Hydrolysis of methyl benzoate from Piper arboreum by Naupactus bipes beetle

A new natural product was isolated from Piper arboreum (Piperaceae) leaves, the methyl 3-geranyl-4-hydroxybenzoate (1). The metabolism of P. arboreum leaves by Naupactus bipes beetle (Germar, 1824 - Coleoptera: Curculionidae) led to the hydrolysis of 1 to 3-geranyl-4-hydroxybenzoic acid (2). The structures of both compounds were determined based on spectroscopic analysis (¹H and 13C NMR, MS, and IR).O 3-geranil-4-hidroxibenzoato de metila (1), um novo produto natural, foi isolado das folhas de Piper arboreum (Piperaceae). O metabolismo das folhas de P. arboreum pelo besouro Naupactus bipes (Germar, 1824 - Coleoptera: Curculionidae) resultou na biotransformação de 1 para o ácido 3-geranil-4-hidroxibenzoico (2). As estruturas dos metabólitos 1 e 2 foram determinadas com base na interpretação dos dados espectroscópicos de EM, IR, RMN de ¹H e de 13C

Biosynthesis of tetrahydrofuran lignans in Virola surinamensis

Através de experimentos de administração in vivo em plântulas de Virola surinamensis, observaram-se as incorporações de fenilalanina e do fenilpropanóide E-isoeugenol no 4-O-metil-5-metoxi-E-isoeugenol (E-isoelemicina) e na lignana tetraidrofurânica verrucosina.The labelled substrates phenylalanine and phenylpropanoid E-isoeugenol were incorporated to 5-methoxy-4-O-methyl-E-isoeugenol (E-isoelemicin) and to the tetrahydrofuran lignan verrucosin in plantlets of Virola surinamensis (Myristicaceae)

Secondary Metabolites from the Phloem of Piper solmsianum (Piperaceae) in the Honeydew of Edessa meditabunda

Introduction The phytochemistry of species of the genus Piper has been studied extensively, including Piper solmsianum. However, no studies have addressed the phytochemistry of the sap content of Piper species. Objective To evaluate the transferring of secondary compounds from the saps of P. solmsianum to the honeydew of Edessa meditabunda. Methodology The honeydew of E. meditabunda and saps of P. solmsianum were analysed by GC-MS, H-1-NMR and LC-MS. Results The lignan (-)-grandisin and the phenylpropanoid (E)-isoelemicin were detected in both saps of P. solmsianum and honeydew of E. meditabunda. Conclusion Analysis of honeydew secreted by the sap-sucking insect E. meditabunda indicated that (-)-grandisin and (E)-isoelemicin are absorbed from the phloem of Piper solmsianum. Copyright (c) 2012 John Wiley & Sons, Ltd

Preferências alimentares de insetos por espécies de Piperaceae, observadas na cidade de São Paulo, Brasil

Piperaceae species have been placed among the basal angiosperm and are adapted to a variety of habitats including moist forests, secondary vegetation and dry high lands. The major anatomical/morphology features are of small trees, vines, and shrubs for Piper species, while the epiphytic and succulent characteristics are predominant forms among Peperomia species. Their secondary chemistry can be mostly represented by amides, phenylpropanoids/lignoids, and chromenes in addition to a phletoria of biosynthetically mixed-origin secondary compounds. Although several amides and lignans are known as insecticides, several phytophagous insects, among which some considered pests of economic importance, have been observed feeding vigorously on Piperaceae species. Herein we describe the feeding preferences of fourteen phytophagous species of Coleoptera, Lepidoptera and Hemiptera over approximately fifty Piperaceae species observed in São Paulo, SP, Brazil, in a long-term basis.As espécies de Piperaceae têm sido posicionadas entre as angiospermas basais e são frequentemente encontradas em habitats diversificados que incluem matas ciliares, vegetação secundária e campos rupestres. As espécies de Piper possuem hábitos de plantas herbáceas, arboretos e trepadeiras enquanto que, no caso de Peperomia, é freqüente o hábito de epífitas e suculentas. As classes de metabólitos secundários que caracterizam espécies de Piperaceae são amidas, fenilpropanóides/lignóides e cromenos, além de diversos outros de origem biossintética mista de menor representatividade. Apesar de muitos desses possuírem atividades inseticidas, diversos insetos fitófagos, alguns considerados pragas de importância econômica, foram observados alimentando-se de espécies de Piperaceae. Neste trabalho são relatadas as preferências alimentares de quatorze espécies fitófagas de Coleoptera, Lepidoptera e Hemiptera sobre aproximadamente cinqüenta espécies de Piperaceae observadas em São Paulo, SP, Brasil, durante um período de quatro anos

Suspensiones celulares y producción de metabolitos secundarios en cultivos in vitro de Piper sp.

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

Portrait of an act: Aesthetics and ethics in The 'Portrait of a Lady' (Henry James)

Five tetrahydrofuran lignans and two known flavones were isolated from the aerial parts of Peperomia blanda. The structures of the isolated lignans were elucidated by interpretation of their spectroscopic data, including by gHMQC and gHMBC. The relative and absolute configurations of the isolates were determined from NOESY interactions and optical properties, respectively. Four of the lignans were diastercomeric whilst one was of mixed biosynthetic origin. All but one of the lignans exhibited high in vitro trypanocidal activity when assayed against epimastigotes of Trypanosoma cruzi strain Y. (C) 2007 Elsevier Ltd. All rights reserved

Uptake of Seeds Secondary Metabolites by Virola surinamensis Seedlings

The major secondary metabolites and fatty acids occurring in the seeds of Virola surinamensis were monitored by GC-MS during germination and seedling development. The role as carbon source for seedling development was indicated considering that both classes of compounds were similarly consumed in the seeds and that no selective consumption of compounds could be detected

Flavones, lignans and terpene from Piper umbellata (Piperaceae)

The phytochemical investigation of Piper umbellata leaves yielded nine compounds including one terpenoid glucoside, five flavones (vitexin 2"-O-β-glucopyranoside, apigenin 8-C-β-D-glucopyranoside,orientin 8-C-β-D-glucopyranoside,5-hydroxy-7,3',4'-trimethoxy-flavone and velutin), two lignans (sesamin e dihydrocubebin) and 4-nerolidylcathecol. Excepting 4-nerolidylcathecol, all compounds have not been described from this species yet

Biotransformation of a tetrahydrofuran lignan by the endophytic fungus Phomopsis Sp.

The biotrasformation of the tetrahydrofuran lignan, (-)-grandisin, by the endophitic fungus Phomopsis sp, obtained from Viguiera arenaria, led to the formation of a new compound determined as 3,4-dimethyl-2-(4'-hydroxy-3',5'-dimethoxyphenyl)-5-methoxy-tetrahydrofuran. The metabolite was evaluated against the parasite Trypanosoma cruzi, the causative agent of Chagas's disease, and showed a trypanocidal activity (IC50 9.8 μmol L-1) similar to the natural precursor (IC50 3.7 μmol L-1).A biotransformação da lignana tetraidrofurânica, (-)-grandisina, pelo fungo endofítico Phomopsis sp, obtido de Viguiera arenaria, conduziu à formação de um novo metabólito caracterizado como 3,4-dimetil-2-(4'-hidróxi-3',5'-dimetóxifenil)-5-metóxi-tetraidrofurano. O metabólito foi analisado contra o parasita Trypanosoma cruzi, o agente causador da doença de Chagas, e mostrou uma atividade tripanocida (IC50 9,8 μmol L-1) similar ao precursor natural (IC50 3,7 μmol L-1).Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP

Clonal propagation, callus induction and biotransformation of precursor feeding in cellular suspension of Piper aduncum L.

Piper aduncum es un arbusto o arbolillo distribuido a lo largo de América en el que se han identificado numerosos compuestos biológicamente activos. Diferentes combinaciones de reguladores de crecimiento fueron ensayadas para la propagación clonal, la inducción y mantenimiento de callos y el establecimiento de suspensiones celulares. Los resultados mostraron una significativa mayor elongación del brote en el tratamiento con medio de cultivo B5 suplementado con AIA 0,02 mg/L y AG3 0,02 mg/L en comparación con otros tratamientos, la inducción de callos en varios tratamientos con BAP o ANA-BAP y el establecimiento de suspensiones celulares en varias combinaciones de auxinas (AIA, ANA o 2,4-D) - citocininas (BAP o KIN). A partir de los callos formados se establecieron suspensiones celulares y estudió la acumulación de metabolitos secundarios. En ese sentido, en suspensiones celulares se examinó el efecto de L-fenilalanina, ácido ferúlico, alcohol coniferílico y eugenol, como precursores en la producción de metabolitos secundarios. La adición de 1,0 o 5,0 mg/L de estos precursores al medio de cultivo MS estimuló la biosíntesis de diversos productos naturales. Como se había asumido, los extractos del medio de cultivo en su fase estacionaria (24 días de cultivo) mostraron la más alta variedad de compuestos acumulados. La identificación de los metabolitos secundarios acumulados en las suspensiones celulares puede proporcionar importante información para la caracterización y estudio de la biosíntesis de los compuestos fenólicos.Piper aduncum is a shrub or small tree distributed throughout the American in which many biologically active compounds were identified. The different combinations of plant growth regulators were tested for clonal propagation, callus induction and maintained and cellular suspension established. The results showed significantly higher shoot elongation in the treatment with B5 medium supplemented with 0.02 mg/L IAA and 0.02 mg/L GA3 compared to the other treatments; callus induction in several tretaments with BAP or NAA-BAP, and cellular suspension with several combinations of auxins (IAA, NAA or 2,4-D) - citokinins (BAP or KIN). From a callus culture, cell suspension were established and their metabolite accumulation studied. In this sense, the effect of L-phenyalanine, ferulic acid, coniferyl alcohol and eugenol, as precursor feeding, on production of secondary metabolites in suspension cultures was examined. The addition of 1.0 or 5.0 mg/L of these precursor feeding to the MS culture medium stimulated the byosinthesis of several natural products. As predicted, extracts from the culture medium at the stationary phase (24 days of culture) showed the highest variety of accumulated compounds. The identification of secondary metabolites accumulated in cell suspension culture may provide important information for characterization and studying phenolic metabolites biosynthesis