RESUMO
Seven diterpenes including two new seco-cembranoid basmanoids A (1) and B (2), and two new labdane basmadanes A (3) and B (4), and three known compounds (-)-dehydro-nor-ambreinolid (5), (13E)-8-hydroxy-13-labden-12-one (6), and 14,15,16-dinor-7-oxolabda-8-ene-13-oic acid (7) were isolated from oriental tobacco Nicotiana tabacum 'YNOTBS1'. Compounds 1-3 and 5 showed anti-tobacco mosaic virus (TMV) activity with inhibition rates in the range of 30-69% at the concentration of 1 mg/mL. However, none of them exhibited any inhibitory effects against nitric oxide (NO) production in LPS and IFN-γ-induced RAW 264.7 murine macrophages and anti-proliferative activities against cancer cell lines SMMC-7721 and A-549.
Assuntos
Diterpenos , Vírus do Mosaico do Tabaco , Animais , Camundongos , Estrutura Molecular , Nicotiana , Linhagem Celular Tumoral , Diterpenos/farmacologiaRESUMO
A new isoquinoline alkaloid(1) has been isolated from the whole plant of Thalictrum glandulosissimum by using various chromatographic techniques, including silica gel, sephadex, MCI-gel resin, and RP-HPLC, and its structure was determined as 1-(6-hydroxy-7-methylisoquinolin-1-yl) ethantone by physicochemical properties and spectroscopic data. This compound was evaluated for anti-tobacco mosaic virus(TMV) activity. The results showed that it had prominent anti-TMV activity with inhibition rates of 28.4%. This rate was closed to that of positive control.
Assuntos
Alcaloides , Antivirais , Thalictrum , Vírus do Mosaico do Tabaco , IsoquinolinasRESUMO
A new isoquinoline alkaloid(1) has been isolated from the whole plant of Thalictrum glandulosissimum by using various chromatographic techniques, including silica gel, sephadex, MCI-gel resin, and RP-HPLC, and its structure was determined as 1-(6-hydroxy-7-methylisoquinolin-1-yl) ethantone by physicochemical properties and spectroscopic data. This compound was evaluated for anti-tobacco mosaic virus(TMV) activity. The results showed that it had prominent anti-TMV activity with inhibition rates of 28.4%. This rate was closed to that of positive control.
Assuntos
Alcaloides , Antivirais , Isoquinolinas , Thalictrum , Vírus do Mosaico do TabacoRESUMO
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 isolates (1-3) including one new sterol and two new flavonoids together with three known sterols (4-6) were isolated from the leaves of Nicotiana tabacum. Their structures were determined mainly by spectroscopic methods, including extensive 1D and 2D NMR techniques. All compounds were evaluated for their anti-tobacco mosaic virus and cytotoxic activities. The results showed that compounds 2 and 3 exhibited high anti-TMV activity with inhibition rate of 34.2 and 33.4%, respectively, which were roughly equivalent to that of positive control. The cytotoxicities of compounds 1 and 4-6 against five human tumour cell lines were also tested, and tested compounds showed weak inhibitory activities against some tested human tumour cell lines.
Assuntos
Antivirais/farmacologia , Produtos Biológicos/química , Nicotiana/química , Folhas de Planta/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Antivirais/química , Produtos Biológicos/farmacologia , Linhagem Celular Tumoral , Avaliação Pré-Clínica de Medicamentos , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Vírus do Mosaico do Tabaco/efeitos dos fármacosRESUMO
A new naphthaldehyde derivative has been isolated from Comastoma pulmonarium by using various chromatographic techniques, including silica gel, Sephadex LH-20, MCI-gel resin and RP-HPLC. This compounds was determined as 5-methoxy-2-methyl-7-(2-oxopropyl)naphthalene-1-carbaldehyde(1) by NMR, MS, IR and UV spectra. This compound was also evaluated for its anti-tobacco mosaic virus (anti-TMV) activity. The result showed that it showed high anti-TMV activity with inhibition rate of 32.8%. The inhibition rate is close to that of positive control (ningnanmycin).
Assuntos
Aldeídos/farmacologia , Antivirais/farmacologia , Gentianaceae/química , Naftalenos/farmacologia , Vírus do Mosaico do Tabaco/efeitos dos fármacos , Aldeídos/isolamento & purificação , Antivirais/isolamento & purificação , Cromatografia Líquida de Alta Pressão , Naftalenos/isolamento & purificação , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , NicotianaRESUMO
Three new isoflavones, 7-acetyl-4',6-dimethoxy-isoflavone (1), 7-acetyl-4'-hydroxy-6-methoxy-isoflavone (2) and 7-acetyl-6,8-dimethoxy-4'-hydroxy-isoflavone (3), together with five known flavones (4-8), were isolated from the Pueraria montana var. lobata (Willd.). Their structures were elucidated by spectroscopic methods, including extensive 1D- and 2D NMR techniques. Compounds 1-8 were evaluated for their anti-tobacco mosaic virus (anti-TMV) activities. The results showed that compounds 1 and 2 exhibited high anti-TMV activities with inhibition rates of 36.8 and 33.6%, respectively. The inhibition rates are higher than that of positive control. The other compounds also showed potential anti-TMV activities with inhibition rates in the range of 21.8~28.4%, respectively. The cytotoxicities of compounds 1-3 against five human tumour cell lines (NB4, A549, SHSY5Y, PC3 and MCF7) were also tested. The results revealed that compounds 1-3 showed weak inhibitory activities against some tested human tumour cell lines with IC50 values in the range of 1.2-3.6 µM.
Assuntos
Isoflavonas/isolamento & purificação , Pueraria/química , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Antivirais/isolamento & purificação , Antivirais/farmacologia , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais , Flavonas/química , Flavonas/isolamento & purificação , Flavonas/farmacologia , Humanos , Isoflavonas/química , Isoflavonas/farmacologia , Estrutura Molecular , Vírus do Mosaico do Tabaco/efeitos dos fármacosRESUMO
A new naphthaldehyde derivative has been isolated from Comastoma pulmonarium by using various chromatographic techniques, including silica gel, Sephadex LH-20, MCI-gel resin and RP-HPLC. This compounds was determined as 5-methoxy-2-methyl-7-(2-oxopropyl)naphthalene-1-carbaldehyde(1) by NMR, MS, IR and UV spectra. This compound was also evaluated for its anti-tobacco mosaic virus (anti-TMV) activity. The result showed that it showed high anti-TMV activity with inhibition rate of 32.8%. The inhibition rate is close to that of positive control (ningnanmycin).
Assuntos
Aldeídos , Farmacologia , Antivirais , Farmacologia , Cromatografia Líquida de Alta Pressão , Gentianaceae , Química , Naftalenos , Farmacologia , Compostos Fitoquímicos , Farmacologia , Nicotiana , Vírus do Mosaico do TabacoRESUMO
Three new isobenzofurans (1-3), together with four known phenylpropanoids (4-7) were isolated from the roots of Nicotiana tabacum. Their structures were determined by means of HRESIMS and extensive 1D and 2D NMR spectroscopic studies. Compounds 1-6 were tested for their anti-tobacco mosaic virus (anti-TMV) activities and cytotoxicity activities. The results showed that compounds 5 and 6 exhibited high anti-TMV activities with inhibition rates of 35.1 and 33.4%, respectively. The cytotoxicities of compounds 1-7 against five human tumor cell lines (NB4, A549, SHSY5Y, PC3 were also tested. Compounds 1-7 showed weak inhibitory activities against some tested human tumor cell lines with IC50 values in the range of 3.8-9.6 µM.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Antivirais/farmacologia , Benzofuranos/química , Nicotiana/química , Vírus do Mosaico do Tabaco/efeitos dos fármacos , Antineoplásicos Fitogênicos/química , Antivirais/química , Benzofuranos/farmacologia , Linhagem Celular Tumoral , Avaliação Pré-Clínica de Medicamentos/métodos , Humanos , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Raízes de Plantas/químicaRESUMO
Three previously unreported anthraquinones, fistulaquinones A-C (1-3), together with three known ones (4-6) were isolated from the twigs of Cassia fistula. Their structures were determined by means of extensive NMR and MS spectroscopic analyses. All the isolated compounds were tested for their anti-tobacco mosaic virus (anti-TMV) activity, and compound 3 showed significant activity with inhibition rate of 34.5% at 20 µM concentration, even more potent than positive control. Additionally, compounds 1-6 exhibited moderate cytotoxicity with IC50 values ranging from 2.8 to 9.4 µM for some tested human tumor cell lines.
Assuntos
Antraquinonas/isolamento & purificação , Antraquinonas/farmacologia , Antivirais/isolamento & purificação , Antivirais/farmacologia , Cassia/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Vírus do Mosaico do Tabaco/efeitos dos fármacos , Antraquinonas/química , Antivirais/química , Citidina/análogos & derivados , Citidina/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Medicamentos de Ervas Chinesas/química , Humanos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Paclitaxel/farmacologia , Folhas de Planta/química , Caules de Planta/químicaRESUMO
Phytochemical investigations on the ethanol extract of the twigs of Garcinia tetralata resulted in the isolation of three new biphenyls, tetralatabiphenyls A-C (1-3), along with three known biphenyl derivatives (4-6). Structural elucidations of 1-3 were performed by spectroscopic methods such as 1D and 2D NMR spectra, in addition to high-resolution mass spectra. Compounds 1-6 were also evaluated for their anti-tobacco mosaic virus (anti-TMV) activity. The results showed that compound 3 showed high anti-TMV activity with inhibition rate of 31.1%. Compounds 1, 2, and 4-6 also showed modest anti-TMV activities with inhibition rates in the range of 18.9-24.5%, respectively.
Assuntos
Antivirais/isolamento & purificação , Antivirais/farmacologia , Compostos de Bifenilo/isolamento & purificação , Compostos de Bifenilo/farmacologia , Garcinia/química , Vírus do Mosaico do Tabaco/efeitos dos fármacos , Antivirais/química , Compostos de Bifenilo/química , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Caules de Planta/químicaRESUMO
Two new sesquiterpenes, nicotianasesterpenes A and B (1 and 2), together with five known sesquiterpenes (3-7) were isolated from the leaves of Nicotiana tabacum. Their structures were determined mainly by spectroscopic methods, including extensive 1D- and 2D-NMR techniques. The anti-tobacco mosaic virus (anti-TMV) activities of compounds 1-7 were evaluated. The results revealed that compound 1 exhibited high anti-TMV activities with inhibition rates of 33.6%. This rate is high than that of positive control. The other compounds also showed potential activities with inhibition rates in the range of 18.8-28.4%, respectively.
RESUMO
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.
Assuntos
Antivirais/química , Compostos de Bifenilo/química , Nicotiana/química , Vírus do Mosaico do Tabaco/efeitos dos fármacos , Antivirais/farmacologia , Compostos de Bifenilo/farmacologia , Estrutura Molecular , Doenças das Plantas/virologia , Folhas de Planta/químicaRESUMO
Fifteen new seco-pregnane steroidal glycosides cynanosides A-O (1-15) together with twenty-seven known ones were isolated from the roots of Cynanchum atratum. The structures of 1-15 were determined by extensive analysis of spectroscopic data. The anti-tobacco mosaic virus (TMV) activity of these steroidal glycosides was screened by the conventional half-leaf method, enzyme-linked immunosorbent assay, and Western blot methods, most of them showed potent anti-TMV activity. Among them, compounds 1, 7, 13, 28 and 31 showed significantly anti-TMV activity with an IC50 value of 20.5, 18.6, 22.0, 19.2 and 22.2 µg/mL, respectively, and were much more effective than the positive control, ningnanmycin (IC50=49.6 µg/mL).