A series of novel 1-(substituted-phenyl)-3-(4,5-dihydro-1,3-oxazol-2-yl)-9H-β-carboline (8a-8i) and 1-(substituted-phenyl)-3-(5,6-dihydro-4H-1,3-oxazin-2-yl)-9H-β-carboline (9a-9h) derivatives, as well as their respective N-(chloroalkyl)-1-(substituted-phenyl)-9H-β-carboline-3-carboxamide precursors (6a-6i and 7a-7h), were synthesized and evaluated for their in vitro antileishmanial activity against promastigote and intracellular amastigote forms of Leishmania amazonensis. Compounds 8d, 8i, 9e and 9h exhibited significant activity for both promastigote and amastigote forms, with IC50 (50% inhibitory concentration) values ranging from 2.9 to 23.0 µM. In addition, spin label electron paramagnetic resonance (EPR) spectroscopy studies were carried out for the most active compounds against L. amazonensis promastigotes. The studies indicated that the tested compounds cause strong stiffness in the parasite plasma membrane and are capable of inducing internal metalloproteins oxidation of the parasite, resulting in their cross-linking to skeletal proteins. Compounds 8d and 8i produced the largest effect, showing that the presence of oxazoline group at C-3 of β-carboline nucleus is important for antileishmanial activity.

The essential oil of roots of Jatropha ribifolia, obtained by hydrodistillation, was characterized in terms of its chemical composition by chromatographic method with flame ionization detection (GC-FID) and gas chromatography coupled to electron ionization mass spectrometry (GC-MS). The analyses and identification pointed by mass fragmentation pattern and retention index revealed the presence of 49 compounds, representing 91.4% of the total oil, with 39.5% of monoterpenes, 43.0% of sesquiterpenes and 8.5% of phenylpropanoids. The major compounds of the oil were β-pinene (9.2%), isoeugenol methyl ether (8.5%), vatirenene (8.4%), α-gurjunene (7.0%), endo-8-hydroxy-cycloisolongifolene (6.6%), α-pinene (6.4%) and p-menth-1-en-8-ol (5.2%). The fractionation by preparative thin layer chromatography (TLC) allowed obtaining five fractions (F1-F5) with different compound contents from the original oil. Some essential oil components showed a significant increase in their levels after fractionation, as borneol (17.9%, F1), 3-thujopsanone (19.1%, F4), isoeugenol methylether (21.2%, F2), 8-oxo-9H-cycloisolongifolene (21.4%, F4), 8-cis-5(1H)-azulenone,2,4,6,7,8,8a-hexahydro-3,8-dimethyl-4-(1-methylethylidene) (23.1%, F4) e endo-8-hydroxy-cycloisolongifolene (38.6%, F2). These fractions and oil were tested in vitro against nine human cancer cell lines by sulforhodamine B assay. The Jatropha oil was more effective in inhibiting the growth of cells NCI-H460 (drug resistant ovarian; GI50 6.2 µg mL–1) and OVCAR-3 (ovarian; GI508.0 µg mL–1). The cancer cells line PC-3 (prostate) was more sensitive to the effects of the fractions showing significant values of GI50 such as for fraction F1, F2 and F4 (< 0.25 µg mL–1). In general the antiproliferative activity of the fractions was more pronounced than that of crude oil.

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.

No presente trabalho descrevemos a síntese e a avaliação da atividade antiproliferativa, frente a linhagens de células tumorais humanas, de derivados do R-(+)-limoneno (3-18) contendo uma unidade tiouréia substituída. Os derivados com substituintes arílicos (3-6) exibiram atividade citostática frente a todas linhagens testadas, com inibição de 50% do crescimento celular (GI50) em concentrações na faixa de 2,5 a 24 µmol L-1. Os compostos 3, 10, 12 e 16 foram os mais ativos, com GI50 na faixa de 0,41 a 3,0 mmol L-1, frente a diferentes linhagens celulares.

A series of R-(+)-limonene derivatives bearing a substituted thiourea moiety (3-13) and five S-methyl analogs (14-18) were synthesized and evaluated for their in vitro antiproliferative activity against human cancer cell lines. Compounds bearing aromatic substituents (3-6) exhibit cytotastic activity in the full panel of cell lines tested, with GI50 values in the range of 2.5 to 24 µmol L-1. Compounds 3, 10, 12 and 16 were the most active with GI50 values in the range of 0.41 to 3.0 µmol L-1, against different cell lines.