RESUMO
Six new acylated flavonoid glycosides namely barringosides J - O (1-6) along with tephrokaempferoside and barringoside D were isolated from the branches and leaves of Barringtonia pendula. The structural elucidation was confirmed by extensive analysis of their spectroscopic data including HRQTOFMS, 1D and 2D NMR experiments. Moderate inhibitory effects on LPS-induced NO production in RAW264.7 cells were observed for barringosides M (4) and N (5) with IC50 values of 48.40 ± 3.01 and 56.61 ± 3.87 µM, whereas weak inhibition was found for compounds 1-3, 6, and 7 with IC50 values ranging from 64.91 ± 3.68 to 79.80 ± 3.90 µM.
Assuntos
Barringtonia , Flavonoides , Animais , Camundongos , Flavonoides/farmacologia , Flavonoides/química , Lipopolissacarídeos/farmacologia , Óxido Nítrico , Barringtonia/química , Estrutura Molecular , Glicosídeos/farmacologia , Glicosídeos/química , Células RAW 264.7RESUMO
Using combined chromatographic methods, two new sesquiterpene glucosides, vulgarosides A (1) and B (2), and two known analogs ainsliaside E (3) and pumilaside A (4) were isolated from the aerial parts of Artemisia vulgaris. Their chemical structures were established by spectroscopic methods, including one and two-dimensional nuclear magnetic resonance (1 D and 2 D-NMR) spectroscopy and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS). In addition, their cytotoxicity on five human cancer cell lines, including KB (epidermoid carcinoma), HepG2 (hepatocarcinoma), MCF7 (breast carcinoma), SK-Mel-2 (melanoma), and LNCaP (prostate cancer) was also evaluated by the SRB assay. However, none of the tested eudesmane sesquiterpene glycosides showed significant cytotoxicity (IC50>100 µM).
Assuntos
Artemisia , Neoplasias , Sesquiterpenos de Eudesmano , Sesquiterpenos , Humanos , Artemisia/química , Glucosídeos/química , Sesquiterpenos de Eudesmano/farmacologia , Sesquiterpenos de Eudesmano/análise , Sesquiterpenos/farmacologia , Sesquiterpenos/análise , Componentes Aéreos da Planta/química , Estrutura MolecularRESUMO
Using combined chromatographic separation techniques, three new triterpenoids named lycomclavatols A-C (1-3), a new natural product, methyl lycernuate-A (4), as well as seven known compounds (5-11), were isolated from the methanol extract of the whole plants of Lycopodium clavatum. Their chemical structures were established based on 1 D/2D NMR and HR-ESI-MS spectroscopic analyses. Among the isolates, compound 1 exhibited inhibitory activity on NO production in LPS-stimulated BV2 cells (IC50 = 36.0 µM). In addition, 1 was cytotoxic against both HepG2 and A549 cancer cell lines, with IC50 values of 40.7 and 87.0 µM, respectively. Compounds 10 and 11 showed cytotoxicity on only HepG2 and A549 cells, with IC50 values of 91.2 and 57.6 µM, respectively. Our results contribute to understanding more the secondary metabolites produced by L. clavatum and provide a scientific rationale for further investigations of anti-inflammatory and anticancer effects for this valuable medicinal plant.
Assuntos
Lycopodium , Plantas Medicinais , Triterpenos , Lycopodium/química , Triterpenos/farmacologia , Triterpenos/química , Óxido Nítrico/metabolismo , Plantas Medicinais/química , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Concentração Inibidora 50RESUMO
Phytochemical investigation of the branches and leaves of Alchornea annamica led to isolation of ten secondary metabolites, including two new megastigmane glucosides alnamicosides A (1) and B (2). The structure elucidation was confirmed by 1 D and 2 D NMR, ECD as well as HR-QTOF-MS experiments. The megastigmane derivatives 1 - 3 exhibited inhibitory effects on LPS-induced NO production in RAW264.7 cells with IC50 values of 78.72 ± 1.90, 77.40 ± 9.40 and 82.16 ± 4.56 µM, respectively. This is the first report on chemical constituents and biological activity of the plant A. annamica.
Assuntos
Euphorbiaceae , Animais , Euphorbiaceae/química , Camundongos , Compostos Fitoquímicos/análise , Extratos Vegetais/química , Folhas de Planta/química , Células RAW 264.7RESUMO
Phytochemical investigation of a methanol extract of Panax pseudoginseng flower buds resulted in the isolation of 22 dammarane-type triterpenoid saponins, including three new compounds, pseudoginsenosides A-C (1-3), and 19 known analogs. Their chemical structures were identified by the comprehensive spectroscopic methods, including 1 D and 2 D NMR and mass spectra. In addition, their cytotoxic effects toward three human carcinoma cell lines, including liver (HepG2), breast (MCF7), and lung (A549) were also evaluated.
Assuntos
Antineoplásicos , Panax , Saponinas , Triterpenos , Antineoplásicos/análise , Flores/química , Humanos , Estrutura Molecular , Panax/química , Saponinas/química , Triterpenos/química , DamaranosRESUMO
Sixteen sesquiterpenoids (1 - 16), including two new compounds namely saussucostusosides A and B (1 and 2), were isolated from the roots of Saussurea costus by various chromatographic separations. Their structures were elucidated by 1 D and 2 D NMR and HR-QTOF-MS experiments. Among isolated compounds, costunlide (6), 3ß-[4-hydroxymethacryloyloxy]-8α-hydroxycostunolide (10) and 11ß,13-dihydrozaluzanin C (16) exhibited potent inhibitory effects on LPS-induced NO production in RAW264.7 cells with IC50 values of 7.08 ± 0.34, 2.40 ± 0.06 and 5.55 ± 0.24 µM, respectively.
Assuntos
Saussurea/química , Sesquiterpenos/isolamento & purificação , Animais , Espectroscopia de Ressonância Magnética Nuclear de Carbono-13 , Concentração Inibidora 50 , Lipopolissacarídeos/farmacologia , Camundongos , Óxido Nítrico/biossíntese , Extratos Vegetais/química , Raízes de Plantas/química , Espectroscopia de Prótons por Ressonância Magnética , Células RAW 264.7 , Sesquiterpenos/químicaRESUMO
Two new megastigmane glucosides namely trewiosides A (1) and B (2), along with 20α-hydroxypregn-4-en-3-one ß-D-glucopyranoside (3), sugeroside (4), and schizandriside (5) were isolated from the branches and leaves of Alchornea trewioides. The structure elucidation was confirmed by extensive analysis of the one and two dimensional (1 and 2D) NMR, electronic circular dichroism (ECD) as well as high resolution electrospray ionization quadrupole time-of-flight (HR-ESI-QTOF) mass spectra. Noteworthily, the isolation of compounds 1 and 2 represents the second finding of megastigmane derivatives with a methoxycarbonyl group at C-5 to date. In addition, compound 3 showed weak cytotoxicity against three human cancer cell lines as A549 (lung carcinoma), HepG2 (hepatocarcinoma), and MCF7 (breast carcinoma). Besides, compounds 2 and 3 exhibited moderate inhibitory effects on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 cells. Whereas, the remaining compounds 1, 4 and 5 showed weak inhibitory activity.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Euphorbiaceae/química , Óxido Nítrico/antagonistas & inibidores , Extratos Vegetais/farmacologia , Folhas de Planta/química , Animais , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Teoria da Densidade Funcional , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Lipopolissacarídeos/antagonistas & inibidores , Lipopolissacarídeos/farmacologia , Camundongos , Óxido Nítrico/biossíntese , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Células RAW 264.7RESUMO
Using various chromatographic separations, three new acylated flavonoid glycosides, namely barringosides G-I (1-3), were isolated from the water-soluble extract of Barringtonia racemosa branches and leaves. The structure elucidation was performed by extensive analysis of the 1D and 2D NMR and HR-QTOF-MS data. Of the isolated compounds, barringoside I (3) showed moderate inhibitory effects on LPS-induced NO production in RAW264.7 cells with an IC50 of 52.48 ± 1.04 µM.
Assuntos
Barringtonia/química , Flavonoides/química , Flavonoides/farmacologia , Acilação , Animais , Glicosídeos/química , Glicosídeos/farmacologia , Lipopolissacarídeos/química , Lipopolissacarídeos/farmacologia , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Camundongos , Estrutura Molecular , Óxido Nítrico/metabolismo , Extratos Vegetais/química , Folhas de Planta/química , Células RAW 264.7RESUMO
Two new guaiane sesquiterpene lactones, vulgarolides A and B (1 and 2), were isolated from Artemisia vulgaris aerial parts using various chromatographic separations. The structure elucidation was performed by combination of spectroscopic experiments including 1D and 2D NMR, HR ESI MS, and CD. Their in vitro cytotoxic activities against five human cancer cell lines were also evaluated using SRB method.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Artemisia/química , Sesquiterpenos de Guaiano/química , Sesquiterpenos de Guaiano/farmacologia , Linhagem Celular Tumoral , Dicroísmo Circular , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Espectroscopia de Ressonância Magnética , Modelos Moleculares , Componentes Aéreos da Planta/química , Espectrometria de Massas por Ionização por ElectrosprayRESUMO
Six iridoid derivatives (1-6), including two new compounds myrmecodoides A and B (1 and 2), were isolated from the ant-plant Myrmecodia tuberosa. Their structures were determined on the basis of spectroscopic data ((1)H and (13)C NMR, HSQC, HMBC, (1)H-(1)H COSY, NOESY and HR-ESI-MS) and by comparison with the literature values. Among isolates, 3 and 4 exhibit weak antibacterial effect against Staphylococcus aureus subsp. aureus with MIC value of 100.0 µg/mL.
Assuntos
Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Iridoides/farmacologia , Rubiaceae/química , Animais , Antibacterianos/química , Antibacterianos/farmacologia , Iridoides/química , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Tubérculos/química , Espectrometria de Massas por Ionização por Electrospray , Staphylococcus aureus/efeitos dos fármacos , VietnãRESUMO
OBJECTIVE: To identify inhibitors of nitric oxide production and NF-κB activity from Chromolaena odorata (C. odorata). METHODS: The compounds isolated from the aerial parts of C. odorata by bioassay-guided fractionation were investigated for their inhibitory effects on the NO production and NF-κB activity in LPS-stimulated RAW264.7 cells. RESULTS: Six fatty acids (S)-coriolic acid (1), (S)-coriolic acid methyl ester (2), (S)-15,16-didehydrocoriolic acid (3), (S)-15,16-didehydrocoriolic acid methyl ester (4), linoleamide (5) and linolenamide (6) were isolated. All compounds inhibited the NO production at concentrations consistent with those required for NF-κB inhibition. Compound 2 was the most active with the IC(50) values of 5.22 and 5.73 µM. The addition of a double bond in the fatty chain decreased the inhibitory effects while the methyl esterification increased the activities. CONCLUSIONS: The fatty acid components in C. odorata with NF-κB inhibitory activity could explain the anti-inflammation property of this plant in traditional medicine. This study could also contribute to the better use of C. odorata for human health care.