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1.
Zhongguo Zhong Yao Za Zhi ; 45(2): 347-351, 2020 Jan.
Artigo em Chinês | MEDLINE | ID: mdl-32237317

RESUMO

Eight compounds were isolated from the ethyl acetate extraction of Prunus mume by column chromatography. On the basis of physicochemical properties and spectrum analysis, these compounds were identified as isoquercitrin-6″-O-benzoate(1), pinoresinol(2), naringin(3), ethyl-ß-D-glucopyranoside(4), astragalin(5), quercetin(6), hypericin(7), and rutin(8). Among them, compound 1 was a new natural product, and compounds 2-5 were isolated from this plant for the first time. In vitro study, compounds 1, 3, 5-8 could significantly increase the cell survival ratio.

2.
Nat Prod Res ; : 1-5, 2019 Nov 10.
Artigo em Inglês | MEDLINE | ID: mdl-31709825

RESUMO

The cortex root of Paeonia ostii, is used as a traditional Chinese medicine for treating female diseases. Phytochemical investigation of the water-soluble fraction of the plant led to the isolation of two new acetoisovanillone glycosides: acetoisovanillone-3-O-ß-D-glucopyranoside (1) and 2-hydroxy-acetoisovanillone-3-O-ß-D-glucopyranoside (2). Their structures were elucidated by extensive spectroscopic methods.

3.
Front Chem ; 7: 434, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31281809

RESUMO

Podophyllotoxin has long been used as an active substance for cytotoxic activity. Fourteen novel biotinylated podophyllotoxin derivatives were designed, synthesized, and evaluated for cytotoxic activity for this study. The synthesized compounds were evaluated for cytotoxic activity in the following human cancer cell lines, SW480, MCF-7, A-549, SMMC-7721, and HL-60 by MTT assay. Most of them exhibited potent cytotoxic effects and compound 15 showed the highest cytotoxic activity among the five cancer cell lines tested, having its IC50 values in the range of 0.13 to 0.84 µM. Apoptosis analysis revealed that compound 15 caused obvious induction of cell apoptosis. Compound 15 significantly down-regulated the expression level of the marker proteins (caspase-3 and PARP) in H1299 and H1975 cells, activated the transcription of IRE1α, increased the expression of GRP78 and XBP-1s, and finally induced apoptosis of H1299 cells. In vivo studies showed that 15 at a dose of 20 mg/kg suppressed tumor growth of S180 cell xenografts in icr mice significantly. Further molecular docking studies suggested that compound 15 could bind well with the ATPase domain of Topoisomerase-II. These data suggest that compound 15 is a promising agent for cancer therapy deserving further research.

4.
Nat Prod Res ; : 1-8, 2019 Jul 15.
Artigo em Inglês | MEDLINE | ID: mdl-31305141

RESUMO

Five new natural compounds (1-5) along with four known ones, involving dibenzo-α-pyrone derivatives, a benzo-γ-pyrone derivative and an amide-type compound were obtained from Alternaria alternata, an endophyte isolated from Paeonia lactiflora. The structures of these isolates were elucidated by intensive analysis of spectroscopic data including NMR, HRMS (ESI and EI), UV and IR spectra. Compounds (1-4) were evaluated for their cytotoxicities against five selected human tumourtumour cell lines (A-549, MDA-MB-231, MCF-7, KB and KB-VIN), and compound 3 exhibited activities against MDA-MB-231and MCF-7 with IC50 values of 20.1 µM and 32.2 µM.

5.
Nat Prod Res ; : 1-7, 2019 May 14.
Artigo em Inglês | MEDLINE | ID: mdl-31084217

RESUMO

One new benzophenone (1) and one new 1,3-diphenylpropane (2) were obtained from the fibrous roots of Anemarrhena asphodeloides Bge. Their structures were determined by comprehensive 1D, 2D NMR and HRESIMS data. By comparing the calculated ECD curves and OR with the experimental data the absolute configurations were determined. The antitumor activity of all isolates was evaluated against two human hepatoma carcinoma cells (HepG2 and Hep3B) in vitro. The results demonstrated that compound 1 and 2 showed potent cytotoxicity against HepG2 and Hep3B cells.

6.
Zhongguo Zhong Yao Za Zhi ; 44(7): 1392-1396, 2019 Apr.
Artigo em Chinês | MEDLINE | ID: mdl-31090296

RESUMO

Five compounds were isolated from the fibrous roots of Anemarrhena asphodeloides by silica gel, Sephadex LH-20 and semi-HPLC column chromatography. On the basis of physic-chemical properties and spectroscopic data analysis, these compounds were identified as methyl 2-[2,4-dihydroxy-3-(4-hydroxybenzoyl)-6-methoxyphenyl]acetate(1), 4-[formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]butanoate(2), perlolyrine(3),syringaresinol-4'-O-ß-D-glucoside(4) and 4',6-dihydroxy-4-methoxybenzophenone-2-O-(2″),3-C-(1″)-1″-desoxy-α-L-fructofuranoside(5). Among them, 1 was a new benzophenone. Compounds 2-5 were isolated from this plant for the first time. Compound 1 was tested for neuroprotective effects against H_2O_2-induced damage in SH-SY5 Y cells.


Assuntos
Anemarrhena/química , Benzofenonas/farmacologia , Fármacos Neuroprotetores/farmacologia , Raízes de Plantas/química , Benzofenonas/isolamento & purificação , Linhagem Celular , Cromatografia Líquida de Alta Pressão , Humanos , Fármacos Neuroprotetores/isolamento & purificação , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia
7.
Nat Prod Res ; 33(15): 2133-2138, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-30822136

RESUMO

A new steroid lactone aspergilolide (1), and nine known compounds helvolic acid (2), verruculogen (3), tryprostatin B (4), 13-oxofumitremorgin B (5), fumitremorgin C (6), demethoxy fumitremorgin C (7), terezine D (8), aszonalenin (9), 12, 13-dihydroxy-fumitremorgin C (10) from cultures of the endophytic fungus Aspergillus sp. MBL1612. Their chemical structures were determined by a series of extensive spectroscopic methods. All of the compounds were isolated from this genus for the first time. The cytotoxicity against five human cancer cell lines of new compound were detected.


Assuntos
Aspergillus/metabolismo , Lactonas/metabolismo , Paeonia/microbiologia , Esteroides/biossíntese , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Lactonas/química , Lactonas/farmacologia , Análise Espectral/métodos , Esteroides/química , Esteroides/farmacologia
8.
J Asian Nat Prod Res ; 21(5): 426-434, 2019 May.
Artigo em Inglês | MEDLINE | ID: mdl-30404553

RESUMO

Two new 11-methoxyl substituted triterpenoids, named as mimengosides J (1) and K (2), along with seven known compounds, were isolated from the fruits of Buddleja lindleyana. Their structures were elucidated on the basis of spectroscopic analysis. In addition, the new ones were evaluated for protective effects against damage of SH-SY5Y cells induced by 1-methyl-4-phenylpyridinium ion (MPP+) and the results indicated that those may be one of the candidate compositions of Buddleja lindleyana for the treatment of neurodegenerative disease.


Assuntos
Buddleja/química , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/farmacologia , Triterpenos/química , Triterpenos/farmacologia , 1-Metil-4-fenilpiridínio/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Autoantígenos , Sobrevivência Celular/efeitos dos fármacos , Colágeno Tipo IV , Frutas/química , Humanos , Estrutura Molecular , Neuroblastoma , Neurônios/efeitos dos fármacos
9.
Bioorg Med Chem Lett ; 29(2): 234-237, 2019 01 15.
Artigo em Inglês | MEDLINE | ID: mdl-30509782

RESUMO

A series of biotinylated camptothecin derivatives were designed and synthesized. The key to the synthesis was achieved by employing an esterification reaction and click chemistry. All of the new derivatives were tested for cytotoxicity against five human tumor cell lines, including HL-60, SMMC-7721, A-549, MCF-7, and SW480 with IC50 values ranging from 0.13 to 21.53 µM. Most of the derivatives exhibited potent cytotoxicity, especially compound 17 (IC50 = 0.13-3.31 µM) and compound 18 (IC50 = 0.23-1.48 µM), which exhibited the highest potencies. The structure-activity relationships (SARs) of the biotinylated camptothecin derivatives were discussed for exploring novel anticancer agents.


Assuntos
Antineoplásicos/farmacologia , Camptotecina/farmacologia , Antineoplásicos/síntese química , Antineoplásicos/química , Camptotecina/síntese química , Camptotecina/química , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Química Click , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Estrutura Molecular , Relação Estrutura-Atividade
10.
Nat Prod Res ; 33(9): 1298-1303, 2019 May.
Artigo em Inglês | MEDLINE | ID: mdl-29873265

RESUMO

Two new Erythrina alkaloids, 10-oxo-erythrinine (1) erythrinine N-oxide (2) together with 23 known ones were obtained from the flowers of Erythrina corallodendron. The structures were determined based on analysis of their spectroscopic data. All compounds were first isolated from plants of Erythrina corallodendron.


Assuntos
Alcaloides/isolamento & purificação , Erythrina/química , Alcaloides/química , Flores/química
11.
Fitoterapia ; 131: 204-208, 2018 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-30385400

RESUMO

Five novel globoscinic acid derivatives, aspergilates A-E (1-5) have been isolated from endophytic fungus Aspergillus sp. derived from Paeonia ostii. The structures of aspergilates A-E were determined by in-depth analyses of NMR spectra, HRESIMS and CD experiments. The absolute configurations of compounds 2-5 were determined by the ECD calculations based on quantum chemistry. Cytotoxic activities against five selected tested tumor cell lines of 1-5 were evaluated.


Assuntos
Aspergillus/química , Paeonia/microbiologia , Linhagem Celular Tumoral , China , Endófitos/química , Humanos , Estrutura Molecular , Raízes de Plantas/microbiologia , Metabolismo Secundário
12.
Drug Des Devel Ther ; 12: 3393-3406, 2018.
Artigo em Inglês | MEDLINE | ID: mdl-30349193

RESUMO

Background: Podophyllotoxin is a potent cytotoxic agent and serves as a useful lead compound for the development of antitumor drugs. Several podophyllotoxin-derived antitumor agents, including etoposide, are currently in clinical use; however, their therapeutic efficacy is often limited due to side effects and the development of resistance by cancer cells. Previous studies have shown that 4ß-1,2,3-triazole derivatives of podophyllotoxin exhibit more potent anticancer activity and better binding to topoisomerase-II than etoposide. The effect of dimerization of such derivatives on the anticancer activity has not been studied. Methods: Two moieties of podophyllotoxin were linked at the C-4 position via 1,2,3-triazole rings to give a series of novel dimeric podophyllotoxin derivatives. 4ß-Azido-substituted podophyllotoxin derivatives (23 and 24) were coupled with various dipropargyl functionalized linkers by utilizing the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction to provide dimeric products in very good yield. The in vitro anticancer activity of the synthesized compounds was evaluated by MTT assay against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW480). The normal BEAS-2B (lung) cell line was also included for study in order to evaluate the cancer selectivity of the most active compound as compared with normal cells. Results: A group of 16 dimeric podophyllotoxin derivatives with different linkers were synthesized and structurally characterized. Most compounds do not show significant cytotoxicity (IC50 > 40 mM) against all five cancer cell lines. However, one compound (29) which bears a perbutyrylated glucose residue on the glycerol linker is highly potent against all five cancer cell lines tested, with IC50 values ranging from 0.43 to 3.50 µM. This compound (29) also shows good selectivity towards cancer cell lines as compared with the normal BEAS-2B (lung) cell line, showing selectivity indexes from 4.4 to 35.7. Conclusion: The anticancer activity of dimeric podophyllotoxin derivatives is generally speaking not improved as compared to their monomeric counterparts, and the potency of these dimeric derivatives can be largely affected by the nature of the linker between the two moieties. Among the synthesized derivatives, compound 29 is significantly more cytotoxic and selective towards cancer cells than etoposide and cisplatin, which are currently in clinical use. Compound 29 is a promising anticancer drug and needs further studies.


Assuntos
Antineoplásicos Fitogênicos/síntese química , Antineoplásicos Fitogênicos/farmacologia , Podofilotoxina/análogos & derivados , Podofilotoxina/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Proliferação de Células/efeitos dos fármacos , Células Cultivadas , Dimerização , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Estrutura Molecular , Podofilotoxina/síntese química , Podofilotoxina/isolamento & purificação , Podophyllum/química , Relação Estrutura-Atividade
13.
Nat Prod Res ; 31(7): 797-801, 2017 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-27798974

RESUMO

Four new glucosides, named as gigantol-5-O-ß-d-glucopyranoside (1), 9,10-dihydro-aphyllone A-5-O-ß-d-glucopyranoside (2), ficusal-4-O-ß-d-glucopyranoside (3), botrydiol-15-O-ß-d-glucopyranoside (4), together with eight known compounds (5-12) were isolated from the n-BuOH extract of the stems of Dendrobium fimbriatum Hook. Their structures were elucidated by the analyses of spectroscopic data.


Assuntos
Dendrobium/química , Glicosídeos/química , Glucosídeos/química , Glicosídeos/isolamento & purificação , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Extratos Vegetais/química , Caules de Planta/química
14.
Fitoterapia ; 115: 122-127, 2016 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-27693740

RESUMO

Four new cycloartane triterpenoids, 1α,3ß-dihydroxy-16-keto-24(31)-en-cycloartane (1), 31-methoxyl-passifloic acid (2), cyclopassifloside XIV (3), and cyclopassifloside XV (4), together with six known compounds (5-10) were isolated from Passiflora edulis Sims. Their structures were elucidated on the basis of extensive spectroscopic analysis. All the compounds were evaluated for protective effects against damage of PC12 cell induced by glutamate according to traditional usage of the herbal medicine, and the results indicated that cycloartane triterpenoids maybe one of the active compositions of P. edulis Sims for the treatment of neurodegenerative disease.


Assuntos
Fármacos Neuroprotetores/química , Passiflora/química , Triterpenos/química , Animais , Ácido Glutâmico/efeitos adversos , Estrutura Molecular , Fármacos Neuroprotetores/isolamento & purificação , Células PC12 , Ratos , Triterpenos/isolamento & purificação
15.
Zhong Yao Cai ; 38(4): 758-60, 2015 Apr.
Artigo em Chinês | MEDLINE | ID: mdl-26672342

RESUMO

OBJECTIVE: To study the flavonoids in the fruits of Buddleja lindleyana. METHODS: The compounds were separated by repeated silica gel, RP-18 and Sephadex LH-20. Their structures were elucidated on the basis of chemical evidence and spectral data. RESULTS: Five flavonoids were isolated and identified as luteolin (1), tricin (2), acacetin (3), acacetin-7-O-ß-D-glucopyranoside (4) and linarin(5). CONCLUSION: Compounds 3,4 and 5 are isolated from fruits of Buddleja lindleyana for the first time. Compound 2 is isolated from fruits of Buddleja lindleyana for the first time.


Assuntos
Buddleja/química , Flavonoides/química , Frutas/química , Compostos Fitoquímicos/química , Flavonas , Flavonoides/isolamento & purificação , Glicosídeos , Luteolina , Compostos Fitoquímicos/isolamento & purificação
16.
Fitoterapia ; 100: 11-8, 2015 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-25447160

RESUMO

One new phenanthrene, aphyllone A (1) and four new bibenzyl derivatives, aphyllone B (2) and aphyllals C-D (3-5), together with nine known compounds (6-14), were isolated from the stems of Dendrobium aphyllum (Roxb.) C. E. Fischer. The structures of these new compounds were elucidated by means of extensive spectroscopic analyses, and the absolute configuration of compound 1 was determined by single crystal X-ray diffraction and quantum calculations. Compounds 6, 8 and 14 inhibited NO production at the concentration of 25 µM in LPS-stimulated RAW264.7 cells with the inhibition (%) of 32.48, 35.68, and 38.50. Compound 2 possessed significant DPPH radical scavenging activity with scavenging percentage of 87.97% at the concentration of 100 µg/mL.


Assuntos
Dendrobium/química , Fenantrenos/química , Fenóis/química , Animais , Bibenzilas/química , Bibenzilas/isolamento & purificação , Linhagem Celular , Linhagem Celular Tumoral , Depuradores de Radicais Livres/química , Depuradores de Radicais Livres/isolamento & purificação , Humanos , Macrófagos/efeitos dos fármacos , Camundongos , Estrutura Molecular , Óxido Nítrico/biossíntese , Fenantrenos/isolamento & purificação , Fenóis/isolamento & purificação , Caules de Planta/química
17.
Bioorg Med Chem Lett ; 24(22): 5268-73, 2014 Nov 15.
Artigo em Inglês | MEDLINE | ID: mdl-25316316

RESUMO

The bioassay-guided chemical investigation of the stems of Dendrobium fimbriatum Hook led to the isolation of seven first reported bibenzyl dimers with a linkage of a methylene moiety, fimbriadimerbibenzyls A-G (1-7), together with a new dihydrophenanthrene derivative (S)-2,4,5,9-tetrahydroxy-9,10-dihydrophenanthrene (8) and thirteen known compounds (9-21). The structure of the new compound was established by spectroscopic analysis. Biological evaluation of bibenzyl derivatives against five human cell lines indicated that seven of those compounds exhibited broad-spectrum and cytotoxic activities with IC50 values ranging from 2.2 to 21.2 µM. Those rare bibenzyl dimers exhibited cytotoxic activities in vitro and the cytotoxicity decreased as the number of oxygen-containing groups in the structure decreases.


Assuntos
Bibenzilas/química , Dendrobium/química , Antioxidantes/química , Antioxidantes/isolamento & purificação , Antioxidantes/toxicidade , Bibenzilas/isolamento & purificação , Bibenzilas/toxicidade , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Dendrobium/metabolismo , Dimerização , Humanos , Espectroscopia de Ressonância Magnética , Conformação Molecular , Caules de Planta/química , Caules de Planta/metabolismo
18.
Molecules ; 18(11): 13992-4012, 2013 Nov 13.
Artigo em Inglês | MEDLINE | ID: mdl-24232736

RESUMO

A series of 4ß-triazole-linked glucose podophyllotoxin conjugates have been designed and synthesized by employing a click chemistry approach. All the compounds were evaluated for their anticancer activity against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, SW480) using MTT assays. Most of these triazole derivatives have good anticancer activity. Among them, compound 35 showed the highest potency against all five cancer cell lines tested, with IC50 values ranging from 0.59 to 2.90 µM, which is significantly more active than the drug etoposide currently in clinical use. Structure-activity relationship analysis reveals that the acyl substitution on the glucose residue, the length of oligoethylene glycol linker, and the 4'-demethylation of podophyllotoxin scaffold can significantly affect the potency of the anticancer activity. Most notably, derivatives with a perbutyrylated glucose residue show much higher activity than their counterparts with either a free glucose or a peracetylated glucose residue.


Assuntos
Antineoplásicos/síntese química , Antineoplásicos/farmacologia , Podofilotoxina/química , Triazóis/química , Antineoplásicos/química , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Humanos , Estrutura Molecular
19.
J Asian Nat Prod Res ; 15(12): 1256-64, 2013.
Artigo em Inglês | MEDLINE | ID: mdl-24205813

RESUMO

Three new stilbenoids, 1-(4'-hydroxybenzyl)-imbricatin, (E)-4'-hydroxy-2',3,3',5-tetramethoxystilbene, and (E)-3,4'-dihydroxy-2,6-bis(4-hydroxybenzyl)-2',3',5-trimethoxystilbene, together with 15 known stilbene derivatives, were isolated from Pholidota yunnanensis. Their structures were elucidated by spectroscopic methods and by comparison of their NMR data with those of related compounds. Furthermore, the inhibitory activities on nitric oxide (NO) production of the isolated compounds were examined in murine macrophages (RAW 264.7) activated by lipopolysaccharide. The cytotoxicity of 18 compounds was determined by the 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium assay. Among the tested compounds, eight stilbenoids, including three dihydrophenanthrenes, three stilbenes, and one bibenzyl derivative showed inhibitory effects on NO production without cytotoxicity with IC50 values ranging from 4.07 to 7.77 µM, as compared to MG-132, which was used as a positive control (IC50 of 0.10 µM). One dihydrophenanthrene, phoyunnanin C, showed cytotoxic effects at the test concentrations.


Assuntos
Macrófagos/efeitos dos fármacos , Óxido Nítrico/antagonistas & inibidores , Orchidaceae/química , Estilbenos/isolamento & purificação , Estilbenos/farmacologia , Animais , Lipopolissacarídeos/farmacologia , Camundongos , Estrutura Molecular , Óxido Nítrico/biossíntese , Ressonância Magnética Nuclear Biomolecular , Fenantrenos/química , Fenantrenos/farmacologia , Estilbenos/química
20.
Fitoterapia ; 91: 224-230, 2013 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-24060906

RESUMO

Five new diterpenoids named excocarinols A-E (1-5) including three pimaranes, one cleistanthane, and one nor-beyerane, together with nine known compounds, were isolated from the EtOAc extract of the Chinese ethnodrug Gua-jing-ban (Excoecaria acerifolia Didr.). Their structures were elucidated by the analysis of spectroscopic data including 1D, 2D NMR and HR-MS. The anti-HIV-1 bioassay on the diterpenoids showed that excocarinol A (1) exhibited moderate anti-HIV-1 activity with EC50 5.58 µM and SI (Selection Index) over 112.71.


Assuntos
Fármacos Anti-HIV/farmacologia , Diterpenos/farmacologia , Medicamentos de Ervas Chinesas/farmacologia , Euphorbiaceae/química , HIV-1/efeitos dos fármacos , /química , /farmacologia , Fármacos Anti-HIV/química , Fármacos Anti-HIV/isolamento & purificação , Diterpenos/química , Diterpenos/isolamento & purificação , Medicamentos de Ervas Chinesas/química , Estrutura Molecular
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