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1.
Chem Biol Interact ; 330: 109167, 2020 Oct 01.
Artigo em Inglês | MEDLINE | ID: mdl-32603660

RESUMO

Recently, it has been shown that drimane-type sesquiterpenoids isolated from Zygogynum pancheri, a species native to New Caledonia, possessed significant α-amylase inhibitory activities. To further explore their antidiabetic potential, we investigated the effect of 1ß-O-(E-cinnamoyl)-6α-hydroxy-9epi-polygodial (D) and 1ß-E-O-p-methoxycinnamoyl-bemadienolide (L), two of the most active compounds of the series, on diabetic model rats. Compounds D and L (2 mg kg/day) were daily and orally administrated for 30 days to streptozotocin (STZ) (150 mg/kg) induced male diabetic Wistar rats. Animals were allocated into five groups of six rats. Comparatively to diabetic rats, treatments with D and L compounds were able to significantly (P < 0.05) decrease Fasting Blood Glucose (FBG) (70.15%, 71.02%), serum total cholesterol (46.27% and 39.38%), triglycerides (56.60% and 58.15%), creatinine (37.31% and 36.49%) and uric acid levels (67.76% and 69.68%), respectively. Compounds D and L also restored the altered plasma enzyme (aspartate aminotransferase, AST (47.83% and 43.20%), alanine aminotransferase, ALT (49.76% and 48.35%, alkaline phosphatase, ALP (72.78% and 73.21%)) and lactate dehydrogenase, LDH (47.95% and 53.93%) levels to near normal, respectively. Administration of Glymepiride, significantly (p < 0.05) reduced FBG (73.94%) in STZ induced diabetic rats. Additionally, the compounds D and L exhibited inhibitory effects in vivo on lipase activity of diabetic rats (54.83% and 52.25%), respectively. The outcomes of this study suggested that these two drimanes could be considered as efficient hypoglycemic, hypolipidemic and antiobesity agents for diabetes management and its complications.


Assuntos
Diabetes Mellitus Experimental/tratamento farmacológico , Fitoterapia/métodos , Extratos Vegetais/farmacologia , Sesquiterpenos Policíclicos/isolamento & purificação , Animais , Fármacos Antiobesidade/isolamento & purificação , Fármacos Antiobesidade/farmacologia , Hipoglicemiantes/isolamento & purificação , Hipoglicemiantes/farmacologia , Hipolipemiantes/isolamento & purificação , Hipolipemiantes/farmacologia , Masculino , Nova Caledônia , Extratos Vegetais/química , Sesquiterpenos Policíclicos/farmacologia , Ratos , Ratos Wistar , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Winteraceae/química
2.
J Chromatogr A ; 1624: 461155, 2020 Aug 02.
Artigo em Inglês | MEDLINE | ID: mdl-32540056

RESUMO

The topic in the present paper is to prepare molecularly imprinted polymer (MIP) using the template molecule with low purity. For the first time, a surrounding of macromolecular crowding was established to promote the formation of the complex of the template with functional monomer efficiently thus highly pure template molecule was unnecessary. In this study, the MIP monolith was synthesized using low purity lactucopicrin as template in place of highly pure one, and polystyrene was used as macromolecular crowding agent. 4-Vinylpyridine and ethyleneglycol dimethacrylate were used as functional monomer and crosslinker, respectively. Polymerization parameters, including the ratio of functional monomer/template, various template concentrations, and PS concentration on the affinity of the resulting MIP were systematically investigated. For the lactucopicrin MIP made with the purity of lactucopicrin of 92%, the imprinting factor can be up to 2.2. The resulting MIP was filled in solid phase extraction (SPE) cartridge to purify lactucopicrin from the crude extract of Cichorium glandulosum Boiss. et Huet. After two cycles of MIP SPE for the crude extract, the highest recovery and purity of lactucopicrin was 64.8% and 97.8%, respectively. The results indicated that the use of macromolecular crowding agent is an effective method for improving the performance of the MIP prepared with the template of low purity, particularly valuable to the cases in which the highly pure target molecule is hard to be obtained.


Assuntos
Impressão Molecular , Polímeros/química , Asteraceae/química , Reagentes para Ligações Cruzadas/química , Lactonas/química , Lactonas/isolamento & purificação , Metacrilatos/química , Polimerização , Poliestirenos/química , Piridinas/química , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Extração em Fase Sólida
3.
J Chromatogr A ; 1624: 461191, 2020 Aug 02.
Artigo em Inglês | MEDLINE | ID: mdl-32540059

RESUMO

Trapping volatiles is a convenient way to study aroma compounds but it is important to determine which volatile trapping method is most comprehensive in extracting the most relevant aroma components when investigating complex food products. Awareness of their limitations is also crucial. (Un)targeted metabolomic approaches were used to determine the volatile profiles of two commercial flavourings. Four trapping techniques were tested as was the addition of salt to the mixture. Comprehensiveness and repeatability were compared and SBSE proved particularly suitable for extracting components such as polysulfides, pyrazines and terpene alcohols, and provided an overall broader chemical spectrum. SPME proved to be more suitable in extracting sesquiterpenes and DHS in extracting monoterpenes. Adding salt to the sample had only quantitative effects on volatiles as detected by SPME. These results help clarify the advantages and limitations of different trapping techniques and hence deliver a valuable decision tool for food matrix analysis.


Assuntos
Aromatizantes/análise , Cromatografia Gasosa-Espectrometria de Massas , Aromatizantes/química , Aromatizantes/isolamento & purificação , Metabolômica , Monoterpenos/isolamento & purificação , Odorantes , Pirazinas/isolamento & purificação , Sesquiterpenos/isolamento & purificação , Microextração em Fase Sólida/métodos , Sulfetos/isolamento & purificação , Terpenos/isolamento & purificação , Compostos Orgânicos Voláteis/análise
4.
PLoS One ; 15(6): e0234661, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32544201

RESUMO

Xanthoxylin was the main compound (content 44.92% of total volatiles) in the leaves of Luodian B. balsamifera, which might be the key cause of failure in collecting essential oil (EO) of the leaves using general hydrodistillation in Clevenger apparatus. A modified hydrodistillation equipped with Clevenger apparatus was designed for isolating EO from the leaves. Six EOs of Luodian B. balsamifera harvested once a month from September to next February were collected successfully. The main components of EOs were δ-elemene, α-cubenene, caryophyllene, caryophyllene epoxide, γ-eudesmol, xanthoxylin, and α-eudesmol. The EOs of Luodian B. balsamifera collected from October to December had higher antioxidant activities (ACs). Combining the principal component analysis of chemical components with the results of ACs and the yields of six EOs, the leaves of Luodian B. balsamifera were suitable to be harvested in November and December to obtain EO with high quality.


Assuntos
Antioxidantes/isolamento & purificação , Asteraceae/química , Óleos Voláteis/química , Antioxidantes/farmacologia , China , Destilação/instrumentação , Destilação/métodos , Óleos Voláteis/farmacologia , Folhas de Planta/química , Óleos Vegetais/química , Óleos Vegetais/farmacologia , Sesquiterpenos Policíclicos/isolamento & purificação , Estações do Ano , Sesquiterpenos/isolamento & purificação
5.
Zhongguo Zhong Yao Za Zhi ; 45(3): 579-583, 2020 Feb.
Artigo em Chinês | MEDLINE | ID: mdl-32237516

RESUMO

This study is to investigate the chemical constituents from the whole plant Corydalis edulis. The chemical constituents were separated and purified by macroporous resin D101, silica gel, Sephadex LH-20, ODS, and semi-preparative HPLC. Their structures were determined by physicochemical properties and spectroscopic data. Four compounds were isolated from the dichloromethane and water extracts of the whole plant C. edulis, and identified as 6'-ß-D-xylosylicariside B2(1),(3S,5R,6S,7E)-5,6-epoxy-3-hydroxy-7-megastigmen-9-one(2), loliolide(3), and 5,5'-dimethoxybiphenyl-2,2'-diol(4), respectively. Compound 1 is a new compound, of which the absolute configuration was established by electronic circular dichroism(ECD) calculations. Compound 4 is obtained from the plants of Papaveraceae family for the first time. Compounds 2 and 3 are firstly isolated from the Corydalis genus.


Assuntos
Corydalis/química , Glicosídeos/isolamento & purificação , Sesquiterpenos/isolamento & purificação , Cromatografia Líquida de Alta Pressão , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação
6.
Artigo em Inglês | MEDLINE | ID: mdl-31911205

RESUMO

Due to the biological features of sesquiterpene coumarins and incomparable interest in therapeutics application of natural products, extraction of sesquiterpene coumarins from asafoetida have gained highly attention. One of the most important problems is removal of sulfur containing compounds which are co-existed with sesquiterpene coumarins. So employment of new methods for selective extraction and cleanup of sesquiterpene coumarins is very substantial. In this study using dummy molecularly imprinting technique, 7-hydroxycoumarin-imprited polymer was synthesized and after evaluation of binding properties of polymers, the optimum one was used as sorbent in solid phase extraction. Afterwards dummy molecularly imprinting solid phase extraction (DMISPE) method was calibrated for simultaneous extraction of galbanic acid, 7-isopentenyloxy coumarin and auraptene from aqueous media before high performance liquid chromatography with UV detector (HPLC-UV) analysis. The recovery was in the range of 68.32%-84.69%, which were in the acceptable range compared to previous works. Finally, the calibrated DMISPE method was used for extraction and cleanup of sesquiterpene coumarins from asafetida plant. The concentration of isosamarcandin, kellerin and farnesiferol in asafoetida extract was obtained 0.8, 2.7, and 5 µg/mL, respectively, using standard addition method.


Assuntos
Cumarínicos/isolamento & purificação , Ferula/química , Impressão Molecular/métodos , Sesquiterpenos/isolamento & purificação , Extração em Fase Sólida/métodos , Cromatografia Líquida de Alta Pressão , Cumarínicos/análise , Cumarínicos/química , Extratos Vegetais/química , Reprodutibilidade dos Testes , Sesquiterpenos/análise , Sesquiterpenos/química
7.
Org Biomol Chem ; 18(4): 642-645, 2020 01 28.
Artigo em Inglês | MEDLINE | ID: mdl-31916553

RESUMO

Photeroids A (1) and B (2), two structurally fascinating meroterpenoids, were isolated from the deep-sea-derived fungus Phomopsis tersa FS441. Their structures were sufficiently established by a comprehensive interpretation of the spectroscopic data, NMR spectra, and ECD calculation. Photeroids A and B represented the first phenolic sesquiterpene meroterpenoids featuring a highly fused 6/6/6/6 tetracyclic ring system derived through a rarely-occurring hetero-Diels-Alder reaction via an orthoquinone methide intermediate. Additionally, they were also evaluated for their cytotoxic activities against four human cancer cells, wherein compounds 1 and 2 exhibited moderate cytotoxic activities.


Assuntos
Ascomicetos/química , Fenóis/farmacologia , Sesquiterpenos/farmacologia , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Linhagem Celular Tumoral , Compostos Heterocíclicos de 4 ou mais Anéis/química , Compostos Heterocíclicos de 4 ou mais Anéis/isolamento & purificação , Compostos Heterocíclicos de 4 ou mais Anéis/farmacologia , Humanos , Fenóis/química , Fenóis/isolamento & purificação , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação
8.
Int J Mol Sci ; 21(2)2020 Jan 19.
Artigo em Inglês | MEDLINE | ID: mdl-31963919

RESUMO

Terpenoids play vital roles in tea aroma quality and plants defense performance determination, whereas the scenarios of genes to metabolites of terpenes pathway remain uninvestigated in tea plants. Here, we report the use of an integrated approach combining metabolites, target gene transcripts and function analyses to reveal a gene-to-terpene network in tea plants. Forty-one terpenes including 26 monoterpenes, 14 sesquiterpenes and one triterpene were detected and 82 terpenes related genes were identified from five tissues of tea plants. Pearson correlation analysis resulted in genes to metabolites network. One terpene synthases whose expression positively correlated with farnesene were selected and its function was confirmed involved in the biosynthesis of α-farnesene, ß-ocimene and ß-farnesene, a very important and conserved alarm pheromone in response to aphids by both in vitro enzymatic assay in planta function analysis. In summary, we provided the first reliable gene-to-terpene network for novel genes discovery.


Assuntos
Alquil e Aril Transferases/genética , Camellia sinensis/enzimologia , Proteínas de Plantas/genética , Terpenos/isolamento & purificação , Monoterpenos Acíclicos/isolamento & purificação , Alcenos/isolamento & purificação , Alquil e Aril Transferases/metabolismo , Camellia sinensis/genética , Perfilação da Expressão Gênica , Regulação da Expressão Gênica de Plantas , Redes Reguladoras de Genes , Metabolômica , Proteínas de Plantas/metabolismo , Sesquiterpenos/isolamento & purificação , Terpenos/química
9.
Chem Commun (Camb) ; 56(10): 1517-1520, 2020 Feb 04.
Artigo em Inglês | MEDLINE | ID: mdl-31919484

RESUMO

The pseudoguaianelactones A (1) and B (2), two novel sesquiterpene lactones with an unprecedented [5,7,7] ring system featuring an α-methylene-γ-lactone moiety, together with a new pseudoguaianelactone C (3) were isolated from the roots of Lindera glauca. Pseudoguaianelactones A-C (1-3) inhibited nitric oxide (NO) production, with IC50 values ranging from 1.38 to 4.00 µM. Moreover, all compounds significantly suppressed the production of pro-inflammatory mediators (TNF-α, IL-6, IL-1ß and PGE2) and the protein expression of the enzymes iNOS and COX-2.


Assuntos
Anti-Inflamatórios/química , Ciclo-Oxigenase 2/metabolismo , Lindera/química , Óxido Nítrico Sintase Tipo II/metabolismo , Sesquiterpenos/química , Animais , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Cristalografia por Raios X , Citocinas/metabolismo , Lindera/metabolismo , Lipopolissacarídeos/farmacologia , Macrófagos/citologia , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Camundongos , Conformação Molecular , Óxido Nítrico/metabolismo , Raízes de Plantas/química , Raízes de Plantas/metabolismo , Células RAW 264.7 , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia
10.
Chem Biodivers ; 17(2): e1900544, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31840372

RESUMO

Geranium species are widely used in traditional medicine of Balkan. The aim of this work was to investigate and compare chemical composition of volatile fractions obtained by hydrodistillation from aerial parts of G. macrorrhizum, G. phaeum, G. sanguineum, G. robertianum, G. palustre, G. pyrenaicum, G. columbinum and G. lucidum as well as from underground parts of G. macrorrhizum and G. phaeum, originated from Vlasina plateau in South Eastern Serbia. The volatiles were analyzed using GC/MS and GC-FID. G. palustre volatiles have been studied for the first time with ß-selinene (18.6 %) as a characteristic compound. The cluster analysis revealed separation of volatiles into two main groups. Volatile fractions of G. macrorrhizum were separated from all other samples due to high sesquiterpene content (92.3 % in aerial and 94.6 % in underground parts). The volatile fractions of other samples were mainly composed of sesquiterpenes (10.8-61.8 %), diterpenes (12.9-43.0 %) and fatty acids and their derivatives (6.6-21.6 %) with the exception of volatile fraction of G. phaeum underground parts which was dominated only by fatty acids and their derivatives (76.6 %). The results presented in this article contribute to the knowledge on the chemistry of this genus and advances the knowledge on flora of southeast Serbia.


Assuntos
Geranium/química , Compostos Orgânicos Voláteis/química , Análise por Conglomerados , Cromatografia Gasosa-Espectrometria de Massas , Geranium/metabolismo , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/metabolismo , Sérvia , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Compostos Orgânicos Voláteis/análise
11.
Fitoterapia ; 140: 104422, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31756377

RESUMO

Peniterester (1), a new tricyclic sesquiterpene, together with 6 known compounds (2-7) were isolated from the secondary metabolites of an artificial mutant Penicillium sp. T2-M20 which was obtained from the parental strain Penicillium sp. T2-8 via UV irradiation as well as nitrosoguanidine (NTG) induction. Peniterester was only produced by the mutant T2-M20 on the basis of LC-MS analysis. Meanwhile, the results of in vitro bioactivities screening indicated that peniterester owned obvious antibacterial activities against Bacillus subtilis, Escherichia coli and Staphylococcus aureus with MICs of 8.0, 8.0 and 4.0 µg/mL, respectively.


Assuntos
Antibacterianos/farmacologia , Penicillium/química , Sesquiterpenos/farmacologia , Antibacterianos/isolamento & purificação , Bacillus subtilis/efeitos dos fármacos , Linhagem Celular Tumoral , China , Escherichia coli/efeitos dos fármacos , Gastrodia/microbiologia , Humanos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Rizoma/microbiologia , Metabolismo Secundário , Sesquiterpenos/isolamento & purificação , Staphylococcus aureus/efeitos dos fármacos
12.
Fitoterapia ; 140: 104406, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31698061

RESUMO

One new quinoline alkaloid (1), two new bisabolane-type sesquiterpene derivatives (2 and 3), and a new natural product (4) along with ten known compounds (514) were isolated from the deep sea-derived fungus Aspergillus sp. SCSIO06786 which cultured on solid rice medium. Three new structures were elucidated by analysis of 1D/2D NMR data and HR-ESI-MS. The absolute configurations of 2 and 3 were established by comparison of the experimental and reported ECD values. Compounds 11-13 exhibited moderate selective inhibitory activities against the tested pathogenic bacteria with MIC values among 3.13-12.5 µg/mL.


Assuntos
Alcaloides/isolamento & purificação , Aspergillus/química , Sesquiterpenos Monocíclicos/isolamento & purificação , Quinolinas/isolamento & purificação , Água do Mar/microbiologia , Sesquiterpenos/isolamento & purificação , Alcaloides/farmacologia , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Bactérias/efeitos dos fármacos , Sedimentos Geológicos/microbiologia , Oceano Índico , Testes de Sensibilidade Microbiana , Estrutura Molecular , Sesquiterpenos Monocíclicos/farmacologia , Quinolinas/farmacologia , Sesquiterpenos/farmacologia
13.
Phytochemistry ; 170: 112196, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31731238

RESUMO

Seven previously undescribed sesquiterpene lactones, three known sesquiterpene lactones (ixerin D, 15-p-hydroxyphenylacetyllactucin, and 15-p-hydroxyphenylacetyllactucin-8-sulfate), and two known quinic acid derivatives (3-O-feruloylquinic acid and 3,5-di-O-caffeoylquinic acid) were isolated from Sonchus palustris L. roots. Four formerly undescribed compounds were elucidated to be 3ß,14-dihydroxycostunolide-3-O-ß-D-glucopyranosyl-(2-O-p-hydroxyphenylacetyl)-14-O-p-hydroxyphenylacetate, 15-p-methoxyphenylacetyllactucin, 15-p-methoxyphenylacetyllactucin-8-sulfate, and 8-p-hydroxyphenylacetyllactucin-15-sulfate. Additionally, three undescribed conjugates of lactucin and a eudesmanolide type sesquiterpenic acid, sonchpalustrin, 4″-O-methylsonchpalustrin, and isosonchpalustrin, were characterized. The structures of the newly discovered natural products were elucidated using 1D and 2D NMR spectroscopy and UHPLC-HRMS. 15-p-Hydroxyphenylacetyllactucin and 15-p-methoxyphenylacetyllactucin showed significant in vitro cytotoxicity against CEM and BJ cells with IC50 values ranging from 3.9 to 9.8 µM. Compounds 3 and 4 showed also strong anti-inflammatory activity in vitro.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Asteraceae/química , Lactonas/farmacologia , Compostos Fitoquímicos/farmacologia , Sesquiterpenos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Proliferação de Células/efeitos dos fármacos , Células Cultivadas , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Lactonas/química , Lactonas/isolamento & purificação , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação
14.
Fitoterapia ; 140: 104415, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31704260

RESUMO

Four new sesquiterpenoids, phellinignins A-D (1-4), together with four known ones (5-8), were isolated from cultures of the fungus Phellinus igniarius. The structures were established by extensive spectroscopic methods including MS, NMR, and the single crystal X-ray diffraction. Compounds 1-3 and 5-8 are tremulane sesquiterpenoids, while compound 4 possesses a new carbon skeleton that might derive from an illudane framework. Compounds 1, 2, 4, and 5 showed certain cytotoxicities to three human cancer cell lines.


Assuntos
Antineoplásicos/farmacologia , Basidiomycota/química , Sesquiterpenos/farmacologia , Antineoplásicos/isolamento & purificação , Linhagem Celular Tumoral , China , Humanos , Estrutura Molecular , Sesquiterpenos Policíclicos , Sesquiterpenos/isolamento & purificação
15.
Nat Prod Res ; 34(7): 903-908, 2020 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-30856347

RESUMO

A new allo-cedrane sesquiterpene glycoside (1) and nine known compounds (2-10) were isolated from the ethanol extract of the fruit of Illicium simonii Maxim. Their structures were elucidated by spectroscopic methods, including 1D-, 2D-NMR, and HRESIMS. The absolute configuration of compound 1 was confirmed by CD experiments. Among them, compounds 1, 4, 5, and 7 displayed moderate anti-inflammatory activities by use of an in vitro bioassay.


Assuntos
Frutas/química , Glicosídeos/isolamento & purificação , Illicium/química , Sesquiterpenos/isolamento & purificação , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Glicosídeos/química , Estrutura Molecular , Sesquiterpenos/química , Análise Espectral
16.
Nat Prod Res ; 34(3): 351-358, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-30580601

RESUMO

A new sesquiterpene (1) and a new monoterpene (2), together with thirteen known compounds (3-15) were isolated from an ethanol extract of the roots of Aristolochia debilis Sieb. et Zucc. The structures of compounds 1 and 2 were elucidated using HR-ESI-MS, 1D and 2D NMR spectroscopy. Anti-inflammatory effects of the isolated compounds were evaluated in terms of inhibition of nitric oxide, tumour-necrosis factor-α and interleukin-6 production in lipopolysaccharide-stimulated RAW264.7 cells. Compounds 1-9 and 12-15 significantly inhibited the levels of NO, TNF-α and IL-6 in LPS-induced RAW264.7 cells from concentrations of 3 µM to 30 µM.


Assuntos
Anti-Inflamatórios/isolamento & purificação , Aristolochia/química , Monoterpenos/isolamento & purificação , Raízes de Plantas/química , Sesquiterpenos/isolamento & purificação , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Interleucina-6/antagonistas & inibidores , Interleucina-6/biossíntese , Lipopolissacarídeos , Camundongos , Estrutura Molecular , Monoterpenos/química , Monoterpenos/farmacologia , Óxido Nítrico/antagonistas & inibidores , Óxido Nítrico/biossíntese , Células RAW 264.7 , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Análise Espectral/métodos , Fator de Necrose Tumoral alfa/antagonistas & inibidores , Fator de Necrose Tumoral alfa/biossíntese
17.
Nat Prod Res ; 34(4): 553-557, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-30317858

RESUMO

Urease inhibition potential of compound (1), guaiane-type sesquiterpene (2), confertin (3) and scopoletin (4) was carried out with high throughout mechanism-based assay. These compounds were isolated from Hypochaeris radicata L., an Asteraceae family member. The pure compounds were screened for their urease and carbonic anhydrase inhibitory activities. The ethyl acetate fractions were subjected to column chromatography, which resulted in the isolation and purification of four compounds (1-4). On evaluation, compounds (1-4) exhibited selective activity against urease enzyme with an IC50 value of 180.11 ± 2.00, 27.18 ± 0.80, 24.12 ± 0.2 and 30.12 ± 1.10 µM respectively. The compounds (1-4) were found to be inactive against carbonic anhydrase enzyme. Thiourea was used as standard inhibitor (21 ± 0.14 µM) of urease enzyme.


Assuntos
Asteraceae/química , Compostos Fitoquímicos/análise , Extratos Vegetais/química , Urease/antagonistas & inibidores , Inibidores Enzimáticos/isolamento & purificação , Inibidores Enzimáticos/farmacologia , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/farmacologia , Sesquiterpenos/análise , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia
18.
Nat Prod Res ; 34(3): 425-428, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-30450961

RESUMO

Phytochemical investigation of Illicium micranthum led to the isolation of two new prenylated C6-C3 compounds, 12-O-methyl-2,3-dehydroillifunone C (1) and illiciminone A (2), together with three known analogues (3-5) and one known sesquiterpene lactone (6). The structures were established by extensive spectroscopic characterization and the reported data. All the isolates were evaluated for their acetylcholinesterase (AChE) inhibition activity. Compound 5 showed weak inhibitory activity (46.0%) at 50 µM concentration.


Assuntos
Illicium/química , Inibidores da Colinesterase/química , Inibidores da Colinesterase/isolamento & purificação , Lactonas/química , Lactonas/isolamento & purificação , Estrutura Molecular , Prenilação , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Análise Espectral
19.
Planta Med ; 86(1): 55-60, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31622995

RESUMO

Chemical investigation of the stems of Dulacia egleri resulted in the isolation of eglerisine (1: ), a compound with a rare sesquiterpenoid tropolone skeleton. Its structure was determined by analysis of spectrometric and spectroscopic data, including HRESIMS, 1D, and 2D NMR. The antiproliferative effects of eglerisine were tested in human leukemia lineages. In the Kasumi-1 lineage, an acute myeloid leukemia cell line, eglerisine reduced cell metabolism, as determined by the resazurin assay. Eglerisine did not induce cell death by either apoptotic or necrotic mechanisms. However, a reduction of the absolute number of cells was observed. Eglerisine induced cell cycle arrest after 72 h of treatment by phosphorylation of H2AX histone, reducing the S phase and increasing the G2 phase of the cell cycle.


Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Proliferação de Células/efeitos dos fármacos , Olacaceae/química , Extratos Vegetais/farmacologia , Sesquiterpenos/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Ciclo Celular/efeitos dos fármacos , Linhagem Celular Tumoral , Histonas/metabolismo , Humanos , Leucemia Mieloide Aguda , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Sesquiterpenos/química , Sesquiterpenos/farmacologia
20.
Nat Prod Res ; 34(7): 943-949, 2020 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-30760039

RESUMO

Saussurea involucrata, known for the abundant bioactive components, is a precious traditional Chinese medicine. In this study, a novel guaiane sesquiterpenoid glycoside named (1R, 5R, 6R, 7R, 8S, 11S)-11, 13-dihydrodehydrocostuslactone-8-O-6'-2''(E)-butenoyl-ß-D-glucopyranoside (1), together with seven known compounds (2-8) were isolated from the dried aerial part of S. involucrata. Their structures were elucidated by spectroscopic and physico-chemical analyses. The antioxidant and anti-inflammatory activities of compound 1 were investigated. And compound 1 showed weak radical scavenging activity and low inhibitory activity on nitric oxide (NO) production.


Assuntos
Glicosídeos/isolamento & purificação , Medicina Tradicional Chinesa , Saussurea/química , Sesquiterpenos/isolamento & purificação , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Antioxidantes/química , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Depuradores de Radicais Livres/química , Depuradores de Radicais Livres/isolamento & purificação , Depuradores de Radicais Livres/farmacologia , Glicosídeos/química , Glicosídeos/farmacologia , Óxido Nítrico/antagonistas & inibidores , Extratos Vegetais/química , Sesquiterpenos/química , Sesquiterpenos/farmacologia
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