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1.
Chem Biodivers ; 16(12): e1900495, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31755643

RESUMO

Fifteen diterpenoids (1-15), including three undescribed ones with ent-atisane skeleton, eupnerias G-I (1-3), were obtained from Euphorbia neriifolia. Compounds 1-3 were established through comprehensive spectroscopic analysis. Compounds 4 and 5 exhibited obvious anti-HIV-1 effect, and their EC50 were 6.6±3.2 and 6.4±2.5 µg mL-1 , respectively. Compound 6 exhibited moderate cytotoxicity on HepG2 and HepG2/Adr cells with IC50 at 13.70 and 15.57 µm, respectively. In addition, compound 15 exhibited significant cytotoxicity on HepG2 cell lines (IC50 =0.01 µm), while it did not show any cytotoxicity against HepG2/Adr cell lines.


Assuntos
Fármacos Anti-HIV/química , Diterpenos/química , Euphorbia/química , Fármacos Anti-HIV/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Diterpenos/farmacologia , Resistencia a Medicamentos Antineoplásicos/efeitos dos fármacos , Euphorbia/metabolismo , HIV-1/efeitos dos fármacos , Humanos , Conformação Molecular , Relação Estrutura-Atividade
2.
Nat Prod Res ; : 1-9, 2019 Jan 29.
Artigo em Inglês | MEDLINE | ID: mdl-30691300

RESUMO

Six new compounds, including three terpenoids (1-3) and three lignans (4-6), were isolated from the 95% EtOH extract of the twigs of Tripterygium hypoglaucum. Their structures were determined on the basis of extensive spectroscopic analysis. 9'-O-benzoyl-lariciresinol (4) showed weak cytotoxicity against HepG2/Adr cells, with an IC50 value of 30.1 µM in vitro.

3.
Nat Prod Res ; 33(21): 3083-3088, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-30427740

RESUMO

A new protostane-type triterpenoid bearing an oxetane ring in the side-chain, named alisol W (1), has been obtained from the dried rhizome of Alisma plantago-aquatica subsp. orientale. The structure and absolute configuration of compound 1 was determined from extensive spectroscopic analysis. In addition, the vasorelaxant activity and the inhibition on 11ß-HSD1 of compound 1 were also evaluated, however, it didn't show remarkable effects.


Assuntos
Alisma/química , Triterpenos/isolamento & purificação , 11-beta-Hidroxiesteroide Desidrogenase Tipo 1/antagonistas & inibidores , Humanos , Estrutura Molecular , Rizoma/química , Análise Espectral , Triterpenos/química , Vasodilatadores/análise
4.
Chem Biodivers ; 15(5): e1700560, 2018 May.
Artigo em Inglês | MEDLINE | ID: mdl-29569369

RESUMO

Three new compounds (1 - 3), including two euphane type triterpenes, 24,24-dimethoxy-25,26,27-trinoreuphan-3ß-ol (1) and (24S)-24-hydroperoxyeupha-8,25-dien-3ß-ol (2), and an ent-atisine diterpene, ent-atisane-3α,16α,17-triol (3), were isolated from an acetone extract of the stems of Euphorbia antiquorum, together with eight known diterpenes (4 - 11). The structures of compounds (1 - 11) were elucidated using NMR and MS spectroscopic methods. Compound 7 showed moderate activity against HIV-1 replication in vitro (EC50 = 1.38 µm).


Assuntos
Fármacos Anti-HIV/farmacologia , Euphorbia/química , HIV-1/efeitos dos fármacos , Terpenos/farmacologia , Fármacos Anti-HIV/química , Fármacos Anti-HIV/isolamento & purificação , Linhagem Celular Transformada , Transformação Celular Viral/efeitos dos fármacos , Relação Dose-Resposta a Droga , Humanos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Relação Estrutura-Atividade , Terpenos/química , Terpenos/isolamento & purificação , Replicação Viral/efeitos dos fármacos
5.
Nat Prod Res ; 32(21): 2571-2576, 2018 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-29359583

RESUMO

Onosmanones A (1) and B (2), two novel quinonoid xanthenes with two geranyl groups, have been isolated from the whole plants of Onosma paniculatum. Their structures were elucidated on the basis of one- and two-dimensional NMR techniques.


Assuntos
Boraginaceae/química , Xantenos/química , China , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Xantenos/isolamento & purificação
6.
Phytochemistry ; 145: 40-47, 2018 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-29080411

RESUMO

Six previously undescribed diterpenoids, named euphorantins S-T and euphorneroids A-D, including ingol and ent-atisane types, along with eleven known diterpenoids, were isolated from Euphorbia neriifolia. Their structures were elucidated on the basis of extensive NMR analysis and high resolution mass spectrometry. Euphorneroid D and ent-3-oxoatisan-16α,17-acetonide exhibited moderate anti-HIV-1 activities, with EC50 values of 34 µM (SI = 2.3) and 24 µM (SI = 1.9), respectively.


Assuntos
Fármacos Anti-HIV/farmacologia , Diterpenos/farmacologia , Euphorbia/química , HIV-1/efeitos dos fármacos , Casca de Planta/química , Caules de Planta/química , Fármacos Anti-HIV/química , Fármacos Anti-HIV/isolamento & purificação , Linhagem Celular , Diterpenos/química , Diterpenos/isolamento & purificação , Relação Dose-Resposta a Droga , Humanos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Relação Estrutura-Atividade
7.
Planta Med ; 83(17): 1368-1373, 2017 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-28662527

RESUMO

Three new compounds (1 - 3), including a sesterterpenoid, aspterpenacid C (1), with an unusual 5/3/7/6/5 pentacyclic skeleton, together with seven known ones (4 - 10), were isolated from the ethanol extract of the traditional Chinese medicinal plant Swertia bimaculata. Their structures were elucidated on the basis of the methods of spectroscopic NMR, MS, and computational chemistry. The structure of 1 was further confirmed by single-crystal X-ray diffraction analysis. Compounds 1 - 10 were tested for activities on the inhibition of nitric oxide production and HIV-1 replication in vitro. Compound 1 exhibited moderate activity in inhibiting nitric oxide production (IC50 = 16.1 µM) and HIV-1 replication (EC50 = 1.35 µM).


Assuntos
Fármacos Anti-HIV/isolamento & purificação , Fármacos Anti-HIV/farmacologia , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Medicamentos de Ervas Chinesas/farmacologia , HIV-1/efeitos dos fármacos , Swertia/química , Animais , Fármacos Anti-HIV/química , Anti-Inflamatórios/química , China , Medicamentos de Ervas Chinesas/química , Camundongos , Estrutura Molecular , Óxido Nítrico/antagonistas & inibidores , Células RAW 264.7 , Replicação Viral/efeitos dos fármacos
8.
J Agric Food Chem ; 65(22): 4456-4463, 2017 Jun 07.
Artigo em Inglês | MEDLINE | ID: mdl-28494582

RESUMO

Six new highly oxygenated grayanane diterpenoids, neopierisoids G-L, 1-6, together with 10 known related compounds, 7-16, were identified from the flowers of the poisonous plant Pieris japonica. The structures were elucidated on the basis of comprehensive NMR spectroscopy and mass analysis. The relative configurations of 1-6 were elucidated by analysis of ROESY spectra and comparison of NMR data with the analogues. The absolute configurations of 1-6 were established by the X-ray diffraction analysis of 1 and comparison of the CD spectra of 1-6. Compared with the skeleton of the normal grayanane diterpenoids, compounds 1-6 shared an unusual seco A ring moiety. The antifeedant activities of compounds 1-16 against Pieris brassicae were evaluated by using a dual-choice bioassay, and compounds 1-10 with a normal grayanane skeleton showed potent antifeedant activity against P. brassicae. The structure-activity relationships of antifeedant activities of 1-16 against P. brassicae are discussed.


Assuntos
Borboletas/efeitos dos fármacos , Diterpenos/química , Diterpenos/farmacologia , Ericaceae/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Animais , Borboletas/fisiologia , Comportamento Alimentar/efeitos dos fármacos , Flores/química , Estrutura Molecular , Relação Estrutura-Atividade
10.
Planta Med ; 83(7): 631-635, 2017 May.
Artigo em Inglês | MEDLINE | ID: mdl-27852095

RESUMO

Four new naphthoquinones (1-4), including a dimeric one, shikometabolin G (1), together with six known ones (6-10), were isolated from the methanol extract of Onosma paniculatum. Their structures were established based on the analysis of NMR and MS spectroscopic data. All of the compounds were evaluated for inhibitory effects on NO production in murine macrophage RAW 264.7 cells. Compounds 2, 3, 5, 6, 7, 8, and 10 displayed good activity on the inhibition of NO production (IC50 = 0.4-16.5 µM), suggesting the potential property of anti-inflammation.


Assuntos
Anti-Inflamatórios não Esteroides/isolamento & purificação , Boraginaceae/química , Medicamentos de Ervas Chinesas/uso terapêutico , Naftoquinonas/isolamento & purificação , Animais , Anti-Inflamatórios não Esteroides/farmacologia , Camundongos , Naftoquinonas/farmacologia , Óxido Nítrico/biossíntese , Raízes de Plantas/química , Células RAW 264.7
11.
Arch Pharm Res ; 39(6): 771-7, 2016 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-27138284

RESUMO

Two new ursane-type triterpenoid saponins, bodiniosides M (1) and N (2), along with three known saponins, oblonganosides I (3), pseudobuxussaponin B (4) and bodinioside A (5), were isolated from the aerial parts of Elsholtzia bodinieri. The structures of compounds 1 and 2 were characterized by spectroscopic data as well as acid hydrolysis and GC analysis as 3-O-ß-D-xylopyranosyl-19α-hydroxy-23-acetoxy-urs-12(13)-en-28-oic acid 28-O-α-L-rhamnopyranosyl-(1-2)-ß-D-glucopyranoside and 3-O-ß-D-glucopyranosyl-2α,19α-dihydroxy-urs-12(13)-en-28,20ß-lactone. Compounds 1 and 5 exhibited potent anti-HCV activities in vitro with a selective index of 6.53 and 4.41, respectively.


Assuntos
Antivirais/isolamento & purificação , Descoberta de Drogas/métodos , Lamiaceae/química , Saponinas/isolamento & purificação , Triterpenos/isolamento & purificação , Animais , Antivirais/farmacologia , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Hepacivirus/efeitos dos fármacos , Estrutura Molecular , Componentes Aéreos da Planta/química , Saponinas/farmacologia , Triterpenos/farmacologia
12.
Fitoterapia ; 109: 224-9, 2016 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-26808916

RESUMO

Seven new vibsane-type diterpenes, vibsanols C-H (1-6) and vibsanin X (7), together with seven analogues, were isolated from the leaves and twigs of Viburnum odoratissimum. The structures of the new compounds were elucidated by extensive spectroscopic methods. All the new compounds were detected for their cytotoxicity. Compound 1 showed significant cytotoxicity against all the tested cell lines (HL-60, SMMC-7721, A-594, MCF-7, and SW-480), with IC50 values of 3.35, 4.41, 5.18, 11.30, and 3.70 µM, respectively. Compounds 4 and 5 also displayed significant cytotoxicity against hepatocellular carcinoma SMMC-7721 cell line, with IC50 values of 3.69 and 3.52 µM, respectively.


Assuntos
Antineoplásicos Fitogênicos/química , Diterpenos/química , Viburnum/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Diterpenos/isolamento & purificação , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Estrutura Molecular , Folhas de Planta/química
13.
J Nat Prod ; 78(2): 330-4, 2015 Feb 27.
Artigo em Inglês | MEDLINE | ID: mdl-25590374

RESUMO

Five selective 11ß-hydroxysteroid dehydrogenase type 1 (11ß-HSD1) competitive inhibitors, hupehenols A-E (1-5), were isolated from Viburnum hupehense. The structure elucidation indicated that compounds 1-5 are new 20,21,22,23,24,25,26,27-octanordammarane triterpenoids. Their structures were established on the basis of NMR spectroscopic and mass spectrometric analysis. Hupehenols A-E (1-5) showed inhibition against human 11ß-HSD1, with hupehenols B (2) and E (5) having IC50 values of 15.3 and 34.0 nM, respectively. Moreover, hupehenols C (3) and D (4) are highly selective inhibitors of human 11ß-HSD1 when compared to murine 11ß-HSD1.


Assuntos
11-beta-Hidroxiesteroide Desidrogenase Tipo 1/antagonistas & inibidores , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Triterpenos/isolamento & purificação , Triterpenos/farmacologia , Viburnum/química , Animais , Medicamentos de Ervas Chinesas/química , Humanos , Camundongos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Componentes Aéreos da Planta/química , Relação Estrutura-Atividade , Triterpenos/química
14.
Plant Physiol Biochem ; 70: 504-11, 2013 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-23860230

RESUMO

Our previous study showed that citrate excretion coupled with a concomitant release of protons was involved in aluminum (Al) resistance in the broad bean. Furthermore, genes encoding plasma membrane (PM) H(+)-ATPase (vha2) and the 14-3-3 protein (vf14-3-3b) were up-regulated by Al in Al-resistant (YD) broad bean roots. In this study, the roles of PM H(+)-ATPase (E.C. 3.6.3.6) and the 14-3-3 protein in the regulation of citrate secretion were further investigated in Al-resistant (YD) and Al-sensitive (AD) broad bean cultivars under Al stress. The results showed that greater citrate exudation was positively correlated with higher activities of PM H(+)-ATPase in roots of YD than AD. Real-time RT-PCR analysis revealed that vha2 was clearly up-regulated by Al in YD but not in AD roots, whereas the transcription levels of vf14-3-3b were elevated in a time-dependent manner in both YD and AD roots. Immunoprecipitation and Western analysis suggested that phosphorylation and interaction with the vf14-3-3b protein of the VHA2 were enhanced in YD roots but not in AD roots with increasing Al treatment time. Fusicoccin or adenosine 5'-monophosphate increased or decreased the interaction between the phosphorylated VHA2 and the vf14-3-3b protein, followed by an enhancement or reduction of the PM H(+)-ATPase activity and citrate exudation in both cultivars under Al stress conditions, respectively. Taken together, these results suggested that Al enhanced the expression and interaction of the PM H(+)-ATPase and the 14-3-3 protein, which thereby led to higher activity of the PM H(+)-ATPase and more citrate exudation from YD plants.


Assuntos
Proteínas 14-3-3/metabolismo , Alumínio/efeitos adversos , Membrana Celular/metabolismo , Ácido Cítrico/metabolismo , Proteínas de Plantas/metabolismo , ATPases Translocadoras de Prótons/metabolismo , Vicia faba/metabolismo , Adaptação Fisiológica/genética , Monofosfato de Adenosina/farmacologia , Alumínio/metabolismo , Regulação da Expressão Gênica de Plantas , Genes de Plantas , Glicosídeos/farmacologia , Fosforilação , Proteínas de Plantas/genética , ATPases Translocadoras de Prótons/genética , Estresse Fisiológico/genética , Transcrição Genética/efeitos dos fármacos , Regulação para Cima , Vicia faba/efeitos dos fármacos , Vicia faba/genética
15.
Chem Biodivers ; 9(6): 1213-20, 2012 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-22700239

RESUMO

Two new polycyclic polyprenylated acylphloroglucinols (PPAPs), androforin A and hyperandrone A, together with twelve known compounds, were isolated from the aerial parts of Hypericum androsaemum. Their structures were established by detailed spectral analysis. In the cytotoxic assay, 1,4-O-diferuloylsecoisolariciresinol showed activities comparable with those of cisplatin, and acetyloleanolic acid exhibited moderate inhibitory effects against HL-60, SMMC-7721, A-549, MCF-7, and SW480 cancer cell lines.


Assuntos
Hypericum/química , Floroglucinol/análogos & derivados , Floroglucinol/química , Compostos Policíclicos/química , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Células HL-60 , Humanos , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Conformação Molecular , Floroglucinol/isolamento & purificação , Floroglucinol/toxicidade
16.
Fitoterapia ; 83(6): 1072-5, 2012 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-22609685

RESUMO

Three new norditerpenoids, castanol A-C (1-3), along with eighteen known diterpenoids, were isolated from Salvia castanea Diels f. pubescens. Their structures were elucidated by extensive spectroscopic analysis. All compounds were evaluated for their cytotoxic activities against five human cancer cell lines. The known compounds neo-tanshinlactone (12) and methyltanshinoate (17) exhibited significant cytotoxic activities against some cells.


Assuntos
Antineoplásicos Fitogênicos/uso terapêutico , Diterpenos/isolamento & purificação , Furanos/uso terapêutico , Pironas/uso terapêutico , Salvia/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Diterpenos/química , Diterpenos/farmacologia , Diterpenos/uso terapêutico , Furanos/isolamento & purificação , Furanos/farmacologia , Humanos , Estrutura Molecular , Neoplasias/tratamento farmacológico , Fitoterapia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Extratos Vegetais/uso terapêutico , Pironas/isolamento & purificação , Pironas/farmacologia
17.
Chem Pharm Bull (Tokyo) ; 59(10): 1250-3, 2011.
Artigo em Inglês | MEDLINE | ID: mdl-21963634

RESUMO

Four new acylphloroglucinols with an unusual 6/6/5 spirocyclic skeleton, hyperbeanols A-D (1-4), were isolated from the methanol extract of Hypericum beanii along with 16 known compounds. Their structures were established on the basis of spectroscopic and X-ray diffraction analysis. Hyperbeanols A-C were three stereoisomers different only at the relative configuration of C-4 and C-13, which were distinguished by the nuclear Overhauser effect spectroscopy (NOESY) spectroscopic data in combination with the single X-ray analysis of hyperbeanol A (1). The cytotoxic activity of hyperbeanols A-D against the cancer cell lines SK-BR-3, HL-60, SMMC-7721, PANC-1, MCF-7, and K562 was also evaluated.


Assuntos
Antineoplásicos Fitogênicos/química , Hypericum/química , Floroglucinol/análogos & derivados , Fitoterapia , Extratos Vegetais/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Avaliação Pré-Clínica de Medicamentos , Ensaios de Seleção de Medicamentos Antitumorais , Células HL-60 , Humanos , Estrutura Molecular , Floroglucinol/química , Floroglucinol/metabolismo , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Estereoisomerismo
18.
Chem Pharm Bull (Tokyo) ; 59(4): 496-8, 2011.
Artigo em Inglês | MEDLINE | ID: mdl-21467682

RESUMO

Two new oleanane triterpenoids (1-2) and one new vibsane-type diterpenoid (3), together with 7 known compounds (4-10), were isolated from the leaves of Viburnum chingii. The structures of compounds 1-3 were elucidated by means of spectroscopic methods including extensive 1D- and 2D-NMR technique. Cytotoxicity of compounds 1-10 were tested against HL-60, SMMC-7721, A-549, SK-BR-3, and PANC-1 cell lines. Compound 3 showed significant cytotoxicity against HL-60, SK-BR-3, and PANC-1 cell lines.


Assuntos
Antineoplásicos Fitogênicos/química , Diterpenos/química , Ácido Oleanólico/química , Triterpenos/química , Viburnum/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/toxicidade , Linhagem Celular Tumoral , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Diterpenos/toxicidade , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Espectroscopia de Ressonância Magnética , Conformação Molecular , Ácido Oleanólico/isolamento & purificação , Ácido Oleanólico/farmacologia , Ácido Oleanólico/toxicidade , Folhas de Planta/química , Triterpenos/isolamento & purificação , Triterpenos/toxicidade
19.
J Asian Nat Prod Res ; 13(2): 105-10, 2011 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-21279873

RESUMO

Two new triterpenoids, ursa-12-sene-3ß,11ß-diol 3-O-palmitate (1) and ursa-12-sene-1ß,3ß,11α-triol 3-O-palmitate (2), were isolated from the 70% aqueous acetone extract of the aerial parts of Viburnum betulifolium, together with the artificial diene derivative of 2, ursa-12-dien-1ß,3ß-diol 3-O-palmitate (2a). Their structures were characterized by various spectroscopic methods, including 1D NMR, 2D NMR, and HR-ESI-MS.


Assuntos
Medicamentos de Ervas Chinesas/isolamento & purificação , Palmitatos/isolamento & purificação , Triterpenos/isolamento & purificação , Viburnum/química , Medicamentos de Ervas Chinesas/química , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Palmitatos/química , Triterpenos/química
20.
Chem Pharm Bull (Tokyo) ; 58(6): 868-71, 2010 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-20523003

RESUMO

Phytochemical investigation on the methanol extract of Brainea insignis led to the isolation of 16 phenolic compounds, including an unusual flavanol coupled with phenylpropyl and shikimic acid units, brainicin (1), and a new flavonol acylglycosides brainoside B (2). The structures of new compounds were elucidated on the basis of extensive spectroscopic analysis. Compounds 1-5 were evaluated for their cytotoxic effects. However, none of the compounds showed significant cytotoxic activity against the HL-60, A549, SMMC-7721, MCF-7, SW480 cell lines (IC(50) > 40 microM).


Assuntos
Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Citotoxinas/química , Citotoxinas/farmacologia , Gleiquênias/química , Fenóis/química , Fenóis/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Citotoxinas/isolamento & purificação , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Neoplasias/tratamento farmacológico , Fenóis/isolamento & purificação
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