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1.
Chem Pharm Bull (Tokyo) ; 68(1): 96-99, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-31902905

RESUMO

Chemical investigation of the aerial parts of Andrographis paniculata resulted in isolation of nine compounds, including a new ent-labdane diterpenoid, andrographic acid methyl ester (1), a new chalcone glucoside, pashanone glucoside (5), and seven known metabolites, andrograpanin (2), andrographolide (3), andropanolide (4), andrographidine A (6), andrographidine F (7), 6-epi-8-O-acetyl-harpagide (8), and curvifloruside F (9). Their chemical structures were elucidated based on comprehensive analyses of the spectroscopic data, including NMR and MS. Among the isolated compounds, andropanolide exerted cytotoxicity toward LNCaP, HepG2, KB, MCF7, and SK-Mel2 carcinoma cells, with IC50 values ranging from 31.8 to 45.9 µM. In addition, andropanolide significantly inhibited the overproduction of nitric oxide (NO) in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages, with an IC50 value of 13.4 µM.


Assuntos
Andrographis/química , Diterpenos/química , Flavonoides/química , Andrographis/metabolismo , Animais , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Humanos , Lipopolissacarídeos/toxicidade , Macrófagos/citologia , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Espectroscopia de Ressonância Magnética , Camundongos , Conformação Molecular , Óxido Nítrico/metabolismo , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/metabolismo , Células RAW 264.7
2.
J Asian Nat Prod Res ; 22(2): 193-200, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-30755033

RESUMO

Using various chromatographic separations, four steroids including one new C20 steroid namely dendrodoristerol (1), were isolated from the Vietnamese nudibranch mollusk Dendrodoris fumata. The structure elucidation was confirmed by combination of spectroscopic experiments including 1D and 2D NMR, HR QTOF MS, and CD. Compound 1 was found to exhibit significant in vitro cytotoxic activity against six human cancer cell lines as HL-60, KB, LU-1, MCF-7, LNCaP, and HepG2. In addition, 1 induced HL-60 cancer cell death by apoptosis and necrosis.

3.
Nat Prod Res ; 34(2): 261-268, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-30580613

RESUMO

A new [7.7]paracyclophane (1), together with eight known compounds (2-9), were isolated from a MeOH extract of the sea snail Planaxis sulcatus (Born, 1780). Their structures were elucidated by HR-ESI-MS and NMR techniques as well as comparison with those reported in literatures. The absolute configuration of metabolite 1 was determined using ECD spectroscopy. Among nine compounds, 1 exhibited significant cytotoxicity toward all eight cancer cells tested with IC50 values between 1.81 and 3.80 µg/mL.[Figure: see text].

4.
Nat Prod Res ; : 1-6, 2019 Dec 10.
Artigo em Inglês | MEDLINE | ID: mdl-31821052

RESUMO

In our search for anti-inflammatory constituents from Vietnamese plants, the methanolic extract of Helicteres viscida was found to exhibit inhibitory effect on LPS-induced NO production in RAW264.7 cells. Phytochemical investigation of this plant led to isolation of four sulphated flavones (1-4), including one new compound 5,3',4'-trihydroxy-7-methoxy-8-O-sulphate flavone (1), and two pregnane-type steroids (5 and 6), including one new compound 7-epi-heligenin B (5). Their structures were elucidated by 1D and 2D NMR as well as HR-QTOF-MS experiments. Among isolated compounds, heligenin B (6) exhibited potent inhibitory effect on LPS-induced NO production in RAW264.7 cells with IC50 of 1.23 ± 0.05 µM. The activity of 6 was comparable to that of the positive control cardamonin.

5.
Nat Prod Res ; : 1-8, 2019 Dec 02.
Artigo em Inglês | MEDLINE | ID: mdl-31790291

RESUMO

Three new triterpene saponins including two lupane-types and an ursane-type were isolated from the leaves of Trevesia palmata. Their structures were determined as 2α,3ß,23-trihydroxylup-20(29)-en-28-oic acid 3-O-α-L-arabinopyranoside (1), 2α,3ß,23-trihydroxylup-20(29)-en-28-oic acid 3-O-[α-L-arabinopyranoside]-28-O-[ß-D-glucopyranosyl] ester (2), and 2α,3ß,23-trihydroxyurs-12-en-28-oic acid 3-O-[α-L-arabinopyranoside]-28-O-[ß-D-glucopyranosyl(1→2)-ß-D-glucopyranosyl] ester (3) by analysis of their HR-ESI-MS, 1D and 2D NMR spectra. The 2α,3ß,23-trioxygenated pentacyclic triterpenes were uncommonly found in the nature. At concentration of 100 µM, compounds 1-3 inhibited NO production in LPS activated BV2 cells with inhibitory rates of 17.4 ± 1.8%, 33.1 ± 1.2%, and 11.7 ± 2.2%, respectively. But, they did not significantly inhibit yeast α-glucosidase activity.

6.
J Nat Prod ; 82(11): 3196-3200, 2019 Nov 22.
Artigo em Inglês | MEDLINE | ID: mdl-31646862

RESUMO

Two novel C19 terpenoids (1, 2) with an unprecedented carbon skeleton (A) were isolated from a Stelletta sp. sponge collected from Vietnamese waters. Their structures and absolute configurations were established by extensive NMR, MS, and ECD analyses together with quantum chemical modeling and biogenetic considerations. The probable pathways of biogenesis of 1 and 2 from isomalabaricane triterpenoids are discussed. Compounds 1 and 2 significantly increase the production of reactive oxygen species in murine peritoneal macrophages.

7.
Nat Prod Res ; : 1-7, 2019 Sep 11.
Artigo em Inglês | MEDLINE | ID: mdl-31507227

RESUMO

Two new pregnane glycosides, gyminosides A and B (1 and 2) and three known, tinctoroside B (3), tinctoroside C (4), and gymnepregoside F (5) were isolated from the leaves of Gymnema inodorum (Lour.) Decne. Their structures were elucidated by physical and chemical methods and comparing with those reported in the literature. All these compounds were evaluated for α-glucosidase assay. Compound 5 exhibited the most anti α-glucosidase activity with inhibitory percentage of 63.7 ± 3.9% at the concentration of 200 µM. Compounds 1-4 showed moderate anti α-glucosidase activity with inhibitory percentage ranging from 40.0 to 52.1%.

8.
Nat Prod Res ; : 1-7, 2019 Aug 12.
Artigo em Inglês | MEDLINE | ID: mdl-31402701

RESUMO

Sixteen sesquiterpenoids (1 - 16), including two new compounds namely saussucostusosides A and B (1 and 2), were isolated from the roots of Saussurea costus by various chromatographic separations. Their structures were elucidated by 1 D and 2 D NMR and HR-QTOF-MS experiments. Among isolated compounds, costunlide (6), 3ß-[4-hydroxymethacryloyloxy]-8α-hydroxycostunolide (10) and 11ß,13-dihydrozaluzanin C (16) exhibited potent inhibitory effects on LPS-induced NO production in RAW264.7 cells with IC50 values of 7.08 ± 0.34, 2.40 ± 0.06 and 5.55 ± 0.24 µM, respectively.

9.
Nat Prod Res ; : 1-5, 2019 Jul 19.
Artigo em Inglês | MEDLINE | ID: mdl-31322428

RESUMO

The MeOH extract of the Vietnamese octocoral Dendronephthya mucronata afforded four bicyclic lactones (1-4), including three new compounds namely dendronephthyones A-C (1-3), after subjecting it on various chromatographic separations. The structures of the isolated compounds were established by spectroscopic experiments including 1D, 2D NMR, CD and HR-QTOF-MS. In addition, compounds 1-4 were found to exhibit selective cytotoxicity against the HeLa human cancer cell line with IC50 values of 32.48 ± 2.15, 30.12 ± 1.86, 35.14 ± 1.57 and 14.45 ± 1.34 µM, respectively.

10.
Nat Prod Res ; : 1-6, 2019 Jan 24.
Artigo em Inglês | MEDLINE | ID: mdl-30676065

RESUMO

Using various chromatographic separations, three new acylated flavonoid glycosides, namely barringosides G-I (1-3), were isolated from the water-soluble extract of Barringtonia racemosa branches and leaves. The structure elucidation was performed by extensive analysis of the 1D and 2D NMR and HR-QTOF-MS data. Of the isolated compounds, barringoside I (3) showed moderate inhibitory effects on LPS-induced NO production in RAW264.7 cells with an IC50 of 52.48 ± 1.04 µM.

11.
Nat Prod Res ; 33(3): 400-406, 2019 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-29595068

RESUMO

A new stereoisomer Meso-araguspongine C together with nine reported macrocyclic bis-quinolizidine alkaloids araguspongines A, C, E, L, N-P, petrosin, and petrosin A were isolated from marine sponge Xestospongia muta. Stereochemistry of meso-araguspongine C (2) and araguspongines N-P (3-5) were established by their NMR data and conformational analyses. Both araguspongine C (1) and meso-araguspongine C (2) exhibited great cytotoxic activity towards HepG-2, HL-60, LU-1, MCF-7, and SK-Mel-2 human cancer cells (IC50 in the range of 0.43-1.02 µM). At a concentration of 20 µM, isolated compounds (1-10) also showed modest inhibitory effects (from 7.6 to 40.8%) on the NO production in LPS activated RAW264.7 macrophages.


Assuntos
Alcaloides/isolamento & purificação , Quinolizidinas/isolamento & purificação , Quinolizinas/isolamento & purificação , Xestospongia/química , Alcaloides/química , Animais , Linhagem Celular Tumoral , Humanos , Lipopolissacarídeos , Compostos Macrocíclicos/isolamento & purificação , Camundongos , Conformação Molecular , Óxido Nítrico/antagonistas & inibidores , Óxido Nítrico/biossíntese , Células RAW 264.7
12.
Nat Prod Res ; 33(5): 628-634, 2019 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-29143535

RESUMO

Using various chromatographic separations, sixteen compounds, including one new triterpene saponin named aegicoroside A (1), were isolated from the leaves of the Vietnamese mangrove Aegiceras corniculatum. Their structures were determined by spectroscopic methods such as 1D and 2D NMR and HR-ESI-MS. The cytotoxic activities of the isolated compounds against MCF7 (breast), HCT116 (colon), B16F10 (melanoma), and A549 (adenocarcinoma) cancer cell lines were also evaluated. Strong cytotoxicity was observed for sakurasosaponin (2) against all four cancer cell lines and for sakurasosaponin methyl ester (3) against MCF7, A549, and HCT116 cell lines with IC50 values ranging from 2.89 ± 0.02 to 9.86 ± 0.21 µM.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Primulaceae/química , Saponinas/farmacologia , Triterpenos/farmacologia , Células A549 , Antineoplásicos Fitogênicos/isolamento & purificação , Ensaios de Seleção de Medicamentos Antitumorais , Células HCT116 , Humanos , Células MCF-7 , Melanoma Experimental , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Folhas de Planta/química , Saponinas/isolamento & purificação , Triterpenos/isolamento & purificação , Vietnã
13.
Chem Pharm Bull (Tokyo) ; 66(11): 1023-1026, 2018 Nov 01.
Artigo em Inglês | MEDLINE | ID: mdl-30135325

RESUMO

Seven anthraquinones including two new compounds namely capillasterquinones A and B (1 and 2) and one new butenolide namely capillasterolide (8) were isolated and structurally elucidated from the crinoid Capillaster multiradiatus. The inhibitory effect of compounds 1-8 on lipopolysaccharide (LPS)-induced nitric oxide (NO) production as well as inhibition of 1 on expressions of inducible nitric oxide synthase (iNOS) and cyclooxygenase 2 (COX-2) proteins in RAW264.7 cells were also evaluated. As the obtained results, capillasterquinone A (1) showed strong NO production inhibitory activity with an IC50 of 5.89±0.11 µM. In addition, compound 1 reduced the LPS-induced iNOS and COX-2 expressions in a dose-dependent manner.


Assuntos
4-Butirolactona/análogos & derivados , Antraquinonas/farmacologia , Equinodermos/química , Inibidores Enzimáticos/farmacologia , 4-Butirolactona/química , 4-Butirolactona/isolamento & purificação , 4-Butirolactona/farmacologia , Animais , Antraquinonas/química , Antraquinonas/isolamento & purificação , Ciclo-Oxigenase 2/metabolismo , Relação Dose-Resposta a Droga , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Lipopolissacarídeos/antagonistas & inibidores , Lipopolissacarídeos/farmacologia , Camundongos , Estrutura Molecular , Óxido Nítrico/antagonistas & inibidores , Óxido Nítrico/metabolismo , Óxido Nítrico Sintase Tipo II/antagonistas & inibidores , Óxido Nítrico Sintase Tipo II/metabolismo , Células RAW 264.7 , Relação Estrutura-Atividade
14.
Steroids ; 138: 57-63, 2018 10.
Artigo em Inglês | MEDLINE | ID: mdl-30018002

RESUMO

Using various chromatographic separations, seventeen steroids including seven new compounds, verrucorosteroids A-F (1-6) and verrucorosterone (7), were isolated from the Vietnamese gorgonian Verrucella corona. Their structures were elucidated by spectroscopic analysis, including HR QTOF MS, 1D and 2D NMR. Among isolates, verrucorosterone (7), 5,6α-epoxy-3ß-hydroxy-(22E)-ergosta-8,22-dien-7-one (14), and 5,6α-epoxy-3ß-hydroxy-(22E)-ergosta-8(14),22-dien-7-one (15) showed significant cytotoxicity (IC50 values ranging from 12.32 ±â€¯1.47 to 33.77 ±â€¯1.28 µM) against eight human cancer cell lines as LNCaP (prostate cancer), HepG2 (hepatoma cancer), KB (epidermoid carcinoma), MCF-7 (breast cancer), SK-Mel2 (melanoma), HL-60 (acute leukemia), LU-1 (lung cancer), and SW480 (colon adenocarcinoma).


Assuntos
Antozoários/química , Antineoplásicos/química , Antineoplásicos/farmacologia , Animais , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Células HL-60 , Humanos , Estrutura Molecular , Esteroides
15.
Molecules ; 23(5)2018 05 03.
Artigo em Inglês | MEDLINE | ID: mdl-29751557

RESUMO

Two new polyhydroxysteroidal glycosides, anthenosides A1 (1) and A2 (2), and one previously known steroidal glycoside anthenoside A (3) were isolated from extract of the tropical starfish Anthenea aspera. Structures of 1⁻3 were determined by analysis of the spectroscopic data as well as chemical transformations. As a result, the structure of anthenoside A has been revised and the structures of 1 and 2 were established. Glycosides 1⁻3 contain a 2-acetamido-2-deoxy-4-O-methyl-ß-d-glucopyranosyl residue, found in the starfish steroidal glycosides for the first time. All the isolated compounds slightly inhibited cell viability of human cancer T-47D cells and did not show cytotoxic effects against RPMI-7951 cells. Glycoside 1 slightly inhibited colony formation of human cancer RPMI-7951 cells by 16% while compound 2 decreased the number of colonies of T-47D cells by 40%.


Assuntos
Glicosídeos/química , Monossacarídeos/química , Estrelas-do-Mar/química , Esteroides/química , Animais , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Humanos , Hidrólise , Espectroscopia de Ressonância Magnética , Estrutura Molecular
16.
Nat Prod Res ; 32(9): 1039-1043, 2018 May.
Artigo em Inglês | MEDLINE | ID: mdl-28934865

RESUMO

Using various chromatographic separations, three triterpene tetraglycosides (1-3), including one new compound, namely stichorrenoside E (1) along with thelenotoside B (2) and deacetyl thelenotoside B (3), were isolated from the MeOH extract of the Vietnamese sea cucumber Stichopus horrens. Their structures were confirmed by spectroscopic experiments, such as 1D and 2D NMR and HR-ESI-MS. Deacetylated thelenotoside B (3) is firstly isolated as a natural product. Among these compounds, thelenotoside B (2) showed strong cytotoxicities against five human cancer cell lines as HepG2, KB, LNCaP, MCF7 and SK-Mel2 with the IC50 values from 0.95 ± 0.08 to 1.90 ± 0.13 µM, whereas stichorrenoside E (1) and deacetyl thelenotoside B (3) exhibited significant activities with the IC50 values from 6.87 ± 0.25 to 11.62 ± 1.05 µM.


Assuntos
Antineoplásicos/química , Antineoplásicos/farmacologia , Glicosídeos/química , Stichopus/química , Triterpenos/química , Animais , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais , Glicosídeos/farmacologia , Células Hep G2 , Humanos , Concentração Inibidora 50 , Células MCF-7 , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Espectrometria de Massas por Ionização por Electrospray , Triterpenos/farmacologia
17.
J Asian Nat Prod Res ; 20(8): 752-756, 2018 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-28942674

RESUMO

Two new guaiane sesquiterpene lactones, vulgarolides A and B (1 and 2), were isolated from Artemisia vulgaris aerial parts using various chromatographic separations. The structure elucidation was performed by combination of spectroscopic experiments including 1D and 2D NMR, HR ESI MS, and CD. Their in vitro cytotoxic activities against five human cancer cell lines were also evaluated using SRB method.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Artemisia/química , Sesquiterpenos de Guaiano/química , Sesquiterpenos de Guaiano/farmacologia , Linhagem Celular Tumoral , Dicroísmo Circular , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Espectroscopia de Ressonância Magnética , Modelos Moleculares , Componentes Aéreos da Planta/química , Espectrometria de Massas por Ionização por Electrospray
18.
Nat Prod Res ; 32(15): 1798-1802, 2018 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-29144177

RESUMO

Using various chromatographic separations, eight sesquiterpenoids (1-8), including one new compound 3ß,5α-dihydroxyeudesma-4(15),11-diene (1), were isolated from the MeOH extract of the Vietnamese soft coral Sinularia erecta. The structure elucidation was confirmed by spectroscopic experiments including 1D and 2D NMR and HR-ESI-MS. The cytotoxic activities against three human cancer cell lines (A-549, HeLa and PANC-1) of all isolated compounds were evaluated by MTT-based colorimetric assays. Compound 1 exhibited selective cytotoxicity against the A549 cell line with IC50 of 14.79 ± 0.91 µM.


Assuntos
Antozoários/química , Antineoplásicos/farmacologia , Sesquiterpenos de Eudesmano/farmacologia , Sesquiterpenos/farmacologia , Animais , Antineoplásicos/química , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais , Células HeLa , Humanos , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Sesquiterpenos/química , Sesquiterpenos de Eudesmano/química , Sesquiterpenos de Guaiano
19.
Nat Prod Res ; 32(1): 54-59, 2018 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-28511566

RESUMO

Five polar steroid derivatives, including one new glycosylated polyhydroxysteroid namely polyacanthoside A (1), were isolated from the water-soluble materials from the MeOH extract of the Vietnamese starfish Astropecten polyacanthus using various chromatographic separations. The structure elucidation was confirmed by spectroscopic experiments such as HR-ESI-MS, 1D and 2D NMR. Among the isolated compounds, (20R,24S)-3ß,6α,8,15ß,24-pentahydroxy-5α-cholestane (3) showed significant cytotoxic effect against five human cancer cell lines as HepG2, KB, LNCaP, MCF7 and SK-Mel2 with the IC50 values from 18.03 ± 2.63 to 21.59 ± 3.23 µM.


Assuntos
Antineoplásicos/farmacologia , Estrelas-do-Mar/química , Esteroides/química , Esteroides/farmacologia , Animais , Antineoplásicos/química , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais/métodos , Humanos , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Espectrometria de Massas por Ionização por Electrospray
20.
Biomed Res Int ; 2018: 3120972, 2018.
Artigo em Inglês | MEDLINE | ID: mdl-30643798

RESUMO

Degalactotigonin (1) and three other steroidal compounds solasodine (2), O-acetyl solasodine (3), and soladulcoside A (4) were isolated from the methanolic extract of Solanum nigrum, and their chemical structures were elucidated by spectroscopic analyses. The isolated compounds were evaluated for cytotoxic activity against human pancreatic cancer cell lines (PANC1 and MIA-PaCa2) and lung cancer cell lines (A549, NCI-H1975, and NCI-H1299). Only degalactotigonin (1) showed potent cytotoxicity against these cancer cell lines. Compound 1 induced apoptosis in PANC1 and A549 cells. Further study on its mechanism of action in PANC1 cells demonstrated that 1 significantly inhibited EGF-induced proliferation and migration in a concentration-dependent manner. Treatment of PANC1 cells with degalactotigonin induced cell cycle arrest at G0/G1 phase. Compound 1 induced downregulation of cyclin D1 and upregulation of p21 in a time- and concentration-dependent manner and inhibited EGF-induced phosphorylation of EGFR, as well as activation of EGFR downstream signaling molecules such as Akt and ERK.


Assuntos
Apoptose/efeitos dos fármacos , Pontos de Checagem do Ciclo Celular/efeitos dos fármacos , Sistema de Sinalização das MAP Quinases/efeitos dos fármacos , Neoplasias Pancreáticas , Saponinas/farmacologia , Solanum nigrum/química , Esteroides/farmacologia , Células A549 , Receptores ErbB/metabolismo , Humanos , Neoplasias Pancreáticas/tratamento farmacológico , Neoplasias Pancreáticas/metabolismo , Neoplasias Pancreáticas/patologia , Proteínas Proto-Oncogênicas c-akt/metabolismo , Saponinas/química , Esteroides/química
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