Smoke of Capsicum baccatum L. var. baccatum (Solanaceae) repels nymphs of triatoma infestans (Klug) (Hemiptera: Reduviidae) / Humo de capsicum baccatum L. var. baccatum (Solanaceae) repele las ninfas de Triatoma infestans (Klug) (Hemiptera: Reduviidae)

Control of the Chagas disease vector, Triatoma infestans (Klug) (Hemiptera: Reduviidae) with synthetic pesticides in Bolivia has become increasingly inefficient due to the development of resistance in the insects. In the Chaco region of Bolivia, guaraní populations have approached the problem by fumigating their houses with the smoke of native plants. Through interviews and field work with local guides, the main plant used by the guaraníes was collected and later identified as Capsicum baccatumL. var. baccatum (Solanaceae). In choice bioassays, filter papers exposed to the smoke of the plant repelled nymphs of T. infestans. Activity remained significant after storing the exposed filter papers for 9 days. Chemical analysis of smoke and literature data suggested that capsaicinoids present in the smoke were responsible for the repellent effect. The data presented provide a rationale for the use of C. baccatumvar. baccatumto control the Chagas vector bythe guaraní populations.

El control del vector de la enfermedad de Chagas, Triatoma infestans (Klug) (Hemiptera: Reduviidae) con plaguicidas sintéticos en Bolivia se ha vuelto cada vez más ineficiente debido al desarrollo de resistencias en los insectos. En la región del Chaco de Bolivia, las poblaciones guaraníes han abordado el problema fumigando sus casas con el humo de las plantas nativas. A través de entrevistas y trabajo de campo con guías locales, se recogió la principal planta utilizada por los guaraníes y posteriormente se identificó como Capsicum baccatumL. var. baccatum (Solanaceae). En bioensayos selectos, los papeles de filtro expuestos al humo de la planta repelieron a las ninfas de T. infestans. La actividad siguió siendo significativa después de almacenar los papeles de filtro expuestos durante 9 días. El análisis químico del humo y los datos de la literatura sugieren que los capsaicinoides presentes en el humo eran responsables del efecto repelente. Los datos presentados proporcionan una justificación para el uso de C. baccatum var. baccatum para el control del vector Chagas por las poblaciones guaraníes.

Potenciais candidatos a novos agentes antineoplásicos: síntese e avaliação da atividade antitumoral de análogos ureídicos e tioureidicos da capsaicina / New potential antineoplastic candidates: synthesis and antitumoral evaluation of urea and thiourea capsaicin analogues

As neoplasias malignas, doenças mundialmente conhecidas como câncer, possuem um dos tratamentos mais onerosos, tóxicos e de baixa seletividade na terapêutica atual. Adicionalmente, o contínuo crescimento da incidência da doença também representa em uma grande problemática. Os produtos de origem natural se apresentam como alternativas para o tratamento de diversas doenças, incluindo o câncer. A capsaicina, produto natural proveniente das pimentas do gênero Capsicum, apresenta propriedades antineoplásicas, portanto, pode ser utilizada como protótipo para obtenção de análogos. Quatro séries foram planejadas e sintetizadas, obtendo-se compostos ureídicos e tioureídicos. A estratégia sintética se baseou na reação da piperonilamina ou vanililamina com isocianatos ou isotiocianatos, ligados a substituintes aromáticos ou alquílicos. Vinte e sete análogos foram sintetizados com rendimentos variando entre 22 a 90 %. Todos os compostos apresentaram aspecto sólido variando a cor de branco a levemente amarelados. Para a caracterização das substâncias obtidas foram utilizados dados de RMN 1H e 13C, ponto de fusão e a determinação de pureza foi realizada mediante HPLC. Todos os compostos foram submetidos a ensaios de avaliação da atividade citotóxica por redução do MTT contra linhagens de células cancerígenas e células sadias. Os compostos RPF652, RPF 512 - 514) apresentaram atividade comparável ou superior ao protótipo com valores de IC50 na faixa de micromolar. Os resultados apontados pela modelagem molecular indicam que descritores eletrônicos como Ehomo e Elumo podem estar associados à atividade do composto, ClogP (3,92) pode favorecer melhor permeabilidade na membrana celular, e o maior número de sítios de acepção de ligação de hidrogênio podem corroborar com a citotoxidade em linhagem A2058. Particularmente, o análogo RPF652 apresentou atividade pronunciada com valores de IC50 de 55, 67, e 87 µM contra as células A2058, SK-MEL 25, e U87, respectivamente, o que representa atividade de superior à capsaicina. Como uma tendência o composto RPF652 causou parada no ciclo de linhagem B-RAF B16F10 não levando a célula à morte. Porém esta linhagem não apresenta mutação no códon V600E. Em contraponto, o análogo RPF652 apresentou maior potência contra linhagem V600EB-RAF A2058 mutada, indicando possível seletividade em linhagens que apresentam a mutação no códon V600E da proteína B-RAF. Ademais, novos esforços devem ser concentrados no análogo RPF652 para melhor elucidação mecanística de sua atividade

Malignant neoplasms have one of the most expensive, non-selective and toxic treatment of present times. This situation, combined with the rising incidence rate, represents a major problem for humanity. The use of natural products can be an alternative for treatment of several diseases, including cancer. Capsaicin is a natural product derived from Capsicum peppers, with reported anticancer activity and can be used as prototype for the design of new molecules with remarkable activity. Capsaicin analogues were designed and synthesized in four series of derivatives, replacing the prototype amide bond with urea and thiourea functions. The synthetic approach builds the urea/ thiourea scaffold using the reaction of piperonyl/ vanilyl amine with alkyl and aryl isocyanides/ isothiocyanides. Twenty-seven new compounds were obtained with yields from 22 to 90 %, and were fully characterized using 1H and 13C NMR, the purity was determined by melting point and HPLC. All of the obtained compounds were evaluated in MTT cytotoxic assays against different cancer cell-lines (B16F10, A2058, SK-MEL 25 and U-87), and compared with healthy human cells (T75). Additionally, the most active compound was submitted to a cell cycle arrest assay. The thiourea derivative RPF652 was the most active compound, and the urea derivatives RPF512, RPF513 and RPF514 showed good micromolar IC50 values. This results, when correlated with several in silico-calculated properties for the obtained molecules, suggests that ClogP, Ehomo, Elumo and the number of hydrogen-bond acception sites may be correlated to the anticancer activity reported. RPF652 especially, showed IC50 values with superior activity and better selectivity index when compared with capsaicin. The cell-cycle assay of RPF652 showed significant arrest in V600E-codon B-RAF non-mutated cell lines (B16F10) without killing it. V600E-codon B-RAF mutated cells A2058, were significantly more sensitive to the compound. These findings may suggest some insights about the mechanism of action and targets of this compounds

Chronotropic, inotropic and lusitropic effects of capsaicin on isolated rat Atria

This work includes results on chronotropic, inotropic and lusitropic changes induced by capsaicin on isolated rat atria. As regards spontaneous frequency, it was stimulated from 10(-9) M up to 7 x 10(-7) M of capsaicin. A simultaneous depression in developed force (F) showed a signigicant correlation with this positive chronotropic effect up to 7 X 10(-8) M of capsaicin, which is the result of the negative staircase phenomenon in the rat heart. The correlation was lost at 2 and 7 x 10(-7) M of capsaicin since in spite of the sustained increase in atrial rate the decrease in F was reversed and then depressed again at 2 and 7x 10(-6) M of capsaicin without changes in frequency. A concentration of capsaicin that overcome the negative staircase phenomenon, 5 x 10(-7) M, was tested as unique dose resulting in stimulation of the chronotropic, inotropic and lusitropic states of the atria. Percentual differences with respect to control values were maximal after 1-3 minutes for frequency (10+3 per cent), F (29+4 per cent), maximal velocity of force development (+F=50+12 per cent) (in all cases +F and -F,bold indicates +F and -F, respectively) and maximal velocity of relaxation (-F=64+13 per cent); a positive lusitropic effect was significant after 8-10 minutes (+F/-F=-17+7 per cent). Capsaicin did not affect the rat atria in the presence of 10(-6) M of ruthenium red, a blocker of capsaicin activation of sensory nerves, indicating that the stimulatory effects were entirely mediated by the release of neurotransmitters and that this concentration of capsaicin was not deleterous "per se". Capsaicin elicited similar inotropic responses in electrically driven isolated atria (+F=41+9 per cent) but the positive lusitropic effect was lost suggesting that capsaicin-induced increases in -F are limited at a frequency higher than the spontaneous frequency (11+6 vs. 32+4 per cent, respectively). 10(-6) M of CGRP8(-37), an antagonist of CGRP1 receptors, suppress the stimulatory effects of capsaicin on atrial contraction. In summary, atrial rate as compared to atrial contraction is more sensitive to the neurotransmitter released by capsaicin, which results in mechanical effects expressing the negative staircase phenomenon in the rat at low concentrations of capsaicin. The positive chronotropic, inotropic and lusitropic responses elicited by capsaicin are mediated by the reelease of neurotransmitters from sensory fibbers and no deletereous effects...

Capsaicinóides em Capsicum annuum L. e Capsicum frutescens L. e avaliaçäo do teor em capsaicina em Capsicum annuum L., do Rio Grande do Sul / Capsaicinoids in Capsicum annuum L. and Capsicum frutescens, L. and determination of capsaicin contents in C. annuum, L. of Rio Grande do Sul

Os capsaicinóides de frutos maduros de Capsicum frutescens L. e Capsicum annuum L. foram cromatografados em camada delgada e eluídos de placas ativadas de sílica Gel G com ciclohexano, clorofórmio e ácido acético (7:2:1). A determinaçäo espectrofotométrica indireta do conteúdo em capsaicina nos frutos de Capsicum annuum L. Foi o método aplicado após purificaçäo preliminar por CCD. O teor de capsaicina em Capsicum annuum foi 0,174 por cento