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1.
J Pharm Pharmacol ; 72(7): 969-978, 2020 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-32246778

RESUMO

OBJECTIVES: To screen the cytotoxic activity of six secondary metabolites isolated from soil fungus Aspergillus niger. Importantly, to investigate the mechanism that pyoluteorin induced human triple-negative breast cancer MDA-MB-231 cells apoptosis in vitro. METHODS: The cell viability assay was tested with CTG assay. Cell cycle, apoptosis and intracellular reactive oxygen species (ROS) production assay were tested with flow cytometry. Additionally, intracellular ROS production assay and mitochondrial membrane potential assay were determined with laser scanning confocal microscopy. The expression of apoptosis-related proteins was determined with Western blot. KEY FINDINGS: Pyoluteorin displayed significantly selective cytotoxicity against human triple-negative breast cancer MDA-MB-231 cells (IC50  = 0.97 µm) with low toxicity against human breast epithelial cell MCF-10A. It was found that pyoluteorin could arrest MDA-MB-231 cells cycle at G2 /M phase and induce cell apoptosis. Further experiments demonstrated that the apoptosis-inducing effect of pyoluteorin was related to reduction of mitochondrial membrane potential, accumulation of ROS and change of apoptosis-related protein expressions. CONCLUSION: Our studies revealed that pyoluteorin had potent proliferation inhibition against MDA-MB-231 cells through arresting cell cycle at G2 /M phase and inducing caspase-3-dependent apoptosis by mitochondrial pathway, implying that pyoluteorin may be a potential lead compound for drug discovery of human triple-negative breast cancer.

2.
Fitoterapia ; 144: 104596, 2020 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-32333960

RESUMO

Seven oleanane-type triterpenoid saponins, tunicosaponins B-D (1-3), F-I (4-7), along with eight known triterpenoid saponins (8-15), were isolated from the roots of Psammosilene tunicoides. The structures of compounds 1-7 were determined by comprehensive spectroscopic analysis, including 1D and 2D NMR techniques, mass spectrometry and chemical methods. Triterpene glycosides have been considered as major active constituents of P. tunicoides. This work provides a more complete insight into the saponin constituents of P. tunicoides.

3.
Fitoterapia ; 142: 104530, 2020 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-32114035

RESUMO

A new azo compound, penoxalin (1), a new isochroman carboxylic acid, penisochroman B (3), two new natural products, penisochroman A (2) and 2,6-dihydroxy-4-[(2R)-2-hydroxyheptyl] benzoic acid (4), together with four known compounds (5-8) were isolated from wetland soil fungus Penicillium oxalicum GY1. All structures were elucidated by extensive NMR spectroscopic evidences together with mass spectrometry. The absolute configuration of penoxalin (1) was determined by calculated ECD spectrum, while the absolute configuration of new natural product penisochroman A (2) was established for the first time by single crystal X-ray diffraction. In addition, all compounds were evaluated for their cytotoxic activity in vitro. 2, 6-Dihydroxy-4-[(2R)-2-hydroxyheptyl] benzoic acid (4) displayed significant cytotoxicity against human esophageal carcinoma cells OE19 with an IC50 value of 5.50 µM.

4.
Nat Prod Bioprospect ; 10(1): 13-21, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31786736

RESUMO

Eight new triterpenoids were isolated from Ainsliaea latifolia. The structures of these compounds were elucidated by interpretation of spectroscopic data, including HRESIMS and NMR data. Compounds 4-6 are identified as rare trinorcucurbitane or tetranorcucurbitane triterpenoids. The absolute configurations of compounds 1 and 2 were confirmed by Snatzke's method. All compounds were evaluated for their inhibition against cyclooxyenase-2 (COX-2), in which compound 4 showed significant inhibitory effect against COX-2 with IC50 value of 3.98 ± 0.32 µM, comparable to that of positive control NS-398 (IC50 4.14 ± 0.28 µM).

5.
Nat Prod Res ; 33(2): 274-279, 2019 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-29540070

RESUMO

Three new sesquiterpenes: 4-acrylic-6-methyl-α-tetralone (1), ainsliaea acid A (2) and ainsliaea acid B (3), together with 8 known compounds (4-11) were isolated from the whole herb of Ainsliaea glabra and their structures were established by means of 1D and 2D NMR spectroscopy and HR-ESIMS. Compounds 1-6 were tested for the inhibition of nuclear factor kappa B (NF-κB) in the 293-NF-κB-luciferase reporter cell line induced by lipopolysaccharide (LPS), and compound 2 was further tested for the production of tumor necrosis factor-α (TNF-α), interleukin-1ß (IL-1ß), IL-6 and IL-10 in RAW264.7 macrophages induced by LPS. The isolated compound 2 exhibited significant anti-inflammatory activity.


Assuntos
Anti-Inflamatórios/isolamento & purificação , Asteraceae/química , Sesquiterpenos/isolamento & purificação , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Citocinas/efeitos dos fármacos , Lipopolissacarídeos/farmacologia , Macrófagos/metabolismo , Camundongos , Estrutura Molecular , NF-kappa B/antagonistas & inibidores , Extratos Vegetais/química , Células RAW 264.7 , Sesquiterpenos/química , Sesquiterpenos/farmacologia
6.
Org Lett ; 20(23): 7567-7570, 2018 12 07.
Artigo em Inglês | MEDLINE | ID: mdl-30421929

RESUMO

Vlasoulamine A (1), an unprecedented sesquiterpene lactone dimer featuring a fully hydrogenated pyrrolo[2,1,5- cd]indolizine core, and vlasoulones A and B (2 and 3), a pair of epimeric dimers formed from a proposed Diels-Alder [4 + 2] cycloaddition between a germacrane sesquiterpene lactone and a eudesmane sesquiterpene, were isolated from the roots of Vladimiria souliei. Their structures and absolute configurations were established by NMR, MS, and single-crystal X-ray spectroscopic analysis. Moreover, 1 exhibited neuroprotective activity when evaluated for glutamate-induced cytotoxicity, nuclear Hoechst 33258 staining, and measuring intracellular reactive oxygen species levels, using a rat pheochromocytoma PC12 cell-based model system.


Assuntos
Antineoplásicos/farmacologia , Asteraceae/química , Lactonas/farmacologia , Fármacos Neuroprotetores/farmacologia , Raízes de Plantas/química , Sesquiterpenos/farmacologia , Animais , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Apoptose/efeitos dos fármacos , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Cristalografia por Raios X , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Ácido Glutâmico/farmacologia , Lactonas/química , Lactonas/isolamento & purificação , Modelos Moleculares , Estrutura Molecular , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/isolamento & purificação , Células PC12 , Ratos , Espécies Reativas de Oxigênio/análise , Espécies Reativas de Oxigênio/metabolismo , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Relação Estrutura-Atividade
7.
Biochem Biophys Res Commun ; 502(2): 202-208, 2018 07 12.
Artigo em Inglês | MEDLINE | ID: mdl-29792864

RESUMO

Delavatine A, an unusual isoquinoline alkaloid isolated from I. delavayi, was first studied for anti-inflammatory effect using lipopolysaccharide (LPS)-induced BV-2 microglia. In the present study, we found that delavatine A substantially suppressed the LPS-induced pro-inflammatory mediators, nitric oxide (NO), and tumor necrosis factor-a (TNF-a), interleukin-6 (IL-6), interleukin-1ß (IL-1ß) in BV-2 microglial cells. These effects resulted from the inhibition of their regulatory genes inducible NO synthase (iNOS), cycloxygenase-2 (COX-2) and TNF-a, IL-6, IL-1ß. In addition, we examined several pathways related to inflammation. The results revealed that delavatine A significantly decreased LPS-induced the activation of nuclear factor-κB (NF-κB) by suppressing the p65 subunits, and the phosphorylation of IκBα, while not related to PI3K/Akt or MAPK pathways.


Assuntos
Citocinas/biossíntese , Isoquinolinas/farmacologia , Microglia/efeitos dos fármacos , NF-kappa B/metabolismo , Alcaloides/farmacologia , Animais , Anti-Inflamatórios não Esteroides/farmacologia , Linhagem Celular , Ciclo-Oxigenase 2/metabolismo , Inibidores de Ciclo-Oxigenase 2/farmacologia , Citocinas/genética , Mediadores da Inflamação/metabolismo , Lipopolissacarídeos/toxicidade , Camundongos , Microglia/metabolismo , Óxido Nítrico/biossíntese , Óxido Nítrico Sintase Tipo II/antagonistas & inibidores , Óxido Nítrico Sintase Tipo II/metabolismo , Transdução de Sinais/efeitos dos fármacos
8.
J Am Chem Soc ; 140(12): 4227-4231, 2018 03 28.
Artigo em Inglês | MEDLINE | ID: mdl-29494142

RESUMO

Hybridaphniphylline B (1) is a Daphniphyllum alkaloid possessing 11 rings and 19 stereocenters. Here we report the first total synthesis of 1 featuring a late-stage intermolecular Diels-Alder reaction of a fully elaborated cyclopentadiene and asperuloside tetraacetate. The diene was prepared on the basis of a scalable route to daphnilongeranin B (4). Claisen rearrangement of an allyl dienol ether was exploited as a key step; the subtle variation of the substrate and use of protic solvents suppressed the undesired Cope rearrangement. Daphniyunnine E (6) and dehydrodaphnilongeranin B (7), two congeners of 4, were also synthesized. The dienophile arose from (+)-genipin through glycosylation and lactonization. A one-pot protocol was developed for the diene formation and Diels-Alder reaction; one of the cycloadducts was converted into 1 through reductive desulfurization and global deacetylation.

9.
Zhongguo Zhong Yao Za Zhi ; 43(1): 100-108, 2018 Jan.
Artigo em Chinês | MEDLINE | ID: mdl-29552818

RESUMO

Application of a combination of various chromatographic techniques including column chromatography over silica gel, Sephadex LH-20, macroporous adsorbent resin, and reversed-phase HPLC, led to the isolation of 173 compounds including irdidoids, monoterpenes, sesquiterpenes, triterpenes, lignans, flavonoids, and simple aromatic derivatives from the ethyl acetate-soluble fraction of the whole plants of Valeriana jatamansi(Valerianaceae), and their structures were elucidated by spectroscopic methods including 1D, 2D NMR UV, IR, and MS techniques. Among them, 77 compounds were new. In previous reports, we have described the isolation, structure elucidation, and bioactivities of 68 new and 25 known compounds. As a consequence, we herein reported the isolation and structure elucidation of the remaining 9 new and 71 known compounds, the structure revision of valeriotriate A(8a), as well as cytotoxicity of some compounds.


Assuntos
Extratos Vegetais/química , Valeriana/química , Acetatos , Cromatografia Líquida de Alta Pressão , Flavonoides/análise , Iridoides/análise , Lignanas/análise , Estrutura Molecular , Monoterpenos/análise , Compostos Fitoquímicos/análise , Sesquiterpenos/análise , Triterpenos/análise
10.
Phytochemistry ; 139: 47-55, 2017 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-28411482

RESUMO

Six previously undescribed C17-guaianolides, a previously undescribed guaianolide alkaloid, and two previously undescribed guaianolides as well as 10 known guaianolides were obtained from an ethanol extract of Ainsliaea yunnanensis Franch. The chemical structures of all previously reported sesquiterpenoids were determined by extensive NMR spectroscopic analysis in combination with a modified Mosher's method. All isolates were in vitro screened for inhibitory effect against nitric oxide release in RAW 264.7 macrophages stimulated by LPS. Zaluzanin C remarkably inhibited the production of nitric oxide with an IC50 value of 6.54 µM.


Assuntos
Alcaloides/isolamento & purificação , Asteraceae/química , Sesquiterpenos de Guaiano/isolamento & purificação , Alcaloides/química , Alcaloides/farmacologia , Animais , Sobrevivência Celular/efeitos dos fármacos , Concentração Inibidora 50 , Lipopolissacarídeos/farmacologia , Macrófagos/efeitos dos fármacos , Camundongos , Estrutura Molecular , Óxido Nítrico/antagonistas & inibidores , Ressonância Magnética Nuclear Biomolecular , Sesquiterpenos de Guaiano/química , Sesquiterpenos de Guaiano/farmacologia
11.
Fitoterapia ; 119: 90-99, 2017 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-28408269

RESUMO

Two new eudesmane sesquiterpenoids, chlorajaponols A-B (1-2), two new guaiane sesquiterpenoids, chlorajaponols C-D (3-4), a new germacrane sesquiterpenoid, chlorajaponol E (5), and a new lindenane sesquiterpenoid, chlorajaponol F (6), along with 8 known sesquiterpenoids and 6 known disesquiterpenoids, were isolated from the whole plant of Chloranthus japonicus. Their structures were established by extensive analysis of NMR spectroscopic data in combination with mass spectrometry. The structures of compounds 1-4 were confirmed by single crystal X-ray diffraction (CuKα radiation). The possible biogenetic pathways of compounds 1-6 were discussed. Chlorajaponol B (2) showed significant inhibition against nitric oxide (NO) release in LPS-induced RAW264.7 macrophages with the IC50 value of 9.56±0.71µM, comparable to that of positive control amino guanidine (8.50±0.35µM). Shizukaol C (18) strongly suppressed the proliferation of three human tumor cell lines MGC803, HepG2, and HL-60 with IC50 values of 4.60±1.05µM, 3.17±0.66µM, and 1.57±0.27µM, respectively.


Assuntos
Anti-Inflamatórios/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Magnoliopsida/química , Sesquiterpenos de Eudesmano/farmacologia , Sesquiterpenos de Guaiano/farmacologia , Animais , Anti-Inflamatórios/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Humanos , Macrófagos/efeitos dos fármacos , Camundongos , Estrutura Molecular , Óxido Nítrico/metabolismo , Células RAW 264.7 , Sesquiterpenos de Eudesmano/isolamento & purificação , Sesquiterpenos de Guaiano/isolamento & purificação
12.
J Am Chem Soc ; 139(15): 5558-5567, 2017 04 19.
Artigo em Inglês | MEDLINE | ID: mdl-28271887

RESUMO

Delavatine A (1) is a structurally unusual isoquinoline alkaloid isolated from Incarvillea delavayi. The first and gram-scale total synthesis of 1 was accomplished in 13 steps (the longest linear sequence) from commercially available starting materials. We exploited an isoquinoline construction strategy and developed two reactions, namely Rh-catalyzed asymmetric hydrogenation of indene-type tetrasubstituted olefins and kinetic resolution of ß-alkyl phenylethylamine derivatives through Pd-catalyzed triflamide-directed C-H olefination. The substrate scope of the first reaction covered unfunctionalized olefins and those containing polar functionalities such as sulfonamides. The kinetic resolution provided a collection of enantioenriched indane- and tetralin-based triflamides, including those bearing quaternary chiral centers. The selectivity factor (s) exceeded 100 for a number of substrates. These reactions enabled two different yet related approaches to a key intermediate 28 in excellent enantiopurity. In the synthesis, the triflamide served as not only an effective directing group for C-H bond activation but also a versatile functional group for further elaborations. The relative and absolute configurations of delavatine A were unambiguously assigned by the syntheses of the natural product and its three stereoisomers. Their cytotoxicity against a series of cancer cell lines was evaluated.


Assuntos
Alcenos/química , Indenos/química , Isoquinolinas/química , Isoquinolinas/síntese química , Paládio/química , Ródio/química , Bignoniaceae/química , Catálise , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Humanos , Hidrogenação , Cinética , Estrutura Molecular , Estereoisomerismo , Relação Estrutura-Atividade
13.
Sci Rep ; 7: 43837, 2017 03 03.
Artigo em Inglês | MEDLINE | ID: mdl-28256560

RESUMO

Vlasouliolides A-D (1-4), four rare sesquiterpene lactone dimers, were isolated from Vladimiria souliei. The common structural characteristic of 1-4 is the C32 skeleton comprising two sesquiterpene lactone units linked by a C11-C13' single bond with one acetyl connected to the C-13 position of one of the two sesquiterpene lactone units. The stereochemistries of 1-4 were assigned by a combination of NOESY correlations and Cu-Κα X-ray crystallographic analyses. Compounds 1-4 strongly inhibited the production of NO in LPS-stimulated RAW 264.7 cells. Furthermore, 1 and 2 inhibited the activation of NF-κB in LPS-induced 293T cells.


Assuntos
Anti-Inflamatórios/farmacologia , Asteraceae/química , Lactonas/farmacologia , Sesquiterpenos/farmacologia , Animais , Anti-Inflamatórios/química , Cristalografia por Raios X , Dimerização , Células HEK293 , Humanos , Lactonas/química , Lipopolissacarídeos/farmacologia , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Camundongos , Estrutura Molecular , Óxido Nítrico/biossíntese , Células RAW 264.7 , Sesquiterpenos/química
14.
J Ethnopharmacol ; 196: 39-46, 2017 Jan 20.
Artigo em Inglês | MEDLINE | ID: mdl-27988396

RESUMO

BACKGROUNDS: Inula helenium L. is an herb with anti-inflammatory properties. Sesquiterpene lactones (SLs), mainly alantolactone (AL) and isoalantolactone (IAL), are considered as its active ingredients. However, the anti-inflammatory effects of SL-containing extracts of I. helenium have not been explored. Here we prepared total SLs from I. helenium (TSL-IHL), analyzed its chemical constituents, and performed cellular and animal studies to evaluate its anti-inflammatory activities. MATERIALS AND METHODS: The chemical profile of TSL-IHL was analyzed by HPLC-UV. Its in vitro effects on the activation of signaling pathways and expression of inflammatory genes were examined by western blotting and quantitative real-time PCR, respectively, and compared with those of AL and IAL. Its in vivo anti-inflammatory effects were evaluated in adjuvant- and collagen-induced arthritis rat models. RESULTS: Chemical analysis showed that AL and IAL represent major constituents of TSL-IHL. TSL-IHL, as well as AL and IAL, could inhibit TNF-α-induced activation of NF-κB and MAPK pathways in b. End3 cells, suppress the expressions of MMP-3, MCP-1, and IL-1 in TNF-α-stimulated synovial fibroblasts, and IL-1, IL-6, and iNOS in LPS-activated RAW 264.7 cells in a dose-dependent manner in the range of 0.6-2.4µg/mL. Oral administration of TSL-IHL at 12.5-50mg/kg could dose-dependently alleviate the arthritic severity and paw swelling in either developing or developed phases of arthritis of rats induced by adjuvant or collagen CONCLUSIONS: These results indicated potentials of TSL-IHL in prevention and therapy of rheumatoid arthritis.


Assuntos
Anti-Inflamatórios/uso terapêutico , Artrite Experimental/tratamento farmacológico , Artrite Reumatoide/tratamento farmacológico , Inula , Lactonas/uso terapêutico , Sesquiterpenos/uso terapêutico , Animais , Anti-Inflamatórios/farmacologia , Artrite Experimental/metabolismo , Artrite Experimental/prevenção & controle , Artrite Reumatoide/metabolismo , Artrite Reumatoide/prevenção & controle , Linhagem Celular , Citocinas/genética , Citocinas/metabolismo , Lactonas/farmacologia , Masculino , Camundongos , Proteínas Quinases Ativadas por Mitógeno/metabolismo , NF-kappa B/metabolismo , Raízes de Plantas , Células RAW 264.7 , Ratos Wistar , Sesquiterpenos/farmacologia
15.
Nat Prod Res ; 31(11): 1263-1269, 2017 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-27687857

RESUMO

Two previously unreported triterpenoids (1 and 2) and four known compounds were isolated from Abies faxoniana. Compound 1 has a α,ß-unsaturated-γ-lactone ring conjugated with the C-22/23 olefin in the C-17 side chain. The structures of the new compounds were established on the basis of spectroscopic data analysis. These compounds were tested for their cytotoxicities against six human tumour cell lines. Compound 1 showed cytotoxic activities against MCF-7 and A549 cells with IC50 values of 7.5 and 8.7 µM, respectively.


Assuntos
Abies/química , Antineoplásicos Fitogênicos/isolamento & purificação , Triterpenos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Humanos , Concentração Inibidora 50 , Estrutura Molecular , Análise Espectral , Triterpenos/química , Triterpenos/farmacologia
16.
J Asian Nat Prod Res ; 19(5): 448-456, 2017 May.
Artigo em Inglês | MEDLINE | ID: mdl-27690644

RESUMO

Two new abietane diterpenoids (1-2) and 13 known compounds (3-15) were characterized from the branches and leaves of Abies faxoniana. The chemical structures of the new diterpenoids (1-2) were determined through the analysis of various 1D/2D NMR techniques. Compound 3 is 151,617-trinor-abietane diterpenoid conjugated with a three-membered epoxide ring. The isolated diterpenoids were tested for their cytotoxicities. Among them, compound 3 exhibited the strongest antiproliferative effect against human hepatoma cell SMMC7721 with an IC50 value of 12.5 µM. To elucidate the preliminary mechanism responsible for compound 3-induced inhibition of cell proliferation, we investigated the effects of compound 3 on apoptosis, cell cycle progression, and reactive oxygen species generation in SMMC7721 cells. The results showed that compound 3 induced cell apoptosis and excessive ROS production, but did not change the cell cycle distribution in SMMC7721 cells.


Assuntos
Abies/química , Abietanos/isolamento & purificação , Abietanos/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Apoptose/efeitos dos fármacos , Carcinoma Hepatocelular/tratamento farmacológico , Neoplasias Hepáticas/tratamento farmacológico , Abietanos/química , Antineoplásicos Fitogênicos/química , Ciclo Celular/efeitos dos fármacos , Humanos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Folhas de Planta/química
17.
Chem Biodivers ; 14(2)2017 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-27611653

RESUMO

Three new sesquiterpenoids, 4α-hydroxyeudesm-11(13)-en-12-yl 3-methylbutanoate (1), diaspanolide E (2), and (13α)-germacra-1(10),4-dien-12,8α-olid-15-oic acid (3), along with eight known sesquiterpenoids (4 - 11), were isolated from the aerial parts of Ainsliaea henryi. The chemical structures of compounds 1 - 3 were elucidated by spectroscopic analysis (1D-, 2D-NMR, MS and HR/MS). All isolates were evaluated for their inhibitory activities against nitric oxide (NO) production in lipopolysaccharide-induced RAW264.7 macrophage cells. Compound 10 exhibited significantly inhibition against NO release with an IC50 value of 6.54 ± 0.16 µm. Also, all isolated compounds were tested for cytotoxicity against three human tumor cell lines A549, MGC803, and HCT116, among which compound 5 significantly inhibited the proliferation of MGC803 cell lines with an IC50 value of 2.2 ± 0.2 µm.


Assuntos
Anti-Inflamatórios/farmacologia , Asteraceae/química , Sobrevivência Celular/efeitos dos fármacos , Macrófagos/efeitos dos fármacos , Extratos Vegetais/farmacologia , Sesquiterpenos/farmacologia , Animais , Humanos , Concentração Inibidora 50 , Lipopolissacarídeos/farmacologia , Camundongos , Estrutura Molecular , Óxido Nítrico/metabolismo , Sesquiterpenos/química , Células Tumorais Cultivadas
18.
J Nat Prod ; 79(10): 2479-2486, 2016 10 28.
Artigo em Inglês | MEDLINE | ID: mdl-27668963

RESUMO

The new highly oxygenated germacranolides cernuumolides A-J (1-10) and the known compounds 11-20 were isolated from Carpesium cernuum. Among these compounds, 1-4 are 11-methoxymethylgermacranolides and 5-7 as well as 11-17 are 2,9-hemiacetal-linked germacranolides. Their structures were elucidated using NMR and HRESIMS analyses, and X-ray diffraction studies were used to confirm the absolute configurations of 1, 2, 5, 6, 8, and 9. Cernuumolides A-J were evaluated for their in vitro cytotoxicity against the A549, HCT116, MDA-MB-231, and BEL7404 cell lines, and 8 exhibited moderate cytotoxicity with IC50 values in the 0.87-2.02 µM range.


Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Asteraceae/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Oxigênio/química , Sesquiterpenos de Germacrano/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Cristalografia por Raios X , Ensaios de Seleção de Medicamentos Antitumorais , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Células HCT116 , Humanos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Sesquiterpenos de Germacrano/química , Sesquiterpenos de Germacrano/farmacologia
19.
Molecules ; 21(8)2016 Aug 08.
Artigo em Inglês | MEDLINE | ID: mdl-27509491

RESUMO

Investigation of the ethanol extract of the whole plant of Ainsliaea yunnanensis led to the isolation of four new dimeric sesquiterpene lactones, ainsliadimer F-I (1-4), together with seven known dimeric sesquiterpene lactones (5-11) and ten sesquiterpenes (12-21). Their structures were elucidated by spectroscopic methods. The relative stereochemistry of ainsliadimer F was further confirmed by single crystal X-ray diffraction analysis. Compounds 1-21 were tested for the inhibition of nuclear factor kappa B (NF-κB) in the 293-NF-κB-luciferase reporter cell line induced by lipopolysaccharide (LPS), and Compounds 5, 18, 20 and 21 were further tested for the production of TNF-α, IL-1ß, IL-6 and IL-10 in RAW 264.7 macrophages induced by LPS. Compounds 5, 18, 20 and 21 exhibited significant activity in anti-inflammatory activity assays.


Assuntos
Anti-Inflamatórios/química , Asteraceae/química , Citocinas/metabolismo , Lactonas/química , Sesquiterpenos/química , Animais , Anti-Inflamatórios/farmacologia , Cristalografia por Raios X , Regulação da Expressão Gênica/efeitos dos fármacos , Lactonas/farmacologia , Lipopolissacarídeos/efeitos adversos , Camundongos , NF-kappa B/antagonistas & inibidores , Células RAW 264.7 , Sesquiterpenos/farmacologia
20.
Fitoterapia ; 113: 110-6, 2016 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-27476617

RESUMO

Two new flavan derivatives tazettones C-D (1-2), one new ß-coumaranone (tazettone E, 3), one new flavan (tazettone F, 4), and one new phenylpropanoid (tazettone G, 5), together with six known flavonoids (6-11), were isolated from the bulbs of Narcissus tazetta var. chinensis Roem. Their structures were elucidated by spectroscopic analysis. In addition, the structures of 1-3 were confirmed by single crystal X-ray diffraction. All isolated compounds were tested for antioxidant activity by Cell Counting Kit-8 (CCK-8) assay. Compounds 6-8 and 10-11 exhibited potent antioxidant activity against H2O2-induced impairment in human SH-SY5Y neuroblastoma cells at tested concentrations.


Assuntos
Antioxidantes/química , Flavanonas/química , Narcissus/química , Raízes de Plantas/química , Antioxidantes/isolamento & purificação , Linhagem Celular Tumoral , Flavanonas/isolamento & purificação , Humanos , Peróxido de Hidrogênio , Estrutura Molecular
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