RESUMO
Two new triterpene fatty acid esters, 3ß-palmityloxy-12,27-cyclofriedoolean-14-en-11α-ol (1) and 3ß-palmityloxy-19α-hydroxyursane (2), together with 3ß-hydroxy-11-oxo-olean-12-enyl palmitate (3) were isolated from the potent anti-inflammatory active fraction of the petroleum ether-soluble part of Cirsium setosum ethanol extract. Compound 1 was found to be a rare 12,27-cyclopropane triterpenoid. Their structures were determined through spectral data analysis combined with literature reports. Furthermore, in vitro experiment, compounds 1-3 exhibited significant inhibitory effects on nitric oxide production in lipopolysaccharide-activated mouse RAW264.7 macrophages.
Assuntos
Anti-Inflamatórios , Cirsium , Ésteres , Lipopolissacarídeos , Óxido Nítrico , Triterpenos , Animais , Camundongos , Cirsium/química , Triterpenos/farmacologia , Triterpenos/química , Triterpenos/isolamento & purificação , Estrutura Molecular , Óxido Nítrico/biossíntese , Óxido Nítrico/antagonistas & inibidores , Células RAW 264.7 , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/química , Lipopolissacarídeos/farmacologia , Ésteres/farmacologia , Ésteres/química , Macrófagos/efeitos dos fármacosRESUMO
Five unusual seco-nortriterpenoids, 3ß-hydroxy-20,21-seco-30-nortaraxastan-20,21-dioic acid (1), 3ß-hydroxy-20,21-seco-30-nortaraxastan-20-oic-21-oate (2), 3ß-hydroxy-20-oxo-21,22-seco-30-nortaraxastan-22-oic acid (3), 3ß-hydroxy-19-oxo-20,21-seco-29,30-nortaraxastan-21-oic acid (4) and 3ß-hydroxy-19-oxo-20,21-seco-19-norlupan-21-oic acid (5) were isolated and elucidated from the anti-inflammatory activity fraction of the ethanol extract of Cirsium setosum. The structures of these compounds were established through spectroscopic methods. Preliminary biological assays showed that compounds 1-5 had significant inhibitory effect on NO production on lipopolysaccharide-stimulated RAW 264.7 cells, and compound 1 showed the strongest anti-inflammatory activity. This type of ring-opening compound is the first seco-triterpenoid structure discovered from the genus of Cirsium.
Assuntos
Anti-Inflamatórios , Cirsium , Óxido Nítrico , Compostos Fitoquímicos , Triterpenos , Células RAW 264.7 , Animais , Camundongos , Cirsium/química , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/isolamento & purificação , Estrutura Molecular , Triterpenos/farmacologia , Triterpenos/isolamento & purificação , Triterpenos/química , Óxido Nítrico/metabolismo , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/isolamento & purificação , Extratos Vegetais/farmacologia , Extratos Vegetais/químicaRESUMO
Two unusual novel iridoid glycosides, cornsecoside A (1) and cornsecoside B (2), were isolated from a 40% ethanol elution fraction of a 50% ethanol extract of Cornus officinalis fruit. Their structures were determined by spectroscopic data analysis combined with hydrolysis and ECD spectroscopy. In addition, compounds 1 and 2 exhibited cytotoxic activity against Bel-7402 cells with IC50 values of 8.12 and 9.31 µM, and were neuroprotective against H2O2-induced SH-SY5Y cell injure at a concentration of 10 µM.
Assuntos
Cornus , Neuroblastoma , Humanos , Glicosídeos Iridoides/farmacologia , Glicosídeos Iridoides/química , Cornus/química , Frutas/química , Peróxido de Hidrogênio/farmacologia , Peróxido de Hidrogênio/análise , Etanol/análise , Glicosídeos/farmacologia , Glicosídeos/químicaRESUMO
Three new ursane-type triterpenoids, 3-oxours-12-en-20, 28-olide (1), 3ß-hydroxyurs-12-en-20, 28-olide (2) and 3ß-hydroxyurs-11, 13(18)-dien-20, 28-olide (3), were isolated from a potent anti-inflammatory and antibacterial fraction of the ethanolic extract of Rosmarinus officinalis. Their structures were elucidated by a combination of extensive 1D- and 2D-NMR experiments, MS data and comparisons with literature reports. Compounds 1-3 exhibited significantly inhibitory effects on nitric oxide production in lipopolysaccharide-activated mouse RAW264.7 macrophages, but no antibacterial activity was found at a concentration of 128 µg·mL-1.
Assuntos
Medicamentos de Ervas Chinesas , Rosmarinus , Triterpenos , Animais , Medicamentos de Ervas Chinesas/química , Camundongos , Estrutura Molecular , Triterpenos/químicaRESUMO
Two new dimeric and trimeric sesquiterpene lactones (1-2), and nine known sesquiterpene lactones (3-11) were isolated from the EtOAc phase of the ethanolic extract of Ainsliaea yunnanensis. Their structures were identified by NMR, IR and HR-ESIMS spectroscopic methods, and compound 1 was confirmed by single crystal X-ray diffraction experiment. All the compounds were tested for their cytotoxic, anti-microbial and anti-inflammatory activities. Compounds 1, 2, 3, 5, 7, 9 and 11 showed very significant selective cytotoxic activities on MDA-MB-468, PANC-1, HEPG2 or A549 cells. Compounds 6 and 11 showed very significant inhibiting effect on Epicoccum sp. (CPCC 400307), Fusarium solani (CPCC 800013) or Bacillus subtilis. Meanwhile, compounds 6 and 7 can inhibit the NLRP3 inflammasome's activation at the concentration of 10 µM.
Assuntos
Asteraceae , Sesquiterpenos , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Asteraceae/química , Inflamassomos , Lactonas/química , Estrutura Molecular , Proteína 3 que Contém Domínio de Pirina da Família NLR , Compostos Fitoquímicos , Extratos Vegetais/química , Sesquiterpenos/químicaRESUMO
Five new secoiridoid glycosides, cornusphenosides E-I (1-5), were isolated and characterized from an active fraction of ethanol extract of the fruits of Cornus officinalis. Their structures were determined by extensive spectroscopic data analysis, including 2 D NMR and HRESIMS experiments. In the preliminary assay, compound 5 (when evaluated at 10 µM) showed the neuroprotective effect against H2O2-induced SH-SY5Y cell damage.
Assuntos
Cornus , Fármacos Neuroprotetores , Cornus/química , Frutas/química , Glicosídeos/química , Peróxido de Hidrogênio , Glicosídeos Iridoides/análise , Glicosídeos Iridoides/farmacologia , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/farmacologiaRESUMO
Five norursane-type triterpenoids, including three novel of 3ß-28-norursa-12,17,19,21-tetraene-3-ol (1), 3ß-28-norursa-12,20(30)-dien-3-ol (2) and 3ß-28-norursa-12,16,20(30)-triene-3-ol (3), as well as two known 3ß-28-norursa-17,19,21-trien-3-ol (4) and 3ß-28-norursa-12-ene-3-ol (5) were isolated from the ethyl acetate dissolved fraction of the ethanol extract from Rosmarinus officinalis. Their structures were elucidated by HR-ESI-MS, IR, 1D- and 2D-NMR spectroscopic methods. Compounds 1-5 exhibited significant inhibitory effect on NO production in LPS-activated RAW264.7 cells, and compounds 2, 3 and 5 shown better anti-inflammatory activity.
Assuntos
Anti-Inflamatórios/farmacologia , Rosmarinus/química , Triterpenos/farmacologia , Animais , Anti-Inflamatórios/isolamento & purificação , China , Camundongos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Componentes Aéreos da Planta/química , Células RAW 264.7 , Triterpenos/isolamento & purificaçãoRESUMO
Searching for PD-1/PD-L1 inhibitor from medicinal plants has become a potential method to discover small molecular cancer immunotherapy drugs. Using PD-1/PD-L1 inhibitory activity assay in vitro, a bioactive fraction was obtained from the ethanol extract of Gymnadenia conopsea. A sensitive UPLC-HRMS/MS method was established for the rapid screening and identification of compositions from bioactive fraction. Based on the characteristic fragmentation patterns of standards analysis and extracted ion chromatogram (EIC) method, 46 compounds were rapidly screened and identified (including 35 succinic acid ester glycosides and 11 other compounds), among which 17 compounds were tentatively identified as new compounds.
Assuntos
Etanol , Receptor de Morte Celular Programada 1 , Antígeno B7-H1 , Cromatografia Líquida de Alta Pressão , Estrutura MolecularRESUMO
Gymnadenia conopsea R. Br. is a traditional Tibetan medicinal plant that grows at altitudes above 3000 m, which is used to treat neurasthenia, asthma, coughs, and chronic hepatitis. However, a comprehensive configuration of the chemical profile of this plant has not been reported because of the complexity of its chemical constituents. In this study, a rapid and precise method based on ultra-high performance liquid chromatography (UPLC) combined with an Orbitrap mass spectrometer (UPLC-Orbitrap-MS/MS) was established in both positive- and negative-ion modes to rapidly identify various chemical components in the tubers of G. conopsea for the first time. Finally, a total of 91 compounds, including 17 succinic acid ester glycosides, 9 stilbenes, 6 phenanthrenes, 19 alkaloids, 11 terpenoids and steroids, 20 phenolic acid derivatives, and 9 others, were identified in the tubers of G. conopsea based on the accurate mass within 3 ppm error. Furthermore, many alkaloids, phenolic acid derivates, and terpenes were reported from G. conopsea for the first time. This rapid method provides an important scientific basis for further study on the cultivation, clinical application, and functional food of G. conopsea.
Assuntos
Orchidaceae/química , Tubérculos/química , Espectrometria de Massas em Tandem/métodos , Cromatografia Líquida de Alta Pressão , Ésteres/química , Glicosídeos/química , Compostos Fitoquímicos/análise , Extratos Vegetais/química , Ácido Succínico/químicaRESUMO
Using a cell-based cytotoxicity assay, two new polyhydroxylated sterols, 16(S),22(S)-epoxy-3ß,5α,6ß,20(R),23(R),25-hexahydroxy-7-ergostene and 3ß,7ß,8α,25-tetrahydroxy-5,22E-ergostadiene were isolated from the ethyl acetate portion of the ethanolic extract of Monascus purpureus. Their structures were elucidated by spectroscopic analysis and in comparison with those reported in the literature. Both compounds showed cytotoxic activity against the lung adenocarcinoma (A549) with IC50 values of 12.6 and 18.5 µM, exhibited moderate activities against human ovarian cancer (A2780), with IC50 values of 8.8 and 9.4 µM.
Assuntos
Antineoplásicos/farmacologia , Fermentação , Monascus/química , Oryza/metabolismo , Esteróis/farmacologia , Células A549 , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Hidroxilação , Conformação Molecular , Monascus/metabolismo , Esteróis/química , Esteróis/isolamento & purificação , Relação Estrutura-Atividade , Células Tumorais CultivadasRESUMO
Guided by TNF-α secretion inhibitory activity assay, four taraxastane-type triterpenoids, including two new ones, 22-oxo-20-taraxasten-3ß, 30-diol (1) and 22α-hydroxy-20-taraxasten-30ß, 30-triol (2), have been obtained from an active fraction of the petroleum ether-soluble extract of the the medicinal and edible plant Cirsium setosum. Their structures were elucidated by spectroscopic data and CD data analysis. In the TNF-α secretion inhibitory activity assay, compounds 1 and 2 were active with the IC50 of 2.6 and 3.8 µmol·L-1, respectively. In addition, compounds 1 and 2 showed moderately selective cytotoxicity against the human ovarian cancer (A2780) and colon cancer (HCT-8) cell lines.
Assuntos
Cirsium/química , Plantas Comestíveis/química , Plantas Medicinais/química , Triterpenos/química , Animais , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Éter/química , Humanos , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Camundongos , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Triterpenos/isolamento & purificação , Triterpenos/farmacologia , Fator de Necrose Tumoral alfa/metabolismoRESUMO
Three previously undescribed iridoids, cornusfurals Aâ»C, were isolated from the ethanolic extracts of fruits of Cornus officinalis. Their structures were elucidated by spectroscopic methods, including one-dimensional and two-dimensional nuclear magnetic resonance, ultraviolet spectroscopy, infrared spectroscopy, and mass spectrometry. The neuroprotective activity was evaluated by measuring corticosterone-induced damage in PC12 cells. The results showed that cornusfural B decreased corticosterone-induced PC12 cell damage compared with that in model cells.
Assuntos
Cornus/química , Corticosterona/efeitos adversos , Iridoides/isolamento & purificação , Iridoides/farmacologia , Neurônios/citologia , Animais , Etanol/química , Etanol/isolamento & purificação , Frutas/química , Iridoides/química , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular , Neurônios/efeitos dos fármacos , Neuroproteção , Células PC12 , Extratos Vegetais/química , Ratos , Espectrofotometria InfravermelhoRESUMO
Four new iridoid glycosides named cornusphenosides A-D (1-4) were isolated from an ethanol extract of the fruits of Cornus officinalis (shan zhu yu). The structures of these compounds were elucidated on the basis of spectroscopic data (UV, IR, HRESIMS, and 1D and 2D NMR) and chemical evidence. The neuroprotective effects of compounds 1-4 were also assessed in vitro.
Assuntos
Cornus/química , Glicosídeos Iridoides/isolamento & purificação , Frutas/química , Humanos , Glicosídeos Iridoides/química , Glicosídeos Iridoides/farmacologia , Espectroscopia de Ressonância Magnética , Fármacos Neuroprotetores/farmacologia , Extratos Vegetais/análiseRESUMO
A new sesquiterpenoid ester glycoside (1) and a new monoterpenoid ester glycoside (2) have been isolated from an ethanol extract of the twigs of Litsea cubeba. Their structures were elucidated by extensive 1D- and 2D-NMR experiments, and the absolute configurations were determined by chemical methods, specific rotation, and a combination of experimental and theoretically calculated electronic circular dichroism spectra. Compound 1 exhibited selective cytotoxicity against A549 and HCT-8 cell lines with the IC50 values of 8.9 and 9.6 µM, respectively.
Assuntos
Glicosídeos/química , Litsea/química , Terpenos/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Humanos , Estrutura MolecularRESUMO
Four new monacolin analogs, monacolin T (1), monacolin U (2) 6a-O-methyl-4,6-dihydromonacolin L (3), and 6a-O-ethyl-4,6-dihydromonacolin L (4) were isolated from the ethanolic extract of Monascus purpureus-fermented rice. Their structures were determined by a combination of 1D, 2D NMR experiments (1H-1HCOSY, HSQC, HMBC, and ROESY), and mass spectrometry. In vitro cytotoxic assay, all compounds were inactive at the concentration of 10 µM.
Assuntos
Monascus/química , Naftalenos/isolamento & purificação , Oryza/microbiologia , Ensaios de Seleção de Medicamentos Antitumorais , Fermentação , Estrutura Molecular , Naftalenos/químicaRESUMO
A new oxacyclododecindione-type macrolactone, (13R,14S,15R)-13-hydroxy-14-deoxyoxacyclododecindione (1), has been obtained from the solid cultures of the fungus Exserohilum rostratum, a fungal strain endophytic in Gymnadenia conopsea. Its structure, including the absolute configuration, was extensively established by 1D and 2D NMR data, the modified Mosher method, and a combination of experimental and theoretically calculated electronic circular dichroism (ECD) spectra. Compound 1 showed weak selective cytotoxicity against the A549 lung cell line with an IC50 value of 9.2 µM.
Assuntos
Ascomicetos/química , Endófitos/fisiologia , Lactonas/farmacologia , Orchidaceae/microbiologia , Células A549 , Antineoplásicos/química , Antineoplásicos/farmacologia , Ascomicetos/fisiologia , Sobrevivência Celular/efeitos dos fármacos , Humanos , Lactonas/química , Estrutura MolecularRESUMO
Four new taraxastane-type triterpenoids acids 3ß,22α-dihydroxy-20-taraxasten-30-oic acid (1), 3ß-hydroxy-22-oxo-20-taraxasten-30-oic acid (2), 3-oxo-22α-hydroxy-20- taraxasten-30-oic acid (3), and 3ß,19ß-dihydroxy-20-taraxasten-30-oic acid (4) were isolated and characterized from Cirsium setosum (Willd.) MB. Their structures were determined by the combination of 1D and 2D NMR experiments ((1)H-(1)HCOSY, HSQC, HMBC and ROESY) and mass spectrometry. Compound 2 exhibited potent selective cytotoxicity against human ovarian cancer cell line A2780 with an IC50 value of 3.9 µM.
Assuntos
Cirsium/química , Triterpenos/isolamento & purificação , Medicamentos de Ervas Chinesas/química , Humanos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Triterpenos/química , Triterpenos/farmacologiaRESUMO
AIM: To investigate the protective effect of glutamine (Gln) on intestinal injury and the bacterial community in rats exposed to hypobaric hypoxia environment. METHODS: Sprague-Dawley rats were divided into control, hypobaric hypoxia (HH), and hypobaric hypoxia + Gln (5.0 g/kg BW·d) (HG) groups. On the first 3 d, all rats were placed in a normal environment. After the third day, the HH and HG groups were transferred into a hypobaric chamber at a simulated elevation of 7000 m for 5 d. The rats in the HG group were given Gln by gavage daily for 8 d. The rats in the control and HH groups were treated with the same volume of saline. The intestinal morphology, serum levels of malondialdehyde (MDA), superoxide dismutase (SOD), interleukin-6 (IL-6), tumor necrosis factor-α (TNF-α), interferon-gamma (IFN-γ) and diamino oxidase (DAO) were examined. We also evaluated the expression levels of occludin, toll-like receptor 4 (TLR4), nuclear factor-κB p65 (NF-κB p65) and myeloid differentiation factor 88 (MyD88), and examined the bacterial community in caecal contents. RESULTS: Hypobaric hypoxia induced the enlargement of the heart, liver, lung and kidney, and caused spleen atrophy. Intestinal villi damage was also observed in the HH group. Supplementation with Gln significantly alleviated hypobaric-induced damage to main organs including the intestine, increased serum SOD (1.14 ± 0.03 vs 0.88 ± 0.04, P < 0.05) and MDA (8.35 ± 1.60, P < 0.01) levels and decreased serum IL-6 (1172.13±30.49 vs 1407.05 ± 34.36, P < 0.05), TNF-α (77.46 ± 0.78 vs 123.70 ± 3.03, P < 0.001), IFN-γ (1355.42 ± 72.80 vs 1830.16 ± 42.07, P < 0.01) and DAO (629.30 ± 9.15 vs 524.10 ± 13.34, P < 0.001) levels. Moreover, Gln significantly increased occludin (0.72 ± 0.05 vs 0.09 ± 0.01, P < 0.001), TLR4 (0.15 ± 0.05 vs 0.30 ±0.09, P < 0.05), MyD88 (0.32 ± 0.08 vs 0.71 ± 0.06, P < 0.01), and NF-κB p65 (0.16 ± 0.04 vs 0.44 ± 0.03, P < 0.01) expression levels and improved the intestinal bacterial community. CONCLUSION: Gln treatment protects from intestinal injury and regulates the gut flora imbalance in hypoxia environment. These effects may be related to the TLR4/MyD88/NF-κB signaling pathway.
Assuntos
Bactérias/efeitos dos fármacos , Glutamina/farmacologia , Hipóxia/tratamento farmacológico , Intestinos/efeitos dos fármacos , Animais , Bactérias/classificação , Bactérias/crescimento & desenvolvimento , Citocinas/sangue , Citoproteção , Modelos Animais de Doenças , Hipóxia/imunologia , Hipóxia/metabolismo , Hipóxia/microbiologia , Hipóxia/patologia , Mediadores da Inflamação/sangue , Mucosa Intestinal/metabolismo , Intestinos/imunologia , Intestinos/microbiologia , Intestinos/patologia , Masculino , Malondialdeído/sangue , Fator 88 de Diferenciação Mieloide/metabolismo , Ratos Sprague-Dawley , Transdução de Sinais/efeitos dos fármacos , Superóxido Dismutase/sangue , Fatores de Tempo , Receptor 4 Toll-Like/metabolismo , Fator de Transcrição RelA/metabolismoRESUMO
OBJECTIVE: To analyze the chemical constituents of low polar components from ethanol extract of Ainsliaea yunnanensis. METHODS: The air-dried stems and leaves of Ainsliaea yunnanensis were extracted with ethanol using ultrasonic extration. After removal of solvent under reduced pressure, the residue was suspended in H2O, and then partitioned sequentially with petroleum ether, EtOAc and n-BuOH, respectively. Then the petroleum ether fraction was chromatographed on normal phase silica gels eluting with a gradient increasing Me2 CO in petroleum ether. Then the components of low polarity were separated from the petroleum ether-Me2CO(50:1 - 20: 1) fraction and identified by GC-MS, and the relative contents of the components were determined with area percentage method. RESULTS: 50 constituents were identified from the low polar components of Ainsliaea yunnanensis. CONCLUSION: The research provides a theoretical basis for the study of chemical constituents and pharmaceutical activities of Ainsliaea yunnanensis.
Assuntos
Antioxidantes/análise , Asteraceae/química , Cromatografia Gasosa-Espectrometria de Massas/métodos , Terpenos/análise , Anti-Inflamatórios não Esteroides/análise , Anti-Inflamatórios não Esteroides/isolamento & purificação , Antioxidantes/isolamento & purificação , Estrutura Molecular , Folhas de Planta/química , Caules de Planta/química , Solventes/química , Terpenos/isolamento & purificaçãoRESUMO
Two new monacolin analogs, monacolins O (1) and P (2), along with three known analogs, have been isolated from the ethanolic extract of Monascus purpureus-fermented rice. Their structures and absolute configurations were elucidated by spectroscopic methods, especially 2D NMR and CD spectral analyses as well as chemical method. Both 1 and 2 were tested against five tumor cell lines, and compound 1 exhibited selective cytotoxic activity against A2780 and A549 cell lines, with IC50 values of 3.7 and 8.0 µM, respectively.