RESUMO
Three new sesquiterpenes, methyl 4-isopropyl-7-methoxy-6-methylnaphthalene-1-carboxylate (1), methyl 2-hydroxy-4-isopropyl-7-methoxy-6-methylnaphthalene-1-carboxylate (2), and methyl 2-hydroxy-6-(hydroxymethyl)-4-isopropyl-7-methoxynaphthalene-1-carboxylate (3), together with three known sesquiterpenes (4-6), were isolated from the stems of Nicotiana tabacum. Their structures were determined by means of HRESIMS and extensive 1D and 2D NMR spectroscopic studies. The results showed that compounds 2, 3, and 5 exhibited high anti-TMV activity with inhibition rates of 33.6, 35.8, and 36.7%. Compounds 1-6 showed weak inhibitory activities against some tested human tumor cell lines (NB4, A549, SHSY5Y, PC3, and MCF7) with IC50 values in the range of 6.7-9.6 µM.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Nicotiana/química , Sesquiterpenos/farmacologia , Antineoplásicos Fitogênicos/química , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Humanos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Sesquiterpenos/químicaRESUMO
Three new phenolic compounds, nicotphenols A-C (1-3), together with 14 known phenols (4-17), were isolated from the leaves of Nicotiana tabacum. Their structures were established by means of spectroscopic methods, including extensive 1D and 2D NMR techniques. Compounds 1-3 were tested for their anti-HIV-1 activities and cytotoxicities. They all showed significant cytotoxic abilities and modest anti-HIV-1 activities, respectively.
Assuntos
Fármacos Anti-HIV/isolamento & purificação , Fármacos Anti-HIV/farmacologia , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Nicotiana/química , Fenóis/isolamento & purificação , Fenóis/farmacologia , Fármacos Anti-HIV/química , Medicamentos de Ervas Chinesas/química , Testes de Sensibilidade Microbiana , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Fenóis/química , Folhas de Planta/químicaRESUMO
Two new triterpenoids, 3-O-(4',5'-dihydroxybenzoyl)-lup-20(29)-en (1) and 3-O-(6'-desmethysyringyl)-13α-methyl-27-norolean-14-en-3ß-ol (2), were isolated from the leaves and twigs of Orophea yunnanensis. Their structures were identified by extensive spectroscopic experiments (NMR and MS) and comparison with literature data. Compounds 1 and 2 exhibited the moderate inhibitory activity against Sclerotinia sclerotiorum, Ceratocystis fimbriata and Verticillium dahliae Kleb with MIC values from 50 to 25 µg/mL, and also displayed the weak activity selectively against tested bacteria strains with MIC values from 100 to 50 µg/mL.
Assuntos
Annonaceae/química , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Triterpenos/química , Triterpenos/farmacologia , Ascomicetos/efeitos dos fármacos , Avaliação Pré-Clínica de Medicamentos , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Estrutura Molecular , Folhas de Planta/química , Caules de Planta/química , Espectrometria de Massas por Ionização por ElectrosprayRESUMO
Three unreported sesquiterpenes possessing two new skeletons, tabasesquiterpenes A-C (1-3), together with three known sesquiterpenes (3-6) were isolated from the leaves of Nicotiana tabacum. Their structures were determined mainly by spectroscopic methods, including extensive 1D- and 2D-NMR techniques. Compounds 1-6 were evaluated for their anti-tobacco mosaic virus (anti-TMV) activities. The results showed that compound 2 exhibited high anti-TMV activity with inhibition rate of 35.2%, which were higher than that of positive control (ningnanmycin). The other compounds also showed potential anti-TMV activity with inhibition rates in the range of 20.5-28.6%.
Assuntos
Antivirais/química , Nicotiana/química , Folhas de Planta/química , Sesquiterpenos/química , Vírus do Mosaico do Tabaco/efeitos dos fármacos , Antivirais/isolamento & purificação , Estrutura Molecular , Extratos Vegetais/química , Sesquiterpenos/isolamento & purificaçãoRESUMO
Four new flavones, tobaflavones E-H (1-4), together with two known flavones (5 and 6), were isolated from the leaves of Dali Tiandeng tobacco (a variety of Yunnan local air cured tobacco). Their structures were elucidated by spectroscopic methods, including extensive 1D- and 2D NMR techniques. Compound 2 is the first naturally occurring flavone bearing a (4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)methyl moiety. These compounds were also evaluated for their anti-tobacco mosaic virus (anti-TMV) activity. The results revealed that compounds 1 and 2 exhibited high anti-TMV activity with inhibition rate of 35.3% and 39.6%, respectively. The rates are higher than those of positive control. The other compounds also showed potential anti-TMV activity with inhibition rates in the range of 18.7-28.4%, respectively.
Assuntos
Antivirais/farmacologia , Flavonas/farmacologia , Nicotiana/química , Vírus do Mosaico do Tabaco/efeitos dos fármacos , Antivirais/isolamento & purificação , China , Flavonas/isolamento & purificação , Estrutura Molecular , Folhas de Planta/químicaRESUMO
Five new biphenyls, tababiphenyls A-E (1-5), together with five known ones (5-10), were isolated from the leaves of Nicotiana tabacum, of which compound 1 possessed a seldom reported 6-carbons unit in biphenyls. Their structures were established on the basis of extensive spectroscopic analyses. All compounds were tested for their anti-tobacco mosaic virus (anti-TMV) activities. The results showed that compounds 3 and 5 exhibited high anti-TMV activities with inhibition rate of 48.4% and 32.1%, respectively, which were higher than that of positive control (ningnanmycin). The other compounds also showed potential anti-TMV activities with inhibition rates in the range of 18.6-28.7%, respectively.