RESUMO
Investigation of the leaves' extract of Cinnamomum tenuifolium (Lauraceae) led to the isolation of one novel benzodioxocinone, 2,3-dihydro-6,6-dimethylbenzo-[b][1,5]dioxocin-4(6 H)-one (1). The structure was determined through in-depth spectroscopic and mass-spectrometric analyses. The antioxidant potential was evaluated using the following in vitro method: scavenging of 1,1-diphenyl-2-picrylhydrazyl radical. We also detected the anti-proliferative effect of 1 on human oral cancer cells and its IC(50) is 107.7 µM.
Assuntos
Antioxidantes/química , Antioxidantes/farmacologia , Cinnamomum/química , Folhas de Planta/química , Compostos de Bifenilo/química , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Humanos , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Picratos/químicaRESUMO
A novel homosesquiterpenoid, burmanol (1), along with 16 known compounds, including one triterpenoid, one quinol, two chlorophylls, two coumarins, two steroids, three lignans and five benzenoids were obtained from the stems of Cinnamomum burmanii (Lauraceae). The structures of these compounds were determined on the basis of spectroscopic analysis.
Assuntos
Cinnamomum/química , Caules de Planta/química , Sesquiterpenos/análise , Clorofila/análise , Cumarínicos/análise , Lignanas , Estrutura Molecular , Sesquiterpenos/química , Esteroides/análise , Triterpenos/análiseRESUMO
(-)-Anonaine (1), (-)-asimilobine (2), (-)-nuciferine (3), (-)-anolobine (4), (-)-romerine (5), (-)-N-acetylanonaine (6), liriodenine (7), (+)-syringaresinol (8), N-trans-feruloyltyramine (9), N-cis-feruloyltyramine (10), scopoletin (11), 4-acetonyl-3,5-dimethoxy-p-quinol (12), vanillin (13), vanillic acid (14), syringic acid (15), beta-sitosterol (16) and stigmasterol (17) were isolated from branches of Michelia champaca L. In addition, a cell proliferation assay of five of the isolated compounds on human breast and lung cancer cells showed that liriodenine (7) was the strongest inhibitor.
Assuntos
Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Magnoliaceae/química , Caules de Planta/química , Antineoplásicos Fitogênicos/uso terapêutico , Neoplasias da Mama/tratamento farmacológico , Linhagem Celular Tumoral , Feminino , Humanos , Neoplasias Pulmonares/tratamento farmacológicoRESUMO
A novel amide, cinnabutamine (1), along with five known amides, cinnaretamine (2), N-trans-caffeoyl-5-hydroxytyramine (3), N-trans-feruloyltyramine (4), N-trans-feruloyl-5-methoxytyramine (5) and N-cis-feruloyl-5-methoxytyramine (6), were isolated from the stems of Cinnamomum burmannii (Lauraceae). Their structures were characterized and identified by spectral analysis.
Assuntos
Amidas/química , Cinnamomum/química , Caules de Planta/química , Estrutura MolecularRESUMO
Pressafonin A (1) and pressafonin B (2), two new Michelia monoterpenic esters, have been isolated from Michelia compressa (Maxim.) Sargent var. formosana Kanehira (Magnoliaceae), and their structures are determined on the basis of spectroscopic analysis.
Assuntos
Ácidos Aristolóquicos/química , Magnoliaceae/química , Folhas de Planta/química , Espectroscopia de Ressonância Magnética , Estrutura MolecularRESUMO
Pressalanine A (1), a new Michelia aristolactam, and pressalanine B (2), a new Michelia dioxoaporphine, have been isolated from Michelia compressa var. lanyuensis (Magnoliaceae), and these structures were determined on the basis of spectroscopic analysis.
Assuntos
Ácidos Aristolóquicos/isolamento & purificação , Magnoliaceae/química , Folhas de Planta/química , Estrutura Molecular , Análise Espectral/métodosRESUMO
Two new diterpenoids, 14,18-dihydroxyabieta-8,11,13-trien-7-one (1) and 13-acetyl-14,18-dihydroxy-podocarpa-8,11,13-triene (2), together with eight known compounds, i.e., gaultheric acid (3), vanillic acid (4), 4-hydroxybenzoic acid (5), cinnamic acid (6), stearic acid (7), palmitic acid (8), beta-sitosterol (9), and stigmasterol (10), were isolated from the MeOH extract of the whole plant of Gaultheria itoana Hayata (Ericaceae). The structures of the new constituents were elucidated by spectroscopic methods (UV, IR, and 1D- and 2D-NMR) and by mass spectrometry (HR-ESI-MS). Among them, 1 and 2 were demonstrated to exhibit significant cytotoxic activity against the LNCaP cell line.
Assuntos
Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Diterpenos/química , Diterpenos/isolamento & purificação , Gaultheria/química , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Cinamatos/química , Cinamatos/isolamento & purificação , Cinamatos/farmacologia , Diterpenos/farmacologia , Humanos , Neoplasias Pulmonares/tratamento farmacológico , Neoplasias Pulmonares/patologia , Espectroscopia de Ressonância Magnética , Metanol/química , Estrutura Molecular , Ácido Palmítico/química , Ácido Palmítico/isolamento & purificação , Ácido Palmítico/farmacologia , Parabenos/química , Parabenos/isolamento & purificação , Parabenos/farmacologia , Extratos Vegetais/química , Sitosteroides/química , Sitosteroides/isolamento & purificação , Sitosteroides/farmacologia , Espectrometria de Massas por Ionização por Electrospray , Ácidos Esteáricos/química , Ácidos Esteáricos/isolamento & purificação , Ácidos Esteáricos/farmacologia , Estigmasterol/química , Estigmasterol/isolamento & purificação , Estigmasterol/farmacologia , Ácido Vanílico/química , Ácido Vanílico/isolamento & purificação , Ácido Vanílico/farmacologiaRESUMO
Three new butanolides, tenuifolide A (1), isotenuifolide A (2), and tenuifolide B (3), a new secobutanolide, secotenuifolide A (4), and one new sesquiterpenoid, tenuifolin (5), along with 16 known compounds were isolated from the stems of Cinnamomum tenuifolium. Their structures were determined by spectroscopic analyses. Compound 4 was found to induce apoptotic-related DNA damage, increase sub-G1 cells, and inhibit the growth of human prostate cancer cells, DU145. In addition, treatment with 4 significantly increased intracellular H2O2 and/or peroxide. The results show that 4 induced (a) noticeable reduction of mitochondrial transmembrane potential (DeltaPsim); (b) significant increase in the ratio of cytochrome c concentration (cytosol/mitochondria); and (c) subsequent activation of caspase-9/caspase-3. Antiproliferation caused by 4 was found to markedly decrease when pretreated with caspase-9/caspase-3 inhibitor. In ROS scavenging, antioxidant, NADPH oxidase, and NO inhibitor studies, pretreatment of DU145 cells with either DPI, dexamethasone, L-NAME, or mannitol decreased 4-induced intracellular DCF fluorescence of ROS. These results suggest that an increase of H2O2 and/or peroxide by 4 is the initial apoptotic event and 4 has anticancer effects on DU145 cells.