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1.
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
2.
J Chromatogr A ; 1621: 461054, 2020 Jun 21.
Artigo em Inglês | MEDLINE | ID: mdl-32204880

RESUMO

The enantioselective separation of newly prepared, pharmacologically significant isopulegol-based ß-amino lactones and ß-amino amides has been studied by carrying out high-performance liquid chromatography on diverse amylose and cellulose tris-(phenylcarbamate)-based chiral stationary phases (CSPs) in n-hexane/alcohol/diethylamine or n-heptane/alcohol/ diethylamine mobile phase systems. For the elucidation of mechanistic details of the chiral recognition, seven polysaccharide-based CSPs were employed under normal-phase conditions. The effect of the nature of selector backbone (amylose or cellulose) and the position of substituents of the tris-(phenylcarbamate) moiety was evaluated. Due to the complex structure and solvation state of polysaccharide-based selectors and the resulting enantioselective interaction sites, the chromatographic conditions (e.g., the nature and content of alcohol modifier) were found to exert a strong influence on the chiral recognition process, resulting in a particular elution order of the resolved enantiomers. Since no prediction can be made for the observed enantiomeric resolution, special attention has been paid to the identification of the elution sequences. The comparison between the effectiveness of covalently immobilized and coated polysaccharide phases allows the conclusion that, in several cases, the application of coated phases can be more advantageous. However, in general, the immobilized phases may be preferred due to their increased robustness. Thermodynamic parameters derived from the temperature-dependence of the selectivity revealed enthalpically-driven separations in most cases, but unusual temperature behavior was also observed.


Assuntos
Amilose/análogos & derivados , Celulose/análogos & derivados , Cromatografia Líquida de Alta Pressão/métodos , Monoterpenos Cicloexânicos/química , Amidas/química , Amidas/isolamento & purificação , Amilose/química , Celulose/química , Lactonas/química , Lactonas/isolamento & purificação , Fenilcarbamatos , Estereoisomerismo , Temperatura , Termodinâmica
3.
J Nat Med ; 74(3): 584-590, 2020 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-32207026

RESUMO

Three new 5,6-dihydro-α-pyrones derivatives, named (S)-rugulactone (1) pulchrinervialactone A (2), and pulchrinervialactone B (4), along with one known pyrone, cryptobrachytone C (3), and three known amide derivatives (5-7) have been isolated from the leaves of Cryptocarya pulchrinervia. The structures of 1-7 were elucidated based on extensive spectroscopic data and comparison with literatures. The configurations of compounds 3 and 4 were established by single crystal X-ray diffraction analysis. This is also the first report in finding (S)-rugulactone (1) as a natural product. In addition, the preliminary cytotoxic activity of the isolated compounds was evaluated against P-388 cells using the [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] assay. All the pyrones, except compound 4, were active significantly inhibiting the growth of P-388 cells, while the amides derivatives (5-7) showed moderate to weak activities. Therefore, compounds 1-3 could be potentially examined further for anticancer agents.


Assuntos
Antineoplásicos/farmacocinética , Proliferação de Células/efeitos dos fármacos , Cryptocarya/química , Lactonas/farmacologia , Pironas/farmacologia , Animais , Antineoplásicos/isolamento & purificação , Linhagem Celular Tumoral , Lactonas/isolamento & purificação , Camundongos , Estrutura Molecular , Neoplasias/tratamento farmacológico , Folhas de Planta/química , Pironas/isolamento & purificação
4.
J Chromatogr A ; 1620: 461004, 2020 Jun 07.
Artigo em Inglês | MEDLINE | ID: mdl-32143875

RESUMO

In the present study, a fast multiresidue method determining three novel fungicides fenpicoxamid, isofetamid, and mandestrobin in cereals was developed and validated for the first time using ultrahigh-performance liquid chromatography coupled to tandem mass spectrometry (UHPLC-MS/MS). Samples were extracted by QuEChERS (Quick, Easy, Cheap, Effective, Rugged, and Safe) methodology, and cleaned up using the disposable pipette extraction (DPX) tips containing primary secondary amine (PSA) and silica gel modified with zirconium oxide (Z-Sep) in less than 1 min. Linearity (r > 0.99) of three fungicides in the calibration range of 0.001-0.1 µg mL-1 was satisfactory. Mean recoveries (n = 15) from all matrices were between 84.8% and 100.3% as the corresponding intra-day and inter-day relative standard deviations (RSDs) were less than 10.6%. Limits of quantitation (LOQs) of all analytes in different matrices were defined at 0.01 mg kg-1. The results indicate this method can serve as a sensitive and rapid approach to monitoring contents of fenpicoxamid, isofetamid, and mandestrobin in cereals.


Assuntos
Acetamidas/análise , Cromatografia Líquida de Alta Pressão/métodos , Grão Comestível/química , Fungicidas Industriais/análise , Resíduos de Praguicidas/análise , Espectrometria de Massas em Tandem/métodos , Tiofenos/análise , Fracionamento Químico/instrumentação , Fungicidas Industriais/química , Fungicidas Industriais/isolamento & purificação , Lactonas/análise , Lactonas/química , Lactonas/isolamento & purificação , Resíduos de Praguicidas/química , Resíduos de Praguicidas/isolamento & purificação , Piridinas/análise , Piridinas/química , Piridinas/isolamento & purificação , Zircônio/química
5.
Phytochemistry ; 171: 112248, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-31918304

RESUMO

The phytochemical investigation of the twig and leaf extracts of Goniothalamus tamirensis led to the isolation and identification of 15 compounds including three rare previously undescribed styryllactones, goniotamirenones A-C, together with 12 known compounds. (Z)-6-Styryl-5,6-dihydro-2-pyranone and 5-(1-hydroxy-3-phenyl-allyl)-dihydro-furan-2-one are reported here for the first time as previously undescribed natural products. Their structures were elucidated by spectroscopic methods. Goniotamirenone A was synthesized via a [2 + 2] cycloaddition reaction of 6-styrrylpyran-2-one in quantitative yield. The absolute configurations of goniotamirenones B and C were identified from experimental and calculated ECD data, while the absolute configurations of (-)-5-acetoxygoniothalamin, (-)-isoaltholactone, parvistone E, and 5-(1-hydroxy-3-phenyl-allyl)-dihydro-furan-2-one were identified by single-crystal X-ray diffraction analysis using Cu Kα radiation. The absolute configurations of the other related compounds were determined from comparisons of their ECD spectra with relevant compounds reported in the literature. (-)-5-Acetoxygoniothalamin exhibited potent cytotoxicity against the colon cancer cell line (HCT116) with an IC50 value of 8.6 µM which was better than the standard control (doxorubicin, IC50 = 9.7 µM), while (Z)-6-styryl-5,6-dihydro-2-pyranone was less active with an IC50 value of 22.1 µM.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Goniothalamus/química , Lactonas/farmacologia , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/farmacologia , Estirenos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Proliferação de Células/efeitos dos fármacos , Cristalografia por Raios X , Teoria da Densidade Funcional , Ensaios de Seleção de Medicamentos Antitumorais , Células HCT116 , Humanos , Lactonas/química , Lactonas/isolamento & purificação , Modelos Moleculares , Estrutura Molecular , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Estirenos/química , Estirenos/isolamento & purificação
6.
Fitoterapia ; 140: 104444, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31790768

RESUMO

Alpinia zerumbet (Pers.) B.L.Burtt & R.M.Sm. (Zingiberaceae) is a perennial plant native to the East Indies and is widely distributed in South America, Oceania, and Asia. The mature fruits of the plant have been used in traditional medicine in China. In this study, we compared the chemical constituents in the methanol extracts of the leaves, the placenta, the pericarps, and the seeds obtained from the same plant using LC-MS, and we examined the NO inhibitory activities of the respective extracts and the isolated compounds. As a result of LC-MS analyses, kavalactone derivatives (1-6) were detected in the methanol extracts of the leaves, placenta, and pericarps. Of these, compound 6 was identified as a new asymmetrical cyclobutane dimer of 5,6-dehydrokawain. Quantitative analysis showed that the total amounts of kavalactone derivatives were highest in the methanol extract of the pericarps. Moreover, the results of measurements of the anti-inflammatory activity revealed that the pericarps extract showed the strongest activity. The compounds responsible for the anti-inflammatory activity of the extracts from A. zerumbet were identified. Of these, five were known kavalactone derivatives and one was a new kavalactone derivative (aniba dimer C). The results showed that the pericarps of A. zerumbet are a rich source of kavalactone derivatives, and that the pericarps of A. zerumbet can be utilized as an important medicinal resource.


Assuntos
Alpinia/química , Anti-Inflamatórios/farmacologia , Lactonas/farmacologia , Animais , Anti-Inflamatórios/isolamento & purificação , Células Cultivadas , Hepatócitos/efeitos dos fármacos , Japão , Lactonas/isolamento & purificação , Estrutura Molecular , Óxido Nítrico/metabolismo , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/química , Folhas de Planta/química , Ratos
7.
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
8.
Planta Med ; 86(1): 26-31, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31711251

RESUMO

Kava, the extract of the roots of Piper methysticum, has been traditionally consumed in the South Pacific islands for its natural relaxing property. Epidemiological data suggests that kava consumption may reduce human cancer risk, and in vitro and in vivo models suggest chemopreventive potential against carcinogen-induced tumorigenesis. Therefore, knowledge about its molecular mechanisms and responsible ingredient(s) for these beneficial properties will better guide kava's use for the management of these disorders. Psychological stress typically results in increased production of stress hormones, such as norepinephrine (NE), which activate adrenergic receptors (ARs). Psychological stress has also been associated with increased cancer incidence and poor clinical outcomes in cancer patients. Mechanistically, binding of NE to ARs induces intracellular calcium influx, which activates downstream signaling pathways involved in both stress and cancer development. In this study, we characterized the effect of kava and its components, 3 fractions and 6 major kavalactones, on NE-induced intracellular calcium influx in H1299, a human non-small cell lung carcinoma cell line. Results show that kava extract effectively inhibits NE-mediated intracellular calcium influx in H1299 cells, potentially through antagonizing ß-AR signaling. This inhibitory activity is recapitulated by the major kavalactones in kava. Among the 6 major kavalactones, DHK demonstrated the best potency. Taken together, our study suggests a novel mechanism through which kava and its ingredients potentially offer the anxiolytic and cancer-preventive activity.


Assuntos
Ansiolíticos/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , Cálcio/metabolismo , Kava/química , Lactonas/farmacologia , Neoplasias Pulmonares/prevenção & controle , Extratos Vegetais/farmacologia , Ansiolíticos/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Humanos , Lactonas/isolamento & purificação , Neoplasias Pulmonares/metabolismo , Neoplasias Pulmonares/psicologia , Norepinefrina/antagonistas & inibidores , Estresse Psicológico/complicações , Estresse Psicológico/tratamento farmacológico
9.
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
10.
Talanta ; 206: 120248, 2020 Jan 01.
Artigo em Inglês | MEDLINE | ID: mdl-31514863

RESUMO

Metabolomics generate a profile of small molecules from plant extracts, which could be directly responsible for bioactivity effects. Using dry-column flash chromatography enabled a rapid and inexpensive method for the very efficient separation of plant extract with a high resolution. This separation method coupled to NMR and FTIR-based metabolomics is applied to identify bioactive natural products. OPLS multivariate analysis method, was used for correlation the chemical composition of the plant extracts, Amphoricarpos autariatus, with the results of cytotoxic activity against Human cervical adenocarcinoma cell line (HeLa) and epithelial lung cancer cell line (A549). In this way, the highest contribution to the cytotoxic activity was recorded for the guaianolide sesquiterpene lactones named amphoricarpolides. The compounds indicated as bioactive after metabolomics analysis were tested, and their cytotoxic activity were confirmed.


Assuntos
Asteraceae/química , Citotoxinas/análise , Lactonas/análise , Metabolômica/métodos , Sesquiterpenos de Guaiano/análise , Linhagem Celular Tumoral , Cromatografia , Citotoxinas/isolamento & purificação , Citotoxinas/toxicidade , Humanos , Lactonas/isolamento & purificação , Lactonas/toxicidade , Espectroscopia de Ressonância Magnética , Componentes Aéreos da Planta/química , Sesquiterpenos de Guaiano/isolamento & purificação , Sesquiterpenos de Guaiano/toxicidade , Espectroscopia de Infravermelho com Transformada de Fourier
11.
Food Chem ; 311: 125975, 2020 May 01.
Artigo em Inglês | MEDLINE | ID: mdl-31855777

RESUMO

A modified quick, easy, cheap, effective, rugged, and safe method coupled with ultra-high performance liquid chromatography-tandem mass spectrometry was established for the simultaneous detection of five Alternaria toxins (tenuazonic acid, alternariol, alternariol monomethyl ether, altenuene, and tentoxin) in wolfberry. The sample pretreatment conditions including the dilution solvent, the extraction solvent and the QuEChERS purification parameters were optimized. Detection of the five Alternaria toxins was performed in MRM mode under ESI + conditions. The results showed that the five Alternaria toxins exhibitedgood linearity (1-200 µg/L, with correlation coefficients > 0.999). The limits of detection were 0.07-0.24 µg/kg, and the limits of quantification were 0.32-0.77 µg/kg. The trueness was between 73.8% and 111.5%, and the precision was lower than 10%. The established method was effectively used for the determination of five Alternaria toxins in 155 wolfberry samples from Northwest China.


Assuntos
Alternaria/metabolismo , Lycium/microbiologia , Micotoxinas/análise , Espectrometria de Massas em Tandem/métodos , Cromatografia Líquida de Alta Pressão , Lactonas/análise , Lactonas/isolamento & purificação , Limite de Detecção , Micotoxinas/isolamento & purificação , Micotoxinas/metabolismo , Peptídeos Cíclicos/análise , Peptídeos Cíclicos/isolamento & purificação , Reprodutibilidade dos Testes , Ácido Tenuazônico/análise , Ácido Tenuazônico/isolamento & purificação
12.
Fitoterapia ; 139: 104372, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31669720

RESUMO

Four new sesquiterpene lactones, named artemargyinolides A-D (1-4), and seven known sesquiterpenoids (5-11) were isolated from Artemisia argyi. Their structures were elucidated based on the extensive analysis of spectroscopic data. The absolute configuration of 1 was assigned by X-ray crystallographic analysis. Compound 1 is an unprecedented sesquiterpene dimer-monoterpene lactone. The cyclooxygenases (COX-1 and COX-2) inhibitory activities of all isolated compounds were evaluated. Compounds 1, 2, 4, and 6-11 showed inhibitory activity against COX-2 with IC50 values ranging from 35.78 ±â€¯0.39 to 256.07 ±â€¯0.38 µM. However, compounds 7, 9, and 10 exhibited weak inhibitory activity against COX-1 with IC50 values of 465.70 ±â€¯1.53, 281.43 ±â€¯3.56, and 490.45 ±â€¯6.07 µM, respectively. Other compounds are inactive against COX-1. Therefore, compounds 1, 2, 4, 6, 8, and 11 displayed selective COX-2 inhibitory activity.


Assuntos
Artemisia/química , Inibidores de Ciclo-Oxigenase 2/farmacologia , Lactonas/farmacologia , Sesquiterpenos/farmacologia , China , Inibidores de Ciclo-Oxigenase 2/isolamento & purificação , Lactonas/isolamento & purificação , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Folhas de Planta/química , Sesquiterpenos/isolamento & purificação
13.
Am J Chin Med ; 47(6): 1289-1305, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31488032

RESUMO

The roots of Aucklandia lappa have been used in traditional medicine in Asia to treat inflammation and diseases associated with pain, including endometriosis. The aim of this study was to investigate the anti-endometriotic effect of dehydrocostus lactone, an active compound in A. lappa roots, using human endometriotic cells and macrophages stimulated by these cells. Dehydrocostus lactone induced apoptotic cell death in 12Z human endometriotic cells. Dehydrocostus lactone stimulated the activation of caspase-3, -8, and -9, while caspase inhibitors significantly reversed the dehydrocostus lactone-induced cell death in 12Z cells. In addition, dehydrocostus lactone decreased the production of PGE2 and neurotrophins (BDNF, NGF, NT3, and NT4/5), which are regarded as endometriosis-associated pain factors in human endometriotic cells. Moreover, dehydrocostus lactone inhibited the expression of M2 markers (CD206, and Trem-2), IL-10, VEGF, and MMP-2/-9 in endometriosis-associated macrophages (EAMs). Furthermore, dehydrocostus lactone inhibited the Akt and NFκB pathways in both endometriotic cells and EAMs. Taken together, our findings suggest that dehydrocostus lactone, an active compound of A, lappa, has anti-endometriotic activities via induction of apoptosis and downregulation of pain factors in endometriotic cells and inhibition of the alternative activation of EAMs.


Assuntos
Apoptose/efeitos dos fármacos , Endometriose/tratamento farmacológico , Endometriose/imunologia , Endométrio/citologia , Lactonas/farmacologia , Lactonas/uso terapêutico , Ativação de Macrófagos/efeitos dos fármacos , Fitoterapia , Raízes de Plantas/química , Saussurea/química , Sesquiterpenos/farmacologia , Sesquiterpenos/uso terapêutico , Caspases/metabolismo , Linhagem Celular , Dinoprostona/metabolismo , Feminino , Humanos , Interleucina-10/metabolismo , Lactonas/isolamento & purificação , Lectinas Tipo C/metabolismo , Lectinas de Ligação a Manose/metabolismo , Medicina Tradicional , Fatores de Crescimento Neural/metabolismo , Receptores de Superfície Celular/metabolismo , Sesquiterpenos/isolamento & purificação , Estimulação Química
14.
J Food Sci ; 84(10): 2758-2776, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-31509249

RESUMO

The changes of volatile compounds in soy sauce during long-term fermentation (12 months) were investigated using solid-phase microextraction (SPME) and stir bar sorptive extraction (SBSE). A total of 144 and 129 compounds were identified in soy sauce with long-term fermentation by SPME and SBSE, respectively. The contents of most compounds, such as acids, aldehydes, benzene and benzene derivatives, esters, lactones, pyrazines, pyrones, and pyrroles, showed a tendency to increase, whereas those of alcohols and ketones decreased according to long-term fermentation. In addition, principal component analysis and partial least squares discriminant analysis were applied to discriminate soy sauce samples according to fermentation periods and determine key volatile compounds related to long-term fermentation. The initial fermentation stages were mainly associated with some alcohols, ketones, and lactones, whereas the later stages were strongly associated with most esters, some phenols, benzene and benzene derivatives, and pyrroles. Moreover, the key volatile compounds associated with long-term fermentation in soy sauce samples were ethyl 3-methylbutanoate (ethyl isovalerate), ethyl pentanoate (ethyl valerate), 1-octen-3-yl acetate, 3-(methylthio)-1-propanol (methionol), ethyl benzoate, ethyl 2-phenylacetate, 1-(1H-pyrrol-2-yl)ethanone (2-acetylpyrrole), and 5-pentyl-2-oxolanone (γ-nonalactone). PRACTICAL APPLICATION: This study investigated changes of volatile compounds in soy sauce during long-term fermentation (12 months) using solid-phase microextraction and stir bar sorptive extraction. In addition, the key volatile compounds associated with long-term fermentation in soy sauce samples were determined. These results may help to predict the effective contributors related to long-term fermentation of soy sauce and improve the quality of soy sauce during long-term fermentation.


Assuntos
Alimentos de Soja/análise , Compostos Orgânicos Voláteis/química , Álcoois/química , Álcoois/isolamento & purificação , Aldeídos/química , Aldeídos/isolamento & purificação , Fermentação , Cetonas/química , Cetonas/isolamento & purificação , Lactonas/química , Lactonas/isolamento & purificação , Microextração em Fase Sólida , Soja/química , Compostos Orgânicos Voláteis/isolamento & purificação
15.
Chirality ; 31(10): 855-864, 2019 10.
Artigo em Inglês | MEDLINE | ID: mdl-31423667

RESUMO

As an important intermediate of prostaglandins and entecavir, optically pure Corey lactone diol (CLD) has great value in the pharmaceutical industry. In this work, the enantioseparation of (±)-CLD was evaluated using high-performance liquid (HPLC) and supercritical fluid chromatography (SFC). In HPLC, the separations of CLD enantiomers on polysaccharide-based chiral stationary phases with both normal phase and polar organic phase were screened. And the conditions for the enantioseparation were optimized in HPLC and SFC, including the selection of mobile phase, temperature, back-pressure, and other conditions. More important, it was found that the chiral resolutions were greatly enhanced by the increase of the coating amount of ADMPC (amylose tris-(3,5-dimethylphenylcarbamate)) under both HPLC and SFC conditions, which can lead to the increase of the productivity and the decrease of the solvent consumption. The preparations of optically pure CLD were evaluated on a semi-preparative (2 × 25 cm) column packed with 30% ADMPC-coated CSP under HPLC and SFC conditions. Preparative performances in terms of kkd are 1.536 kg racemate/kg CSP/day and 1.248 kg racemate/kg CSP/day in HPLC and SFC, respectively.


Assuntos
Cromatografia Líquida de Alta Pressão/métodos , Cromatografia com Fluido Supercrítico/métodos , Lactonas/química , Lactonas/isolamento & purificação , Amilose/análogos & derivados , Amilose/química , Fenilcarbamatos/química , Espectroscopia de Infravermelho com Transformada de Fourier , Estereoisomerismo , Temperatura
16.
J Appl Microbiol ; 127(5): 1468-1478, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31403229

RESUMO

AIMS: Medicinal plant-associated endophytic fungi are important sources of precious bioactive compounds, contributing more than 80% of the natural drugs for various ailments. The present study was aimed at evaluating the anticancer activity of the crystallized compound alternariol methyl ether (AME) against hepatocellular carcinoma (HCC) both in vitro and in vivo from an endophytic fungus residing in the medicinal plant Vitex negundo. METHODS AND RESULTS: The secondary metabolites from the endophytic fungus Alternaria alternata MGTMMP031 were isolated. Purification and characterization of the compound was performed and the potential compound was identified as AME. The crystal structure of AME was unambiguously confirmed by X-ray analysis. AME has been checked for its antibacterial and anticancer properties which showed its effectiveness against various bacteria and demonstrated marked anti-proliferative activity against the human HCC cells (HUH-7) both in vitro and in vivo. Mode of actions included cell cycle arrest, reducing the level of markers enzymes of liver cancer and preventing tumour growth. CONCLUSIONS: Alternariol methyl ether acts as a potential therapeutic target against HCC. The compound was isolated and the crystal structure was obtained for the first time from the endophytic fungus A. alternata MGTMMP031. In the present study, the crystallized structure of AME was obtained by slow evaporation technique. It can be concluded that AME acts as a potential therapeutic target against HCC. SIGNIFICANCE AND IMPACT OF THE STUDY: Endophytic fungi residing in the medicinal plants have strong biological significance and bioactive compounds from these fungi provide better therapeutic targets against diseases.


Assuntos
Alternaria/química , Antineoplásicos/química , Antineoplásicos/farmacologia , Endófitos/química , Lactonas/isolamento & purificação , Lactonas/farmacologia , Éteres Metílicos/química , Plantas Medicinais/microbiologia , Alternaria/isolamento & purificação , Alternaria/metabolismo , Antineoplásicos/isolamento & purificação , Antineoplásicos/metabolismo , Carcinoma Hepatocelular/tratamento farmacológico , Carcinoma Hepatocelular/fisiopatologia , Pontos de Checagem do Ciclo Celular/efeitos dos fármacos , Cristalização , Endófitos/isolamento & purificação , Endófitos/metabolismo , Humanos , Lactonas/química , Lactonas/metabolismo , Neoplasias Hepáticas/tratamento farmacológico , Neoplasias Hepáticas/fisiopatologia , Éteres Metílicos/isolamento & purificação , Éteres Metílicos/farmacologia , Metabolismo Secundário
17.
Fitoterapia ; 138: 104286, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-31394164

RESUMO

Three new compounds including two depsidones (simplicildones J and K) and one dihydroxanthenone (globosuxanthone E) together with nine known compounds were obtained from the crude extracts of two endophytic fungi Simplicillium lanosoniveum (J.F.H. Beyma) Zare & W. Gams PSU-H168 and PSU-H261 which were isolated from the leaves of Hevea brasiliensis. The structures were elucidated by spectroscopic evidence. The absolute configuration of globosuxanthone E was established by means of experimental and calculated TDDFT ECD data. Simplicildone K exhibited antibacterial activity against Staphylococcus aureus and methicillin-resistant S. aureus with equal MIC values of 128 µg/mL. Simplicildone K and globosuxanthone E displayed antifungal activity against Cryptococcus neoformans ATCC90113 with the same MIC values of 32 µg/mL. In addition, known botryohordine C and simplicildone A showed phosphodiesterase 5 inhibitory activity with the IC50 values of 5.69 and 9.96 µM, respectively, and were noncytotoxic toward noncancerous Vero cells.


Assuntos
Depsídeos/farmacologia , Hevea/microbiologia , Hypocreales/química , Lactonas/farmacologia , Xantonas/farmacologia , Animais , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Chlorocebus aethiops , Cryptococcus neoformans/efeitos dos fármacos , Depsídeos/isolamento & purificação , Endófitos/química , Lactonas/isolamento & purificação , Staphylococcus aureus Resistente à Meticilina/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Inibidores da Fosfodiesterase 5/isolamento & purificação , Inibidores da Fosfodiesterase 5/farmacologia , Folhas de Planta/microbiologia , Tailândia , Células Vero , Xantonas/isolamento & purificação
18.
Molecules ; 24(14)2019 Jul 23.
Artigo em Inglês | MEDLINE | ID: mdl-31340585

RESUMO

The stems of Dendrobium loddigesii, a Chinese herb, are often used to treat diabetes and its polar extract is rich in shihunine, a water-soluble Orchidaceae alkaloid, but little is known about the anti-diabetes effects and mechanism of shihunine. This study investigated the anti-diabetic effect of a shihunine-rich extract of D. loddigesii (DLS) based on 3T3-L1 cells and db/db mice. The underlying mechanisms were primarily explored using Western blot analysis and immunohistochemical staining. The 3T3-L1 cell experiments showed that DLS can reduce the intracellular accumulation of oil droplets as well as triglycerides (p < 0.001) and promote the 2-[N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino]-2deoxyglucose (2-NBDG) uptake of 3T3-L1 cells (p < 0.001). The animal experiments confirmed that after 8 weeks of DLS treatment, the body weight, fasting blood sugar, and serum lipid levels of mice were significantly lowered, and the oral glucose tolerance test and serum insulin level were significantly improved compared to the no-treatment diabetes mellitus group. Further histomorphology observation led to the conclusion that the quantities of islet cells were significantly increased and the increase in adipose cell size was significantly suppressed. The immunohistochemical test of pancreatic tissue revealed that DLS inhibited the expression of cleaved cysteine aspartic acid-specific protease 3 (cleaved caspase-3). Western blot experiments showed that DLS had agonistic effects on adenosine monophosphate (AMP)-activated protein kinase phosphorylation (p-AMPK) and increased the expression levels of peroxisome proliferator-activated receptor α (PPARα) and glucose transporter 4 (GLUT4) in liver or adipose tissues. These data suggest that the shihunine-rich extract of D. loddigesii is an anti-diabetic fraction of D. loddigesii. Under our experimental condition, DLS at a dose of 50 mg/kg has good anti-diabetic efficacy.


Assuntos
Glicemia/efeitos dos fármacos , Dendrobium/química , Diabetes Mellitus Experimental/tratamento farmacológico , Hipoglicemiantes/farmacologia , Lactonas/farmacologia , Extratos Vegetais/farmacologia , Pirrolidinas/farmacologia , Células 3T3-L1 , 4-Cloro-7-nitrobenzofurazano/análogos & derivados , 4-Cloro-7-nitrobenzofurazano/metabolismo , Proteínas Quinases Ativadas por AMP/genética , Proteínas Quinases Ativadas por AMP/metabolismo , Animais , Transporte Biológico , Glicemia/metabolismo , Caspase 3/genética , Caspase 3/metabolismo , Desoxiglucose/análogos & derivados , Desoxiglucose/metabolismo , Diabetes Mellitus Experimental/genética , Diabetes Mellitus Experimental/metabolismo , Diabetes Mellitus Experimental/fisiopatologia , Jejum , Regulação da Expressão Gênica , Teste de Tolerância a Glucose , Transportador de Glucose Tipo 4/genética , Transportador de Glucose Tipo 4/metabolismo , Hipoglicemiantes/isolamento & purificação , Lactonas/isolamento & purificação , Gotículas Lipídicas/química , Gotículas Lipídicas/efeitos dos fármacos , Masculino , Camundongos , Camundongos Transgênicos , PPAR alfa/genética , PPAR alfa/metabolismo , Extratos Vegetais/química , Caules de Planta/química , Pirrolidinas/isolamento & purificação , Transdução de Sinais , Triglicerídeos/antagonistas & inibidores , Triglicerídeos/metabolismo
19.
Molecules ; 24(15)2019 Jul 26.
Artigo em Inglês | MEDLINE | ID: mdl-31357563

RESUMO

Andrographis paniculata (AP) has been widely used in China for centuries to treat various diseases, and especially to treat inflammation. Diterpenoid lactones are the main anti-inflammatory components of AP. However, systematic chemical composition and biological activities, as well as key pharmacophores, of these diterpenoid lactones from AP have not yet been clearly understood. In this study, 17 diterpenoid lactones, including 2 new compounds, were identified by spectroscopic methods, and most of them attenuated the generation of TNF-α and IL-6 in LPS-induced RAW 274.7 cells examined by ELISA. Pharmacophores of diterpenoid lactones responsible for the anti-inflammatory activities were revealed based on the quantitative structure-activity relationship (QSAR) models. Moreover, new compounds (AP-1 and AP-4) exerted anti-inflammatory activity in LPS microinjection-induced zebrafish, which might be correlated with the inhibition of the translocation of NF-κB p65 from cytoplasm to nucleus. Our study provides guidelines for future structure modification and rational drug design of diterpenoid lactones with anti-inflammatory properties in medical chemistry.


Assuntos
Andrographis/química , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Diterpenos/química , Lactonas/química , Lactonas/farmacologia , Componentes Aéreos da Planta/química , Animais , Anti-Inflamatórios/isolamento & purificação , Sobrevivência Celular/efeitos dos fármacos , Lactonas/isolamento & purificação , Lipopolissacarídeos/imunologia , Macrófagos/efeitos dos fármacos , Macrófagos/imunologia , Macrófagos/metabolismo , Camundongos , Modelos Moleculares , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Relação Quantitativa Estrutura-Atividade , Células RAW 264.7 , Análise Espectral , Peixe-Zebra
20.
Chem Biodivers ; 16(9): e1900266, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31298476

RESUMO

Two new spliceostatin analogs, designed as spliceostatins J and K (1 and 2), were isolated and identified from the culture of Pseudomonas sp., along with two known ones, FR901464 (3) and spliceostatin E (4). Their structures were elucidated by detailed interpretation of their spectroscopic data, especially 2D-NMR and HR-ESI-MS. Spliceostatin J (1) represented the first example of spliceostatins bearing an unusual hexahydrofuro[3,4-b]furan moiety. Biological assay showed all the isolated compounds except 1 displayed potent cytotoxic activities against two cancer cell lines (MDA-MB-231 and A-549). Structure-activity-relationship studies revealed that the tetrahydropyran ring in spliceostatin analogs was necessary for their bioactive retention.


Assuntos
Antineoplásicos/farmacologia , Furanos/farmacologia , Lactonas/farmacologia , Pseudomonas/química , Pironas/farmacologia , Células A549 , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Furanos/química , Furanos/isolamento & purificação , Humanos , Lactonas/química , Lactonas/isolamento & purificação , Estrutura Molecular , Piranos/química , Piranos/isolamento & purificação , Piranos/farmacologia , Pironas/química , Pironas/isolamento & purificação , Compostos de Espiro/química , Compostos de Espiro/isolamento & purificação , Compostos de Espiro/farmacologia , Relação Estrutura-Atividade
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