Um novo alcalóide benzofenantridínico, 6-acetonil-N-metil-diidrodecarina foi isolado das raízes de Zanthoxylum riedelianum juntamente com lupeol, 6-acetonildiidroqueleritrina e 6-acetonildiidroavicina. As estruturas dessas substâncias foram estabelecidas com base na análise dos dados espectrométricos de IV, EM e RMN incluindo experimentos 2D.A new benzophenanthridine alkaloid, 6-acetonyl-N-methyl-dihydrodecarine was isolated from Zanthoxylum riedelianum roots together with lupeol, 6-acetonyldihydrochelerythrine and 6-acetonyldihydroavicine. The structures were established from the IR, MS and NMR spectral data, including 2D-NMR experiments. Keywords: Zanthoxylum riedelianum, Rutaceae, benzophenanthridine alkaloids IntroductionThe Zanthoxylum genus (Rutaceae) is composed by more than 200 species and largely distributed around the world. 1 Chemically, this genus is characterized by alkaloids, 2-7 cumarins, 5,6,8 lignans, 4,9,10 amides 11,12 and terpenes. 5,6,13,14 Ongoing studies have shown that Zanthoxylum exhibit a range of biological activities such as antichagas, 2 tripanocidal, 9 antiplasmodial, 7 anti-HIV 13 and antiinflammatory, 8,10 as well as antihelmintic. 12 Z. riedelianum is used in folk medicine as a decoction against different types of inflammations, rheumatism and skin stains. 15 Previous works reported the identification of terpenes from the essential oil 14 and lignans from the leaves and the stem bark. 10 In this work we report the isolation and structural elucidation of a novel benzophenanthridine alkaloid, namely, 6-acetonyl-N-methyl-dihydrodecarine (1), together with two known alkaloids 6-acetonyldihydrochelerythrine (2) and 6-acetonyldihydroavicine (3) from the roots of Z. riedelianum. Experimental General proceduresMelting points were uncorrected. IR spectra were recorded on FTIR-Bomem-MB/100 model spectrophotometer using NaCl film. NMR spectra in CDCl 3 , were recorded on Bruker ARX-400 (400 MHz for 1 H and 100 MHz for 13 C); Bruker AC-200 (200 MHz for 1 H and 50 MHZ for 13 C) and Varian-Mercury 300 (300 MHz for 1 H and 75 MHz for 13 C) spectrometers, using tetramethylsilane (TMS) as internal standard. Electron Ionization Mass Spectra (ESI-MS) was undertaken employing a Quatro LC-Micromass UK model spectrometer. Optical rotations were determined on a Perkin-Elmer 341 polarimeter. CC: silica gel (Merck 70-230 mesh ASTM); TLC: silica gel G 60 and silica gel 60 PF 254 (Merck) were used to analyze the fractions collected from column chromatography (CC) with visualization by UV (254 and 366 nm), Dragendorff´s reagent and exposure to iodine vapor. Plant materialZanthoxylum riedelianum (Engl.) was collected in Rio Manso Highway, km 22, Chapada dos Guimarães, Mato 6-Acetonyl-N-methyl-dihydrodecarine, a New Alkaloid from Zanthoxylum riedelianum J. Braz. Chem. Soc. 380 Grosso State, Brazil. A voucher specimen (No. 24.080) was deposited at Universidade Federal de Mato Grosso Central Herbarium. Extraction and isolationDried roots (3.0 kg) were powdered and extracted with hexane and methanol by mac...

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-The potential insecticidal of oils from southwestern Amazon plants against Spodoptera frugiperda (J. E. Smith, 1797) (Lepidoptera: Noctuidae) was investigated. Initial bioassays were performed with undiluted oils from 11 plant species. The efficacy of the oils was evaluated against eggs and third-instar caterpillars of S. frugiperda. The oils of Copaifera sp. (Leguminosae), Orbignya phalerata (Arecaceae), and Carapa guianensis (Meliaceae) displayed a high efficacy against the caterpillars and were used in subsequent concentration-response bioassays, at concentrations established through preliminary tests. The highest nonlethal concentrations of oils and the lowest lethal concentrations were calculated. A completely randomized design was adopted in both bioassays. The LC 50 of the oils varied from 7.50 to 60.84% (v/v). Copaifera sp. oil had the highest toxicity and was 6.84-fold more toxic than O. phalerata oil and 8.11-fold more toxic than Carapa guianensis oil. In general, oils from Copaifera sp., O. phalerata, and Carapa guianensis were effective in controlling S. frugiperda caterpillars under laboratory conditions, and are good candidates for use in integrated management programs of corn pests.

Recebido em 24/8/08; aceito em 19/11/08; publicado na web em 2/4/09 SALICYLATES ISOLATED FROM LEAVES AND STEMS OF Salix martiana Leyb. (SALICACEAE). Salix martiana Leyb. is an endemic species from the Amazon river floodplain areas (varzeas), of the State of Amazonas. Stems and leaves were extracted with dichloromethane, methanol and hydro-alcohol and these extracts were fractionated by using conventional chromatographic techniques. The major substances isolated, salicin and trichocarposide (6-0-p-coumaroyl salicin), were determined through analyses of NMR 1D (1 H and 13 C) and NMR 2D (gHSQC and gHMBC). These compounds were isolated for the first time in Salix martiana Leyb. (Salicaceae). The percentage of these compounds in S. martiana is very high. The extracts were analyzed for their DPPH antioxidant capacity and the methanolic from the leaves and the hydro-alcoholic from the stems were the more active.

RESUMOEste artigo descreve o isolamento dos triterpenos lupeol, taraxerol, lupen-3-ona e esqualeno obtido do extrato diclorometânico das folhas da espécie Minquartia guianensis Aubl., pertencente à família Olacaceae. Estes terpenóides foram isolados através de técnicas cromatográficas e identificados utilizando Ressonância Magnética Nuclear (RMN) de 1 H e de 13 C. Na literatura disponível, este é o primeiro relato destes triterpenos em M. guianensis.PALAVRAS CHAVE: Triterpenos, Minquartia guianensis, Olacaceae. Triterpenes from the leaves of Minquartia guianensis Aubl. (Olacaceae)ABSTRACT This article describes the isolation of the triterpenes lupeol, taraxerol, lupen-3-one and squalene from the dichloromethane extract of the leaves of Minquartia guianensis Aubl. belonging to the Olacaceae family. These terpenoids were isolated through chromatographic techniques and identified using 1 H and 13 C Nuclear Magnetic Resonance (NMR). At the best of our knowledge, this is the first report of these triterpenes in M. guianensis.

RESUMENEsta investigación tiene el objetivo de hacer una selección de especies vegetales que son propias de la región Amazónica con potencial de uso en el manejo integrado de la oruga militar tardía Spodoptera frugiperda (J.E. Smith) (Lepidoptera: Noctuidae). Para tal, fue evaluado la eficiencia de extractos hidroalcohólicos de 15 especies vegetales que se son de la región. Los extractos fueron producidos a partir de las hojas, o de la cáscara, o de liana de las plantas. La eficiencia de los extractos (30 mg.mL -1 ) fue evaluada sobre huevos y larvas de 3º instar de S. frugiperda. Se constató una variación de respuesta de la oruga militar tardía entre los extractos hidroalcohólicos. El extracto de la cáscara de Calycophyllum spruceanum (Benth.) Hook. f. ex K. Schum. presentó mayor eficiencia en los huevos, y el extracto de las hojas de Bauhinia forficata Link presentó mayor eficiencia en las larvas. Estos resultados son fundamentales para el manejo de la oruga militar tardía, toda vez que, los efectos nocivos reducen las pérdidas en la producción de maíz en las primeras fases del desarrollo del S. frugiperda. Se concluye que los extractos de C. spruceanum y B. forficata fueron los más eficientes para los huevos y larvas de la oruga militar tardía.Palabras clave: Spodoptera frugiperda, insecticidas botánicos, manejo integrado de plagas. ABSTRACTThis study aimed to screen plant species from the Amazon region for the potential to be used in the integrated management of the fall armyworm Spodoptera frugiperda (J.E. Smith) (Lepidoptera: Noctuidae). For this purpose, the efficiency of the hydroalcoholic extracts of 15 plant species from the Amazon region was evaluated. The extracts were obtained from plant leaves, bark, or vines. The efficiency of the extracts (30 mg·mL −1 ) was evaluated on eggs and third instar larvae of S. frugiperda. A range of reactions of the fall armyworm to the hydroalcoholic extracts was observed. The extract obtained from the bark of Calycophyllum spruceanum (Benth.) Hook. f. ex K. Schum. presented the highest efficiency against the eggs, whereas the extract obtained from the leaves of Bauhinia forficata Link was most efficient against the larvae. These findings are essential for the management of fall armyworms because the deleterious effects in the initial stages of S. frugiperda development significantly reduce maize production. In conclusion, the extracts of C. spruceanum and B. forficata were more efficient for eggs and larvae of the fall armyworm, respectively.

The essential oil (EO) from the leaves of Onychopetalum periquino, obtained by hydrodistillation, was analyzed by gas chromatography coupled with mass spectrometry (GC-MS), and also was investigated for its larvicidal activity against Aedes aegypti larvae. Thirteen compounds, representing 91.31% of the crude oil, were identified.Major compounds were sesquiterpenes, including β-elemene (53.16%), spathulenol (11.94%) and β-selinene (9.25%). The EO showed high larvicidal activity with a lethal concentration (LC 50 ) of 63.75 μg/mL and 100% mortality at 200 μg/mL. These results represent the first report about the chemical composition of O. periquino and the first larvicidal evaluation with Onychopetalum species.

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