This paper evaluates CHCl3 and CH3OH extracts of the stem bark, branches and leaves of Drimys brasiliensis and drimane sesquiterpenes isolated from the stem bark against strains of Leishmania amazonensis and Leishmania braziliensis promastigotes and Plasmodium falciparum trophozoites. All of the extracts and compounds were tested in cell lines in comparison with reference standards and cell viability was determined by the XTT method. The CHCl3 and CH3OH extracts from the stem bark and branches yielded promising results against two strains of Leishmania, with 50% inhibitory concentrations (IC50) values ranging from 39-100 µg/mL. The CHCl3 extract of the stem bark returned IC50 values of 39 and 40.6 µg/mL for L. amazonensis and L. braziliensis, respectively. The drimanes were relatively effective: 1-β-(p-coumaroyloxy)-polygodial produced IC50 values of 5.55 and 2.52 µM for L. amazonensis and L. braziliensis, respectively, compared with 1-β-(p-methoxycinnamoyl)-polygodial, which produced respective IC50 values of 15.85 and 17.80 µM. The CHCl3 extract demonstrated activity (IC50 of 3.0 µg/mL) against P. falciparum. The IC50 values of 1-β-(p-cumaroyloxyl)-polygodial and 1-β-(p-methoxycinnamoyl)-polygodial were 1.01 and 4.87 µM, respectively, for the trophozoite strain. Therefore, the results suggest that D. brasiliensis is a promising plant from which to obtain new and effective antiparasitic agents.

A fração diclorometano obtida pelo particionamento do extrato hidroalcoólico obtido das folhas e flores de Vernonia scorpioides (Asteraceae) resultou no isolamento e caracterização de um novo poliacetileno, 5-octa-2,4,6-triinil-furan-2(5H)-ona. A determinação estrutural foi baseada em dados de espectrometria de Ressonância Magnética Nuclear mono e bidimensionais, de Massas e de Infravermelho. Foi investigado o potencial antitumoral e genotóxico do novo poliacetileno e os resultados encontrados sugerem genotoxicidade e citotoxicidade, onde a morte celular ocorreu via apoptose, envolvendo um mecanismo dependente de caspase.

The dichloromethane fraction obtained from hydroalcoholic crude extract of leaves and flowers of Vernonia scorpioides (Asteraceae) was investigated, resulting in the isolation and structure elucidation of a new polyacetylene namely 5-octa-2,4,6-triynyl-furan-2(5H)-one. The structure of the isolated compound was determined based on IR, NMR (1D and 2D) and MS spectrometric data. The antitumor potential, including cytotoxicity to tumor cells and genotoxicity, was investigated. The results suggest that apoptotic cell death may have occurred, at least in part, via a caspase-dependent mechanism.

From the resinous exudate of twigs end leaves of Larrea nitida, two lignans nor isoguaiacine 1 and meso-nor-dihydroguaiaretic acid 2 and ferulic acid 3 were isolated. The antioxidant activities of resin and pure compounds were assesed by bleaching of the ABTS derived radical-cation

The phytochemical investigation of the chloroformic and methanolic extracts of the Baccharis pseudotenuifolia led to the isolation of triterpenes, steroids and flavonoids. From chloroformic extract were isolated oleanolic acid and alpha-spinasterol while from methanolic extract were isolated the flavonoids: hispidulin, naringenin, 3'-methoxy-luteolin, apigenin, kaempferol, eriodyctiol, aromadendrin, quercetin, 3'-methoxy-quercetin, quercetin-3-O-rhamnoside and quercetin-3-O-glucoside. The structure of these compounds were identified by IR, CG/MS, ¹H and 13C NMR spectral analysis and comparison with literature. In addition, the extracts were evaluated by means of Brine Shrimp Lethality test and the highier activity was observed in the chloroformic extract.

The present paper describes the chemical composition and biological activities of artichoke cultivated in Brazil. Our studies demonstrated that glycosyl flavonoids (cynaroside and scolymoside), are the major constituents, along with cynaropicrin, a sesquiterpene lactone, and the triterpene lupeol. Cynarin, which is the main compound described for artichoke, was detected in very low concentration. Hexanic fraction exhibited considerable cytotoxicity and diuretic activities.

Dois tetranortriterpenos, sendo um inédito e dois novos derivados do acido dihidrocinâmico foram obtidos da madeira de Hortia colombiana. Suas estruturas foram elucidadas por RMN, e as configurações relativas estabelecidas através de experimentos de nOe diferencial. Em adição, foram isolados aloxantoxiletina, nerolidol, epoxinerolidol, três conhecidos derivados do acido dihidrocinâmico e duas amidas.

A novel tetranortriterpenoid and two dihydrocinnamic acid derivatives were obtained from the wood of Hortia colombiana. Their structures were elucidated by detailed NMR investigations and the relative configurations established by Difference NOE experiments. In addition, alloxanthoxyletin, nerolidol, epoxynerolidol, three known dihydrocinnamic acid derivatives and two amides were isolated. Detailed analysis of NMR data of Hortiolide A, whose structure was previosly established by X ray, are also provided.

Um novo ácido triterpenóide pentacíclico foi isolado a partir de folhas e frutos de Vochysia ferruginea. A estrutura do novo composto foi elucidada por espectroscopia de RMN como sendo o ácido 2alfa,3beta,6beta-triidroxiolean-12-en-28-óico (ácido 6beta-hidroximaslínico, 1). Além do novo triterpenóide, foram isolados das folhas e frutos o glicosídeo de beta-sitosterol e três misturas contendo os triterpenóides conhecidos uvaol e eritrodiol, ácidos ursólico e oleanólico e os ácidos 2alfa,3beta-diidroxiurs-12-en-28-óico e o respectivo isômero oleanólico (ácido maslínico ou cratególico). Nos frutos, a bellericagenina A e o seu éster (28 -> 1) beta-D-glicopiranosílico (bellericasídeo A) estão presentes em elevados teores.

A novel oleane acid was isolated from the leaves and the fruits of Vochysia ferruginea. The structure of the new triterpenoid was elucidated by NMR spectroscopy as 2alpha,3beta,6beta-trihydroxyolean-12-en-28-oic acid (6beta-hydroxymaslinic acid, 1). In addition, beta-sitosterol-glucoside and three mixtures containing known triterpenoids, uvaol and erythrodiol, ursolic and oleanolic acids, 2alpha,3beta-dihydroxyurs-12-en-28-oic acid and its respective oleanolic isomer (maslinic or crategolic acid), were isolated from the leaves and the fruits of Vochysia ferruginea. In the fruits, bellericagenin A and its (28 -> 1) beta-D-glucopyranosyl ester (bellericaside A) were present in high amount.

Um novo triterpeno lupânico, ácido divergióico, além de beta-sitosterol, ácidos betulínico, serícico e 24-hidroxitormêntico, e o éster (28 -> 1) beta-D-glucopiranosílico do último, foram obtidos a partir da casca do caule de Vochysia divergens. A estrutura do ácido divergióico foi elucidada por meio de técnicas espectroscópicas, e caracterizada como sendo o ácido 2alfa,3beta,6beta-trihidroxi-lup-20(29)-en-28-óico.

A new lupane triterpene, divergioic acid, has been isolated from the stem bark of Vochysia divergens together with beta-sitosterol, betulinic, sericic and 24-hydroxytormentic acids and the (28 -> 1) beta-D-glucopyranosyl ester of the latter. The structure of divergioic acid was elucidated by spectroscopic techniques and characterized as 2alpha,3beta,6beta-trihydroxy-lup-20(29)-en-28-oic acid.

O estudo de correlação entre estrutura-retenção (QSRR) foi usado para relacionar a retenção cromatográfica de diferentes cumarinas substituídas as suas características estruturais. Diferentes parâmetros estruturais foram selecionados tais como: descritores topológicos, geométricos, eletrônicos, químico-quânticos e físico-químicos para encontrar uma equação que melhor explique o comportamento cromatográfico destes compostos. O método proposto por Dimov que classifica os descritores em diferentes grupos de acordo com seus valores de coeficientes de correlação foi utilizado neste estudo. As melhores equações de correlação linear múltipla foram obtidas com os seguintes descritores: área total (A T), índice do estado eletrotopológico (S-O-) e orbital molecular ocupado de maior energia (E HOMO), mostrando que a retenção experimental, usando fase estacionária de baixa polaridade está relacionada principalmente com fatores relacionados a forma e também eletrônicos. Os modelos selecionados apresentaram uma boa predictabilidade, a qual foi estabelecida através dos valores do coeficiente de correlação de validação cruzada (r²cv). As equações encontradas podem ser utilizadas para auxiliar na elucidação da estrutura ou retenção cromatográfica de cumarinas similares às estudadas.

Quantitative structure-retention relationships (QSRR) were used in this study to relate the chromatographic retention of different substituted coumarins to molecular structure. Different structural parameters were selected, such as topological, geometric, electronic, quantum-chemical and physico-chemical descriptors, in order to find an equation that fitted the chromatographic retention of these compounds. The method proposed by Dimov that classifies the descriptors in different groups in agreement with their values of correlation coefficients was analysed. Significant correlation equations were obtained with the following molecular descriptors: the total surface area (A T), the electrotopological state index (S(-o-)) of the oxygen in position 1 of coumarin, and the highest occupied molecular orbital energy (E HOMO), showing that the experimental retention, using stationary phases with low polarity, was related with the shape and electronic factors of the solutes. The models found have a good predictive ability as established by cross-validation r²cv values and thus, can be used to aid in the elucidation of the structure or the chromatographic retention of similar coumarins.