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1.
J Chromatogr A ; 1625: 461332, 2020 Aug 16.
Artigo em Inglês | MEDLINE | ID: mdl-32709358

RESUMO

Two structural isomeric pentacyclic triterpenes, oleanolic acid and ursolic acid, were considered as the models for the quality control of many traditional Chinese herbal medicines and they have been proved to own important pharmacological activities. In the present work, liquid chromatographic and liquid-liquid chromatographic separation with high peak resolution of structural isomeric oleanolic acid and ursolic acid using hydroxypropyl-ß-cyclodextrin as mobile phase additive was successfully achieved, respectively. A high peak resolution, RS=8.143, was achieved for the two structural isomeric compounds by conventional reverse phase high performance liquid chromatography, which was greatly improved compared with the published values. Meanwhile, a biphasic solvent system composed of n-hexane-ethyl acetate-0.1 mol/L hydroxypropyl-ß-cyclodextrin (9:1:10, v/v) was selected for liquid-liquid chromatography, which provided a high peak resolution, RS = 6.573, for analytical apparatus and Rs = 8.500 for semi-preparative apparatus after optimization by liquid-liquid extractions. Two elution modes including reverse phase mode and normal phase mode were investigated for preparative separation of two acids from crude exact of Eriobotrya japonica Thunb. Furthermore, the inclusion complex between each of the two structural isomers and hydroxypropyl-ß-cyclodextrin were also investigated for high performance liquid chromatography and liquid-liquid chromatography, respectively, in which formation constants were determined for oleanolic acid and ursolic acid.


Assuntos
2-Hidroxipropil-beta-Ciclodextrina/química , Cromatografia Líquida/métodos , Ácido Oleanólico/química , Ácido Oleanólico/isolamento & purificação , Triterpenos/química , Triterpenos/isolamento & purificação , Cromatografia de Fase Reversa , Eriobotrya/química , Isomerismo , Solventes , Temperatura , Termodinâmica , beta-Ciclodextrinas/química
2.
PLoS One ; 15(6): e0235221, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32584888

RESUMO

Ficus krishnae stem bark and leaves are used for diabetes treatment in traditional medicines. Stem bark of F. krishnae was sequentially extracted with hexane, methanol and water, and these extracts were tested for their antihyperglyceamic activity by oral glucose tolerance test (OGTT) in overnight fasted glucose loaded normal rats. Hexane extract showed significant glucose lowering activity in OGTT, and the triterpene alcohols (cycloartenol+24-methylenecycloartanol) (CA+24-MCA) were isolated together from it by activity guided isolation and characterized by NMR and mass spectroscopy. The ratio of the chemical constituents CA and 24-MCA in (CA+24-MCA) was determined as 2.27:1.00 by chemical derivatization and gas chromatographic quantification. (CA+24-MCA) in high fat diet-streptozotocin induced type II diabetic rats showed significant antidiabetes activity at 1 mg/kg and ameliorated derailed blood glucose and other serum biochemical parameters. Cytoprotective activity of (CA+24-MCA) from glucose toxicity was evaluated in cultured RIN-5F cells by MTT assay and fluorescent microscopy. (CA+24-MCA) in in vitro studies showed enhanced cell viability in RIN-5F cells and significant protection of beta cells from glucose toxicity. Both in in vivo and in vitro studies (CA+24-MCA) showed enhancement in insulin release from the beta cells. In short term toxicity studies in mice (CA+24-MCA) did not show any conspicuous toxic symptoms. The combination of the phytosterols (CA+24-MCA) obtained through activity guided isolation of the stem bark of F. krishnae showed significant activity, and therefore is a promising candidate for new generation antidiabetes drug development.


Assuntos
Diabetes Mellitus Experimental/tratamento farmacológico , Ficus/química , Hipoglicemiantes/uso terapêutico , Fitosteróis/química , Triterpenos/química , Animais , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Diabetes Mellitus Experimental/induzido quimicamente , Ficus/metabolismo , Teste de Tolerância a Glucose , Hipoglicemiantes/química , Hipoglicemiantes/farmacologia , Insulina/metabolismo , Fígado/metabolismo , Masculino , Camundongos , Conformação Molecular , Fitosteróis/isolamento & purificação , Fitosteróis/uso terapêutico , Caules de Planta/química , Caules de Planta/metabolismo , Ratos , Ratos Wistar , Triterpenos/isolamento & purificação , Triterpenos/uso terapêutico
3.
J Pharmacol Sci ; 143(3): 165-175, 2020 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-32387002

RESUMO

yeyachun and danshen exist as Chinese patent medicine, Xuemai Tong, and are clearly effective at alleviating liver fibrosis (LF). Previous studies have indicated that triterpenoids from yeyachun (EFT), and phenolic acids from danshen (SMP) are effective in the treatment of LF. The regulation of intestinal flora is an effective method for treating LF. The aim of this study was to investigate the effect of a mixture of EFT and SMP on carbon tetrachloride (CCl4) induced LF. Our results showed the mixture significantly decreased liver damage and fibrosis index, and maintained liver tissue composition, compared to the model group. Moreover, the imbalance of symptoms of intestinal flora was improved. The mixture also caused changes to metabolites of gut flora. Furthermore, the expression of CD68 in liver tissues from the treated groups was significantly decreased when compared to the model group. However, no significant difference was observed from microstructure of gut tissues and LPS concentrations in the serum between mixture treated mice and model mice. This study suggests that the mixture of EFT and SMP had a significant effect on CCl4 induced LF, and the mechanism of this action, at least in part, involved the regulation of intestinal flora and their metabolites.


Assuntos
Tetracloreto de Carbono/efeitos adversos , Medicamentos de Ervas Chinesas/farmacologia , Medicamentos de Ervas Chinesas/uso terapêutico , Microbioma Gastrointestinal/efeitos dos fármacos , Hidroxibenzoatos/farmacologia , Hidroxibenzoatos/uso terapêutico , Cirrose Hepática/tratamento farmacológico , Cirrose Hepática/microbiologia , Fitoterapia , Salvia miltiorrhiza/química , Triterpenos/farmacologia , Triterpenos/uso terapêutico , Animais , Antígenos CD/metabolismo , Antígenos de Diferenciação Mielomonocítica/metabolismo , Modelos Animais de Doenças , Medicamentos de Ervas Chinesas/isolamento & purificação , Fígado/metabolismo , Cirrose Hepática/induzido quimicamente , Cirrose Hepática/metabolismo , Masculino , Camundongos Endogâmicos ICR , Triterpenos/isolamento & purificação
4.
Arch Microbiol ; 202(7): 1677-1685, 2020 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-32285166

RESUMO

Triterpenoid compounds are important bioactivity materials. Morchella is an abundant medicinal fungi found worldwide. In this study, we optimised the isolation and purification of triterpenoid compounds from Morchella mycelium fermentation. The results showed that the triterpenoid compounds yield was 35.22 mg/g, and we also identified two triterpenoid compounds using high-performance liquid chromatography. In addition, we evaluated the anti-tumour and antioxidant activity of the products, and the results showed that triterpenoid compounds from Morchella mycelium fermentation showed good bioactivity. The IC50 values of four cancer cell lines treated with the triterpenoid compounds for 48 h were 7.20, 14.96, 4.41, and 13.43 mg/mL, respectively. Morphological changes associated with the apoptosis of PC-3 cells were observed using confocal scanning laser microscopy after treatment with triterpenoid compounds for 48 and 72 h. The triterpenoid compounds also exhibited DPPH radical, hydroxyl, and ABTS-free radical scavenging activities in vitro. These results suggest that triterpenoid compounds from Morchella mycelium fermentation, which are found in functional foods and used in the field of pharmacology, might be excellent products for the treatment of cancer and age-related illnesses.


Assuntos
Ascomicetos/química , Micélio/química , Triterpenos/isolamento & purificação , Triterpenos/farmacologia , Antineoplásicos/farmacologia , Antioxidantes/farmacologia , Linhagem Celular Tumoral , Forma Celular/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Cromatografia Líquida de Alta Pressão , Fermentação , Humanos , Radical Hidroxila/química , Concentração Inibidora 50 , Células PC-3
5.
Food Chem ; 319: 126582, 2020 Jul 30.
Artigo em Inglês | MEDLINE | ID: mdl-32199144

RESUMO

An ultrasound-assisted supercritical carbon dioxide (USC-CO2) procedure was developed for the extraction of ursolic acid, oleanolic acid and oridonin from Rabdosia rubescens, with yields that were 9.84-10.46 and 15.43-21.10% higher than those of the conventional SC-CO2 and heat-reflux extractions, respectively. USC-CO2 uses a shorter extraction time (1.83-2.09 times) and less organic solvent (3.39-173.25 times) to operate at a lower extraction temperature (5-16 °C). The dominant component in the extract was oridonin, which may indicate that the kinetic behavior in the extraction system is predominated by that of oridonin. Furthermore, the USC-CO2 and conventional SC-CO2 dynamic extraction kinetics of oridonin from R. rubescens were well described by the second-order rate and Fick's second law models. The extraction rate constant, energy of activation for diffusion, Biot number and thermodynamic parameters were deduced from the data obtained. These results provide valuable insights into the USC-CO2 and conventional SC-CO2 procedures.


Assuntos
Fracionamento Químico/métodos , Diterpenos de Caurano/isolamento & purificação , Isodon/química , Ácido Oleanólico/isolamento & purificação , Triterpenos/isolamento & purificação , Dióxido de Carbono/química , Cromatografia Líquida de Alta Pressão , Diterpenos de Caurano/análise , Química Verde , Cinética , Ácido Oleanólico/análise , Extratos Vegetais/química , Plantas Medicinais/química , Reprodutibilidade dos Testes , Solventes/química , Espectrometria de Massas em Tandem , Triterpenos/análise , Ultrassom
6.
J Chromatogr A ; 1620: 461010, 2020 Jun 07.
Artigo em Inglês | MEDLINE | ID: mdl-32173025

RESUMO

In this paper, adsorption mechanism of triterpenoid saponins in reversed-phase liquid chromatography (RPLC) and hydrophilic interaction liquid chromatography (HILIC) was proposed based on the study of the retention behavior of mogroside V as test substance. The change of peak shape of mogroside V and its influencing factors was first investigated. As the increase of sample loading, a tailing peak of mogroside V was observed in MeOHH2O of both two modes. It was the fronting peak in ACNH2O of HILIC while there was a transition from fronting peak to tailing peak in ACNH2O of RPLC that was largely affected by column temperature and ACN concentration. The adsorption isotherm of mogroside V in ACNH2O of RPLC was fitted by Moreau model, where a monolayer adsorption with large inter-molecular interaction was formed on the C18 surface. While in ACNH2O of HILIC, the adsorption of mogroside V was in accordance with BET model, showing multilayer adsorption behavior. In MeOHH2O of both HILIC and RPLC, there was always monolayer adsorption, which was fitted by Langmuir model. At last, by choosing the suitable chromatographic mode, controlling the key factors such as the solvent concentration and column temperature, and predicting the broadening trend of peak, three methods were screened out, namely, C18 column with 22% ACN (30 °C), Click XIon column with 90% MeOH or 70% ACN, to get mogroside V of purity greater than 98% from Siraitia grosvenorii extract. Among them, the RPLC method of 22% ACN that showed the highest loading sample per hour (1.92%) and the lowest solvent consumption emerged as the best approach.


Assuntos
Cromatografia Líquida/métodos , Cromatografia de Fase Reversa/métodos , Interações Hidrofóbicas e Hidrofílicas , Saponinas/isolamento & purificação , Triterpenos/isolamento & purificação , Adsorção , Saponinas/química , Solventes , Temperatura , Triterpenos/química
7.
Food Chem ; 315: 126217, 2020 Jun 15.
Artigo em Inglês | MEDLINE | ID: mdl-32007812

RESUMO

This study investigated the direct citric acid hydrolysis extraction method to optimize phytosterols extraction from hickory husk. Single factor experiments followed by a three-level three-factor Box-Behnken experiments were performed. The optimal extraction parameters were determined as: pH of 2.0, liquid-to-solid ratio of 17.12: 1 mL/g, and temperature of 55.81 °C. Practical experiments were carried out in triplicate, and subsequently yielded phytosterols of 912.452 ± 17.452 µg/g DW, in good consistence with the predicted extraction yield of 902.874 µg/g DW. The conductivity of the extract was also found to play effective role under direct citric acid hydrolysis and recorded 36.30 ± 1.08 µs/cm at optimum extraction condition. ß-Sitosterol stigmasterol, campsterol, ergosterol and lupeol were detected as main PSs and triterpenoids in hickory husk using UPLC-Triple-TOF/MS. Finally, the comparison between direct hydrolysis extraction and traditional solvent extraction showed that this new method was more effective and eco-friendlier to extract both free and conjugated phytosterols.


Assuntos
Carya/química , Modelos Teóricos , Fitosteróis/isolamento & purificação , Triterpenos/isolamento & purificação , Ácido Cítrico/química , Ergosterol/química , Ergosterol/isolamento & purificação , Concentração de Íons de Hidrogênio , Hidrólise , Triterpenos Pentacíclicos/química , Triterpenos Pentacíclicos/isolamento & purificação , Fitosteróis/química , Sitosteroides/química , Sitosteroides/isolamento & purificação , Estigmasterol/química , Estigmasterol/isolamento & purificação , Triterpenos/química
8.
J Agric Food Chem ; 68(7): 2041-2053, 2020 Feb 19.
Artigo em Inglês | MEDLINE | ID: mdl-31967813

RESUMO

Cyclocarya paliurus is commonly used for the prevention and treatment of hypertension, diabetes, and inflammation in South China. Although research on the anti-inflammatory effects of C. paliurus leaves has been reported, no active anti-inflammatory compounds have been identified. In the present study, RAW 264.7 cells were used to establish a bioactivity-guided identification model to verify the inhibitory effects of C. paliurus leaves on inflammation and identify the anti-inflammatory constituents. The active fraction was isolated to yield 18 dammarane triterpenoid saponins, including 11 new 3,4-seco-dammarane triterpenoid saponins (1-11), the structures of which were identified on the basis of analyses of nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS) and comparison with literature data. Compounds 7, 8, 10, and 11 showed strong inhibition on nitric oxide (NO) productions, with IC50 values ranging from 8.23 to 11.23 µM. These four compounds significantly decreased the secretion of tumor necrosis factor-alpha (TNF-α), prostaglandin E2 (PGE2), and interleukin 6 (IL-6) in lipopolysaccharide-activated RAW 264.7 cells. Furthermore, compound 7 decreased the expression of the proteins cyclooxygenase-2 (COX-2), inducible nitric-oxide synthase (iNOS), and nuclear factor kappa-B (NF-κB/p65). In addition, the structure-activity relationships of the isolates were investigated. The results suggest that 3,4-seco-dammarane triterpenoid saponins may be used as potential anti-inflammatory drugs and warrant further investigation.


Assuntos
Anti-Inflamatórios/farmacologia , Juglandaceae/química , Extratos Vegetais/farmacologia , Saponinas/farmacologia , Triterpenos/farmacologia , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Interleucina-6/genética , Interleucina-6/imunologia , Macrófagos/efeitos dos fármacos , Camundongos , NF-kappa B/genética , NF-kappa B/imunologia , Óxido Nítrico Sintase Tipo II/genética , Óxido Nítrico Sintase Tipo II/imunologia , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Folhas de Planta/química , Células RAW 264.7 , Saponinas/química , Saponinas/isolamento & purificação , Triterpenos/química , Triterpenos/isolamento & purificação , Fator de Necrose Tumoral alfa/genética , Fator de Necrose Tumoral alfa/imunologia
9.
Phytochemistry ; 171: 112229, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-31901474

RESUMO

Seven undescribed cycloartane triterpenoids, pseudolarnoids A-G, together with ten known ones, were isolated from the seeds of Pseudolarix amabilis (J. Nelson) Rehder. Their structures were elucidated on the basis of spectroscopic analysis, X-ray crystallography, and ECD data. Pseudolarnoids A-C are cycloartane triterpenoids with a unique 16S, 23R-spirolactone moiety. Pseudolarnoids F, G, and pseudolarolide C demonstrated potent antiviral effects on HSV-1 in vitro.


Assuntos
Antivirais/farmacologia , Herpesvirus Humano 1/efeitos dos fármacos , Vírus da Influenza A Subtipo H3N2/efeitos dos fármacos , Compostos Fitoquímicos/farmacologia , Triterpenos/farmacologia , Antivirais/química , Antivirais/isolamento & purificação , Cristalografia por Raios X , Testes de Sensibilidade Microbiana , Modelos Moleculares , Conformação Molecular , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Pinaceae/química , Triterpenos/química , Triterpenos/isolamento & purificação
10.
Phytochemistry ; 171: 112228, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-31911265

RESUMO

A previously undescribed taraxerene-type triterpenoid possessing a class of rare natural taraxerene triterpenoid possessing skeleton with 14, 28-lactone, two undescribed oleane-type triterpenoids, and twenty-five known triterpenoids were isolated from Liquidambar formosana (Hamamelidaceae). The structures of undescribed compounds were determined on the basis of 1D and 2D NMR spectroscopic, HR-ESI-MS, and X-ray crystallographic data analysis. Among the isolates, ursolic acid, 3,6-dion-20(29)-lupen-28-oic acid, and 3-oxo-12α-hydroxyoleanan-28,13ß-olide induced a significant apoptosis in SMMC7721 cells in the flow cytometer experiment with apoptosis rates of 94.5%, 57.3% and 89.9% at 8.0 µM, respectively, exhibiting near equivalent apoptosis-inducing abilities to that positive drug taxol (apoptotic rate of 71.2% at 1.4 µM). Mechanism studies suggested that these three compounds could regulate the mitochondrial pathway by up-regulating the expressions of pro-apoptotic factors (Bad and Bax) and activating caspase-3 and caspase-9 to induce apoptosis. Further studies indicated that the pro-apoptotic effects of these three compounds were associated with PI3K-AKT pathway inhibition. Taken together, these studies provide evidence that triterpenoids from L. Fructus are promising candidates for the hepatocellular carcinoma therapy.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Apoptose/efeitos dos fármacos , Liquidambar/química , Compostos Fitoquímicos/farmacologia , Inibidores de Proteínas Quinases/farmacologia , Triterpenos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Proliferação de Células/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Fosfatidilinositol 3-Quinases/metabolismo , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Inibidores de Proteínas Quinases/química , Inibidores de Proteínas Quinases/isolamento & purificação , Proteínas Proto-Oncogênicas c-akt/antagonistas & inibidores , Proteínas Proto-Oncogênicas c-akt/metabolismo , Transdução de Sinais/efeitos dos fármacos , Triterpenos/química , Triterpenos/isolamento & purificação , Células Tumorais Cultivadas
11.
Phytochemistry ; 170: 112201, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31778881

RESUMO

Nine undescribed triterpenoids (jughopenoids A-I), including seven nortriterpenoids and two normal triterpenoids, together with fourteen known analogues, were isolated from the barks of Juglans hopeiensis Hu. The structures of the undescribed triterpenoids were established by integrated spectroscopic analysis and single crystal X-ray diffraction. Jughopenoid A represented an unprecedented lupane-type nortriterpenoid with a five-membered lactone ring A. Selected isolates were tested for their cytotoxic effects against human HT-29 colon carcinoma, human HepG2 hepatocellular carcinoma, and human PC-3 prostate cancer cell lines. Their immunosuppressive activities against ConA-induced T cell proliferation and LPS-induced B cell proliferation were also evaluated.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Juglans/química , Compostos Fitoquímicos/farmacologia , Casca de Planta/química , Triterpenos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Cristalografia por Raios X , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Células HT29 , Células Hep G2 , Humanos , Modelos Moleculares , Estrutura Molecular , Células PC-3 , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Relação Estrutura-Atividade , Triterpenos/química , Triterpenos/isolamento & purificação
12.
Prep Biochem Biotechnol ; 50(3): 302-315, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-31755817

RESUMO

When ingested as a dietary supplement, Ganoderma lucidum spore powders (GLSP) provide various health benefits such as enhanced immunity, liver protection and anti-cancer effects. In this study, triterpenoid extraction from GLSP was achieved using an ultrasound-assisted process which was optimized using response surface methodology (RSM). Ultrasound-assisted extraction (UAE) was also compared to the most conventional chemical extraction method. For UAE, optimum extraction conditions were found to be ethanol concentration = 95% v/v; solvent to solid ratio = 50:1 mL/g; ultrasound time = 5.4 min; ultrasound power = 564.7 w, and ultrasound probe distance = 8.2 cm. At optimal UAE conditions, no significant differences were found between experimental (0.97 ± 0.04 %) and predicted values (99%); which indicates appreciable correlation at the 97% confidence interval. The findings show the application of Box-Behnken design (BBD) to predict and optimize triterpenoid yield for UAE of triterpenoid from GLSP. Furthermore, glucose consumption was 2.68 times that of control samples when tested with insulin-resistant HepG2 cell, showing potential use in type 2 diabetes. In addition, triterpenoid extracts show good biocompatibility and inhibition of antioxidant activity.


Assuntos
Reishi/química , Esporos Fúngicos/química , Triterpenos , Ondas Ultrassônicas , Triterpenos/química , Triterpenos/isolamento & purificação
13.
Nat Prod Res ; 34(8): 1061-1067, 2020 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-30663364

RESUMO

From the MeOH extract of the Vietnamese sea cucumber Holothuria edulis, eight triterpene glycosides (1-8), including one new compound namely holothurin A5 (1), were isolated by using various chromatographic separations. Their structures were established by spectroscopic experiments including 1D, 2D NMR and HR-ESI-MS. Holothurin A5 (1) has a hydroperoxy group at C-25. To the best of our knowledge, this is the first report of this group in triterpene saponins obtained from sea cucumbers to date. In addition, the in vitro cytotoxicity against five human cancer cell lines (HepG2, KB, LNCaP, MCF7 and SK-Mel2) of all isolated compounds was also evaluated using SRB assays.


Assuntos
Glicosídeos/isolamento & purificação , Holothuria/química , Pepinos-do-Mar/química , Triterpenos/isolamento & purificação , Animais , Linhagem Celular Tumoral , Citotoxinas/química , Citotoxinas/isolamento & purificação , Citotoxinas/farmacologia , Glicosídeos/química , Humanos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Saponinas/química , Saponinas/isolamento & purificação , Triterpenos/química , Vietnã
14.
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
15.
Nat Prod Res ; 34(7): 915-922, 2020 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-30600711

RESUMO

The continuing studies on the fruits of Stauntonia brachyanthera led to the isolations of 6 normal and nor-oleanane triterpenoids, including two new compounds, brachyantheoraside B10 (1) and brachyantheraside C1 (2). Compounds 1-3 showed inhibitory activity on lipopolysaccharide (LPS)-induced nitric oxide production in RAW 264.7 macrophages with the IC50 values of 27.04, 26.22, and 21.41 µM, respectively, which were all stronger than that of indomethacin. The study not only revealed a new type of nor-oleanane triterpenoids, but also confirmed the anti-inflammation abilities of three type nor-oleanane triterpenoids as the inhibitors of NO production.


Assuntos
Anti-Inflamatórios/isolamento & purificação , Ácido Oleanólico/análogos & derivados , Ranunculales/química , Triterpenos/farmacologia , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Frutas/química , Concentração Inibidora 50 , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Camundongos , Estrutura Molecular , Óxido Nítrico/antagonistas & inibidores , Óxido Nítrico/biossíntese , Ácido Oleanólico/química , Ácido Oleanólico/isolamento & purificação , Células RAW 264.7 , Triterpenos/química , Triterpenos/isolamento & purificação
16.
Nat Prod Res ; 34(6): 810-815, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-30388899

RESUMO

Friedelan-3-one (1) and friedelane-3,16-dione (2) isolated from leaves and branches of Maytenus robusta Reissek were subjected to structural modifications via nucleophilic addition to the carbonyl group and Baeyer-Villiger oxidation in order to synthesize potential cytotoxic compounds. The oximes friedelane-3-hydroxyimino (3) and 3-hydroxyiminofriedelan-16-one (4) together with the lactones friedelane-3,4-lactone (5) and 3,4-lactonefriedelan-16-one (6) were characterized by IR and NMR spectroscopic analyses. Compounds 4 and 6 are reported for the first time. Cytotoxic screening via MTT assay in human leukemia cell lines (THP-1 and K562) demonstrated no significant improvement of compounds 3-6 when compared to the starting materials. Only compounds 3 and 5 demonstrated an improvement against K562 cells. However, the same assay on ovarian and breast cancer cell lines (TOV-21G and MDA-MB-231) showed a reduction in the IC50 for compounds 4-6, indicating that ring A modifications may enhance the biological potential.


Assuntos
Antineoplásicos/farmacologia , Celastraceae/química , Citotoxinas/isolamento & purificação , Iminas/química , Lactonas/química , Triterpenos/química , Antineoplásicos/síntese química , Antineoplásicos/isolamento & purificação , Linhagem Celular Tumoral , Citotoxinas/síntese química , Citotoxinas/farmacologia , Humanos , Iminas/síntese química , Lactonas/síntese química , Folhas de Planta/química , Relação Estrutura-Atividade , Triterpenos/isolamento & purificação
17.
Nat Prod Res ; 34(4): 482-488, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-30445837

RESUMO

Two new ceanothane triterpenes, 3,7-O,O-dibenzoyl ceanothic acid methylester (1) and 3-O-acetyl-7-O-benzoyl ceanothic acid methylester (2), along with nine known compounds (3-11), were isolated from the roots of Colubrina asiatica. The isolated compounds were identified by spectroscopic evidence. Compounds 1 and 2 showed antimalarial activity against Plasmodium falciparum with IC50 values of 4.67 and 3.07 µg/mL, respectively. Compound 2 also showed antimycobacterial activity against Mycobacterium tuberculosis (MIC 6.25 µg/mL). In addition, compounds 1, 2, 10 and 11 showed cytotoxicity against three cancer cell lines (KB, NCI-H187 and MCF-7) with IC50 values ranging from 8.32 to 46.72 µg/mL.


Assuntos
Colubrina/química , Extratos Vegetais/química , Raízes de Plantas/química , Triterpenos/farmacologia , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antimaláricos/química , Antimaláricos/isolamento & purificação , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Concentração Inibidora 50 , Estrutura Molecular , Mycobacterium tuberculosis/efeitos dos fármacos , Plasmodium falciparum/efeitos dos fármacos , Triterpenos/química , Triterpenos/isolamento & purificação
18.
Nat Prod Res ; 34(6): 773-781, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-30445848

RESUMO

New allelochemicals were identified through bio-guided fractionation from the ethyl acetate of seeds extracts, which was the most autotoxic compared to the other plant parts. Phytochemical investigation of the seeds extracts of C. arabica by spectroscopy analyses has led to identify two new dammarane type triterpenes (4 and 9), with nine known analogues (1 - 3, 5 - 8, 10 and 11), a new cucurbitane triterpene (12), acylated dehydrodiconiferyl alcohol (13), and three highly oxygenated flavonols (14-16). The most autotoxic compounds on germination and seedling growth were elucidated as dammarane type triterpenes. However, less autotoxic effect was recorded by an inhibition under 50% for most of the identified flavonoids. These results suggest that those autotoxic substances may be used as a new bio-herbicide that may contribute to manage the distribution of C. arabica in agronomic field.[Formula: see text].


Assuntos
Cleome/efeitos dos fármacos , Herbicidas/isolamento & purificação , Feromônios/farmacologia , Triterpenos/isolamento & purificação , Flavonóis/isolamento & purificação , Germinação/efeitos dos fármacos , Glicosídeos/isolamento & purificação , Herbicidas/química , Extratos Vegetais/química , Plântula/efeitos dos fármacos , Sementes/química , Triterpenos/química , Triterpenos/farmacologia
19.
Nat Prod Res ; 34(2): 204-209, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-30580617

RESUMO

A new oleanane triterpenoid, 2α,3ß,6ß,23,29-pentahydroxyolean-12-en-28- oic acid (1), was isolated from the roots of Rhodomyrtus tomentosa, together with four known oleanane triterpenoids (2-5) and two known ursane triterpenoids (6-7). The structure of compound 1 was determined by extensive NMR and HR-ESI-MS data analysis. Compounds 4-5 showed cytotoxicity against PC12 cell lines at a concentration of 50 µM, and compound 1 exhibited moderate neuroprotective activity against corticosterone induced PC12 cell death at the same concentration.


Assuntos
Myrtaceae/química , Ácido Oleanólico/análogos & derivados , Raízes de Plantas/química , Triterpenos/isolamento & purificação , Animais , Citotoxinas/química , Citotoxinas/isolamento & purificação , Humanos , Hidroxilação , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/isolamento & purificação , Ácido Oleanólico/química , Ácido Oleanólico/isolamento & purificação , Células PC12 , Ratos , Espectrometria de Massas por Ionização por Electrospray , Triterpenos/química , Triterpenos/farmacologia
20.
Nat Prod Res ; 34(2): 217-224, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-30580625

RESUMO

The chemical composition of Gynostemma burmanicum King ex Chakrav. was investigated for the first time in this study. Nine dammarane glycosides (1‒9) were isolated from the EtOH extract of the aerial parts of G. burmanicum. Their structures were elucidated by 1D and 2D NMR spectroscopic interpretation as well as by chemical studies. The new compounds were 3ß,20S-dihydroxydammar-24-ene-3-O-ß-D-glucopyranosyl-20-O-[ß-D-xylopyranosyl-(1→6)-ß-D-glucopyranoside] (1), 3ß,12ß,20S-trihydroxydammar-24-ene-3-O-ß-D-xylopyranosyl-20-O-[ß-D-xylopyranosyl-(1→6)-ß-D-glucopyranoside] (2), and 12-oxo-3ß,20S-dihydroxydammar-24-ene-3-O-[ß-D-glucopyranosyl(1→2)-ß-D-glucopyranosyl]-20-O-[ß-D-xylopyranosyl-(1→6)-ß-D-glucopyranoside] (3).


Assuntos
Glicosídeos/isolamento & purificação , Gynostemma/química , Triterpenos/isolamento & purificação , Glicosídeos/química , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Extratos Vegetais/química , Saponinas/química , Saponinas/isolamento & purificação , Triterpenos/química
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