A series of β-carboline derivatives with amino or guanidinium were synthesized and evaluated in vitro against anti-Mycobacterium tuberculosis and for antiproliferative activities against nine human cancer cell lines. The compounds 1-(4-hydroxyphenyl)-3-carboxamide(ethylamine) β-carboline (24.9 µg mL-1) and 1-(4-methoxyphenyl)-3-carboxamide(ethylamine) β-carboline (26.9 µg mL-1) were the most active against M. Tuberculosis (MTB). Compounds 1-(4-hydroxyphenyl)-3-carboxamide(ethylamine) β-carboline and 1-(4-methoxyphenyl)-3-carboxamide(propylamine) β-carboline, which had the same substituted groups, inhibited the growth of all human tumor cell lines with growth inhibitory activity (GI50) values from 1.37 to 9.20 mmol L-1. Also in this series, compounds 1-(4-hydroxyphenyl)-3-carboxamide(propylamine) β-carboline and 1-(3-nitrophenyl)-3-carboxamide(propylamine) β-carboline demonstrated significant activity against NCI/ADR cells. Among compounds with a terminal guanidine group, compounds 1-(4-hydroxyphenyl)-3-carboxamide(ethyl)guanidine β-carboline (27.8 µg mL-1) and 1-(3-nitrophenyl)-3-carboxamide(ethyl)guanidine β-carboline (37.4 µg mL-1) demonstrated the greatest activity against MTB. Additionally, compounds 1-(4-methoxyphenyl)-3-carboxamide(ethyl)guanidine β-carboline (GI50 = 0.45 mmol L-1) effectively inhibited growth and was highly selective against NCI/ADR. The in silico study revealed that 1-(4-hydroxyphenyl)-3-carboxamide(ethylamine) β-carboline, 1-(4-methoxyphenyl)-3-carboxamide(ethylamine) β-carboline, 1-(4-hydroxyphenyl)-3-carboxamide(propylamine) β-carboline, 1-(4-methoxyphenyl)-3-carboxamide(propylamine) β-carboline and 1-(3-nitrophenyl)-3-carboxamide(propylamine) β-carboline compounds follow the rules established by Lipinski, suggesting that this compound has no problems with oral bioavailability.

O uso de culturas de cobertura pode reduzir ou até mesmo eliminar o uso de fertilizantes nitrogenados, contribuindo para uma agricultura mais sustentável e garantindo a conservação dos recursos naturais. Assim, o objetivo deste trabalho foi avaliar o uso de culturas de cobertura para incrementar a produção de biomassa de plantas de Serjania marginata. O experimento foi realizado na Universidade Federal da Grande Dourados, em Dourados-MS, de dezembro de 2009 a fevereiro de 2011. Um delineamento de blocos casualizados foi usado, em parcelas subdivididas, com quatro repetições, sendo avaliadas, nas parcelas, três espécies de leguminosas tropicais (mucuna (Stizolobium aterrimum), crotalária (Crotalaria spectabilis) e feijão-de-porco (Canavalia ensiformes)) e uma parcela controle (sem culturas de cobertura), e, nas subparcelas, foi avaliada a adição ou não de nitrogênio (N) (aos 150 dias após o transplante (DAT)). As plantas de S. marginata, em cada subparcela, foram colhidas aos 240 e 350DAT. Mucuna e feijão-de-porco apresentaram a maior acumulação de biomassa fresca (média de 37,61t ha-1) e seca (média de 6,39t ha-1) da parte aérea no florescimento, comparado com a crotalária (21,92 e 4,63t ha-1, respectivamente). A contribuição das culturas de cobertura como prováveis fontes de N somente foi observada para mucuna e feijão-de-porco, as quais promoveram um aumento no índice de clorofila, área foliar, e massa fresca e seca de folhas e caule de plantas de S. marginata na ausência de N. Em folhas de S. marginata, somente a mucuna contribuiu significativamente para um aumento nos níveis de N, enquanto um aumento nos níveis de K foi observado com todos os tratamentos com culturas de cobertura, comparados com o controle. O pré-cultivo com mucuna e feijão-de-porco promoveu um aumento nos níveis de P em folhas de S. marginata. Portanto, mucuna e feijão-de-porco foram as culturas de cobertura mais promissoras para o cultivo de S. marginata, melhorando a produção de biomassa e provavelmente a economia de N.

The use of cover crops can reduce or even eliminate the use of nitrogenous fertilizers, contributing to a more sustainable agriculture and ensuring the conservation of natural resources. Thus, the aim of this research was to evaluate the use of cover crops to improve the biomass yield of Serjania marginata plants. The experiment was carried out at the Federal University of Grande Dourados, in Dourados-MS, from December 2009 to February 2011. A split plot design was used in a randomized block design with four replications, being evaluated in plots three species of tropical legumes (Stizolobium aterrimum, Crotalaria spectabilis and Canavalia ensiformes, and one control plot (without cover crops), and in subplots the addition or not of nitrogen (N) (at 150 days after transplant (DAT)). Plants of S. marginata in each subplot were harvested at 240 and 350 DAT. S. aterrimum and C. ensiformes showed higher accumulation of fresh (average of 37.61t ha-1) and dry (average of 6.39t ha-1) biomass of shoot in flowering, compared with the C. spectabilis (21.92 and 4.63t ha-1, respectively). The contribution of cover crops as a likely source of N only was observed for S. aterrimum and C. ensiforme, which promoted an increase in chlorophyll index, leaf area, fresh and dry weight of leaves and stem of S. marginata plants, in absence of N. In leaves of S. marginata, only C. ensiformes contributed significantly to an increase in N levels, while an increase in K levels was observed with all cover crop treatments, when compared to control. Pre-cultivation with S. aterrimum and C. ensiformes provided an increase in P levels in leaves of S. marginata. Therefore, S. aterrimum and C. ensiformes were the most promising cover crops for growing of S. marginata, improving the biomass yield and probably the N economy.

O extrato etanólico das folhas de Paullinia elegans Cambess., Sapindaceae, e as frações n-hexano, clorofórmio, acetato de etila e hidroetanólica, obtidas de seu fracionamento, foram avaliadas quanto às suas atividades anti-edematogênica e sequestradora de radicais livres. O extrato etanólico e a fração hexano produziram inibição significativa (74,4 e 76,0%, respectivamente) do edema da orelha induzido pelo óleo de cróton em ratos, em doses de 5 mg/orelha. As frações acetato de etila e hidroetanólica mostraram atividade sequestradora de radicais livres no ensaio de DPPH, com IC50 de 36,7 e de 30,1 µg/mL, respectivamente. O fracionamento dos extratos pelo uso de métodos cromatográficos resultou no isolamento do epifriedelanol, ácido 3-O-acetil oleanólico, mistura do stigmasterol 3-β-O-glucopiranosídeo e sitosterol 3-β-O-glucopiranosídeo, canferol, canferol 3,7-O-α-diramnopiranosídeo, canferol 3-O-α-ramnopiranosídeo e 2-O-metil-chiro-inositol. Os compostos foram identificados com base na comparação de seus dados espectroscópicos de RMN com os da literatura.

Ethanol extract of the leaves of Paullinia elegans Cambess., Sapindaceae, and its hexane, chloroform, ethyl acetate, and hydroethanol fractions were evaluated for their antiedematogenic and free radical scavenging activities. The ethanol extract and the hexane fraction produced statistically significant inhibition (74.4 and 76.0%, respectively) of the ear edema induced by croton oil in mice, observed at doses of 5 mg/ear. The ethyl acetate and hydroethanol fractions showed significant radical scavenging effect in the DPPH assay, with IC50 of 36.7 and 30.1 µg/mL, respectively. Fractionation of the extracts through chromatographic methods afforded epifriedelanol, oleanolic acid 3-O-acetyl, a mixture of stigmasterol 3-β-O-glucopyranoside and sitosterol 3-β-O-glucopyranoside, kaempferol 3,7-O-α-dirhamnopyranoside, kaempeferol-3-O-α-rhamnopyranoside and 2-O-methyl-chiro-inositol. The compounds were identified on the basis of their NMR spectral data and comparison with those of literature.

Com o propósito de aumentar a atividade anticâncer demonstrada anteriormente pelas 1-fenilssubstituído-3-(2-tioxo-1,3,4-oxadiazol-5-il) β-carbolinas 1a-c, neste trabalho foram realizadas a síntese e a avaliação in vitro da atividade antitumoral de novas bases de Mannich 2-7(a-c), derivadas da introdução de diferentes grupos alquilamino(metil) na unidade 1,3,4-oxadiazol de 1a-c. Os derivados 1a-c e 2-7(a-c) foram também avaliados quanto às atividades antibacteriana e antifúngica. Adicionalmente, um estudo in silico das propriedades de ADME dos novos compostos sintetizados 2-7(a-c) foi realizado pela avaliação de seus parâmetros de Lipinski e de dados de área de superfície topológica polar (TPSA) e de porcentagem de absorção (% ABS).

With the purpose of activity enhancement of 1-substituted phenyl-3-(2-thioxo-1,3,4-oxadiazol-5-yl) β-carbolines 1a-c, reported as potential antitumor agents in our previous study, herein we report the synthesis and antitumor activity evaluation of several novel Mannich bases 2-7(a-c), by the introduction of different alkylamino(methyl) groups in the 1,3,4-oxadiazole unity of 1a-c. The antimicrobial activities of 1a-c and of 2-7(a-c) were also evaluated. Additionally, an in silico study of the ADME properties of novel synthesized β-carboline derivatives 2-7(a-c) was performed by evaluation of their Lipinski's parameters and topological polar surface area (TPSA) and percentage of absorption (% ABS) data.