RESUMO
Seven new cucurbitane-type triterpenoids, kuguaovins A-G (1-7), and five known ones were isolated from the rattans of wild Momordica charantia. Their structures were established by spectroscopic data analyses, including 1D and 2D NMR, IR, and MS techniques. The absolute configurations of the cucurbitanes were determined from NOESY data and partially by X-ray crystallographic analysis. In pharmacological studies, compounds 1-7 and 9-12 exhibited weak anti-inflammatory effects (IC50 = 15-35 µM), based on an anti-NO production assay.
Assuntos
Anti-Inflamatórios não Esteroides/farmacologia , Glicosídeos/farmacologia , Momordica charantia/química , Extratos Vegetais/farmacologia , Triterpenos/farmacologia , Animais , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Camundongos , Estrutura Molecular , Óxido Nítrico/antagonistas & inibidores , Óxido Nítrico/biossíntese , Extratos Vegetais/química , Células RAW 264.7 , Espectrofotometria Infravermelho , Difração de Raios XRESUMO
Glaulactams A-C (1-3), which possess a novel skeleton, as well as the known compound daphmanidin B (4), were isolated from the leaves of Daphniphyllum glaucescens and separated using ion-exchange chromatography aided by NMR fingerprinting. Their structures, including their absolute configurations, were elucidated by spectroscopic analyses and time-dependent density-functional-theory-calculated electronic circular dichroism spectra; the data were subsequently analyzed to gain insight into the respective biogenetic relationships between the isolates, which exhibited anti-H1N1 and immunosuppressive activities.
Assuntos
Alcaloides/isolamento & purificação , Daphniphyllum/química , Alcaloides/química , Alcaloides/farmacologia , Alcaloides/uso terapêutico , Animais , Antivirais/química , Antivirais/isolamento & purificação , Antivirais/farmacologia , Antivirais/uso terapêutico , Cromatografia por Troca Iônica , Dicroísmo Circular , Citocinas/metabolismo , Células Dendríticas/efeitos dos fármacos , Cães , Avaliação Pré-Clínica de Medicamentos , Feminino , Vírus da Influenza A Subtipo H1N1/efeitos dos fármacos , Vírus da Influenza A Subtipo H1N1/fisiologia , Camundongos , Camundongos Endogâmicos C57BL , Estrutura Molecular , Óxido Nítrico/metabolismo , Ressonância Magnética Nuclear Biomolecular , Extratos Vegetais/química , Folhas de Planta/química , Replicação Viral/efeitos dos fármacosRESUMO
In an attempt to study the chemical constituents from the twigs and leaves of Flueggea virosa, a new terpenoid, 9(10â20)-abeo-ent-podocarpane, 3ß,10α-dihydroxy-12-methoxy-13- methyl-9(10â20)-abeo-ent-podocarpa-6,8,11,13-tetraene (1), as well as five known compounds were characterized. Their structures were elucidated on the basis of spectroscopic analysis. In addition, the structure of dehydrochebulic acid trimethyl ester was revised as (2S,3R)-4E-dehydrochebulic acid trimethyl ester based on a single-crystal X-ray diffraction study. The in vitro anti-hepatitis C virus (anti-HCV) activity and cytotoxicity against Huh7.5 cells for the isolated compounds were evaluated.
Assuntos
Antivirais , Benzopiranos , Euphorbiaceae/química , Hepacivirus , Hepatite C/tratamento farmacológico , Maleatos , Raízes de Plantas/química , Antivirais/química , Antivirais/isolamento & purificação , Antivirais/farmacologia , Benzopiranos/química , Benzopiranos/isolamento & purificação , Benzopiranos/farmacologia , Linhagem Celular , Hepatite C/metabolismo , Humanos , Maleatos/química , Maleatos/isolamento & purificação , Maleatos/farmacologiaRESUMO
Trapa natans L., called water chestnut or water caltrop, is a floating aquarium plant. Its fruits are widely used as food. Two new tannins, 1 and 2, one new neolignan, 14, one new norlignan, 17, and 20 known compounds, 3-13, 15, 16, and 18-24 were isolated from T. natans pericarps in this study. The 1, 2, 14, and 17 structures were elucidated using a chemical method and extensive spectral evidence. A series of hydrolyzable tannins, 1-8, a lignin, 13, a flavonoid, 16, a norlignan, 17, and phenolic compounds, 18, 20, 21, and 24 resulted in the enhanced glucose uptake activity in C2C12 myotubes. Compounds 4 and 5 significantly increased GLUT4 protein expression in C2C12 myotubes. In addition, 4 and 5 improved the phosphorylation of AMPK, AKT(S473), and AKT(T308). The involvement of AMPK and PI3K in the mechanism of action of compounds 4 and 5 was confirmed by use of AMPK and PI3K inhibitors, which completely suppressed the 4- and 5-mediated activities of glucose uptake in C2C12 myotubes. We also demonstrated that 4 and 5 could increase GLUT4 protein levels in plasma membranes.
Assuntos
Hipoglicemiantes , Lythraceae , Animais , Camundongos , Adenilato Quinase/metabolismo , Linhagem Celular , Cromatografia Líquida de Alta Pressão , Glucose/metabolismo , Hipoglicemiantes/uso terapêutico , Fosfatidilinositol 3-Quinases/metabolismo , Proteínas Proto-Oncogênicas c-akt/metabolismo , Análise Espectral/métodosRESUMO
Five new 5ß,19-epoxycucurbitane triterpenoids, taikugausins A-E (1-5), together with 5ß,19-epoxy-25-methoxycucurbita-6,23-diene-3ß,19-diol (6), have been isolated and characterized from the 70â% EtOH extract of the fresh fruits of Momordica charantia. The chemical structures of compounds 1-6 were elucidated on the basis of extensive spectroscopic analyses, especially 2D NMR (HMQC, HMBC, and NOESY) experiments and HRESIMS data. The relationship between NMR chemical shifts and the configuration of C-19 with an OMe group in 5ß,19-epoxycucurbitane are described. Among them, compounds 3 and 4 exhibited remarkable anti-inflammatory activities by the inhibition of nitric oxide production at the concentration of 10 µg/mL. In addition, 3 and 4 also showed moderate cytotoxicity against WiDr, Hep G2, MCF-7, and HEp-2 human tumor cell lines.
Assuntos
Anti-Inflamatórios não Esteroides/farmacologia , Momordica charantia/química , Animais , Anti-Inflamatórios não Esteroides/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Relação Dose-Resposta a Droga , Avaliação Pré-Clínica de Medicamentos , Células Hep G2/efeitos dos fármacos , Humanos , Macrófagos/efeitos dos fármacos , Espectroscopia de Ressonância Magnética , Camundongos , Estrutura Molecular , Óxido Nítrico/metabolismo , Saponinas/química , Saponinas/farmacologia , Triterpenos/química , Triterpenos/farmacologiaRESUMO
Two new steroidal saponins, named drangustosides A-B (1-2), together with eight known compounds were isolated and characterized from the MeOH extract of Dracaena angustifolia Roxb. The structures of compounds were assigned based on 1D and 2D NMR spectroscopic analyses, including HMQC, HMBC, and NOESY. Compounds 1 and 2 showed anti-inflammatory activity by superoxide generation and elastase release by human neutrophils in response to fMLP/CB.
Assuntos
Anti-Inflamatórios/farmacologia , Dracaena/química , Extratos Vegetais/farmacologia , Saponinas/química , Anti-Inflamatórios/química , Células Cultivadas , Humanos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Neutrófilos/efeitos dos fármacos , Elastase Pancreática/antagonistas & inibidores , Elastase Pancreática/química , Extratos Vegetais/química , Saponinas/farmacologia , Esteroides/química , Esteroides/farmacologia , Superóxidos/químicaRESUMO
This paper reports that bioassay-guided fractionations of EtOH extract of Momordica charantia fruits led to the isolation of 15 cucurbitane-type triterpene glycosides including 4 new compounds, kuguaosides A-D (1-4), along with 11 known ones, charantoside A (5), momordicosides I (6), F1 (7), F2 (8), K (9), L (10), and U (11), goyaglycosides-b (12) and -d (13), 7ß,25-dihydroxycucurbita-5,23(E)-dien-19-al 3-O-ß-d-allopyranoside (14), and 25-hydroxy-5ß,19-epoxycucurbita-6,23-dien-19-on-3ß-ol 3-O-ß-d-glucopyranoside (15). Their structures were elucidated on the basis of spectroscopic analyses and chemical methods. This study also established the HPLC-ELSD fingerprinting profile of an antiproliferative fraction of which 11 main peaks were identified. Biological evaluation showed that several isolated cucurbitane-type triterpene glycosides had antiproliferative activities against MCF-7, WiDr, HEp-2, and Doay human tumor cell lines. In addition, compound 14 showed potent hypoglycemic activities by glucose uptake assay.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Frutas/química , Glicosídeos/farmacologia , Hipoglicemiantes/farmacologia , Momordica charantia/química , Triterpenos/farmacologia , Animais , Linhagem Celular , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Cromatografia Líquida de Alta Pressão , Glicosídeos/química , Glicosídeos/isolamento & purificação , Humanos , Camundongos , Estrutura Molecular , Extratos Vegetais/química , Triterpenos/química , Triterpenos/isolamento & purificaçãoRESUMO
Seventeen compounds, quercetin-3-O-α-l-rhamnoside (1), kaempferol-3-O-α-L-rhamnoside (2), apigenin-7-O-ß-D-glucuronide (3), apigenin 7-O-ß-D-glucuronide methyl ester (4), apigenin 7-O-ß-D-glucuronide ethyl ester (5), chrysoeriol (6), apigenin (7), kaempferol (8), luteolin (9), quercetin (10), methyl 3,4-dihydroxybenzoate (11), p-coumaric acid (12), 4-hydroxybenzoic acid (13), hydroquinone (14), protocathehuic acid (15), gallic acid (16), and indole-3-carboxylic acid (17), were isolated from the ethanol extract of Taiwanese Cardiospermum halicabum. All chemical structures were determined by physical and extensive spectroscopic analyses such as (1) H Nuclear Magnetic Resonance spectroscopy (NMR), (13)C NMR, (1)H-(1)H Correlation spectroscopy ((1)H-(1)H COSY), Heteronuclear Multiple Quantum Coherence spectroscopy (HMQC), Heteronuclear Multiple-bond Correlation spectroscopy (HMBC), and Nuclear Overhauser Effect spectroscopy (NOESY), as well as comparison with literature values. Furthermore, the High-Performance Liquid Chromatography- Photodiode Array Detector (HPLC-DAD) fingerprint profile was established for the determination of major constituents in the EtOAc extract and retention times of the isolated compounds. All isolated compounds were also evaluated for antiinflammatory and antioxidant activities.
RESUMO
Seven new compounds including three flavanone glycosides, visartisides A-C (1-3), three glycoside acyl esters, visartisides D-F (4-6), and one diphenylpropane glycoside, (4'-hydroxy-2',3',6',3''-tetramethoxy-1,3-diphenylpropane)-4''-O-beta-d-glucopyranoside (7), along with four known flavanone glycosides (8-11) were isolated from the leaves and stems of Viscum articulatum. The structure elucidation of 1-7 was based on spectroscopic data analysis. Biological evaluation showed that 1, 2, and 10 exhibited antioxidant activity using a DPPH method and that compounds 1, 3, and 11 were active in a lipopolysaccharide-induced nitric oxide assay.