ABSTRACT Piperaceae species can be found worldwide in tropical and subtropical areas and many of them have been used for centuries in traditional folk medicine and in culinary. In Brazil, species of Piperaceae are commonly used in some communities as local anesthetic and analgesic. Countrified communities have known some species of the genus Ottonia as "anestesia" and it is a common habit of chewing leaves and roots of Ottonia species to relief toothache. The purpose of this study is to report our findings on new molecules entities obtained from the roots of Ottonia anisum Spreng, in which local anesthetic activity (sensory blockage) is demonstrated for the first time in vivo guinea pig model. Phytochemical investigation led to the isolation of three amides (pipercallosidine, piperine and valeramide) and in an enriched mixture of seven amides (valeramide, 4,5-dihydropiperlonguminine, N-isobutil-6-piperonil-2-hexenamide, piperovatine, dihydropipercallosidine, pipercallosidine and pipercallpsine). Our findings demonstrated the anesthetic potential for the methanolic extract from roots, its n-hexane partition and amides from O. anisum and it is in agreement with ethnobotanical survey.

RESUMO O presente estudo foi projetado para investigar as atividades antioxidante, antinociceptiva e anti-inflamatória do extrato etanólico dos galhos de Ageratum fastigiatum. Perfil fitoquímico e teores de fenois totais e flavonoids foram determinados. A atividade antioxidante foi avaliada por 2,2-difenil-1-picril-hidrazila (DPPH) e pelo método de poder de redução do ferro. O efeito antinociceptivo foi avaliado usando os ensaios de contorções abdominais induzidas por ácido acético, formalina, placa quente e imersão da cauda; enquanto os testes do edema de pata e pleurisia induzidos por carragenina foram realizados para examinar a atividade anti-inflamatória contra inflamação aguda. O extrato revelou a presença de flavonoides, taninos, cumarinas, terpenos, esteroides e saponina. Teores expressivos de fenóis totais e flavonoides e um promissor efeito antioxidante foram quantificados. Nas doses de 50, 100 e 200 mg/kg, o extrato inibiu as contorções, reduziu ambas as fases do tempo da lambida da pata e aumentou o tempo de reação sobre a placa quente. No teste de imersão da cauda, o extrato (50, 100 e 200 mg/kg) causou uma inibição significativa da dor. Nessas doses, o edema de pata, o volume do exsudato e a migração leucocitária foram significativamente reduzidos. Esses resultados sugerem que A. fastigiatum pode ser uma fonte de substâncias ativas com atividades antioxidante, antinociceptiva e anti-inflamatória, adicionando uma base científica para o uso na medicina popular brasileira.

ABSTRACT The present study was designed to investigate the antioxidant, antinociceptive and anti-inflammatory activities of the ethanol extract from Ageratum fastigiatum branches. Phytochemical screening and total phenol and flavonoid contents were determined. The antioxidant activity was assessed by 2,2-diphenyl-1-pycrilhydrazin (DPPH) and iron reducing power methods. The antinociceptive effect was evaluated using the acetic acid-induced writhing, formalin, hot plate and tail immersion assays; while the carrageenan-induced paw edema and pleurisy tests were performed to examine the anti-inflammatory activity against acute inflammation. The extract revealed the presence of flavonoids, tannins, coumarins, terpenes, sterols and saponins. Expressive levels of total phenols and flavonoids and a promising antioxidant effect were quantified. At the doses of 50, 100 and 200 mg/kg, the extract inhibited the writhing, reduced both phases of paw licking time and increased the reaction time on the hot plate. In the tail immersion test, the extract (50, 100 and 200 mg/kg) caused a significant inhibition of pain. In these doses, the paw edema, exudate volume and leucocyte mobilization were significantly reduced. These results suggest that A. fastigiatum can be an active source of substances with antioxidant, antinociceptive and anti-inflammatory activities, adding scientific support to the appropriate use in the Brazilian folk medicine.

Derivados de benzofenonas despertam grande interesse científico. A família Clusiaceae é conhecida por produzir grandes quantidades dessas substâncias, com vários resíduos isoprênicos em suas estruturas, os quais são responsáveis pela complexidade e variedade estrutural observada nesta classe de substâncias, e também contribuem para suas atividades biológicas. Clusia é um gênero importante pertencente à família Clusiaceae, com 55 benzofenonas poliisopreniladas diferentes identificadas até o momento. Essas substâncias foram analisadas sob perspectivas biossintéticas e quimiossistemáticas, permitindo determinar características relacionadas à sua produção, acumulação e distribuição dentro desse gênero. As benzofenonas poliisopreniladas encontradas em Clusia apresentaram um grau elevado de prenilação, com 2 a 5 unidades isoprênicas e uma maior ocorrência em flores e frutos. A seção Cordylandra mostrou uma ocorrência muito semelhante de derivados de 2,4,6-triidroxibenzofenona e biciclo[3.3.1]nonano-2,4,9-triona, a maioria deles com 4 unidades isoprênicas. Na seção Anandrogyne predominam derivados de 2,4,6-triidroxibenzofenona com 2 unidades isoprênicas, e em Chlamydoclusia predominam os derivados de biciclo[3.3.1]nonano-2,4,9-triona com 4 unidades isoprênicas. Embora altamente preniladas, essas substâncias mostraram índices de oxidação baixos, o que, sob uma perspectiva evolucionária, corrobora o fato de que Clusiaceae é uma família em transição, com alguns aspectos comuns tanto à famílias botânicas basais, quanto derivadas.

Benzophenone derivatives are special metabolites that arouse great scientific interest. The Clusiaceae family is known for producing large amounts of benzophenone derivatives with several isoprene residues on their structures, which are responsible for the observed complexity and structural variety in this class of substances, and also contribute to their biological activities. Clusia is an important genus belonging to Clusiaceae, with 55 different polyisoprenylated benzophenones identified so far. These substances were analyzed from biosynthetic and chemosystematic points of view, allowing the determination of characteristics regarding their production, accumulation and distribution within this genus. Polyisoprenylated benzophenones found in Clusiashowed a high prenylation degree, with 2 to 5 isoprene units and a greater occurrence in flowers and fruits. Section Cordylandra showed a very similar occurrence of 2,4,6-trihydroxybenzophenone derivatives and bicyclo[3.3.1]nonane-2,4,9-trione derivatives, the majority of them with 4 isoprene units. In section Anandrogyne there is a predominance of simple 2,4,6-trihydroxy-benzophenone derivatives, with 2 isoprene units, and in Chlamydoclusia predominates bicyclo[3.3.1]nonane-2,4,9-trione derivatives with 4 isoprene units. Although highly prenylated, these substances showed low oxidation indexes, which from an evolutionary perspective corroborates the fact that Clusiaceae is a family in transition, with some common aspects with both basal and derived botanical families.

Piper aduncum L., Piperaceae, stands out due to its biological activities, however, it is still found in the wild and little is known about its agronomic point of view. The aim of this study was to evaluate the growth and to analyze the chemical composition of essential oils from leaves of P. aduncum collected in two different sites of Cerrado as well as in cultivated plants. The cultivation was installed out in a greenhouse using cuttings of adult specimens. Essential oils were obtained from fresh leaves. Plants from the two studied locations showed erect growth habit and behavior of linear growth. The essential oils composition of P. aduncum from Bocaiuva did not differ between wild and cultivated plants, as the major substance identified as 1,8-cineole. The plants from Montes Claros site showed a distinct concentration for the two samples, being the major substance characterized as transocimene (13.4%) for wild and 1,8-cineole (31.3%) for cultivated plants. Samples from both locations showed a similar essential oil composition in cultivars. Our results showed that P. aduncum cultivation is feasible and the variation in chemical composition of the two sites may indicate an environmental influence, since chemical and isoenzyme analysis did not show great differences.

RESUMOPiper aduncum L. é utilizada na medicina popular para o tratamento de doenças respiratórias e inflamatórias. O objetivo desse estudo foi analisar o óleo essencial das folhas de P. aduncum coletadas no Cerrado brasileiro, Norte de Minas Gerais, assim como avaliar a atividade larvicida desse óleo e de sua substância majoritária. O óleo essencial foi analisado por cromatografia em fase gasosa acoplada à espectrometria de massas e por cromatografia em fase gasosa acoplada a detector por ionização de chamas, que permitiu a caracterização de 23 substâncias (monoterpenos: 90,4%; sesquiterpenos: 7,0%). O componente majoritário foi o 1,8-cineol (53,9%). O óleo essencial desse exemplar mostrou ser muito diferente do óleo da mesma espécie. Larvas de Aedes aegypti foram expostas a diferentes concentrações do óleo essencial e do 1,8-cineol. Após 24h do tratamento com o óleo registrou-se uma taxa de mortalidade de 100% das larvas nas concentrações de 500 e 1,000 ppm. Após 48h a taxa de mortalidade foi de 80% e 50% para as concentrações de 250 e 100 ppm, respectivamente. A CL50 obtida após 24h foi estimada em 289,9 ppm e após 48h foi de 134,1 ppm. A substância majoritária 1,8-cineol não apresentou atividade larvicida.

ABSTRACTPiper aduncum L. is used in folk medicine to treat respiratory and inflammatory diseases. The aim of this study was to analyze the essential oil from leaves ofP. aduncum collected in the Brazilian Cerrado, North of Minas Gerais, as well as to evaluate the larvicidal activity of this oil and of its major constituent. The essential oil was analyzed by gas chromatography coupled to flame ionization detector and gas chromatography coupled to mass spectrometry that allowed characterizing 23 compounds (monoterpenes: 90.4%; sesquiterpenes: 7.0%). The major component was 1,8-cineole (53.9%). This oil showed to be very different from those obtained from the same species. Larvae of A. aegypti were exposed to different concentrations of the essential oil and 1,8-cineole. The mortality rate of 100% was obtained after 24h of treatment with the oil at concentrations of 500 and 1,000 ppm. After 48h of treatment, the mortality rate was 80% and 50% for concentrations of 250 and 100 ppm, respectively. The LC50 obtained after 24h was estimated in 289.9 ppm and after 48h was 134.1 ppm. The major compound 1,8-cineole showed no larvicidal activity.

Inflorescências de bananeira são popularmente conhecidas como "umbigos", e esses são usados no Brasil como complementos nutricionais. No entanto, o valor nutricional das inflorescências (flores masculinas e brácteas) de bananeira nunca foi estudado. Portanto, o material vegetal de Musa acuminata cultivar "ouro" foi coletado no Rio de Janeiro, Brasil e, em seguida, submetido aos procedimentos químicos para determinar a sua composição nutricional. As análises foram realizadas em triplicata. A análise da composição da amostra apresentou teor percentual médio de umidade, proteína, lipídeos e cinza de 8,21, 14,50, 4,04 e 14,43, respectivamente. As inflorescências secas mostraram significativo complemento nutritivo baseado no alto conteúdo de potássio (5.008,26 mg / 100 g) e de fibra 49,83% (lignina, celulose e hemiceluloses) revelando importantes propriedades funcional e nutritiva. Em uma avaliação paralela, o estudo anatômico mostrou elementos fundamentais para o reconhecimento de Musa acuminata, quando reduzida a fragmentos.

Banana inflorescences are popularly known as 'navels,' and they are used in Brazil as nutritional complements. However, the nutritional value of banana inflorescences (male flowers and bracts) has never been studied. Therefore, plant material of Musa acuminata, cultivar "ouro", was collected in Rio de Janeiro state, Brazil, and then submitted to chemical procedures to determine its nutritional composition. The experiment was arranged a completely randomized design and performed in triplicate. The sample composition analysis showed percentual average value for moisture, protein, fat and ash as 8.21, 14.50, 4.04 and 14.43, respectively. The dehydrated inflorescences were found to contain a significant nutritive complement based on their high content of potassium (5008.26 mg / 100 g) and fiber 49.83% (lignin, cellulose and hemicelluloses) revealing important functional and nutritional properties. In a parallel evaluation, the anatomical study revealed key elements for the recognition of Musa acuminata when reduced to fragments.

Leishmaniasis is an infection of viscera or tegument caused by protozoa Leishmania sp. The extensive period required for the treatment, which involves the use of toxic medicines, leads patients to drop treatment increasing the development of resistant forms of Leishmania sp. Lantana camara L., Verbenaceae, is a tropical plant native from America. Folk uses have been described for treatment of tumors, tetanus, rheumatism and malaria. This study evaluates the leishmanicidal activity of the essential oil of leaves from L. camara on promastigote forms of Leishmania chagasi and L. amazonensis and its toxic effects on Artemia salina (brine shrimp test), macrophage cultures and BALB/c mice. The chemical composition was evaluated using the gas chromatography coupled with mass spectrometer (GC-MS). Thirty substances, mostly mono and sesquiterpenes were identified. The most representative constituents were: germacrene D (24.90%), farnesene derivatives (22%) and (E)-cariophylene (14.31%). Bioassays revealed a significant leishmanicidal activity of essential oil against L. amazonensis (IC50 0.25 µg/ mL) and a potential toxic effect on Brine shrimp (LC50 10 µg/mL) and macrophage assays (CC50 4 µg/mL), while there was no toxic manifestation on mice. The data show the relevant potential of L. camara as a source of medicine for leishmaniasis treatment.

Plumbago scandens L. é uma espécie brasileira tropical/subtropical que ocorre ao longo da costa. Quimicamente, é principalmente representada por naftoquinonas, flavonóides, terpenóides e esteróides. objetivo do presente trabalho é estudar mudanças quantitativas da produção metabólica nas raízes de Plumbago scandens durante diferentes estágios de desenvolvimento fisiológico, relativos à floração. Os resultados indicaram a presença de quatro substâncias nos extratos: plumbagina, epi-isoshinanolona, ácido palmítico e sitosterol, independente do estágio de desenvolvimento. A naftoquinona plumbagina tem sempre mostrado ser o componente majoritário de todos os extratos. Naftoquinonas exibiram seus maiores conteúdos durante a floração, enquanto o conteúdo dos dois outros componentes decresceu durante este estágio, revelando um perfil inverso. A composição química modificou dependendo das necessidades da planta.

Plumbago scandens L. is a Brazilian tropical/subtropical species that occurs along the coast. Chemically it is mainly represented by naphthoquinones, flavonoids, terpenoids and steroids. The aim of the present work is to study quantitative changes in the root metabolic production of Plumbago scandens during different physiologic developmental stages relative to floration. The results indicated the presence of four substances in the extracts: plumbagin, epi-isoshinanolone, palmitic acid and sitosterol, independent on developmental stage. The naphthoquinone plumbagin has always showed to be the major component of all extracts. Naphthoquinones exhibited their highest content during floration, while the content of the two others components decreased during this stage, revealing an inverse profile. The chemical composition changed depending on the plant requirements.

Leishmaniasis is one of the most neglected tropical diseases, representing a group of parasitic diseases worldwide spread, occurring in 88 tropical and subtropical countries. Approximately 350 million people live in areas of active transmission of leishmaniasis, with about 1-2 million estimated new cases occurring every year. More than 90% of the cutaneous cases appear in developing countries. Efforts to improve the therapeutic arsenal against leishmaniasis have led to the search for new and cheap range of drugs. In this study, the nerolidol-rich essential oil from Piper claussenianum (Miq.) C. DC., Piperaceae, was assayed on arginase activity of Leishmania amazonensis. The effect of this essential oil on arginase activity levels showed an enzyme inhibition of 62.2%. This result stimulates the scientific interest about the potential value of this plant species on neglected diseases as potential new natural product source of pharmacological interest for the treatment of leishmaniasis.

Um total de vinte extratos de seis espécies de Bromeliaceae brasileiras foram avaliadas quanto a atividade antioxidante, usando-se o método colorimétrico de redução do radical DPPH. De maneira geral, os extratos polares dos rizomas das espécies de Bromeliaceae testadas revelaram melhor perfil antioxidante do que os extratos das folhas e dos frutos das mesmas espécies. Os melhores resultados foram encontrados para os rizomas de Vriesea procera (Mart. ex Schult.f.) Wittm. e Neoregelia cruenta (Graham) L.B. Sm. O extrato bruto metanólico das folhas de Ananas bracteatus (Lindl.) Schult. & Schult. f. apresentou uma atividade significativa, em relação aos extratos de folhas testados, e o processo de purificação desse extrato resultou na identificação de quatro metabólitos: ferulato de 2-glicerila, p-cumarato de 2-glicerila, 5,7,4'-triidroxi-3,3',5'-trimetoxiflavona e 3-O-β-D-glicopiranosil sitosterol.

A total of twenty different extracts from six Brazilian Bromeliaceae species was screened for antioxidant activity by assessment of their capacity to scavenge the DPPH radical. In a general way, the polar rhizome extracts from Bromeliaceae representatives showed better antioxidant results than the extracts from leaves and fruits of the same species. The best results were found for the rhizome extracts of Vriesea procera (Mart. ex Schult.f.) Wittm. and Neoregelia cruenta (Graham) L.B. Sm. Crude methanol extract of Ananas bracteatus (Lindl.) Schult. & Schult. f. leaf had a significant antiradical activity among the leaves extracts assessed its purification afforded four metabolites: 2-O-feruloyl glyceride, 2-O-p-coumaroyl glyceride, 5,7,4'-trihydroxy-3,3',5'-trimethoxyflavone and 3-O-β-D-glucopyranosyl sitosterol.

O estudo fitoquímico do extrato metanólico de galhos de Ouratea hexasperma (Ochnaceae) forneceu dois novos flavonóides, 7-O-β-D-glicopiranosil-6-(3-metilbut-2-enil)-5,4'-diidroxiflavanonol (6-β,β-dimetilalil-7-O-β-D-glucopiranosil-aromadendrina) e 7-O-β-D-glicopiranosil-6-(3-metilbut-2-enil)-3,5,4'-triidroxiflavona (6-β,β-dimetilalil-7-O-β-D-glucopiranosil-kaemperol) além de uma mistura de sitosterol e estigmasterol, lupeol, 3-O-β-D-glicopiranosil-sitosterol e o ácido 2,4-diidroxifenilacético. As estruturas dessas substâncias foram estabelecidas através de análise dos espectros de IV, EM-IES e RMN das substâncias naturais e dos derivados peracetílico e éter dimetílico da nova flavona, além de comparação com dados da literatura.

Chromatographical fractionation of the methanol extract from the branches of Ouratea hexasperma (Ochnaceae) afforded two new flavonoids, 7-O-β-D-glucopyranosyl-6-(3-methylbut-2-enyl)-5,4'-dihydroxyflavanonol (6-β,β-dimethylallylaromadendrin-7-O-β-D-glucoside) and 7-O-β-D-glucopyranosyl-6-(3-methylbut-2-enyl)-3,5,4'-trihydroxyflavone (6-β,β-dimethylallylkaempferol-7-O-β-D-glucoside) besides a mixture of sitosterol and stigmasterol,lupeol, sitosterol-3-O-β-D-glycopyranoside and 2,4-dihydroxyphenylacetic acid. The structures were established by analysis of IR, ESI-MS, and NMR spectra of the natural substances, and those of the dimethyl ether and peracetyl-derivatives of the new flavone, as well as comparison with literature values.

Análise por cromatografia com fase gasosa e cromatografia com fase gasosa acoplada à espectrometria de massas de óleos essenciais obtidos de folhas de Echinodorus grandiflorus ("Chapéu-de-couro") em duas diferentes populações (folhas grandes e folhas pequenas), coletadas mensalmente entre setembro de 1998 e dezembro de 1999, revelou 17 componentes. Fitol foi o constituinte majoritário em ambas populações. Os principais representantes sesquiterpênicos foram (E)-cariofileno, alfa-humuleno e (E)-nerolidol.

Analysis by Gas Chromatography and Gas Chromatography/Mass Spectrometry of the essential oils obtained from leaves of Echinodorus grandiflorus ("Chapéu de couro") from two different populations (Big Leaves and Small Leaves), collected monthly between September 1998 and December 1999 revealed 17 components. Phytol was the major constituent for both populations. The main sesquiterpene representatives are (E)-caryophyllene, alpha-humulene and (E)-nerolidol.

We characterized the chemical constituents of Copaifera duckei oleoresin and used dermal application to Wistar rats to evaluated its possible mutagenic and cytotoxic activities on peripheral blood reticulocytes and bone marrow cells. Chemical characterization of the oleoresin revealed the presence of sesquiterpene hydrocarbons, an unidentified neutral diterpene and diterpene acids. To evaluate mutagenicity evaluation the rats were treated with 10, 25 and 50% of the LD50 dose of the oleoresin for three consecutive days and peripheral blood collected after 0, 24, 48 and 72 h for micronucleus analysis. The rats were humanly sacrificed 24 hours after the last treatment and chromosome preparations made using standard techniques. At the three concentrations and the three time intervals tested we found that there were no statistically significant differences in either the mean number of micronucleated reticulocytes (MNRETs) or the number of chromosomal aberrations as to the negative control. However, at 25 and 50% of the LD50 dose of the oleoresin there was a significant decrease in the mitotic index (MI) as compared to the negative control. Under our experimental conditions, C. duckei V11 oleoresin produced no mutagenic effects on bone marrow cells or in peripheral reticulocytes as assessed by chromosome aberrations and the micronucleus test respectively, but showed cytotoxic activity at high doses.

O gênero Plumbago pertence à família Plumbaginaceae e apresenta uma variedade de atividades biológicas, a maioria atribuída à presença de naftoquinonas. Plumbagina é uma naftoquinona natural que pode ser obtida a partir de raízes de Plumbago scandens L. Na tentativa de descobrir a melhor técnica de extração dessa substância foram usadas, maceração estática, maceração dinâmica, extração com auxílio de ultrassom e extração em Soxhlet. Quatro substâncias foram detectadas qualitativamente: as naftoquinonas plumbagina e epi-isoshinanolona, o ácido palmítico e o sitosterol. Plumbagina foi sempre o componente majoritário em todos os extratos analisados e sua determinação quantitativa foi realizada através de cromatografia com fase gasosa acoplada à espectrometria de massas. A extração em Soxhlet foi a técnica mais eficiente para obtenção de plumbagina, entretanto a longa exposição a temperaturas elevadas favoreceu a degradação da plumbagina.

The Plumbago genus belongs to the Plumbaginaceae family and it is known due to its variety of biological uses, most of them attributed to the presence of naphthoquinones. Plumbagin is a naturally occurring naphthoquinone that can be obtained from roots of Plumbago scandens L. In order to find out the better technique for plumbagin extraction, were applied: static maceration, dynamic maceration, with assistance of ultrasonic waves and in Soxhlet apparatus. Four compounds were qualitatively detected in all extracts: the naphthoquinones plumbagin and epi-isoshinanolone, palmitic acid and sitosterol. Plumbagin was always the major component in all analyzed extracts and it was quantitatively determined by gas chromatograph coupled with mass spectrometer. Soxhlet was the most efficient extraction technique however, prolonged heating time promoted plumbagin degradation.

O óleo essencial das folhas de Piper solmsianum e seu constituinte majoritário (sarisan) foram testados para avaliar suas influências no comportamento de camundongos. O óleo essencial foi obtido por hidrodestilação em aparelho do tipo Clevenger modificado e analisado por CG/ EM. Essa análise mostrou a presença de monoterpenos, sesquiterpenos e arilpropanóides. Sarisan, um análogo da myristicina, foi isolado do óleo para se efetuar os testes farmacológicos. Emulsões do óleo essencial e do sarisan a 5,0% e 10,0% (v/v) foram utilizadas nos testes. Pentobarbital (30 mg/ kg s.c.) ou diazepam (2,5 mg/ kg s.c.) foram testados como padrões na verificação de efeitos depressores e ansiolíticos, respectivamente. O óleo essencial e seu componente majoritário apresentaram efeitos excitantes e depressores nos animais testados.

The essential oil from Piper solmsianum leaves and its major compound (sarisan) were tested to verify their influences upon mice behaviour. The essential oil was obtained by hydrodistillation in a modified Clevenger extractor and analysed by GC/ MS. This analysis revealed in the oil the presence of monoterpenes, sesquiterpenes and of arylpropanoids. The compound sarisan, a myristicin analogue, was isolated from the oil to perform the pharmacological tests. Emulsions of the oil and of sarisan (5.0 and 10.0% v/v) were used in the tests. Pentobarbital (30 mg/ kg s.c.) or diazepam (2.5 mg/ kg s.c.) were tested as standard drugs to verify depressant or anxiolytic effects, respectively. Both essential oil and sarisan showed to have exciting and depressant effects in the tested animals.