RESUMO
Piper tuberculatum (Piperaceae) is a species that accumulates especially amides as secondary metabolites and several biological activities was previously reported. In this article, we report a proteomic study of P. tuberculatum. Bidimensional electrophoresis (2D SDS-PAGE) and mass spectrometry (ESI-Q-TOF) were used in this study. Over a hundred spots and various peptides were identified in this species and the putative functions of these peptides related to defense mechanism as biotic and abiotic stress were assigned. The information presented extend the range of molecular information of P. tuberculatum.(AU)
Piper tuberculatum (Piperaceae) é uma espécie que acumula especialmente amidas como metabólitos secundários e diversas atividades biológicas dessa espécie foram relatadas anteriormente. No presente artigo, relatamos um estudo proteômico dessa espécie. Eletroforese bidimensional (2D SDS-PAGE) e espectrometria de massas (ESI-Q-TOF) foram utilizadas nesse estudos. Mais de cem spots e vários peptídeos foram identificados nesta espécie e as funções putativas desses peptídeos relacionadas a mecanismo de defesa como estresse biótico e abiótico foram atribuídos. As informações apresentadas ampliam a gama de informações moleculares dessa espécie.(AU)
Assuntos
Proteômica , Piperaceae/metabolismo , Eletroforese em Gel Bidimensional , Espectrometria de MassasRESUMO
The essential oils from leaves of Piper malacophyllum (Piperaceae) showed to be mainly composed by two alkenylphenol derivatives: gibbilimbols A and B. After isolation and structural characterization by NMR and MS data analysis, both compounds were evaluated against promastigote/amastigote forms of Leishmania (L.) infantum as well as trypomastigote/amastigote forms of Trypanosoma cruzi. The obtained results indicated that gibbilimbol B displayed potential against the tested parasites and low toxicity to mammalian cells, stimulating the preparation of several quite simple synthetic analogues in order to improve its activity and to explore the preliminary structure-activity relationships (SAR) data. Among the prepared derivatives, compound LINS03003 (n-octyl-4-hydroxybenzylamine) displayed the most potent IC50 values of 5.5 and 1.8 µM against amastigotes of T. cruzi and L. (L.) infantum, respectively, indicating higher activity than the natural prototype. In addition, this compound showed remarkable selectivity index (SI) towards the intracellular forms of Leishmania (SI=13.1) and T. cruzi (SI=4.3). Therefore, this work indicated that preparation of synthetic compounds structurally based in the bioactive natural products could be an interesting source of novel and selective compounds against these protozoan parasites.
Assuntos
Antiprotozoários/síntese química , Fenóis/química , Antiprotozoários/química , Antiprotozoários/farmacologia , Leishmania infantum/efeitos dos fármacos , Óleos Voláteis/química , Fenóis/isolamento & purificação , Fenóis/farmacologia , Piperaceae/química , Piperaceae/metabolismo , Folhas de Planta/química , Folhas de Planta/metabolismo , Relação Estrutura-Atividade , Trypanosoma cruzi/efeitos dos fármacosRESUMO
Os óleos essenciais de P. arboreum, P. dilatatum e P. divaricatum foram obtidos por hidrodestilação e analisados por CG-DIC e CG-EM. Extratos etanólicos foram preparados por extração exaustiva. A atividade antioxidante de óleos e extratos foi avaliada por meio do método de sequestro de radicais livres usando 2,2-difenil-1-picril-hidrazila. Os teores de óleos essenciais foram de 0,98%, 1,50% e 0,99% para P. arboreum, P. dilatatum e P. divaricatum, respectivamente. Esses óleos demonstraram riqueza em sesquiterpenos, sendo os principais componentes: biciclogermacreno (28,7%) e ß-copaen-4-α-ol (13,3%) para P. arboreum; germacreno D (16,7%), α-alaskeno (18,9%) e viridiflorol (12,5%) para P. dilatatum; e germacreno D (9,4%), valenceno (11,1%) e γ-cadineno (11,0%) para P. divaricatum. No teste de atividade antioxidante, com base nas percentagens de sequestro de radicais, foram determinados a concentrações efetivas (CE50) e o Índice de Atividade Antioxidante (IAA). Os seguintes valores de CE50 e IAA foram encontrados: ácido ascórbico (usado como referência) 226,84 µg.mL-1 e 5,30; extrato de P. arboreum 239,60 µg.mL-1 e 4,90, e extrato de P. dilatatum 367,70 µg.mL-1 e 3,20, respectivamente. A metodologia utilizada para a atividade antioxidante mostrou-se inadequada para o extrato da P. divaricatum. Os óleos essenciais não apresentaram atividade antioxidante significativa, entretanto, os extratos etanólicos de P. arboreum e de P. dilatatum apresentaram atividade antioxidante expressiva.
were obtained by means of hydrodistillation and analyzed by GC-FID and GC-MS. The ethanolic extracts were prepared by exhaustive extraction. The antioxidant activity of the oils and extracts were evaluated by applying the free radical scavenging method using the 2,2-diphenyl-1-picrylhydrazyl radical. The yields of the essential oils were 0.98%, 1.50% and 0.99% for P. arboreum, P. dilatatum and P. divaricatum, respectively. The oils are rich in sesquiterpenes, and the main components of P. arboreum are the bicyclogermacrene (28.7%) and ß-copaen-4-α-ol (13.3%); of P. dilatatum, the germacrene D (16.7%), α-alaskene (18.9%) and viridiflorol (12.5%); and of P. divaricatum, the germacrene D (9.4%), valencene (11.1%) and γ-cadinene (11.0%). The antioxidant activity test, based on the percentages of radical scavenging, determined the effective concentrations (CE50) and the Antioxidant Activity Index (AAI). The following CE50 and AAI values were found: 226.84 µg.mL-1 and 5.30 for ascorbic acid (used as the reference), 239.60 µg.mL-1 and 4.90 for P. arboreum, and 367.70 µg.mL-1 and 3.20 for P. dilatatum. The antioxidant evaluation using this methodology is not applicable for the P. divaricatum extract. These essential oils did not present a significant antioxidant activity. However, the ethanolic extracts of P. arboreum and P. dilatatum did show a strong antioxidant
Assuntos
Óleos Voláteis/análise , Piperaceae/metabolismo , Antioxidantes/análise , Plantas MedicinaisRESUMO
Piperaceae is an important family from neotropical American in which many biologically active compounds were identified. A survey of structural diversity and bioactivity reveals that groups of species specialize in the production of amides, phenylpropanoids, lignans and neolignans, benzoic acids and chromenes, alkaloids, polyketides, and a plethora of compounds of mixed biosynthetic origin. With this in mind, several explants obtained from in vitro plantlets were cultured in the presence of different plant growth regulator combinations (IAA, NAA, 2,4-D, DICAMBA, BAP and KIN). The callus induction was depended of Piper species, explant type and plant growth regulator combinations. From a callus culture, cell suspension cultures were established and their growth and metabolite accumulation studied. The achieve results may be useful for further characterization of the activated secondary metabolites pathways in in vitro systems of various Piper species.
Piperaceae es una familia importante de la América neotropical en la que muchos compuestos biológicamente activos han sido identificados. Un estudio general sobre la diversidad estructural y bioactividad reveló que grupos de especies se especializan en la producción de amidas, fenilpropanoides, lignanos y neolignanos, ácidos benzoicos y cromenes, alcaloides, policétidos y una diversidad de compuestos de origen biosintético mixto. Con este conocimiento, diversos explantes obtenidos de plántulas in vitro se cultivaron en presencia de diferentes combinaciones de reguladores de crecimiento (AIA, ANA, 2,4-D, DICAMBA, BAP y KIN). La inducción de callos dependió de la especie de Piper, tipo de explante y las combinaciones de los reguladores de crecimiento. Suspensiones celulares se establecieron a partir de callos y estudiadas en su crecimiento y acumulación de metabolitos. Los resultados alcanzados pueden utilizarse para caracterizar rutas de producción de metabolitos secundarios, en sistemas in vitro, en varias especies de Piper.