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

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

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

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

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

Further monoterpene chromane esters from Peperomia obtusifolia: VCD determination of the absolute configuration of a new diastereomeric mixture

A reinvestigation of the monoterpene chromane ester enriched fraction from Peperomia obtusifolia using chiral chromatography led to the identification of a minor peak, which was elucidated by NMR and HRMS as fenchyl-3,4-dihydro-5- hydroxy-2,7-dimethyl-8-(3″-methyl-2″-butenyl)-2-(4′-methyl- 1′,3′-pentadienyl)-2H-1-benzopyran-6-carboxylate, the same structure assigned to two other fenchyl esters described previously, pointing out a stereoisomeric relationship among them. Further NMR analysis revealed that it was actually a mixture of two compounds, whose absolute configurations were determined by VCD measurements. Although, almost no vibrational transitions could be assigned to the chiral chromane, the experimental VCD spectrum was largely opposite to that obtained for the average experimental VCD [(2S,1‴R,2‴R,4‴S + 2R,1‴R,2‴R,4‴S)/2] for fenchol derivatives. These results allowed us to assign the putative compounds as a racemic mixture of the chiral chromane esterified with the monoterpene (1S,2S,4R)-fenchol, which had not been identified in our early work.Fil: Batista Junior, João Marcos. Universidade Estadual Paulista Julio de Mesquita Filho; BrasilFil: Batista, Andrea N. L.. Universidade Estadual Paulista Julio de Mesquita Filho; BrasilFil: Kato, Massuo J.. Universidade de Sao Paulo; BrasilFil: Bolzani, Vanderlan S.. Universidade Estadual Paulista Julio de Mesquita Filho; BrasilFil: López, Silvia Noelí. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; ArgentinaFil: Nafie, Laurence A.. Syracuse University; Estados UnidosFil: Furlan, Maysa. Universidade Estadual Paulista Julio de Mesquita Filho; Brasi

In vitro antifungal activity of crude extracts of Piper tuberculatum

En la medicina tradicional Peruana Piper tuberculatum Jacq. (Piperaceae) es utilizado en humanos y animales domésticos como antiinflamatorio y desinfectante de heridas. Piper tuberculatum contiene las amidas isobutílicas, pirrolidina, dihidropiridona y piperidina. El objetivo de este trabajo fue investigar la actividad antifúngica de los extractos crudos de inflorescencias, hojas y tallos de plantas silvestres, obtenidos con CH2Cl2:MeOH (2:1), EtOH y decocción y de plantas in vitro obtenido con CH2Cl2:MeOH (2:1). Los extractos crudos exhibieron actividad antifúngica sobre Trichophyton rubrum, Microsporum canis y M. gypseum. La concentración inhibitoria mínima (CIM) observada con los extractos CH2Cl2:MeOH (2:1), EtOH y decocción, sobre Trichophyton rubrum, Microsporum canis y M. gypseum fue 0,1 mg/mL para inflorescencias y hojas, y 0,1 a 0,5 mg/mL para tallos. En plantas in vitro la inhibición en el crecimiento de T. rubrum y M. canis fue 100% en 0,5 mg/mL y para M. gypseum fue 95% en 1,5 mg/mL de concentración.Piper tuberculatum Jacq. (Piperaceae) is used in traditional Peruvian medicine as anti-inflammatory and disinfectant of wounds in humans and domestic animals. This species contains amides bearing isobutyl, pyrrolidine, dihydropyridone and piperidine moieties. The aim of this work was to investigate antifungal activity of crude extracts from the spikes, leaves and stems of wild plants extracted with CH2Cl2:MeOH (2:1), EtOH, decoction, and in vitro plants extracted with CH2Cl2:MeOH (2:1). The crude extracts showed antifungal activity on Trichophyton rubrum, Mycosporum canis y M. gypseum. The minimum inhibitory concentration (MIC) observed with CH2Cl2:MeOH (2:1), EtOH and decoctions extracts against T. rubrum, M. canis and M. gypseum was 0,1 mg/mL for spikes and leaves, and 0,1 to 0,5 mg/mL for stems. The inhibition of growth using in vitro plants on T. rubrum and M. canis was 100% in 0,5 mg/mL, and 95% on M. gypseum 95% using 1,5 mg/mL of concentration