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1.
Biochem Pharmacol ; 180: 114175, 2020 10.
Artigo em Inglês | MEDLINE | ID: mdl-32717226

RESUMO

BACKGROUND: Eugenol, a common phenylpropanoid derivative found in different plant species, has well-described anti-inflammatory effects associated with the development of occupational hypersensitive asthma. Dehydrodieugenol, a dimeric eugenol derivative, exhibits anti-inflammatory and antioxidant activities and can be found in the Brazilian plant species Nectandra leucantha (Lauraceae). The biological effects of dehydrodieugenol on lung inflammation remain unclear. PURPOSE: This study aimed to investigate the effects of eugenol and dehydrodieugenol isolated from N. leucantha in an experimental model of asthma. METHODS: In the present work, the toxic effects of eugenol and dehydrodieugenol on RAW 264.7 cells and their oxidant and inflammatory effects before lipopolysaccharide (LPS) exposure were tested. Then, male BALB/c mice were sensitized with ovalbumin through a 29-day protocol and treated with vehicle, eugenol, dehydrodieugenol or dexamethasone for eight days beginning on the 22nd day until the end of the protocol. Lung function; the inflammatory profile; and the protein expression of ERK1/2, JNK, p38, VAChT, STAT3, and SOCS3 in the lung were evaluated by immunoblotting. RESULTS: Eugenol and dehydrodieugenol were nontoxic to cells. Both compounds inhibited NO release and the gene expression of IL-1ß and IL-6 in LPS-stimulated RAW 264.7 cells. In OVA-sensitized animals, dehydrodieugenol reduced lung inflammatory cell numbers and the lung concentrations of IL-4, IL-13, IL-17, and IL-10. These anti-inflammatory effects were associated with inhibition of the JNK, p38 and ERK1/2, VAChT and STAT3/SOCS3 pathways. Moreover, treatment with dehydrodieugenol effectively attenuated airway hyperresponsiveness. CONCLUSION: The obtained data demonstrate, for the first time, that dehydrodieugenol was more effective than eugenol in counteracting allergic airway inflammation in mice, especially its inhibition of the JNK, p38 and ERK1/2, components of MAPK pathway. Therefore, dehydrodieugenol can be considered a prototype for the development of new and effective agents for the treatment of asthmatic patients.


Assuntos
Asma/tratamento farmacológico , Eugenol/análogos & derivados , Lignanas/uso terapêutico , Sistema de Sinalização das MAP Quinases/efeitos dos fármacos , Pneumonia/tratamento farmacológico , Fator de Transcrição STAT3/antagonistas & inibidores , Proteína 3 Supressora da Sinalização de Citocinas/antagonistas & inibidores , Animais , Asma/metabolismo , Relação Dose-Resposta a Droga , Eugenol/isolamento & purificação , Eugenol/farmacologia , Eugenol/uso terapêutico , Lauraceae , Lignanas/isolamento & purificação , Lignanas/farmacologia , Sistema de Sinalização das MAP Quinases/fisiologia , Masculino , Camundongos , Camundongos Endogâmicos BALB C , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Extratos Vegetais/uso terapêutico , Pneumonia/metabolismo , Células RAW 264.7 , Fator de Transcrição STAT3/metabolismo , Proteína 3 Supressora da Sinalização de Citocinas/metabolismo
2.
J Chromatogr A ; 1625: 461238, 2020 Aug 16.
Artigo em Inglês | MEDLINE | ID: mdl-32709314

RESUMO

In the present study, a novel strategy based on unidirectional freezing and atom transfer radical polymerization combined with activator regenerated by electron transfer (ARGET-ATRP) was applied to synthesizing orderly macroporous monolithic column with restricted-access (RA) property in a 1000µL pipette tip. The RA column was composed of hydrophobic inner column (poly(styrene-co-ethylene glycol dimethacrylate) and hydrophilic outer layer (poly-hydroxyethyl methacrylate chain) which was grafted on the hydrophobic surface by means of the second ARGET-ATRP reaction. The as-prepared RA monolithic tip was connected to a 2mL syringe for directly extracting magnolol and honokiol from rat plasma just by manually pushing operation. The surface morphology and chemical composition of the column were characterized by scanning electronic microscope, infrared spectroscopy and X-ray photoelectron spectroscopy respectively. The determined results of evaluation experiments based on the optimized solid phase extraction conditions showed that the RA column possessed good protein exclusion power, extraction recovery and reusability. The constructed RA-SPE-HPLC/UV method for simultaneously analyzing magnolol and honokiol in rat plasma was validated with quality control (QC) samples at four concentration levels. Good precision (RSDs, 3.39~11.16%) and acceptable accuracy (relative recoveries, 89.52%~108.42%) were obtained for intra- and inter-day assays. The determined results of real rat plasma as well as the standard-addition samples demonstrated the developed method with good accuracy and precision. It can be extrapolated from the experimental results that this simple and cost-efficient RA-SPE method is also suitable for directly extracting other hydrophobic constituents in biological body fluid for therapeutic drug monitoring or pharmacokinetic study.


Assuntos
Compostos de Bifenilo/sangue , Cromatografia Líquida de Alta Pressão/métodos , Lignanas/sangue , Metacrilatos/química , Polietilenoglicóis/química , Animais , Compostos de Bifenilo/isolamento & purificação , Compostos de Bifenilo/normas , Cromatografia Líquida de Alta Pressão/normas , Congelamento , Interações Hidrofóbicas e Hidrofílicas , Lignanas/isolamento & purificação , Lignanas/normas , Controle de Qualidade , Ratos , Reprodutibilidade dos Testes , Extração em Fase Sólida
3.
Chem Biodivers ; 17(4): e2000035, 2020 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-32141193

RESUMO

Fifteen constituents, including one new lignan (schisandroside E) and one new terpenoid (schisandenoid A) as well as nine known lignans and four known terpenoids, were isolated from Schisandra chinensis leaves. The structures of schisandroside E and schisandenoid A were established by entirely meticulous spectroscopic analysis (NMR, MS, CD, IR and UV). All compounds were tested for cytotoxicity against MGC-803, Caco-2 and Ishikawa cell lines. Some compounds showed strong cytotoxicity against these three cancer cell lines with IC50 <1 µm.


Assuntos
Lignanas/química , Schisandra/química , Terpenos/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Humanos , Lignanas/isolamento & purificação , Lignanas/farmacologia , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Conformação Molecular , Extratos Vegetais/química , Folhas de Planta/química , Folhas de Planta/metabolismo , Schisandra/metabolismo , Terpenos/isolamento & purificação , Terpenos/farmacologia
4.
Sci Rep ; 10(1): 5467, 2020 03 25.
Artigo em Inglês | MEDLINE | ID: mdl-32214193

RESUMO

Neolignan licarin A (1) was isolated from leaves of Nectandra oppositifolia (Lauraceae) and displayed activity against trypomastigote forms of the etiologic agent of American trypanosomiasis, Trypanosoma cruzi. Aiming for the establishment of SAR, five different compounds (1a - 1e) were prepared and tested against T. cruzi. The 2-allyl derivative of licarin A (1d) exhibited higher activity against trypomastigotes of T. cruzi (IC50 = 5.0 µM and SI = 9.0), while its heterocyclic derivative 1e displayed IC50 of 10.5 µM and reduced toxicity against NCTC cells (SI > 19.0). However, these compounds presented limited oral bioavailability estimation (<85%, Papp <1.0 × 10-6 cm/s) in parallel artificial membrane permeability assays (PAMPA) due to excessive lipophilicity. Based on these results, different simplified structures of licarin A were designed: vanillin (2), vanillyl alcohol (3), isoeugenol (4), and eugenol (5), as well as its corresponding methyl (a), acetyl (b), O-allyl (c), and C-allyl (d) analogues. Vanillin (2) and its acetyl derivative (2b) displayed expressive activity against intracellular amastigotes of T. cruzi with IC50 values of 5.5 and 5.6 µM, respectively, and reduced toxicity against NCTC cells (CC50 > 200 µM). In addition, these simplified analogues showed a better permeability profile (Papp > 1.0 × 10-6 cm/s) on PAMPA models, resulting in improved drug-likeness. Vanillyl alcohol acetyl derivative (3b) and isoeugenol methyl derivative (4a) displayed activity against the extracellular forms of T. cruzi (trypomastigotes) with IC50 values of 5.1 and 8.8 µM respectively. Based on these results, compounds with higher selectivity index against extracellular forms of the parasite (1d, 1e, 3d, and 4a) were selected for a mechanism of action study. After a short incubation period (1 h) all compounds increased the reactive oxygen species (ROS) levels of trypomastigotes, suggesting cellular oxidative stress. The ATP levels were increased after two hours of incubation, possibly involving a high energy expenditure of the parasite to control the homeostasis. Except for compound 4a, all compounds induced hyperpolarization of mitochondrial membrane potential, demonstrating a mitochondrial imbalance. Considering the unique mitochondria apparatus of T. cruzi and the lethal alterations induced by structurally based on licarin A, these compounds are interesting hits for future drug discovery studies in Chagas disease.


Assuntos
Antiparasitários/isolamento & purificação , Antiparasitários/farmacologia , Produtos Biológicos/isolamento & purificação , Doença de Chagas/tratamento farmacológico , Lauraceae/química , Lignanas/isolamento & purificação , Lignanas/farmacologia , Folhas de Planta/química , Tripanossomicidas/isolamento & purificação , Tripanossomicidas/farmacologia , Trypanosoma cruzi/efeitos dos fármacos , Animais , Antiparasitários/síntese química , Produtos Biológicos/síntese química , Produtos Biológicos/farmacologia , Descoberta de Drogas , Lignanas/síntese química , Estresse Oxidativo/efeitos dos fármacos , Fitoterapia , Espécies Reativas de Oxigênio/metabolismo , Relação Estrutura-Atividade , Tripanossomicidas/síntese química , Trypanosoma cruzi/metabolismo
5.
PLoS One ; 15(2): e0226901, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32084140

RESUMO

Alkaline ionic liquid aqueous solutions were used to extract biphenyl cyclooctene lignans derivatives, and hydrolyze to the free-state biphenyl cyclooctene lignans simultaneously from Schisandra chinensis by microwave-assisted heating. The hydrogen bonds formatted between ionic liquid and water molecular attacks the amorphous region of cellulose. Selective heating by microwave produce the more polar regions, which results in swelling and fragmentation of raw materials near the hot spots. Therefore, ionic liquid-microwave-assisted extraction method of free-state biphenyl cyclooctene lignans was set up. The solid residue after treatment was characterized by infrared spectroscopy and scanning electron microscopy, which showed that cellulose, hemicellulose, and lignin were removed partially. The water content of ionic liquid solution affected its viscosity and diffusivity, and in turns the extraction efficiency of lignans. The IL solutions with different mole fractions of IL were detected by FTIR and Raman spectroscopy, the result shows that IL solutions with higher water contents (>0.6) won't form clusters. The optimum hydrolysis conditions were 0.2 g of ionic liquid catalyst per 5.0 g of S. chinensis fruits, a microwave irradiation power of 600 W, and heating time of 12 min, which gave a yield of free-state biphenyl cyclooctene lignans of 4.12±0.37 mg g-1. Besides, a hydrolysis mechanism of ester-bond biphenyl cyclooctene lignans and decreasing "biomass recalcitrance effect" by ionic liquid microwave-assisted method was proposed.


Assuntos
Compostos de Bifenilo/isolamento & purificação , Ciclo-Octanos/isolamento & purificação , Frutas/química , Lignanas/isolamento & purificação , Extratos Vegetais/química , Schisandra/metabolismo , Hidrólise , Líquidos Iônicos/química , Campos Magnéticos , Micro-Ondas , Água/química
6.
Org Lett ; 22(4): 1380-1384, 2020 02 21.
Artigo em Inglês | MEDLINE | ID: mdl-31999125

RESUMO

(±)-Melipatulinones A-C (1-3), three unique enantiomeric pairs of lignan-phloroglucinol hybrids along with the biogenetically related compound melipatulignan A (4), were isolated from the leaves of Melicope patulinervia. Melipatulinones A (1) and B (2) share a novel spiro[hydrobenzofuran-2,3'-furan] 5/5/6 tricyclic ring system, while melipatulinone C (3) features an unprecedented spiro[cyclopenta[b]hydrofuran-2,3'-furan] 5/5/5 tricyclic framework. Their structures were determined by spectroscopic methods, electronic circular dichroism (ECD) calculations, and X-ray diffraction. Compounds 1-3 exhibited a pancreatic lipase inhibitory effect.


Assuntos
Inibidores Enzimáticos/farmacologia , Lignanas/farmacologia , Lipase/antagonistas & inibidores , Rutaceae/química , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Lignanas/química , Lignanas/isolamento & purificação , Lipase/metabolismo , Conformação Molecular , Pâncreas/enzimologia , Folhas de Planta/química , Estereoisomerismo
7.
Fitoterapia ; 140: 104440, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31783131

RESUMO

Praxelis clematidea (Asteraceae) is a harmful invasive alien weed, which cause huge destruction of ecological environment and economic losses. In this study, 22 compounds were isolated and purified from the whole plant of P. clematidea, including 4 benzofurans (1-4), 18 lignans (5-22), and five of which were new compounds (1, 3, 4, 9, 10). Various spectroscopic analysis methods were utilized to elucidate their chemical structures. The inhibitory effects of the isolated compounds on NO release from BV-2 microglia cells induced by LPS were investigated. Most of the compounds showed pronounced anti-neuroinflammatory activity. Additionally, the new compounds 3, 4 and 10 exhibited significant anti-neuroinflammatory effects, and the biological activities were further confirmed by immunoblotting, quantitative PCR and immunofluorescence staining assays. As results, this study provided a new idea for the further treatment and utilization of P. clematidea as anti-neuroinflammatory agents in health-benefit products.


Assuntos
Asteraceae/química , Benzofuranos/farmacologia , Lignanas/farmacologia , Microglia/efeitos dos fármacos , Animais , Benzofuranos/isolamento & purificação , Linhagem Celular , China , Lignanas/isolamento & purificação , Camundongos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia
8.
Nat Prod Res ; 34(11): 1515-1520, 2020 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-30388890

RESUMO

Chemical investigation of Penthorum chinense resulted in the isolation of two neolignans (1 and 2) together with two known compounds (3 and 4). The structures of compounds 1 and 2 were determined by interpretation of spectroscopic data, and absolute configurations were made based on electronic circular dichroism (ECD). All compounds were evaluated for their antiproliferative activity on hepatic stellate T6 cells (HSC-T6 cells), and 1 and 2 showed moderate activity with IC50 values of 15.3 and 10.1 µM, respectively.


Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Células Estreladas do Fígado/efeitos dos fármacos , Lignanas/isolamento & purificação , Extratos Vegetais/química , Plantas Medicinais/química , Antineoplásicos Fitogênicos/farmacologia , Dicroísmo Circular , Humanos , Concentração Inibidora 50 , Lignanas/química , Lignanas/farmacologia , Estrutura Molecular
9.
Nat Prod Res ; 34(6): 816-822, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-30398365

RESUMO

The chemical constituents of Cupressus macrocarpa were investigated. A new neolignan glycoside (1) in addition to nine known compounds were isolated. The acetylcholinesterase (AChE) inhibitory activity and antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) of different fractions and isolates of C. macrocarpa were evaluated. The light petroleum fraction showed the highest activity in both assays with IC50 value of 88.79 µg/ml and 152.58 µg/ml for the AChE inhibitory activity and MRSA antibacterial activities, respectively. Weak to moderate activity were detected for the isolated compounds.


Assuntos
Antibacterianos/isolamento & purificação , Inibidores da Colinesterase/isolamento & purificação , Cupressus/química , Antibacterianos/farmacologia , Inibidores da Colinesterase/farmacologia , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Lignanas/isolamento & purificação , Lignanas/farmacologia , Staphylococcus aureus Resistente à Meticilina/efeitos dos fármacos , Extratos Vegetais/química , Folhas de Planta/química
10.
Nat Prod Res ; 34(4): 456-463, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-30445834

RESUMO

The phytochemical investigation on the twigs and leaves of Archidendron clypearia (Jack) I.C.N. led to the isolation of three pairs of furolactone-type lignans enantiomers, including a pair of new compounds (1R,5S,6S)-Kachiranol (1a) and (1S,5R,6R)-Kachiranol (1b) and four known compounds (2a/2b and 3a/3b). Separation of the furolactone-type lignans enantiomeric mixtures was achieved using chiral HPLC for the first time. Their structures were determined by spectroscopic analysis and comparison between the experimental and calculated electronic circular dichroism (ECD) spectra. All optical pure compounds were evaluated for their inhibitory effects on ß-amyloid aggregation by ThT assay. Among them, the inhibitory activity of the compound 1b (71.1%) was higher than the positive control (61.0%) and other compounds. In addition, molecular dynamics and molecular docking were employed to explore the binding relationship between the ligand and the receptor.


Assuntos
Fabaceae/química , Lignanas/química , Compostos Fitoquímicos/análise , Agregação Patológica de Proteínas/tratamento farmacológico , Peptídeos beta-Amiloides/efeitos dos fármacos , Dicroísmo Circular , Lignanas/isolamento & purificação , Lignanas/farmacologia , Simulação de Acoplamento Molecular , Estrutura Molecular , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/uso terapêutico , Agregação Patológica de Proteínas/prevenção & controle , Estereoisomerismo
11.
Nat Prod Res ; 34(6): 823-829, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-30557059

RESUMO

Two new lignans mubezhisol (1) and mubezhisal (2), together with twenty six known compounds (3-28) were isolated from water-soluble fraction from the semens of Momordica cochinchinensis. In the subsequent action evaluation, four saponins (4, 6, 13, 27), six lignans (1, 2, 16, 17, 22, 23), and one naphthoquinone (24) exhibited the significant cytotoxicity. The results indicated that various saponins and lignans were mainly responsible for the antitumor activities of Momordicae Semen.


Assuntos
Antineoplásicos/isolamento & purificação , Lignanas/farmacologia , Momordica/química , Saponinas/farmacocinética , Antineoplásicos/química , Antineoplásicos/farmacologia , Lignanas/isolamento & purificação , Extratos Vegetais/química , Saponinas/isolamento & purificação , Saponinas/farmacologia , Sementes/química , Solubilidade , Água
12.
Nat Prod Res ; 34(16): 2276-2282, 2020 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-30580585

RESUMO

A new lignan, named oleralignan (1) and three known componds (+)-syringaresinol (2), (+)-lirioresinol A (3) and monomethyl 3,3',4,4'-tetrahydroxy-δ-truxinate (4) were isolated from the P. oleracea for the first time. The compound (1) were identified by 1D, 2D NMR spectroscopic methods and high resolution electrospray ionization time-of-flight mass spectrometry. In addition, it was found that the four lignans presented the scavenging activities in 1,1-diphenyl-2-picryl-hydrazyl (DPPH) radical quenching assay more than that of hydroxyl anisole (BHA). [Formula: see text].


Assuntos
Antioxidantes/farmacologia , Lignanas/farmacologia , Portulaca/química , Antioxidantes/química , Antioxidantes/isolamento & purificação , Depuradores de Radicais Livres/isolamento & purificação , Depuradores de Radicais Livres/farmacologia , Furanos/isolamento & purificação , Lignanas/isolamento & purificação , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Espectrometria de Massas por Ionização por Electrospray/métodos
13.
Nat Prod Res ; 34(2): 225-232, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-30580619

RESUMO

One new aryldihydronaphthalene-type lignan (1) together with eight known lignans (2-4, 7-11) as well as two caffeic-acid dimers (5, 6) were isolated from an ethanol extract of the whole plant of Corispermum mongolicum Iljin (Chenopodiaceae). The chemical structures of these compounds were determined from 1D and 2D NMR and HR-ESI-MS spectra, and results were compared with data from the literature. This study is the first demonstration of nine compounds (2 and 4-11) isolated from the Chenopodiaceae family, with one of these (3) from the genus Corispermum. Anti-inflammatory effects of the isolated compounds were evaluated in terms of inhibition of production of nitric oxide, tumour necrosis factor-α, and interleukin-6 in lipopolysaccharide-induced RAW 264.7 cells.


Assuntos
Anti-Inflamatórios/isolamento & purificação , Chenopodiaceae/química , Lignanas/isolamento & purificação , Extratos Vegetais/química , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Chenopodiaceae/metabolismo , Interleucina-6/biossíntese , Lignanas/química , Lignanas/farmacologia , Lipopolissacarídeos , Camundongos , Estrutura Molecular , Óxido Nítrico/antagonistas & inibidores , Óxido Nítrico/biossíntese , Células RAW 264.7 , Fator de Necrose Tumoral alfa/biossíntese , Fator de Necrose Tumoral alfa/efeitos dos fármacos
14.
Nat Prod Res ; 34(12): 1756-1762, 2020 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-30580629

RESUMO

Phytochemical investigation on the pericarps of Illicium difengpi lead to the isolation and structure elucidation of a new sesquiterpene, sesquicaranoic acid C (1), a new neolignan, difengpiol C (2), and 10 known compounds. The structures and absolute configurations of two new compounds were determined by a combination of NMR and CD spectroscopic analyses. All isolates were evaluated for their inhibitory effects on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 cells.


Assuntos
Anti-Inflamatórios/isolamento & purificação , Illicium/química , Compostos Fitoquímicos/farmacologia , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Lignanas/química , Lignanas/isolamento & purificação , Lignanas/farmacologia , Lipopolissacarídeos , Camundongos , Estrutura Molecular , Óxido Nítrico/antagonistas & inibidores , Óxido Nítrico/biossíntese , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Extratos Vegetais/química , Células RAW 264.7 , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia
15.
Nat Prod Res ; 34(3): 329-334, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-30587031

RESUMO

A new dibenzocyclooctdiene (1), and a new eupodienone (2) type lignans were isolated along with five known analogues from the whole plant of Gymnotheca involucrata Pei. The structures of the new compounds were elucidated on the basis of detailed spectroscopic analysis. Bioassay results showed that compounds 1 and 2 exhibited no antimicrobial activity against four Gram-positive bacterial strains and four Gram-negative bacteria at the concentration of 1 mg/mL.


Assuntos
Lignanas/isolamento & purificação , Saururaceae/química , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Positivas/efeitos dos fármacos , Lignanas/química , Estrutura Molecular , Análise Espectral/métodos
16.
Nat Prod Res ; 34(3): 390-397, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-30600696

RESUMO

Twenty-seven compounds, including a new diarypropane and two new lignans were isolated from the twigs and leaves of Endocomia macrocoma. Their structures were elucidated by spectroscopic analysis. Cytotoxicity evaluation of the new compounds against five human tumor lines showed no inhibitory effects.[Formula: see text].


Assuntos
Lignanas/isolamento & purificação , Myristicaceae/química , Propano/isolamento & purificação , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Lignanas/química , Lignanas/farmacologia , Estrutura Molecular , Extratos Vegetais/química , Folhas de Planta/química , Propano/química , Propano/farmacologia
17.
Nat Prod Res ; 34(3): 359-368, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-30600708

RESUMO

Phytochemical investigation of the roots of Solanum melongena L. resulted in the isolation of ten terpenes and sixteen lignans, including a new triterpene saponin, officinoterpenoside E (1) and twenty-five known compounds (2-26). All compounds were firstly isolated from S. melongena except 2, 13, 21, 22. The structures of these compounds were determined by 1 D and 2 D NMR spectra referring to the literatures, together with high-resolution mass spectrometric analysis. All compounds were evaluated for the cytotoxicity against three cancer cell lines (HepG2, Hela, and MCF-7) in vitro. The results showed that compounds 1, 6, 20, 25 and 26 exhibited moderate cytotoxicity against HepG2, Hela and MCF-7 cells with IC50 values in the range of 16.8 ± 1.7 to 29.1 ± 1.9 µM. Therefore, these terpenoids and lignans may have potential biological activity, and also seemed to be of great chemotaxonomic value for S. melongena.


Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Citotoxinas/isolamento & purificação , Lignanas/isolamento & purificação , Raízes de Plantas/química , Solanum melongena/química , Triterpenos/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Citotoxinas/farmacologia , Células HeLa , Células Hep G2 , Humanos , Lignanas/química , Lignanas/farmacologia , Células MCF-7 , Estrutura Molecular , Compostos Fitoquímicos/análise , Terpenos/química , Terpenos/isolamento & purificação , Terpenos/farmacologia , Triterpenos/análise , Triterpenos/farmacologia
18.
Nat Prod Res ; 34(9): 1326-1330, 2020 May.
Artigo em Inglês | MEDLINE | ID: mdl-30663367

RESUMO

The composition and the relative variation of secondary metabolites of Paulownia tomentosa S. wood under thermal effect is a little explored area. Wood material was previously thermo-treated at 210 °C for 3 hours using a press vacuum technology. Extractives of untreated and thermo-treated wood material achieved with Soxhlet extraction techniques were obtained. Then the extracts were chromatographed by using thin layer chromatography. Component groups in extracts were determined by gas chromatography in combination with mass spectrometry. In terms of wood change the thermo-treatment of wood induces a darkening of wood color surface (ΔL* = 28.3), an increase of mass loss (3.5%) and an increase of the amount of extractives and lignin content as well as an increase of the chloroform soluble fraction. This work mainly describes the chemical exploration of the extract from paulownia wood, leading to the isolation and identification of episesamin.


Assuntos
Dioxóis/análise , Lamiales/química , Lignanas/análise , Madeira/química , Fracionamento Químico/métodos , Clorofórmio , Cromatografia Líquida de Alta Pressão , Cor , Dioxóis/isolamento & purificação , Cromatografia Gasosa-Espectrometria de Massas/métodos , Lignanas/isolamento & purificação , Lignina/análise , Extratos Vegetais/análise , Extratos Vegetais/química , Temperatura
19.
Nat Prod Res ; 34(13): 1853-1861, 2020 Jul.
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.


Assuntos
Lignanas/isolamento & purificação , Terpenos/isolamento & purificação , Tripterygium/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Furanos/isolamento & purificação , Furanos/farmacologia , Células Hep G2/efeitos dos fármacos , Humanos , Concentração Inibidora 50 , Lignanas/química , Lignanas/farmacologia , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Análise Espectral , Terpenos/química
20.
Nat Prod Res ; 34(20): 2894-2899, 2020 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-30990071

RESUMO

Astragalus ernestii has been used as a substitute for Radix Astragali (Huang-Qi) in southwest China. To better understand the chemical rationale for the medicinal usage, the phytochemistry of A. ernestii was recently studied. As a result, a novel aurone-phenylpropanoid adduct astrernestin (1), together with five known phenoloids calycosin-7-O-ß-D-glucopyranoside (2), 4,4'-dimethoxy-3'-hydroxy-7,9':7',9-diepoxylignan-3-O-ß-D-glucopyranoside (3), syringaresinol-4-O-ß-D-monoglucoside (4), hedyotol D 4″-O-ß-D-glucopyranoside (5) and trifolirhizin (6), were isolated from the roots of A. ernestii. The structure of compound 1 was elucidated by extensive spectroscopic analysis and optical rotation calculation.


Assuntos
Astrágalo (Planta)/química , Benzofuranos/química , Fenóis/química , Raízes de Plantas/química , China , Medicamentos de Ervas Chinesas , Furanos/isolamento & purificação , Glucosídeos/isolamento & purificação , Compostos Heterocíclicos de 4 ou mais Anéis/isolamento & purificação , Isoflavonas/isolamento & purificação , Lignanas/isolamento & purificação , Estrutura Molecular , Fenóis/isolamento & purificação
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