Cytotoxic and Genotoxic Butanolides and Lignans fromAiouea trinervis

Abstract

The ethanolic extracts from the roots, the underground trunk and the leaves of Aiouea trinervis were active in the brine shrimp (Artemia salina) lethality assay (LD (50): 1.93, 0.92 and 262.1 microg/mL, respectively). Fractionation of the extracts led to the isolation of four butanolides, namely (-)-epilitsenolides C (2) and C (1) ( 1 and 2), isoobtusilactone A ( 3) and obtusilactone A ( 4), two of which ( 1 and 2) are reported for the first time as genuine natural products. The lignans (+)-sesamin ( 5) and (+)-methylpiperitol ( 6) and polyprenol-12 ( 7) were isolated as well. Their structures were determined with spectral methods (1D-, 2D-NMR and MS). Compounds 1, 2, 3, 5 and 6 were tested for their cytotoxic activities in Hep (2) human cancer cells. The butanolides 2 and 3 were the most active (IC (50): 5.96 microg/mL and 4.95 microg/mL, respectively) whereas the other compounds showed moderate IC (50) values ranging from 12.20 microg/mL to 25.64 microg/mL. The genotoxic properties of the crude ethanolic extracts and of compounds 3 and 5 were also evaluated in this study on CHO K1 and HTC mammalian cells with single-cell gel electrophoresis (comet assay). The crude extracts as well as the compounds tested induced DNA migration in this assay, which was indicative of DNA damage (genotoxic effect).

Fenilpropanóides e outros constituintes bioativos de Nectandra megapotamica

“…6 A investigação da composição química de lauráceas que ocorrem no Cerrado e Pantanal de Mato Grosso do Sul, incluindo as do gênero Nectandra, tem sido motivo de estudos desenvolvidos por nosso grupo de pesquisa. 7 Nas coletas de plantas realizadas, constatamos a presença de Nectandra megapotamica em diferentes locais das regiões central e sul do estado, porém sempre em matas ciliares. Considerando a possibilidade destas plantas se constituírem numa população genotipicamente distinta das anteriormente estudadas, decidimos investigar a composição química das cascas do caule de um exemplar de N. megapotamica ocorrente em Mato Grosso do Sul.…”

Evaluation of the genotoxic activity of ethanol extract and secondary metabolites isolated from Aiouea trinervis Meisn. (Lauraceae)

“…As previously demonstrated, the fractionation of ethanol extracts (EEs) from the roots, underground trunk, and the leaves of A. trinervis led to the isolation of 4 butanolides (g-lactones), namely (-)-epilitsenolides C-2 and C-1, isoobtusilactone A, and obtusilactone A, and the lignans (+)-sesamin, (+)-methylpiperitol, and polyprenol-12 (Garcez et al, 2005).…”

“…The EEs from leaves and butanolides (isoobtusilactone A and obtusilactone A) that were investigated in this study were produced and supplied by the Chemistry Department at the Federal University of Mato Grosso do Sul (UFMS), Campo Grande, MS, Brazil (see Garcez et al, 2005). The EEs and butanolides were always freshly prepared immediately before use and dissolved in 1% Tween 80 (Labsynth Produtos para Laboratórios Ltda., Diadema, SP, Brazil), 3% ethanol (Proquímios, Rio de Janeiro, RJ, Brazil), and distilled water.…”

“…Aiouea trinervis Meisn., 1864 (Laurales, Lauraceae) is a shrub that grows in the "Cerrado" (a savanna ecosystem) of Mato Grosso do Sul, Brazil, and is considered to be an endangered Brazilian species (Garcez et al, 2005). As previously demonstrated, the fractionation of ethanol extracts (EEs) from the roots, underground trunk, and the leaves of A. trinervis led to the isolation of 4 butanolides (g-lactones), namely (-)-epilitsenolides C-2 and C-1, isoobtusilactone A, and obtusilactone A, and the lignans (+)-sesamin, (+)-methylpiperitol, and polyprenol-12 (Garcez et al, 2005).…”

“…It consists mostly of trees or tree-like shrubs that are rich in biologically active secondary metabolites, such as neolignans, g-lactones, alkaloids, flavonoids, and terpenes. These secondary metabolites have shown different biological properties: cytotoxic (Tsai et al, 2000;Chang et al, 2008) and genotoxic (Garcez et al, 2005).…”