and OMTs was analyzed by Northern blot. The expression of most of these genes increased in response to the induction treatment, showing a similar pattern in both tissues. Although the overall expression levels were higher in the flavedo, the highest inductions were detected in the albedo. In addition, changes in the expression of these genes in response to the infection by P. digitatum were similar to those originated by the induction of resistance treatment.The putative involvement of this pathway was further studied by examining changes in the metabolic profile by means of HPLC. In the treated fruits a greater abundance and a higher concentration of phenolic compounds in the flavedo with respect to the albedo were observed. Flavanones were the only phenolics whose concentration was higher in the internal tissue. Although the coumarin scoparone was the phenolic compound showing the highest increase in response to the treatment, it has to be pointed out that, among the different phenylpropanoids, benzoic acid derivatives were the most affected. Similar changes were detected during the infection of fruits by P. digitatum.The possible antifungal activity of diverse coumarins, flavanones and alkaloids was tested both in vitro and in vivo against different pathogenic fungi. The coumarins scoparone and umbelliferone and the flavanone hesperidin showed the highest in vitro antifungal activity, although none of them inhibited completely the growth of the citrus fungal pathogens analyzed. However, only the coumarins had an effect in vivo delaying the development of P. digitatum in inoculated citrus fruit. On the other hand, addition of some alkaloids detected in citrus tissues to the culture medium significantly reduced the growth of P. digitatum, being caffeine and 1, 2, 3, 4-tetrahydroharmane 3-carboxylic acid (THHCA) the most effective.This is the first work undertaking both a transcriptomic and a metabolomic approach to study changes associated with relevant processes in postharvest pathology. The global results indicate that both the secondary metabolism, mainly phenylpropanoids, and ethylene play important roles in the induction of resistance in citrus fruit against P. digitatum infection.
López, Pinto Javiera Alejandra. « Efecto de Distintos Niveles de Luminosidad sobre la Composición Fenólica y la Expresión Génica de Enzimas de la Ruta Fenilpropanoide en Bayas de var. Carménère ». Tesis, Universidad de Chile, 2008. http://www.repositorio.uchile.cl/handle/2250/101699.
Texte intégralTizziani, Tiago 1989, Ricardo Andrade 1960 Rebelo, Caio Maurício Mendes de 1972 Córdova et Universidade Regional de Blumenau Programa de Pós-Graduação em Química. « Isolamento, caracterização química e avaliação da atividade antimicrobiana de óleo essencial e fenilpropanoides de Drimys angustifolia Miers (Winteraceae) e de derivados semi-sintéticos / ». reponame:Biblioteca Digital de Teses e Dissertações FURB, 2014. http://www.bc.furb.br/docs/DS/2014/357642_1_1.pdf.
Texte intégralCo-orientador: Caio Mauricio Mendes de Cordova.
Dissertação (mestrado) - Universidade Regional Blumenau, Centro de Ciências Exatas e Naturais, Programa de Pós-Graduação em Química.
Silva, Bianca Carvalho da. « Avaliação da toxicidade de quatro solventes e um surfactante, e dos fenilpropanoides eugenol e (E)-cinamaldeído sobre larvas e pupas de Musca domestica Linnaeus, 1758 (Diptera : Muscidae) ». Universidade Federal de Juiz de Fora (UFJF), 2016. https://repositorio.ufjf.br/jspui/handle/ufjf/4062.
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Musca domestica é um importante vetor mecânico de diversos patógenos para humanos e animais de criação, sendo essencial o estudo de novas alternativas de controle mais eficientes e seguras para este díptero. A busca por novas alternativas de inseticidas envolve experimentos que geralmente necessitam do uso de solventes que não interfiram nos resultados da substância testada. Assim, o presente estudo compreendeu duas etapas: investigar a sensibilidade de larvas e pupas de M. domestica aos solventes acetona, etanol, metanol e dimetilsulfóxido (DMSO) e ao surfactante Tween 80 em diferentes tempos de volatilização; e avaliar a toxicidade dos fenilpropanoides eugenol e (E)-cinamaldeído sobre os mesmo estágios deste díptero. Para ambos os experimentos utilizou-se o teste de contato, com 10 repetições (n=10) para cada solvente/surfactante e concentração das substâncias sobre cada estágio. No primeiro experimento foram testados acetona, etanol e metanol em pureza analítica e DMSO e Tween 80 na concentração de 5%. Os tempos avaliados foram zero, cinco, 10 e 15 minutos (23±2°C e 60±10% UR). Os resultados mostraram que o tempo de volatilização produz diferença significativa na mortalidade larval (ML) para os três primeiros solventes testados, e acetona mostrou-se semelhante ao controle após cinco minutos de volatilização (p>0,05). Metanol e etanol mostraram-se semelhantes ao controle após 15 minutos de volatilização (p>0,05). DMSO não apresentou ML significativa (p>0,05), no entanto apresentou percenbtual de mortalidade acumulada (PMA) superiores a 14% (p<0,05). Tween 80 não apresentou diferença na toxicidade sobre as larvas relacionada ao tempo. Para o teste com pupas somente etanol produziu diferença significativa entre os tempos de volatilização, enquanto acetona e metanol diferiram do controle em todos os tratamentos (p<0,05). DMSO e Tween 80 não diferiram significativamente do controle em nenhum tempo (p˃0,05). O surfactante Tween 80 foi o único que não apresentou toxicidade para ambos os estágios na concentração testada, porém acetona foi o solvente que volatilizou mais rapidamente, mostrando menor toxicidade entre aqueles testados em pureza analítica. Para o segundo experimento, foram utilizadas oito concentrações de cada substância para a determinação das concentrações letais (CL50 e CL90). Eugenol apresentou os menores valores de CL50 e CL90, para a eficácia do tratamento larval (ETL) (1,5 e 3,75 mg/mL, respectivamente) enquanto (E)-cinamaldeido apresentou os menores valores de CL50 e CL90 para a eficácia do tratamento pupal (ETP) (18,08 e 78,83 mg/mL, respectivamente). Ambas as substâncias apresentaram atividade larvicida a partir de 2,5 mg/mL e ETL de 100% a partir de 5 mg/mL. Para o tratamento pupal (E)-cinamaldeído diferiu do controle a partir da 13 concentração de 10mg/mL (p<0,05) e ambos os fenilpropanoides causaram má formação em adultos a partir de 10 mg/mL, e maior ETP na concentração de 30 mg/mL, sendo 67,2% para (E)-cinamaldeído e 32% para eugenol. Os produtos testados nesse estudo apresentaram elevado potencial larvicida, além de ambos apresentarem efeitos pupicida e causarem má formação nos adultros provenientes de pupas tratadas. Ainda, é possível sugerir a utilização conjunta de ambas substância para um controle mais eficiente, visto que (E)-cinamaldeído apresentou melhor atividade larvicida, enquanto eugenol teve melhor atividade pupicida. Desta forma, esses fenilpropanoides mostrando-se promissores para o uso no desenvolvimento de formulações mais seguras para a saúde e meio ambiente, sendo possível sua utilização em estratégias de Manejo Integrado de Pragas.
Musca domestica is an important mechanical vector of several pathogens to humans and domestic animals, being essential to study new alternatives to eficiente and safe control against this Diptera. The search for new insecticides alternative involves experiments that generally require the use of solvents that should not interfere in the results of the test substance. Thus, this study involved two stages: to investigate the sensitivity of M. domestica larvae and pupae to the solvents acetone, ethanol, methanol and dimethylsulfoxide (DMSO) and the surfactant Tween 80 at different times of volatilization; and evaluating toxicity of phenylpropanoid eugenol and (E)-cinnamaldehyde against the same stages of this Diptera. For both experiments were used the patch test with 10 repetitions (n=10) for each solvent/surfactant and concentration of substances against each stage. In the first experiment acetone, ethanol and methanol were tested in analytical purity while DMSO and Tween 80 at the concentration of 5%. The times evaluated were zero, five, 10 and 15 minutes (23±2°C and 60±10% RH). The results showed that the volatilization time produces significant difference in larval mortality (LM) for the first three solvents tested, and acetone was similar to the control after five minutes volatilization (p>0.05). Methanol and ethanol were similar to the control after 15 minutes of evaporation (p>0.05). DMSO showed no significant LM (p> 0.05), but its accumulated mortality percenbtual (AMP) was over 14% (p<0.05). Tween 80 showed no difference in toxicity againts larvae related to time. For the pupae test only ethanol produced significant difference between the evaporation time, while acetone and methanol differed from the control in all treatments (p<0.05). DMSO and Tween 80 did not differ significantly from control at any time (p>0.05). The surfactant Tween 80 was the only one that showed no toxicity for both stages at the concentration tested, however the solvent acetone was volatilized more quickly, showing lower toxicity among those tested in analytical purity. For the second experiment, we used eight concentrations of each substance for the determination of lethal doses (LC50 and LC90). Eugenol showed the lowest values of LC50 and LC90 for the effectiveness of larval treatment (ELT) (1.5 and 3.75 mg/mL, respectively) while (E)-cinnamaldehyde had the lowest values of LC50 and LC90 for effectiveness of pupal treatment (EPT) (18.08 and 78.83 mg/mL, respectively). Both substances exhibited larvicidal activity from 2.5 mg/mL and ELT of 100% from 5 mg/mL. For pupal treatment (E)cinnamaldehyde differed from the control from the concentration of 10mg/mL (p <0.05) and both phenylpropanoid caused malformation in adults from 10 mg/mL. The greater EPT was from concentration of 30 mg/mL, being 67.2% for (E)-cinnamaldehyde and 32% for eugenol. 15 The products tested in this study had high potential larvicide, and both present pupicida effects and cause malformation in adultros from treated pupae. Still, it is possible to suggest the combined use of both substance for more efficient control, as (E)-cinamaldeído showed better larvicidal activity, while eugenol had better pupicida activity. Thus, using these phenylpropanoids show promise in the development of safer formulations for health and the environment, and these could be used in Integrated Pest Management strategies.
Costa, Jacqueline Iris Vasconcelos. « Estudo fitoquímico das folhas e caules de piper arboreum aublet (piperacae) ». Universidade Federal da Paraíba, 2015. http://tede.biblioteca.ufpb.br:8080/handle/tede/8854.
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The genus Piper is the largest the family Piperaceae, its species are distributed especially in neotropical region of the globe. The phytochemical research of Piper species originated numerous scientific papers in many parts of the world, which led to the isolation of many bioactive compounds such as kavalactones, lignoids, chromones, flavonoids and chalcones, terpenes, steroids, prenylated benzoic acids, aristolactams, phenylpropanoids and amides. Piper arboreum is an erect shrub with about 4.0 meters high. It is popularly known as “fruto de morcego”, “alecrim-de-Angola”, “pau-de-Angola” or “beto-preto” and used in Brazil, in the form of decoction for the treatment of rheumatism, bronchitis, flu and colds and used against venereal and urinary tract diseases. This work reports the phytochemical study of the leaves and stem of P. arboreum Aublet. Using usual chromatographic methods and spectroscopic techniques of IR, MS, 1H and 13C NMR and comparison with the literature data it was possible to isolate and identify from the leaves and stem of Piper arboreum, a mixture of steroids: β-sitosterol and stigmasterol, four aristolactams: Piperolactam A, Piperolactam B, Piperolactam C and Cefaronone B, three phenylpropanoids: 3,4,5-trimethoxyphenyl-propanoic acid, 3,4-dimethoxyphenyl-propanoic acid and 3,5-dimethoxy-4-hydroxyphenyl-propanoic acid and three amides: Arboreumine, N-(12,14-dimethoxy-13-hydroxydihydrocinamoil)-3-pyridin-2-one and N-[12-(15,16-methylenedioxyphenyl)-8( E),10 (E) -heptadienoil-pyrrolidine. The last two compounds are being reported for the first time in the literature.
O gênero Piper é o maior da família Piperaceae, suas espécies estão distribuídas especialmente na região neotropical do globo terrestre. A investigação fitoquímica de espécies de Piper originou inúmeros trabalhos científicos em várias partes do mundo, o que levou ao isolamento de diversos compostos bioativos tais como cavalactonas, lignoides, cromonas, flavonoides e chalconas, terpenos, esteroides, ácidos benzoicos prenilados, aristolactamas, fenilpropanoides e amidas. Piper arboreum é um arbusto ereto de aproximadamente 4,0 metros de altura. Popularmente é conhecida como fruto de morcego, alecrim-de-Angola, pau-de-Angola ou beto-preto e utilizada no Brasil na forma de decocto para o tratamento de reumatismo, bronquite, gripe e resfriado e empregada contra doenças venéreas e do trato urinário. Este trabalho reporta o estudo fitoquímico das folhas e caule de P. arboreum Aublet. Utilizando-se métodos cromatográficos usuais e técnicas espectroscópicas de IV, EM e RMN de 1H e 13C uni e bidimensionais e a comparação dos dados com a literatura foi possível isolar e identificar das folhas o e do caule de Piper arboreum, uma mistura de esteroides: β-sitosterol e estigmasterol, quatro aristolactamas: Piperolactama A, Piperolactama B, Piperolactama C e Cefaronona B, três fenilpropanoides: Ácido 3,4,5-trimetoxifenil-propanóico, Ácido 3,4,-dimetoxifenil-propanóico e Ácido 3,5-dimetoxi-4-hidroxifenil-propanóico e três amidas: Arboreumina, N-(12,14-dimetoxi-13-hidroxidihidrocinamoil)-3-piridin-2-ona e N-[12-(15,16-metilenedioxifenil)-8(E),10(E)-heptadienoil-pirrolidina. Os dois últimos compostos estão sendo relatados pela primeira vez na literatura.
Canuto, Gisele André Baptista. « Avaliação metabolômica comparativa in vitro de fármaco candidato ao tratamento de leishmaniose ». Universidade de São Paulo, 2016. http://www.teses.usp.br/teses/disponiveis/46/46136/tde-14092016-090130/.
Texte intégralLeishmaniasis is a neglected disease caused by Leishmania parasites, which occurs in more than 90 countries worldwide, affecting millions of people. The disease is treatable but not curable, and the commonly used therapeutic arsenal is limited and consists in the use of highly toxic drugs. The search for new therapies has been encouraged and the use of active compounds, isolated from natural products, such as plants, has been proven effective. For future use of these active compounds in the treatment, it is necessary to understand its mechanism of action. \"Omics\" sciences, specifically metabolomics, which is the comparative analysis of altered metabolites in a biological system after external intervention, has been widely applied for this purpose. The metabolomic approach is multidisciplinary and the analyzes are performed using modern analytical platforms, such as separation techniques coupled to mass spectrometry (MS). Data treatment are performed with advanced statistical tools and altered metabolites are correlated with metabolic pathways. In this work, the mechanism of action, in Leishmania infantum, of an active compound (methyldehydrodieugenol B), isolated from Nectandra leucantha plant, was evaluated by global metabolomics approach with multiplatform analysis (gas and reversed phase liquid chromatography, GC-MS and RPLC-MS, respectively). Optimizations of sample preparation, extraction and derivatization for GC-MS to obtain the maximum number of metabolites in the samples under consideration were performed. L. infantum promastigotes were grown in culture medium and after 72 h they were treated with metildihidrodieugenol B (at a concentration of 58.18 µg x mL-1); after 48 h of treatment, enzyme activity was quenched, cells washed and frozen for further analysis. Methanol:water (1:1) and 100% methanol are used as solvent extractor to assess intracellular metabolites for analysis by GC-MS and RPLC-MS, respectively. Derivatization with O-methoxyamine in pyridine (15 mg x mL-1) at room temperature for 90 min, followed by silylation with BSTFA + 1% TMCS for 30 min at 40°C was performed to make volatile and stable metabolites for analysis by GC- MS. The results of both analytical platforms showed significant differences between treated and non-treated samples with the active substance, and altered metabolites with statistical significance were correlated with Leishmania metabolism. Different amino acids, fatty acids, carbohydrates, and glycerolipids phospholipids were found, mostly decreased with treatment. Due to the complexity of the parasite metabolism and the great diversity of altered metabolites, a multi-target mechanism can be assigned to the methyldehydrodieugenol B. Changes in the metabolism of glycolysis and gluconeogenesis are highlighted, indicating changes in the cell energy sources. Changes in the lipid composition of the parasite plasma membrane were also observed, suggesting variations in its flexibility and fluidity. The results are preliminary, but very important to take the first step into elucidation of the action of this substance in the treatment of leishmaniasis, aiming the search for new pharmaceutical therapies.
Amaral, Lúcio de Paula. « Caracterização química e avaliação biológica do óleo essencial de Nectandra megapotamica (Spreng.) Mez ». Universidade Federal de Santa Maria, 2014. http://repositorio.ufsm.br/handle/1/3779.
Texte intégralNectandra megapotamica (Lauraceae) is abundant in the Deciduos Forest in Santa Maria-RS. Its essential oil (EO) has been studied for biological activities due to its anti-inflammatory, antifungal, antimicrobial, and cytotoxic effects against tumor cells, among others. The presence of phenylpropanoids as well as sedative and anesthetic activities in R. quelen were observed in the prospect of EO of Nectandra megapotamica. As a hypothesis, we considered the seasonal variability and the occurrence of chemical phenotypes for the individuals in the same population of the species with different biological activities for the EO. The objectives of this study were to define the potential of N. megapotamica in a population in Santa Maria-RS for the production of EO; to determine the yield (Y), chemical composition and the seasonal variation of EO; to evaluate the possible occurrence of chemical phenotypes (differentiated chemical composition); to isolate compounds of interest; and to perform tests of biological activities for the EO and for the isolated compound. The EO samples were obtained from fresh leaves, which were initially separated in young (YL) and old leaves (OL) by hydrodistillation in triplicate for three hours. The collections occurred in function of the seasons in two locations in Santa Maria-RS (Morro do Elefante, and in the proximity of the 318 km of BR 158). The respective Y values were determined, and EO samples were analyzed by GC/MS. Some samples were also analyzed by GC-FID, in triplicate. The chemical composition of the EO was analyzed and grouped by multivariate techniques, main components and hierarchical grouping. The EO was also fractionated by CC, for the isolation of a compound, whose identification happened by NMR. The discrepant groups (CG2 and CG5) were tested for allelopathic, insecticide and anesthetic activities in fish. The compound obtained from CG5 was identified as isoelemicin (phenylpropanoid) and also tested for the anesthetic activity. The largest Y for the EO was observed in spring (YL 0.24% and OL 0.14%) during flowering, fruiting and foliation, and the lowest in autumn (YL 0.13% and OL 0.11%) in the rustification and at rest. The major constituents were α-pinene with greater Y in spring and summer (YL 30.81% and OL 35.86%), and bicyclogermacrene with greater Y in autumn and winter (YL 24.19% and OL 21.73%), which formed two large CG. In the CG of bicyclogermacrene, the presence of phenylpropanoids was observed and therefore it constituted a specific group (CG5). However, CG2 presented higher concentration of monoterpenoids. In the biological tests, the allelopathic activity (lower seed germination and seedling development) for L. sativa var. regina, B. subalternans, G. max, A. strigosa, L. multiflorum and O. sativa was observed when the seeds were submitted to the EO. Moreover, the insecticidal activity was observed in N. viridula, and also sedation in R. quelen. The CG5 was superior than CG2, concerning allelopathy in O. sativa; however, both groups were active at the concentration of 15% EO for the other species, which inhibits 100% germination of B. subalternans (QG5) and A. strigosa (both groups). Regarding the insecticidal action of EO at 5%, the CG5 promoted 46.67% mortality of N. viridula, and CG2 only 14.44%. Concering R. quelen, we observed toxicity associated with sedation, both by the EO similar to CG5 and by isoelimicin. The stage of anesthesia was observed at the concentracion of 500 mg L-1 EO; however, the effect was lower than that observed for eugenol (positive control). In conclusion, the species in the population assessed has the potential to produce EO as a source of new bioactive molecules and biological action mechanisms that should consider the toxicity component, which requires further studies.
Nectandra megapotamica (Lauraceae) é abundante na Floresta Estacional Decidual em Santa Maria-RS. O seu óleo essencial (OE) vêm sendo estudado quanto às atividades biológicas, devido a sua ação anti-inflamatória, antifúngica, antimicrobiana, citotóxica contra células tumorais, dentre outras. Na prospecção do OE foram encontrados fenilpropanoides, além de atividades sedativas e anestesicas em Rhamdia quelen. Como hipótese, considerou-se que haja variabilidade sazonal e ocorrência de fenótipos químicos para os indivíduos na mesma população da espécie, com atividade biológica diferenciada para o OE. Os objetivos deste trabalho foram pesquisar o potencial de N. megapotamica, em uma população em Santa Maria, para a produção de OE; determinar o rendimento (R), a composição química e sua variação sazonal; avaliar a possível ocorrência de fenótipos químicos (composição química diferenciada); isolar constituintes de interesse; e por fim, realizar testes de atividades biológicas, para o OE e para o isolado. Os OE foram obtidos de folhas frescas, inicialmente separadas em jovens (FJ) e velhas (FV), por hidrodestilação em triplicata por três horas. As coletas ocorreramem função das estações do ano, em dois locais em Santa Maria-RS (Morro do Elefante e, na proximidade do km 318 da BR 158). Foram determinados os respectivos R, e os OE foram analisados por CG-EM. Algumas amostras também foram analisadas por CG-DIC, em triplicata. A composição química do OE dos indivíduos coletados foi analisada e agrupada por técnicas multivariadas, componentes principais e agrupamento hierárquico. Foi também realizado fracionamento do OE por CC, para o isolamento de uma substância, cuja identificação se deu por RMN. Determinados os grupos químicos (GQ) e o constituinte isolado, os grupos mais discrepantes (GQ2 e GQ5) foram testados quanto a atividade alelopática, inseticida e anestésica em peixes. A isoelemicina foi avaliada para esta última. O maior R do OE foi observado na primavera (FJ 0,24% e FV 0,14%), durante a floração, frutificação e foliação, e o menor no outono (FJ 0,13% e FV 0,11%), na rustificação e repouso. Os constituintes majoritários foram α-pineno, com maior R na primavera e verão (FJ 30,81% e FV 35,86%), e biciclogermacreno, com maior R no outono e inverno (FJ 24,19 e FV 21,73%). Estes formaram dois grandes GQ. No GQ do biciclogermacreno foi observada a presença de fenilpropanoides, que constituíram um grupo específico (GQ5). Já o GQ2 apresentou maiores teores de monoterpenoides. Do OE do GQ5 foi isolada a isoelemicina (fenilpropanoide). Nos testes biológicos realizados foram observadas atividade alelopática (menor germinação de sementes e desenvolvimento de plântulas) para Lactuca sativa cv. regina, Bidens subalternans, Glicine max, Avena strigosa, Lolium multiflorum e Oryza sativa; atividade inseticida em Nezara viridula e sedação em R. quelen. O GQ5 foi superior ao GQ2, nos testes de alelopatia em O. sativa, mas ambos os grupos foram ativos na concentração de 15% de OE para as demais espécies, inibindo100% da germinação de B. subalternans (GQ5) e de A. strigosa (ambos os grupos). Na ação inseticida com 5% do OE, o GQ5 promoveu 46,67% de mortalidade de N. viridula, e o GQ2 apenas 14,44%. Em R. quelen foi observada sedação associada à toxicidade, tanto pelo OE similar ao GQ5 (obtido do segundo local de coleta) como pela isoelemicina. O estágio de anestesia foi observado na concentração de 500 mg L-1 de OE, mas o efeito foi inferior ao observado para o eugenol com 50 mg L-1 (controle positivo). Conclui-se que a espécie, na população avaliada, possui potencial para produzir OE, como fonte de novas moléculas bioativas e mecanismos de ação biológica, que devem considerar a componente de toxicidade, o que exigirá novas pesquisas.
Vélez, Bermúdez Isabel Cristina. « Caracterización funcional del factor de transcripción ZmZIM91 de maíz ». Doctoral thesis, Universitat de Barcelona, 2013. http://hdl.handle.net/10803/110928.
Texte intégralThe regulatory subunit of protein kinase CK2β1 was used as a bait to perform a yeast two-hybrid screening against a cDNA library of drought-stressed maize leaves. Between the interacting partners a putative transcription factor named ZmZIM91 (GATA/Zinc Finger type) was identified. The protein ZmZIM91 has not been previously characterized in maize and there was little information about their homologous in Arabidopsis thus, no fuctional data regarding this group of proteins was available. Sequence analysis and phylogenetic studies show that ZmZIM91 belong to the TIFY family, more specifically at the ZML subfamily. JAZ proteins, which have been widely characterized in Arabidopsis and in other species, also belong to the TIFY family. To make a molecular characterization of ZmZIM91, first of all, it was demonstrated that this protein was an in vitro substrate of the maize protein kinase CK2. In addition, in vivo gel kinase assays suggest that phosphorylation regulates this protein under different treatments as drought or methyl jasmonate (MeJA). Furthermore, were carried out a set of experiments as pull-down, yeast two-hybrid assay and Bimolecular fluorescence complementation, which yielded results as the interaction between ZmZIM91 with the regulatory subunits of the protein kinase ZmCK2, the dimerization of ZmZIM91 and the interaction with JAZ protein, however, it was established that unlike JAZ, ZmZIM91 cannot interact with the E3 ubiquitin ligase COI1. Furthermore, were performed western blot experiments using wild-type maize leaves and the endogenous antibody against ZmZIM91 (produced in this work), also assays of overexpression in maize protoplasts in both using the MeJA hormone, as MeJA and MG132, where it was observed that ZmZIM91 was degraded in the presence of MeJA in one hour and its degradation it is probably through the 26S proteasome pathway. Using a Protein-Array assay, it was established that ZmZIM91 could bind to DNA directly through GATA and GATC motifs. Finally, experiments of chromatin immunoprecipitation and massively parallel sequencing (ChIP-Seq), allowed to determine target genes of the transcription factor ZmZIM91. Between the targets identified, one correspond to the caffeic acid O-methyltransferase (COMT) gene, involved in the biosynthesis of lignin and another is the DFR gene (A1) involved in the biosynthesis of flavonoids. These results were confirmed by ChIP-QPCR, and by transient expression experiments in maize protoplasts where they were identified as highly enriched, It was determined that the ZmZIM91 transcription factor is a repressor of COMT and A1 genes, suggesting a regulatory role of ZmZIM91 in the phenylpropanoid pathway and also as a negative regulator of this pathway. Experiments Chromatin immunoprecipitation (ChIP) with MeJA treatment application at one hour, confirmed that in the presence of this hormone ZmZIM91 loses binding capacity to the COMT and A1 promoters. Moreover, through Bimolecular complementation assays was established the interaction between the transcription factor ZmZIM91 and the ZmMYB31 and ZmMYB42 factors involved in the negative regulation of genes of the phenylpropanoid pathway, which may be acting as a regulatory module to regulate genes such as COMT.
NIEDDU, FRANCESCO. « Caratterizzazione molecolare della famiglia genica della Calcone Sintasi in Olea europaea ed analisi della variabilità genetica in cultivar italiane ». Doctoral thesis, 2010. http://hdl.handle.net/2158/546263.
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