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1.
Anticancer Res ; 40(1): 87-95, 2020 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-31892556

RESUMEN

BACKGROUND/AIM: Very few studies are available about the biological activity of 3-styrylchromones. Our previous study demonstrated the importance of methoxy group at 6-position of the chromone ring and hydroxyl group at 4'-position of phenyl group in styryl moiety. As a sequel of this study, we synthesized fourteen compounds that include eight 3-styrylchromones where methoxy group was introduced at 7-position of chromone rings, and then evaluated their tumor-specificity. MATERIALS AND METHODS: Tumor-specificity (TS) was calculated by relative cytotoxicity against human oral squamous cell carcinoma cell lines versus human normal oral cells. Apoptosis induction and growth arrest were monitored by cell-cycle analysis. Quantitative structure-activity relationship analysis of TS was performed with 3,167 chemical descriptors. RESULTS AND DISCUSSION: Two compounds, 7-methoxy-3-[(1E)-2-phenylethenyl]-4H-1-benzopyran-4-one [7] and 3-[(1E)-2-(4-hydroxyphenyl)ethenyl]-7-methoxy-4H-1-benzopyran-4-one [14] showed higher tumor-specificity than doxorubicin and 5-FU, suggesting the importance of methoxy group in 7-position of the chromone ring. These compounds induced the apoptosis and mitotic arrest in HSC-2 cells. The tumor-specificity of 3-styrylchromone derivatives were most correlated with descriptors for molecule shape and electronic charge. The present study suggested that modification by introducing methoxy group at 7-position, instead at 6-position, further increased the tumor-specificity of 3-styrylchromone.


Asunto(s)
Antineoplásicos/química , Antineoplásicos/farmacología , Cromonas/química , Cromonas/farmacología , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Humanos , Estructura Molecular , Relación Estructura-Actividad Cuantitativa
2.
J Enzyme Inhib Med Chem ; 35(1): 489-497, 2020 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-31914827

RESUMEN

A series of amino acid-sulphonamide conjugates was prepared through benzotriazole mediated coupling reactions and characterised by 1H-NMR, 13C-NMR, MS, and FTIR spectroscopic techniques as well as elemental analysis. The carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activity of the new compounds was determined against four human (h) isoforms, hCA I, hCA II, hCA VA, and hCA XII. Most of the synthesised compounds showed effective in vitro CA inhibitory properties. The new amino acid-sulphonamide conjugates showed potent inhibitory activity against hCA II, some of them at subnanomolar levels, exhibiting more effective inhibitory activity compared to the standard drug acetazolamide. Some of these sulphonamides were also found to be effective inhibitors of hCA I, hCA VA, and hCA XII, with activity from the low to high nanomolar range.


Asunto(s)
Aminoácidos/farmacología , Inhibidores de Anhidrasa Carbónica/farmacología , Anhidrasas Carbónicas/metabolismo , Sulfonamidas/farmacología , Aminoácidos/síntesis química , Aminoácidos/química , Inhibidores de Anhidrasa Carbónica/síntesis química , Inhibidores de Anhidrasa Carbónica/química , Humanos , Isoenzimas/antagonistas & inhibidores , Isoenzimas/metabolismo , Estructura Molecular , Sulfonamidas/síntesis química , Sulfonamidas/química
3.
J Enzyme Inhib Med Chem ; 35(1): 498-505, 2020 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-31914836

RESUMEN

Brain butyrylcholinesterase (BChE) is an attractive target for drugs designed for the treatment of Alzheimer's disease (AD) in its advanced stages. It also potentially represents a biomarker for progression of this disease. Based on the crystal structure of previously described highly potent, reversible, and selective BChE inhibitors, we have developed the fluorescent probes that are selective towards human BChE. The most promising probes also maintain their inhibition of BChE in the low nanomolar range with high selectivity over acetylcholinesterase. Kinetic studies of probes reveal a reversible mixed inhibition mechanism, with binding of these fluorescent probes to both the free and acylated enzyme. Probes show environment-sensitive emission, and additionally, one of them also shows significant enhancement of fluorescence intensity upon binding to the active site of BChE. Finally, the crystal structures of probes in complex with human BChE are reported, which offer an excellent base for further development of this library of compounds.


Asunto(s)
Amidas/farmacología , Butirilcolinesterasa/metabolismo , Inhibidores de la Colinesterasa/farmacología , Colorantes Fluorescentes/farmacología , Amidas/síntesis química , Amidas/química , Animales , Butirilcolinesterasa/aislamiento & purificación , Inhibidores de la Colinesterasa/síntesis química , Inhibidores de la Colinesterasa/química , Cristalografía por Rayos X , Colorantes Fluorescentes/síntesis química , Colorantes Fluorescentes/química , Humanos , Ratones , Modelos Moleculares , Estructura Molecular
4.
J Enzyme Inhib Med Chem ; 35(1): 584-597, 2020 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-31992093

RESUMEN

NorA is the most studied efflux pump of Staphylococcus aureus and is responsible for high level resistance towards fluoroquinolone drugs. Although along the years many NorA efflux pump inhibitors (EPIs) have been reported, poor information is available about structure-activity relationship (SAR) around their nuclei and reliability of data supported by robust assays proving NorA inhibition. In this regard, we focussed efforts on the 2-phenylquinoline as a promising chemotype to develop potent NorA EPIs. Herein, we report SAR studies about the introduction of different aryl moieties on the quinoline C-2 position. The new derivative 37a showed an improved EPI activity (16-fold) with respect to the starting hit 1. Moreover, compound 37a exhibited a high potential in time-kill curves when combined with ciprofloxacin against SA-1199B (norA+). Also, 37a exhibited poor non-specific effect on bacterial membrane polarisation and showed an improvement in terms of "selectivity index" in comparison to 1.


Asunto(s)
Antibacterianos/farmacología , Proteínas Bacterianas/antagonistas & inhibidores , Proteínas Asociadas a Resistencia a Múltiples Medicamentos/antagonistas & inhibidores , Quinolinas/farmacología , Staphylococcus aureus/efectos de los fármacos , Antibacterianos/síntesis química , Antibacterianos/química , Proteínas Bacterianas/metabolismo , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Proteínas Asociadas a Resistencia a Múltiples Medicamentos/metabolismo , Quinolinas/síntesis química , Quinolinas/química , Staphylococcus aureus/metabolismo , Relación Estructura-Actividad
5.
Chem Commun (Camb) ; 56(8): 1271-1274, 2020 Jan 25.
Artículo en Inglés | MEDLINE | ID: mdl-31903456

RESUMEN

A dual-cavity basket 16-, holding six γ-aminobutyric acids at its termini, encapsulates variously sized aromatics 2-7+, including four anthracyclines (8+-11+), driven by the hydrophobic effect and hydrogen bonding (HB). In particular, the formation of stable (K = 1012 M-2) anthracycline complexes [(8+-11+)2⊂16-], assembled into nanoparticles, occurred with positive homotropic cooperativity (α = 4K2/K1 = 1.1 ± 0.3 × 102-1.3 ± 0.7 × 103) in PBS medium. Importantly, weakening the first binding event (K1, i.e. by removing HBs) turned the second one (K2) more favorable. The finding is of interest for developing cooperative nano-antidotes acting as biodetoxifying agents.


Asunto(s)
Antraciclinas/farmacología , Antídotos/farmacología , Antineoplásicos/farmacología , Nanoestructuras/química , Regulación Alostérica/efectos de los fármacos , Antraciclinas/síntesis química , Antraciclinas/química , Antídotos/síntesis química , Antídotos/química , Antineoplásicos/química , Enlaces de Hidrógeno , Interacciones Hidrofóbicas e Hidrofílicas , Modelos Moleculares , Estructura Molecular
6.
Chem Commun (Camb) ; 56(9): 1353-1356, 2020 Jan 30.
Artículo en Inglés | MEDLINE | ID: mdl-31904054

RESUMEN

A novel cyclodextrin molecular tube with one fully modified and one unmodified end was facilely synthesized by selective desilylation of a 6-O-tert-butyldimethylsilylated ß-cyclodextrin dimer possessing multiple linkers. This molecular tube showed a selective inclusion ability toward cis-unsaturated fatty acid esters by utilizing the asymmetric cylindrical nanocavity.


Asunto(s)
Ésteres/química , Ácidos Grasos Insaturados/química , beta-Ciclodextrinas/química , Estructura Molecular , Estereoisomerismo , beta-Ciclodextrinas/síntesis química
7.
Inorg Chem ; 59(2): 1242-1255, 2020 Jan 21.
Artículo en Inglés | MEDLINE | ID: mdl-31910004

RESUMEN

Cytochrome c oxidase (CcO) has a binuclear active site composed of a high-spin heme group and a tris-histidine-ligated copper ion (CuB). By using two different porphyrin models derived by Gunter (H2TPyPP) and us (H2TImPP), we have isolated several mono- and binuclear complexes including one carbonyl and three chloride derivatives which are determined by 100 K single-crystal X-ray. Low-temperature (4 K) EPR and multitemperature (295-25 K) Mössbauer investigations on the products not only confirmed the spin states of the two metal ions (S = 5/2 Fe3+ and S = 1/2 Cu2+) but also revealed the intermolecular interactions and intramolecular couplings which are in accordance with the crystal structural features.


Asunto(s)
Complejo IV de Transporte de Electrones/análisis , Porfirinas/química , Cristalografía por Rayos X , Complejo IV de Transporte de Electrones/metabolismo , Modelos Moleculares , Estructura Molecular , Porfirinas/metabolismo , Temperatura Ambiental
8.
Inorg Chem ; 59(2): 1323-1331, 2020 Jan 21.
Artículo en Inglés | MEDLINE | ID: mdl-31920084

RESUMEN

We first design and synthesize a dendritic aromatic 6-carboxyl linker (H6TDCPB), which is successfully assembled with Cd(II) ion to construct a porous metal-organic framework with a raw Cd6 cluster, {[Cd3(TDCPB)·2DMAc]·DMAc·4H2O}n (namely, complex 1). More interestingly, six adjacent linkers are packed together by π-π-stacking interactions to form an amazing six-molecule accumulation in the crystal structure. By virtue of high stability and luminescent properties, the as-synthesized sample not merely owns an excellent detectable ability but also possesses an outstanding selectivity for nitrofurans with remarkable recursitivity.


Asunto(s)
Antibacterianos/análisis , Colorantes Fluorescentes/química , Mediciones Luminiscentes , Estructuras Metalorgánicas/química , Colorantes Fluorescentes/síntesis química , Estructuras Metalorgánicas/síntesis química , Estructura Molecular
9.
Fitoterapia ; 140: 104441, 2020 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-31778760

RESUMEN

In the present work, we reported the triterpenoids isolated from n-butanol fraction of Kadsura heteroclita which is a Tujia ethnomedicine with trivial name "Xuetong". This effort resulted in the isolation of six unpresented triterpenoids xuetongsu A-F (1-6), along with five known triterpenoids (7-11). The structures of the reported compounds were established on the 1D, and 2D NMR and HRESIMS spectra, along with CD spectroscopic analysis. Moreover, the absolute stereochemistry of compound 7 was determined by X-ray diffraction analysis. Antioxidant and cytotoxic activities were evaluated for all isolated compounds, compound 7 shown weak cytotoxic activity against HL-60 with IC50 value of 50.0 µM.


Asunto(s)
Kadsura/química , Tallos de la Planta/química , Triterpenos/química , China , Células HL-60 , Humanos , Estructura Molecular , Fitoquímicos/química , Fitoquímicos/aislamiento & purificación , Triterpenos/aislamiento & purificación
10.
Fitoterapia ; 140: 104440, 2020 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-31783131

RESUMEN

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


Asunto(s)
Asteraceae/química , Benzofuranos/farmacología , Lignanos/farmacología , Microglía/efectos de los fármacos , Animales , Benzofuranos/aislamiento & purificación , Línea Celular , China , Lignanos/aislamiento & purificación , Ratones , Estructura Molecular , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología
11.
J Agric Food Chem ; 68(1): 258-266, 2020 Jan 08.
Artículo en Inglés | MEDLINE | ID: mdl-31825219

RESUMEN

Screening the volatiles of cempedak [Artocarpus integer (Thunb.) Merr.] pulp for odor-active compounds by aroma extract dilution analysis and gas chromatography (GC)-olfactometry of static headspace samples revealed a total of 55 odorants, among which 47 were identified. Using stable isotopically substituted odorants as internal standards, these compounds were quantitated by GC-mass spectrometry, and odor activity values (OAVs) were calculated as ratios of the natural concentrations in cempedak pulp to the orthonasal odor detection thresholds. An aroma reconstitution model based on the 41 compounds with OAVs >1 in their natural concentrations successfully mimicked the characteristic aroma of cempedak pulp including the pronounced sulfury, oniony note which is intense in cempedak pulp but absent in jackfruit pulp. Further sensory tests finally showed that 2-(methylsulfanyl)propane, 2-(methylsulfanyl)butane, and 2-(methylsulfanyl)pentane are the key compounds responsible for this unique aroma note in cempedak pulp and vitally contribute to the aroma difference between cempedak pulp and jackfruit pulp.


Asunto(s)
Artocarpus/química , Odorantes/análisis , Compuestos Orgánicos Volátiles/química , Aromatizantes/química , Cromatografía de Gases y Espectrometría de Masas , Humanos , Estructura Molecular , Olfatometría , Olfato
12.
J Agric Food Chem ; 68(3): 884-891, 2020 Jan 22.
Artículo en Inglés | MEDLINE | ID: mdl-31825610

RESUMEN

Having a long history of traditional medicinal applications, Papaver somniferum is also known as a source of various pharmacologically highly active opiates. Consequently, their detection from plant extracts is an important analytical task and generally addressed by methods of GC-MS and LC-MS. However, opiates do also show structural similarities to matrix molecules used in matrix-assisted laser desorption ionization (LDI) and may therefore ionize upon simple laser irradiation. Following this analytical approach, the present work thoroughly evaluated the direct detection of opiates by matrix-free LDI in crude extracts of P. somniferum. The method facilitated the identification of 10 reported opiates by their molecular formulas without any chromatographic prepurification. Moreover, a principal component analysis based on LDI-MS data permitted the correct grouping of all extracts according to their inherent chemistry. Concluding experiments on serial dilutions of thebaine further evaluated potential quantitative applications of the method. Overall results highlight the promising potential of LDI-MS for the swift detection of opiates in complex mixtures.


Asunto(s)
Alcaloides Opiáceos/química , Papaver/química , Extractos Vegetales/química , Espectrometría de Masa por Láser de Matriz Asistida de Ionización Desorción/métodos , Rayos Láser , Estructura Molecular , Espectrometría de Masa por Láser de Matriz Asistida de Ionización Desorción/instrumentación
13.
J Agric Food Chem ; 68(1): 88-96, 2020 Jan 08.
Artículo en Inglés | MEDLINE | ID: mdl-31826619

RESUMEN

Solanum rostratum is a worldwide malignant invasive weed, causing serious harm to the ecological environment and biodiversity. Strong chemical defense against herbivorous insects is supposed to be one of the successful invasive mechanisms of this exotic plant. However, the real defense components and their action mechanisms and distributions are still unknown. To address these problems, we bioassay-guided isolated compounds from the aerial part of S. rostratum and determined their structures using high-resolution electrospray ionization mass spectrometry, nuclear magnetic resonance, and electronic circular dichroism calculation. One new and seven known compounds were identified, and all of the isolates exhibited different levels of antifeedant activities, especially compounds 1 and 4. Consistently, compounds 1 and 4 displayed potent inhibitory effects on antifeedant-related enzymes (AchE and CarE). The action mechanisms of active compounds 1 and 4 were revealed by molecular docking and molecular dynamic simulation studies. Furthermore, the distributions of the active compounds in leaves, stems, and flowers were also analyzed by liquid chromatography-mass spectrometry.


Asunto(s)
Conducta Alimentaria/efectos de los fármacos , Insecticidas/farmacología , Mariposas Nocturnas/efectos de los fármacos , Extractos Vegetales/farmacología , Malezas/química , Solanum/química , Animales , Flores/química , Flores/metabolismo , Insecticidas/química , Insecticidas/aislamiento & purificación , Insecticidas/metabolismo , Simulación del Acoplamiento Molecular , Estructura Molecular , Mariposas Nocturnas/fisiología , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/metabolismo , Hojas de la Planta/química , Hojas de la Planta/metabolismo , Malezas/metabolismo , Metabolismo Secundario , Solanum/metabolismo , Espectrometría de Masa por Ionización de Electrospray
14.
Fitoterapia ; 140: 104444, 2020 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-31790768

RESUMEN

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.


Asunto(s)
Alpinia/química , Antiinflamatorios/farmacología , Lactonas/farmacología , Animales , Antiinflamatorios/aislamiento & purificación , Células Cultivadas , Hepatocitos/efectos de los fármacos , Japón , Lactonas/aislamiento & purificación , Estructura Molecular , Óxido Nítrico/metabolismo , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Extractos Vegetales/química , Hojas de la Planta/química , Ratas
15.
Fitoterapia ; 140: 104442, 2020 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-31790769

RESUMEN

Averrhoa carambola L. (Oxalidaceae) was widely cultivated for fruits (star fruit), whereas the value of leaves remains to be discovered. Our study on the leaves yielded five flavan-3-ols (1-5) and two 2-diglycosyloxybenzoates. Their structures were determined by spectroscopic and chemical methods. Epicatechin-(5,6-bc)-4ß-(p-hydroxyphenyl)-dihydro-2(3H)-pyranone (1) and benzyl 2-ß-d-apiofuranosyl-(1 â†’ 6)-ß-d-glucopyranosyloxybenzoate (6) were new structures. 6-(S-2-Pyrrolidinone-5-yl)epicatechin (4) and 6-(R-2-pyrrolidinone-5-yl)epicatechin (5) were obtained as monomeric diastereomer for the first time and their absolute configurations were determined by electronic circular dichroism (ECD) computation. Epicatechin-(7,8-bc)-4α-(p-hydroxyphenyl)-dihydro-2(3H)-pyranone (2), epicatechin-(7,8-bc)-4ß-(p-hydroxyphenyl)-dihydro-2(3H)-pyranone (3), and methyl 2-ß-d-apiofuranosyl-(1 â†’ 6)-ß-d-glucopyranosyloxybenzoate (7) were not previously reported from the genus Averrhoa. Compounds 1-5 showed more potent 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) radical cation and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activities and ferric reducing antioxidant power (FRAP) than l-ascorbic acid. Meanwhile 1 and 3 exhibited lipase and α-glucosidase inhibitory activities, respectively. The results clarified the structures of flavan-3-ols and 2-diglycosyloxybenzoates in the leaves and their antioxidant, lipase, and α-glucosidase inhibitory activities.


Asunto(s)
Antioxidantes/química , Averrhoa/química , Benzoatos/química , Flavonoides/química , Hojas de la Planta/química , Antioxidantes/aislamiento & purificación , Benzoatos/aislamiento & purificación , China , Flavonoides/aislamiento & purificación , Inhibidores de Glicósido Hidrolasas/química , Inhibidores de Glicósido Hidrolasas/aislamiento & purificación , Lipasa/antagonistas & inhibidores , Estructura Molecular , Fitoquímicos/química , Fitoquímicos/aislamiento & purificación
16.
Fitoterapia ; 140: 104445, 2020 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-31790771

RESUMEN

Thallactones A (1) and B (2), enantiomeric aporphine alkaloids with rare cleaved rings A and B, as well as thaliglucine N-oxide (3) and their biosynthetically related precursor, northalphenine (4), were isolated from the whole plant of Thalictrum wangii. Their structures with absolute configurations were elucidated by spectral techniques and electronic circular dichroism (ECD). Moreover, compounds 1, 3, and northalphenine inhibited concanavalin A (Con A)-stimulated proliferation of mice splenocyte significantly in a dose-dependent manner.


Asunto(s)
Aporfinas/farmacología , Inmunosupresores/farmacología , Thalictrum/química , Animales , Aporfinas/aislamiento & purificación , China , Relación Dosis-Respuesta a Droga , Inmunosupresores/aislamiento & purificación , Ratones , Estructura Molecular , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Bazo/citología , Bazo/efectos de los fármacos , Estereoisomerismo
17.
Fitoterapia ; 140: 104422, 2020 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-31756377

RESUMEN

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.


Asunto(s)
Antibacterianos/farmacología , Penicillium/química , Sesquiterpenos/farmacología , Antibacterianos/aislamiento & purificación , Bacillus subtilis/efectos de los fármacos , Línea Celular Tumoral , China , Escherichia coli/efectos de los fármacos , Gastrodia/microbiología , Humanos , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Rizoma/microbiología , Metabolismo Secundario , Sesquiterpenos/aislamiento & purificación , Staphylococcus aureus/efectos de los fármacos
18.
Fitoterapia ; 140: 104432, 2020 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-31759030

RESUMEN

Seven new lignans, cleistonkinins A- E (1-5), cleistonkisides A and B (6-7) were isolated from the fruits of Cleistanthus tonkinensis (Euphorbiaceae), together with five known aryltetralin lignans, cleisindoside B (8), cleistantoxin (9), cleisindoside D (10), neocleistantoxin (11) and polygamain (12). Their structures were established from spectral analysis, including mass spectrometry and 2D-NMR. The absolute configurations of 4-7 were determined by analysis of their experimental CD spectra and comparison with calculated electronic circular dichroism (ECD) spectra. Compounds 2 and 6 had selective inhibition with moderate cytotoxicity against Pan C1 and A549 cell lines, respectively. Cleistantoxin (9) was significantly active against A549, HeLa, Hep3B, Pan C1 and MCF7 cell lines while it was less cytotoxic against HeLa cells. Neocleistantoxin (11) exhibited remarkable inhibition toward A549, HeLa, MCF7 and Pan C1. This is the first report for cytotoxicity of 9 and 11 against A549, Hep3B and Pan C1 cell lines.


Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Euphorbiaceae/química , Frutas/química , Lignanos/farmacología , Antineoplásicos Fitogénicos/aislamiento & purificación , Línea Celular Tumoral , Humanos , Lignanos/aislamiento & purificación , Estructura Molecular , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Vietnam
19.
Fitoterapia ; 140: 104431, 2020 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-31759031

RESUMEN

Two novel heptanornemoralisin-type diterpenoids nornemoralisins A (1) and B (2), together with two known compounds nemoralisin (3) and nemoralisin A (4), were isolated from the stem bark and leaves of Aphanamixis polystachya (Wall.) R. Parker. Their structures were established through comprehensive analyses of NMR spectroscopic data and high resolution mass spectrometric (HR-ESI-MS) data. The absolute configurations of carbon stereocenters were elucidated by circular dichroism (CD) analyses. The four compounds were tested for their potential cytotoxic effects against ACHN, HeLa, SMMC-7721, and MCF-7 cell lines. Nornemoralisins A (1) and B (2) exhibited significant cytotoxicity on ACHN with an IC50 value of 13.9 ± 0.8 and 10.3 ± 0.4 µM, respectively, and other compounds failed to reveal obvious cytotoxicity on the tested cell lines, compared to positive control vinblastine (IC50, 28.0 ± 0.9 µM).


Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Diterpenos/farmacología , Meliaceae/química , Antineoplásicos Fitogénicos/aislamiento & purificación , China , Diterpenos/aislamiento & purificación , Humanos , Estructura Molecular , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Corteza de la Planta/química , Hojas de la Planta/química
20.
Fitoterapia ; 140: 104434, 2020 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-31760067

RESUMEN

Fritillaria cirrhosa bulbus is a Chinese folk herb famous for its antitussive, expectorant, anti-asthma and anti-inflammatory properties, and is widely used to treat respiratory diseases. However, the impacts of F. cirrhosa bulbus on oxidative stress are still unkown. In the present study, we investigated the potential effect and mechanism of six isosteroid alkaloids with different chemical structures from F. cirrhosa bulbus on protection against cigarette smoke-induced oxidative stress in RAW264.7 macrophages. The results showed that six isosteroid alkaloids reduced reactive oxygen species (ROS) production, elevated glutathione (GSH) level and promoted heme oxygenase (HO-1) expression, which is in association with induction of NF-E2-related factor 2 (Nrf2) nuclear translocation and up-regulation of Nrf2 expression. Among these alkaloids, verticinone, verticine, imperialine-3-ß-D-glucoside, delavine and peimisine exhibited more potent effect against CSE-induced oxidative stress than that of imperialine. These findings for the first time demonstrated that F. cirrhosa bulbus may play a protective role in cellular oxidative stress by activating Nrf2-mediated antioxidant pathway. Furthermore, the differences in antioxidant effects of these alkaloids were compared, as well as the corresponding structure-activity relationships were preliminarily elucidated. This suggested that F. cirrhosa bulbus might be a promising therapeutic treatment for the prevent of oxidative stress-related diseases.


Asunto(s)
Alcaloides/farmacología , Fritillaria/química , Estrés Oxidativo/efectos de los fármacos , Humo/efectos adversos , Alcaloides/aislamiento & purificación , Animales , Glutatión/metabolismo , Hemo-Oxigenasa 1/metabolismo , Proteínas de la Membrana/metabolismo , Ratones , Estructura Molecular , Factor 2 Relacionado con NF-E2/metabolismo , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Raíces de Plantas/química , Plantas Medicinales/química , Células RAW 264.7 , Especies Reactivas de Oxígeno/metabolismo , Relación Estructura-Actividad , Productos de Tabaco
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