RESUMO
An unreported prenylated indole derivative hydroxytakakiamide (4) was isolated, together with the previously described ergosterol (1), ergosterol acetate (2), and (3R)-3-(1H-indol-3-ylmethyl)-3, 4-dihydro-1H-1,4-benzodiazepine-2,5-dione (3), from the column fractions of the crude ethyl acetate extract of the culture of a marine sponge-associated fungus, Aspergillus fischeri MMERU 23. The structure of 4 was elucidated by the interpretation of 1D and 2D NMR spectral data and high-resolution mass spectrum. The absolute configuration of the stereogenic carbon in 3 was proposed to be the same as those of the co-occurring congeners on the basis of their biogenetic consideration and was supported by the comparison of its sign of optical rotation with those of its steroisomers. The crude ethyl acetate extract and 2 were evaluated, together with acetylaszonalenin (5) and helvolic acid (6), which were previously isolated from the same extract, for the in vivo antinociceptive activity in the mice model. The crude ethyl acetate extract exhibited antinociceptive activity in the acetic acid-induced writhing and formalin tests, while 2, 5, and 6 displayed the effects in the late phase of the formalin test. On the other hand, neither the crude ethyl acetate extract nor 2, 5, and 6 affected the motor performance of mice in both open-field and rotarod tests. Additionally, docking studies of 2, 5, and 6 were performed with 5-lipoxygenase (5-LOX) and phosphodiesterase (PDE) enzymes, PDE4 and PDE7, which are directly related to pain and inflammatory processes. Molecular docking showed that 6 has low affinity energy to PDE4 and PDE7 targets while retaining high affinity to 5-LOX. On the other hand, while 2 did not display any hydrogen bond interactions in any of its complexes, it achieved overall better energy values than 6 on the three antinociceptive targets. On the other hand, 5 has the best energy profile of all the docked compounds and was able to reproduce the crystallographic interactions of the 5-LOX complex.
Assuntos
Acetatos , Aspergillus , Fungos , Ácido Fusídico/análogos & derivados , Poríferos , Animais , Camundongos , Simulação de Acoplamento Molecular , Ácido Acético , Ergosterol , AnalgésicosRESUMO
The present study describes the seasonal and circadian variations of the major compounds from Lippia alba leaves. SPSS was used to identify, quantify, and associate the variations in the secondary metabolites of this species through HPLC/DAD analysis of the leaves hydroethanolic extracts of six selected L. alba specimens. For the circadian study, the samples were collected at four different daily hours in each year's season. For the seasonal study, the samples were collected monthly from the same individuals for two consecutive years (2018 and 2019). These samples were analyzed and quantified using a validated HPLC method for flavonoids, iridoids, and phenyl ethanoid glycoside. Mussaenoside, acteoside, and tricin-7-O-diglucuronide showed a moderate positive correlation between their biosynthesis and the precipitation index, while epi-loganin had a moderate negative correlation. Acteoside showed a moderate positive correlation between the minimum registered temperature and its production. Compared with previous studies, a drastic reduction (about 95 %) in the production of tricin-7-O-diglucuronide compared with previous study and this difference could be attributed to the plant's aging. Thus, the data demonstrated that lower temperatures and high rainfall could favor the production of the major L. alba active compounds (acteoside and tricin-7-O-diglucuronide) and that older plants harm their production.
Assuntos
Lippia , Folhas de Planta , Estações do Ano , Folhas de Planta/química , Folhas de Planta/metabolismo , Lippia/química , Lippia/metabolismo , Cromatografia Líquida de Alta Pressão , Extratos Vegetais/química , Extratos Vegetais/metabolismoRESUMO
MicroRNAs (miRs) act as important post-transcriptional regulators of gene expression in glial cells and have been shown to be involved in the pathogenesis of neurodegenerative diseases, including Alzheimer's disease (AD). Here, we investigated the effects of agathisflavone, a biflavonoid purified from the leaves of Cenostigma pyramidale (Tul.), on modulating the expression of miRs and inflammatory mediators in activated microglia. C20 human microglia were exposed to oligomers of the ß-amyloid peptide (Aß, 500 nM) for 4 h or to lipopolysaccharide (LPS, 1 µg/mL) for 24 h and then treated or not with agathisflavone (1 µM) for 24 h. We observed that ß-amyloid and LPS activated microglia to an inflammatory state, with increased expression of miR-146a, miR-155, IL1-ß, IL-6, and NOS2. Treatment with agathisflavone resulted in a significant reduction in miR146a and miR-155 induced by LPS or Aß, as well as inflammatory cytokines IL1-ß, IL-6, and NOS2. In cells stimulated with Aß, there was an increase in p-STAT3 expression that was reduced by agathisflavone treatment. These data identify a role for miRs in the anti-inflammatory effect of agathisflavone on microglia in models of neuroinflammation and AD.
Assuntos
Doença de Alzheimer , Biflavonoides , MicroRNAs , Humanos , Biflavonoides/farmacologia , Microglia/metabolismo , Interleucina-6/metabolismo , Lipopolissacarídeos/farmacologia , Doença de Alzheimer/metabolismo , Peptídeos beta-Amiloides/metabolismo , Citocinas/metabolismo , MicroRNAs/genética , Fator de Transcrição STAT3/metabolismoRESUMO
This study describes methodologies for extracting and isolating bergenin, a C-glucoside of 4-O-methylgallic acid found in some plants and it presents various in vitro and in vivo biological activities. Bergenin was previously obtained from the Pelthophorum dubim (Fabaceae) roots with a good yield. Conventional chromatographic procedures of the CHCl3 soluble fraction of the MeOH extract gave 3.62% of this glucoside. An HPLC/DAD method was also developed and validated for bergenin and its precursor, gallic acid quantifications. Microwave extractions with different solvents were tested to optimize the extraction of bergenin, varying the temperature and time. MAE (Microwave Assisted Extraction) was more efficient than conventional extraction procedures, giving a higher yield of bergenin per root mass (0.45% vs. 0.0839%). Molecularly imprinted polymer (MIP) and non-imprinted polymer (NIP) based on bergenin as the template molecule, methacrylic acid, and ethylene glycol dimethacrylate were synthesized and characterized by FTIR and SEM (Scanning Electron Microscopy). Bergenin adsorption experiments using MIP and NIP followed by molecular imprinted solid phase extraction (MISPE) showed that MIP had a higher selectivity for bergenin than NIP. A dendrochronological study using the proposed method for detection and quantification of gallic acid and bergenin in five P. dubium growth rings of a 31-year-old heartwood and in the phelloderm and barks indicated that bergenin was more abundant in the 11-14th growth rings of the heartwood and decreased from the heartwood to the barks.
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ABSTRACT Natural steroids and triterpenes such as b-sitosterol, stigmasterol, lupeol, ursolic and betulinic acids were transformed into its hexanoic and oleic esters, to evaluate the influence of chemical modification towards the cytotoxic activities against tumor cells. The derivatives were evaluated against five tumor cell lines [OVCAR-8 (ovarian carcinoma); SF-295 (glioblastoma); HCT-116 (colon adenocarcinoma); HL-60 (leukemia); and PC-3 (prostate carcinoma)] and the results showed only betulinic acid hexyl ester exhibits cytotoxic potential activity.
Assuntos
Humanos , Triterpenos/farmacologia , Lamiaceae/química , Triterpenos Pentacíclicos/farmacologia , Fabaceae/química , Antineoplásicos/farmacologia , Triterpenos/isolamento & purificação , Triterpenos/química , Ensaios de Seleção de Medicamentos Antitumorais , Lamiaceae/classificação , Concentração Inibidora 50 , Linhagem Celular Tumoral , Ésteres , Triterpenos Pentacíclicos/isolamento & purificação , Triterpenos Pentacíclicos/química , Fabaceae/classificação , Antineoplásicos/isolamento & purificação , Antineoplásicos/químicaRESUMO
ABSTRACT The profile of volatile organic compounds, the glandular and non-glandular trichomes of Plectranthus ornatus, obtained by in vitro cultivation, was evaluated in plants grown in Murashide and Skoog medium supplemented with benylaminopurine at 4.5, 9.0, and 18.0 µM + naphthaleneacetic acid at 5.37 µM, kinetin at 4.7, 9.3 and 18.5 µM + naphthaleneacetic acid (5.37 µM) or Murashide and Skoog 0 medium (as a control). Scanning Electron Microscopy was performed on samples of the third leaf node of the 90 days old plants obtained from treatment with 4.5 or 9.0 µM benylaminopurine, and 4.7 or 9.3 µM kinetin. Headspace Solid Phase Micro-Extraction of the 30, 60 and 90 days old in vitro plants permitted to determinate by GC/MS the composition comprised of 62 compounds. The data were analyzed using Principal Component Analysis and Hierarchical Clustering Analysis and, the major constituents of these oils after treatment and aging were monoterpenes and sesquiterpenes. Morphoanatomical analysis of trichomes, by Scanning Electron Microscopy, enabled the identification of non-glandular trichomes and four types of glandular trichomes, which comprised capitate and peltate glandular trichomes that were distributed on both sides of the leaf. We observed that the regulators influenced qualitative and quantitative profiles of the volatile organic compounds and the number and distribution of hairs on the leaf surface.
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Se reportan los resultados de una investigación cualitativa que tuvo como objetivo describir e interpretar las teorías subjetivas de docentes acerca de su salud laboral. Se trabajó con 46 profesores de cuatro liceos públicos de dos comunas de la Región de Atacama, Chile, que se seleccionaron bajo el criterio de representatividad de casos. Se aplicaron ocho entrevistas en profundidad y seis grupos de discusión. Mediante la técnica de análisis de la Grounded Theory y análisis específico para teorías subjetivas; se encontró que las teorías subjetivas sobre salud laboral docente están relacionadas con los significados subjetivos que los docentes le otorgan a la profesión, enseñanza y aprendizaje de sus estudiantes, y que las características de su estructura y contenido conllevan más bien a una inhibición del autocuidado de su salud laboral. En la discusión se analiza la implicancia que esto tiene para la salud laboral del profesor y se proponen orientaciones que podrían propiciar, a partir del cambio subjetivo, el desarrollo de teorías subjetivas de mayor elaboración y complejidad, que orienten la acción hacia el autocuidado de la salud laboral docente.
The results of a qualitative study aimed to describe and interpret the subjective theories of teachers about their occupational health is reported. We worked with 46 teachers from four public secondary education in the towns of the Atacama Region, Chile, which were selected under the criteria of representativeness of cases. Eight interviews and six focus groups were applied. Through technical analysis of Grounded Theory and subjective theories specific analysis revealed that subjective theories on occupational health teaching are closely related to the subjective meanings that teachers give to the profession, teaching and student learning, and that the characteristics of the structure and content rather lead to an inhibition of self-care in occupational health. In discussing the implications of this for occupational health teacher and guidance that could lead, from subjective change, the development of subjective theories of elaboration and greater complexity, to guide action towards self-care proposed occupational health teacher analyzed.
Assuntos
Humanos , Masculino , Feminino , Adulto , Conhecimentos, Atitudes e Prática em Saúde , Saúde Ocupacional , Professores Escolares/psicologia , Chile , Entrevistas como Assunto , Ensino Fundamental e Médio , Pesquisa Qualitativa , Promoção da Saúde , Doenças Profissionais/prevenção & controleRESUMO
This study describes the isolation and identification of apigenin-7-O-ghicopyranoside, a flavonoid isolated from the flowers of Bellis perennis L., Asteraceae, an species with a broad spectrum of biological activities. The in vitro antioxidant activity and the inhibition of the enzyme acetylcholinesterase were evaluated. The flavonoid showed strong in vitro antioxidant potential, because of the capacity of removal of hydroxyl radicals and nitric oxide, and also prevented the formation of thiobarbituric acid-reactive substances. These parameters were inhibited at the highest concentration of ApG at rates of 77.7%, 72% and 73.4%, respectively, in addition to inhibiting acetylcholinesterase, suggesting potential use in the treatment of neurodegenerative diseases.
Assuntos
Antioxidantes/farmacologia , Asteraceae/química , Inibidores da Colinesterase/farmacologia , Flores/química , Extratos Vegetais/farmacologia , Acetilcolinesterase/efeitos dos fármacos , Asteraceae/classificação , Peroxidação de Lipídeos/efeitos dos fármacos , Extratos Vegetais/isolamento & purificaçãoRESUMO
Approximately 600-700 species of Ipomoea, Convolvulaceae, are found throughout tropical and subtropical regions of the world. Several of those species have been used as ornamental plants, food, medicines or in religious ritual. The present work reviews the traditional uses, chemistry and biological activities of Ipomoea species and illustrates the potential of the genus as a source of therapeutic agents. These species are used in different parts of the world for the treatment of several diseases, such as, diabetes, hypertension, dysentery, constipation, fatigue, arthritis, rheumatism, hydrocephaly, meningitis, kidney ailments and inflammations. Some of these species showed antimicrobial, analgesic, spasmolitic, spasmogenic, hypoglycemic, hypotensive, anticoagulant, anti-inflammatory, psychotomimetic and anticancer activities. Alkaloids, phenolics compounds and glycolipids are the most common biologically active constituents from these plant extracts.
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This work describes the chemical composition and antimicrobial activity of the volatile oils of Ocimum canum and Ocimum selloi, both occurring in Jequié/BA, northeastern Brazil. The plants were collected in the winter/2005 andsummer/2006, the oils extracted by steam distillation and further analyzed by GC-MS. A total of 30 and 31 compounds was identified from the oils of O. selloi and O. canum, respectively. It was observed that the oil content of O. canum showed variation during the seasons, while the oils of O. selloi did not. Methylchavicol and linalool were the main chemical components found in the aerial parts and leaves of O. canum. This finding permitted to characterize this specimen as a new chemotype of O. canum. Regarding the aerial parts of O. selloi, eugenol, 1,8-cineole, transcaryophyllene and linalool were identified as their major components. All extracted oils from the aerial parts showed biological activity against gram-positive cocci - Staphylococcus aureus ATCC 25923 - but only the O. canum one showed activity against gram-negative bacilli - Escherichia coli ATCC 25922.
Este trabalho descreve a composição química e a atividade antimicrobiana dos óleos voláteis de Ocimum canum e Ocimum selloi, que ocorrem em Jequié/BA, nordeste do Brasil. As plantas foram colhidas no inverno de 2005 e verão de 2006 e os óleos extraídos por destilação a vapor foram posteriormente analisados por GC-MS. Um total de 30 e 31 compostos foi identificado a partir dos óleos de O. selloi e O. canum, respectivamente. Foi observado que o teor de óleo de O. canum apresentou variação durante as estações do ano, enquanto o óleo de O. selloi não. Metilchavicol e linalol foram os principais componentes químicos encontrados na parte aérea e folhas de O. canum. Esta descoberta permitiu caracterizar este espécime como um novo quimiotipo de O. canum. Com relação às partes aéreas de O. selloi, eugenol, 1,8-cineol, trans-cariofileno e linalol foram identificadas como os seus principais componentes. Todos os óleos extraídos das partes aéreas apresentaram atividade biológica contra cocos gram-positivo - Staphylococcus aureus ATCC 25923 - mas apenas aquele de O. canum apresentou atividade contra bacilo gram-negativo - Escherichia coli ATCC 25922.
Assuntos
Antibacterianos/química , Escherichia coli/efeitos dos fármacos , Ocimum/química , Óleos Voláteis/química , Óleos de Plantas/química , Staphylococcus aureus/efeitos dos fármacos , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Cromatografia Gasosa-Espectrometria de Massas , Óleos Voláteis/farmacologia , Óleos de Plantas/farmacologia , Estações do AnoRESUMO
Rutaceae is a taxon with species very well distributed in Brazilian semi-arid area, commonly used in folk medicine. Species from this genus have diverse biological activity described in literature. In this work, immunomodulatory and bactericidal activity are described for chloroform and ethyl acetate extracts of three of them (Esenbeckia grandiflora Mart., Pilocarpus spicatus A.St.-Hil. and Galipea simplicifolia Schult.). Initially all the samples had their cytotoxicity evaluated, aiming to determine the LC50. The immunomodulatory potential was evaluated in cultures of murine splenocytes stimulated or not with concanavalin A and in a mixed lymphocyte reaction (MLR) using splenocytes from BALB/c (H-2d) mice immunized with splenocytes from C57Bl/6 (H-2b) mice. Four samples had higher values of lymphoproliferation inhibition in concanavalin A-stimulated cultures and were evaluated in MLR. The antibacterial activity of extracts was also evaluated and the minimal inhibitory concentrations (MIC) for two active samples were 1.0 and 5.0 mg/ml for extracts from Esenbeckia grandiflora Mart. and Galipea simplicifolia Schult., respectively. Thus, our results reinforce data of literature relating biological activity for many species of the Rutaceae family and encourage studies with these species aiming to discover active compounds, candidates to new medicines.
A família Rutaceae apresenta espécies vegetais muito bem distribuídas no Semi-Árido Brasileiro e comumente usadas em medicina popular. Espécies dessa família tem diversas atividades biológicas descritas na literatura. Neste trabalho, atividades imunomoduladora e bactericida são descritas para o extrato acetato de etila e clorofórmico de três espécies da família (Esenbeckia grandiflora Mart., Pilocarpus spicatus A.St.-Hil. e Galipea simplicifolia Schult.). Todas as amostras foram inicialmente avaliadas quanto à sua citotoxicidade, com objetivo de determinar a LC50. O potencial imunomodulador foi avaliado em culturas de esplenócitos murinos estimulados ou não com concanavalina A e também em reação mista linfocitária (RML), usando também esplenócitos de camundongos BALB/c (H-2d) imunizados com esplenócitos de camundongos C57Bl/6 (H-2b). Quatro amostras tiveram os mais elevados valores percentuais de inibição da proliferação de linfócitos ativados pela concanavalina A e foram avaliados em RML. A atividade antibacteriana dos extratos foi também avaliada e a concentração mínima inibitória (CMI) para duas amostras ativas foi de 1.0 e 5.0 mg/mL, respectivamente para as espécies Esenbeckia grandiflora Mart. and Galipea simplicifolia Schult. Assim, os dados aqui apresentados reforçam informações da literatura científica relacionados à atividade biológica para muitas espécies da família Rutaceae e incentivam outros estudos com estas visando descobrir substâncias ativas, potenciais candidatas a novos fármacos.
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The family Boraginaceae is widely distributed in Brazil and in the Northeastern region some species are popularly used to treat symptoms of rheumatism, painful menstruation and dyspepsia. In this work we studied Cordia superba Cham. and C. rufescens A. DC., native from Brazilian Semi-arid region, in order to investigate their immunomodulatory activity. Six extracts were prepared from aerial parts of C. superba and C. rufescens. The cytotoxicity was evaluated using splenocytes from BALB/c mice. The immunomodulatory activity was determined by in vitro assays using activated mouse macrophages and lymphocytes. Peritoneal macrophages obtained from BALB/c mice were stimulated with IFN-gamma and LPS in the presence/absence of the samples. The NO production was measured indirectly through Griess method. Three samples inhibited the production of nitric oxide in values near 50 percent at a concentration of 100 µg/mL. To evaluate the effects of the extracts on lymphocytes, splenocytes from BALB/c mice were incubated with the samples and concanavalin A. Proliferation inhibition was determined by analysis of ³H-thymidine uptake. Samples from the two species had a strong inhibitory activity on lymphocyte proliferation and IL-2 production. Two chloroform extracts prepared from aerial parts of C. rufescens had the lowest IC50 values (7.6 and 11.0 µg/mL).
A família Boraginaceae é amplamente distribuída no Brasil e na região nordeste algumas espécies são usadas popularmente no tratamento de reumatismo, dores menstruais e dispepsias. Neste trabalho foram estudadas as espécies Cordia superba Cham. and C. rufescens A. DC., nativas da região semi-árida brasileira, objetivando investigar a atividade imunomoduladora. Seis extratos foram preparados a partir de partes aéreas das espécies. A citotoxicidade foi avaliada usando culturas de esplenócitos de camundongos BALB/c. A atividade imunomoduladora foi determinada por ensaios in vitro usando macrófagos e linfócitos murinos ativados. Macrófagos peritoneais obtidos de camundongos BALB/c foram estimulados com IFN-gama and LPS na presença/ausência das amostras. A produção de NO foi medida indiretamente através do método de Griess. Três amostras inibiram a produção de NO em valores próximos a 50 por cento (100 µg/mL). Os efeitos das amostras sobre os linfócitos foram avaliados cultivando esplenócitos de camundongos BALB/c em presença destas amostras e de concanavalina A. A proliferação foi determinada pela análise da incorporação de ³H-tritiada. Amostras de duas espécies apresentaram uma forte atividade inibidora sobre a proliferação de linfócitos e sobre a produção de IL-2. Dois extratos clorofórmicos (partes aéreas de C. rufescens) tiveram os menores valores de IC50 (7,6 and 11,0 µg/mL).
Assuntos
Boraginaceae/imunologia , Cordia/imunologia , Extratos VegetaisRESUMO
Este trabalho descreve o isolamento e caracterização de alguns metabólitos presentes nos caules de Davilla rugosa (Dilleniaceae), conhecida vulgarmente como cipó-caboclo e utilizada pela população na medicina tradicional brasileira para diversas enfermidades. O extrato hidrometanólico foi particionado entre hexano, clorofórmio e acetato de etila. Da fase hexânica foram obtidos a friedelina, sitostenona e ácido betulínico. Da fase clorofórmica foram isolados através de técnicas cromatográficas o ácido betulínico e a narigenina. Enquanto que do extrato acetato de etila foram obtidos dois outros flavonóides, quercetina e 4-O-metil taxifolina. As substâncias tiveram suas estruturas elucidadas através da análise de dados no UV e de RMN.
This work describes the first chemical study of the Brazilian medicinal plant Davilla rugosa (Dilleniaceae) popularly known as cipó-caboclo. The hydromethanolic extract of the stems was partitioned between hexane, CHCl3 and EtOAc. Chromagraphic methods of fractions resulted in isolation of friedelin, sitostenone, betulinic acid, narigenin, quercetin and 4-O-methyl taxifolin. The compounds were identified by spectrometric data analyses.
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This work describes the evaluation of the antioxidant activity in the system b-carotene / linoleic acid and radical scavenging effects of the substances epicatechin-(2β→7,4β→8)-epicatechin, epicatechin, epigalocatechin-(2β→7,4β→8)-epicatechin, luteolin 3-β-Dglicopiranoside and crisoeriol 7-β-D-glicopiranoside isolated of the extract AcOEt of the stem of Dioclea lasiophylla, in comparison with the standards n-propyl gallate, BHT and a-tocopherol.
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Se presenta un caso de sexo masculino de 61 años de edad cuya sintomatología comienza aparentemente 3 meses antes: anorexia, pérdida de peso, síndrome febril prolongado, mialgias, polineuropatía periférica, dolor abdominal, anemia, síndrome de insuficiencia renal, esplenomegalia detectado ecográficamente, ascitis, fosfatasas aldalinas elevadas, hipoprotidemia, caídas súbitas del hematocrito, úlcera gástrica con biopsias negativas para malignidad y donde el estudio histopatológico de la pieza operatoria (gastrectomía parcial), confirmó los diagnósticos de enfermedad de Ménétrier o gastropatía hipertrófica, asociada a poliarteritis nodosa. La primera explica la hipoprotidemia, los edemas, la ascitis. La segunda, la insuficiencia renal, la polineuropatía periférica, el compromiso muscular esplénico, hepático y la fiebre; mientras que la úlcera gástrica, las pérdidas de sangre, la anorexia, la pérdida de peso y el dolor abdominal pueden ser explicados por ambas enfermedades. En la bibliografía consultada no se detectó ningún caso con esta misma asociación