RESUMO
Two new baccharane triterpenes, 17,24-epoxy-23-en-baccharan-3-one (1) and 17,24(S)-epoxy-25-en-21-hydroxy-baccharan-3-one (2) were isolated from Rhus chinensis Mill. The structures were established on the basis of UV, IR, HR-ESI-MS, 1D and 2D NMR spectroscopy and X-ray diffraction analysis.
Assuntos
Rhus , Triterpenos , Triterpenos Pentacíclicos , Rhus/química , Triterpenos/farmacologia , Triterpenos/química , Extratos Vegetais , Espectroscopia de Ressonância Magnética , Estrutura MolecularRESUMO
One new sesquiterpene, (6S,7R,11S)-13-carboxy-1(10)-en-dihydroartemisinic acid (1), together with three known sesquiterpenes, ainsliaea acid B (2), mongolicumin B (3), and 11ß,13-dihydroxydeacetylmatricarin (4) were isolated from Taraxacum mongolicum Hand.-Mazz. The structures were established on the basis of UV, IR, HR-ESI-MS, 1D and 2D NMR spectroscopy, ECD spectroscopy, and X-ray diffraction analysis. Compound 1 was found to have potential anti-inflammatory activity and could reduce LPS-induced NO levels in murine macrophage, with inhibitory rate of 37%.
Assuntos
Asteraceae , Sesquiterpenos , Taraxacum , Animais , Camundongos , Taraxacum/química , Espectroscopia de Ressonância Magnética , Macrófagos , Sesquiterpenos/farmacologia , Sesquiterpenos/química , Estrutura MolecularRESUMO
Two new sesquiterpene dimers, lappadimers A and B, were isolated from the roots of Saussurea lappa (Yunmuxiang). Their structures were established on the basis of spectroscopic methods. They were found to have potential anti-inflammatory activity at 10 µM and could reduce LPS-induced NO levels in murine macrophage, with inhibitory rates of 67% and 47%, respectively.
Assuntos
Saussurea , Sesquiterpenos , Animais , Macrófagos , Camundongos , Estrutura Molecular , Extratos Vegetais/farmacologia , Raízes de Plantas/química , Saussurea/química , Sesquiterpenos/química , Sesquiterpenos/farmacologiaRESUMO
Fifteen new water-soluble alkaloids were obtained from the fresh herbs of Portulaca oleracea L. The structures of 15 alkaloids 1-15 were established according to spectroscopic data, and the stereoconfigurations were determined based on experimental and calculated electronic circular dichroism (ECD) data and single crystal X-ray diffraction. Alkaloids 1-15 were found to display good anti-inflammatory activity at 10 µM and could significantly reduce the interleukin-6 (IL-6) and nitric oxide (NO) levels induced by lipopolysaccharide (LPS) in RAW 264.7 macrophages.
Assuntos
Alcaloides/química , Anti-Inflamatórios/química , Portulaca/química , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Alcaloides/uso terapêutico , Animais , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/uso terapêutico , Cristalografia por Raios X , Edema/induzido quimicamente , Edema/tratamento farmacológico , Edema/patologia , Interleucina-6/metabolismo , Lipopolissacarídeos/farmacologia , Macrófagos/citologia , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Masculino , Camundongos , Conformação Molecular , Óxido Nítrico/metabolismo , Extratos Vegetais/química , Portulaca/metabolismo , Células RAW 264.7 , Solubilidade , Água/químicaRESUMO
Four new phenols and one new aminobenzoic acid derivative, with five known phenols were isolated from the roots of Rhus chinensis Mill. Their structures were elucidated by UV, IR, HRESIMS, 1D and 2D NMR spectra, as well as optical rotations. Compound 4 significantly inhibited mouse ear inflammation (inhibitory rate of 44.03%), and significantly extended the time of pain response (extension rate of 48.55%), showing significant anti-inflammatory and analgesic effects in vivo.
Assuntos
Analgésicos , Anti-Inflamatórios , Fenóis , Raízes de Plantas , Rhus , Animais , Raízes de Plantas/química , Camundongos , Estrutura Molecular , Fenóis/isolamento & purificação , Fenóis/farmacologia , Fenóis/química , Rhus/química , Analgésicos/farmacologia , Analgésicos/isolamento & purificação , Analgésicos/química , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/química , Masculino , Dor/tratamento farmacológico , Dor/induzido quimicamente , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Inflamação/tratamento farmacológico , ChinaRESUMO
Nine undescribed geranylgeranylated derivatives (chinensens A-G), including malic acid derivative (A) and phenolic derivatives (B-E), as well as two pairs of enantiomers, [(R), (S)]-chinensens F and [(R), (S)]-chinensens G, were isolated from the roots of Rhus chinensis Mill. Their structures were elucidated by UV, IR, HRESIMS, 1D and 2D NMR spectra, as well as optical rotations. The 95% EtOH extract (95% EXT, 500 mg/kg, p. o.) of the roots of Rhus chinensis and the 95% EtOH fraction (95% FRA, 500 mg/kg, p. o.) from the microporous resin column significantly alleviated indomethacin-induced or water immersion-restraint stress-induced damage in rat gastric mucosa with inhibitory rates from 53% to 89%. The racemic mixture (chinensen G) and its enantiomers [(R), (S)]-chinensens G showed weak activities against H+,K+-ATPase (20%-24%) at a concentration of 0.1 mM, respectively.
Assuntos
Compostos Fitoquímicos , Rhus , Animais , Ratos , Rhus/química , Raízes de Plantas/química , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Mucosa Gástrica/efeitos dos fármacos , Fenóis/química , Fenóis/isolamento & purificaçãoRESUMO
Four new compounds (1-4), together with 23 known compounds (5-27), were isolated from the whole plant of Taraxacum mongolicum. Among them, one racemic mixture (4) was separated with a chiral HPLC column. Their structures were identified by spectroscopic evidence and mass spectrometry. The absolute configurations of compounds 1, 3, and 4 were determined via comparison of their calculated and experimental electronic circular dichroism (ECD) spectra. Compound 3 showed an inhibitory effect against aldose reductase with a 59.1% inhibition. Two known compounds (13 and 27) showed α-glucosidase inhibition of 51.5% and 56.0%, respectively.
Assuntos
Alcaloides , Sesquiterpenos , Taraxacum , Taraxacum/química , Furaldeído , Estrutura Molecular , Fenóis/farmacologia , Alcaloides/farmacologia , Dicroísmo Circular , Sesquiterpenos/farmacologiaRESUMO
Eight previously undescribed compounds, two quinones (1-2), one sesquiterpene (3), and five phenol compounds (4-8), including three enantiomers (6a, 7a, and 8a), along with three corresponding known enantiomers (6b-8b) were isolated from the aerial parts of Morinda umbellata L. Their structures were elucidated by 1D and 2D NMR spectroscopy, X-ray diffraction, and experimental and calculated ECD spectra, respectively. Compound 5 was found to have weak cytotoxity, which inhibited the growth of seven human cancer cell lines (A2780, HeLa, MCF-7, BGC-823, H7420, Ketr3 and SW 1990) with IC50 values from 13.3 to 15.1 µM.
Assuntos
Citotoxinas/toxicidade , Morinda/química , Fenóis/toxicidade , Quinonas/toxicidade , Sesquiterpenos/toxicidade , Linhagem Celular Tumoral , Cromatografia Líquida de Alta Pressão , Cristalografia por Raios X , Citotoxinas/isolamento & purificação , Humanos , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Fenóis/isolamento & purificação , Componentes Aéreos da Planta/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/toxicidade , Quinonas/isolamento & purificação , Sesquiterpenos/isolamento & purificaçãoRESUMO
Ten previously undescribed compounds, including two benzobicyclic ketones, one cycloheptenone oxide derivative, three guaiane-type sesquiterpenes, and four alkaloids, along with one known cycloheptenone oxide derivative, were isolated from the whole plants of Taraxacum mongolicum Hand.-Mazz. Their structures were elucidated by UV, IR, HR-ESI-MS, 1D and 2D NMR spectroscopy, ECD spectroscopy, or X-ray diffraction analysis. Notably, benzobicyclic ketones have never been isolated from nature before. The 70% EtOH-H2O extract of T. mongolicum displayed a significant inhibitory activity (33%) against croton oil-induced mouse ear edema. The two cycloheptenone oxide derivatives exhibited anti-inflammatory activities at 10 µM and significantly reduced the nitric oxide (NO) and interleukin-6 (IL-6) levels in RAW 264.7 macrophages induced by lipopolysaccharide (LPS), with inhibitory rates of 26.4-64.4%.
Assuntos
Alcaloides , Sesquiterpenos , Taraxacum , Alcaloides/farmacologia , Animais , Cetonas/farmacologia , Camundongos , Estrutura Molecular , Óxido Nítrico , Óxidos , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Sesquiterpenos de Guaiano/farmacologiaRESUMO
Four undescribed racemic quinones, umbellatas Q-T, were isolated from the aerial parts of Morinda umbellata L. All enantiomers were separated on a chiral HPLC column, and their structures were elucidated by UV spectroscopy, IR spectroscopy, HR-ESI-MS, 1D and 2D NMR spectroscopy, DP4+ NMR calculations, ECD spectroscopy, and X-ray diffraction. Three of the racemes are polycyclic anthraquinones, and one is a rare racemic trimer of naphthoquinone-bisnaphthohydroquinones. (+)-Umbellata S exhibited potent cytotoxicity (IC50: 6.2-9.3 µM) against the A2780, HeLa, H7420, Ketr3 and SW 1990 human cancer cell lines.