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

Terpenes of the Essential Oil from Ipomoea alba Leaf in Response to Herbivore and Mechanical Injuries

There is no doubt that the chemical composition of plants, including norvolatile and volatile compounds, is widely affected by abiotic and biotic stress. Plants are able to biosynthesize a variety of secondary metabolites against actions of natural enemies, such as herbivores, fungus, virus and bacteria. The present study revealed that the chemical compositions of leaf essential oils from Ipomoea alba underwent quantitative and qualitative alterations both when infested with the grasshopper Elaeochlora trilineata and mechanically damaged. Grasshopper attack and mechanical wounding induced the biosynthesis of nine volatile compounds in leaves of I. alba: cumene, α-ylangene, β-panasinsene, β-gurjunene aromadendrene, β-funebrene, spirolepechinene, cubenol and sclareolide. The amount of germacrene D (33.2% to 20.4%) decreased when the leaves were mechanically damaged; but when the leaves were attacked by a grasshopper, the germacrene D increased from 33.2% to 39.4%. The results showed that I. alba leaves clearly responded to abiotic and biotic stress and contribute to an understanding of plant responses to stress conditions

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

La ocurrencia de fenilpropanoides en las savias de seis especies de Piper (Piperaceae) de Brasil

Las especies de la familia Piperaceae son ampliamente investigadas debido a su importancia biológica, económica y ecológica. Sin embargo, los estudios químicos con las savias de la familia de las Piperaceae no han recibido tanta atención como la mayoría de otras especies de plantas. El presente estudio demostró la presencia de fenilpropanoides en la savia de seis especies de Piperaceae. Este estudio contribuye significativamente al conocimiento químico de la savia vegetal, hasta el momento poco explorado

Chemical composition, circadian rhythm and antibacterial activity of essential oils of piper divaricatum: a new source of safrole

The essential oils from leaves, stems and fruits of Piper divaricatum were analyzed by GC-MS. The tissues showed high safrole content: leaves (98%), fruits (87%) and stems (83%), with yields of 2.0, 4.8 and 1.7%, respectively. This is a new alternative source of safrole, a compound widely used as a flavoring agent and insecticide. The leaf's oil showed antibacterial activity against gram-negative bacteria while safrole was active against Salmonella Typhimurium and Pseudomonas aeruginosa. In addition, the study of circadian rhythm of the safrole concentration in the essential oils of leaves showed a negligible variation of 92 to 98%

Solanum paniculatum root extract reduces diarrhea in rats

Abstract Solanum paniculatum L., Solanaceae, locally known as "jurubeba", is widely used in Brazil for culinary purposes, and in folk medicine to treat of diverse disorder including gastric dysfunctions. In this study we investigated the antidiarrheal activity of S. paniculatum roots extract in rats at different concentrations (125, 250 and 500 mg/kg, p.o) using different experimental models such as castor oil-induced diarrhea, enteropooling and gastrointestinal motility, determined by in vivo experimental models. The major compound of root extract was characterized as chlorogenic acid based in the IR, 1D and 2D NMR analysis. All the extract doses achieved antidiarrheal potency, as indicated by reduced weight of feces in castor oil-induced diarrhea, decreased intestinal motility and significantly inhibited castor oil-induced enteropooling compared to the vehicle group. The highest dose (500 mg/kg) produced greater anti-motility effect and better reduction of enteropooling, similar to the reference drug Loperamide (5 mg/kg). Extract from S. paniculatum L. roots had antidiarrheal activity, as shown by the lower weight of the feces as well as decrease in the accumulation of intestinal fluid and slower transit, justifying the traditional use of plant for diarrhea

UM NOVO COMPLEXO HÍBRIDO FORMADO A PARTIR DE PIPLARTINA E O ÍON VANADILA: SÍNTESE, CARACTERIZAÇÃO E ESTUDO DA ATIVIDADE BIOLÓGICA

The synthesis, characterization and antimicrobial activity of novel vanadium (IV) complex derived of amide natural piplartine is reported. The minimum inhibitory concentrations (MIC) of complex, piplartine and vanadyl sulphate used in the synthesis were determined against six bacteria and one fungus. The complex exhibited good activity with minimal inhibitory concentration values ranging from 156.2 to 625 µg mL-1, it was observed the lowest value for the Escherichia coli bacteria with MIC 156.2 µg mL-1 and Microsporum gypseum fungus with MIC 312.5 µg/mL. In overall, the complex showed better antimicrobial activity than the piplartine. Additionally, the V-PIP complex was completely soluble in water, on the contrary of the piplartine free; which means that the proposal complex consists in a potential candidate to drug

Chemical and biological studies of β-carotene after exposure to Cannabis sativa smoke

Considering the increase in consumption of Cannabis sativa and the use of the compound β-carotene (BC) as supplement, we investigated potential changes in the chemical and biological proprieties of BC after exposure to C. sativa smoke (CSS). Our results showed that the BC exposed to CSS underwent 98.8% degradation and suffered loss of its antiradical activity. The major degradation products identified were 3-hydroxy-2,4,4-trimethylpentyl)2-methylpropanoate and (2-ethyl-3-hydroxyhexyl)2-methylpropanoate compounds. These are found in higher levels in the exhalations of colorectal cancer patients and are similar to the toxic products associated with lipid peroxidation of polyunsaturated fatty acids. In toxicological assays using micro-crustacean Artemia salina the BC was non-toxic, while the BC degraded by CSS had a toxicity of LC50 = 397.35 μg/mL. In Wistar rats, females treated with BC degraded by CSS (BCCSS) showed whitish liver spots, alterations in liver weight and in bilirubin and alkaline phosphatase levels, and decrease in the number of leukocytes associated with atypical lymphocytosis. In male rats, there was an increase in the number of leukocytes when compared to the control group. In the histopathological analysis, the cortical region of the kidneys showed the presence of discrete amorphous eosinophilic material (cylinders) in the lumen of the proximate and distal convoluted tubules. In general, the BC in contact with CSS undergoes chemical changes and exhibits toxicity to rats and Artemia salina. Keywords: Cannabis sativa smoke, β-Carotene, Toxicity, Degradatio

A NOVEL HYBRID COMPLEX FORMED FROM THE PIPLARTINE AND VANADIL ION: SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL ACTIVITY STUDY

<p></p><p>The synthesis, characterization and antimicrobial activity of novel vanadium (IV) complex derived of amide natural piplartine is reported. The minimum inhibitory concentrations (MIC) of complex, piplartine and vanadyl sulphate used in the synthesis were determined against six bacteria and one fungus. The complex exhibited good activity with minimal inhibitory concentration values ranging from 156.2 to 625 µg mL-1, it was observed the lowest value for the Escherichia coli bacteria with MIC 156.2 µg mL-1 and Microsporum gypseum fungus with MIC 312.5 µg/mL. In overall, the complex showed better antimicrobial activity than the piplartine. Additionally, the V-PIP complex was completely soluble in water, on the contrary of the piplartine free; which means that the proposal complex consists in a potential candidate to drug.</p><p></p