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1.
Sci Rep ; 13(1): 14923, 2023 09 10.
Artículo en Inglés | MEDLINE | ID: mdl-37691048

RESUMEN

Many studies have explored the extraction of bioactive compounds from different onion solid wastes, such as bulb, skin, and peel. However, onion leaves have received limited attention despite their potential as a valuable source of nutraceutical compounds. This study aimed to valorise, for the first time, the agricultural waste in the form of spring onion leaves (CN, Cipollotto Nocerino) to obtain antioxidant-rich polyphenolic extracts. A Box-Behnken design (BBD) was used to assess the impact of microwave-assisted extraction (MAE) variables (temperature, time, extraction volume, and ethanol concentration) on total polyphenol content (TPC) measured by Folin-Ciocalteu method and the antioxidant power determined by FRAP assay. Response surface methodology (RSM) was applied, and regression equations, analysis of variance, and 3D response curves were developed. Our results highlighted that the TPC values range from 0.76 to 1.43 mg GAE g-1 dw, while the FRAP values range from 8.25 to 14.80 mmol Fe(II)E g-1 dw. The optimal extraction conditions predicted by the model were 60 °C, 22 min, ethanol concentration 51% (v/v), and solvent volume 11 mL. These conditions resulted in TPC and FRAP values of 1.35 mg GAE g-1 dw and 14.02 mmol Fe(II)E g-1 dw, respectively. Furthermore, the extract obtained under optimized conditions was characterized by UHPLC-ESI-Orbitrap-MS analysis. LC/MS-MS platform allowed us to tentatively identify various compounds belonging to the class of flavonoids, saponins, fatty acids, and lipids. Finally, the ability of CN optimal extract to inhibit the intracellular reactive oxygen species (ROS) release in a hepatocarcinoma cell line using an H2O2-induced oxidative stress model, was evaluated. The results highlighted the potential of CN extract as a valuable source of polyphenols with significant antioxidant properties, suitable for various applications in the food and pharmaceutical industries.


Asunto(s)
Compuestos de Bifenilo , Cebollas , Picratos , Hojas de la Planta , Cebollas/química , Hojas de la Planta/química , Extractos Vegetales/química , Residuos Sólidos , Compuestos de Bifenilo/aislamiento & purificación , Picratos/aislamiento & purificación , Microondas , Células Hep G2 , Humanos , Tecnología Química Verde
2.
Pharmacol Res Perspect ; 10(2): e00914, 2022 04.
Artículo en Inglés | MEDLINE | ID: mdl-35171536

RESUMEN

Despite advantages of arsenic trioxide (ATO) in oncological practice, its clinical applications have been hampered by severe cardiotoxicity. The general mechanism of ATO-induced cardiotoxicity has been attributed to its damage to mitochondria, resulting in cardiac remodeling. Honokiol (HKL) is a naturally occurring compound derived from Magnolia bark. Previous studies have demonstrated that HKL exerts cardio-protective effects on ischemia/reperfusion (I/R) or chemical-induced cardiotoxicity by counteracting the toxic effects on mitochondria. The present study was conducted to investigate whether HKL pretreatment protects against ATO-induced cardiac oxidative damage and cell death. For the in vitro study, we evaluated the effects of ATO and/or Honokiol on reactive oxygen species (ROS) production and apoptosis induction in primary cultured cardiomyocytes; for the in vivo study, BALB/c mice were administrated with ATO and/or HKL for a period of 4 weeks, myocardial apoptosis, cardiac function, and cardiac remodeling (cardiac hypertrophy and cardiac fibrosis) were assessed at the end of administration. Our results demonstrated Honokiol pretreatment alleviated the ATO-induced boost in ROS concentration and the following apoptosis induction in primary cultured cardiomyocytes. In the mouse model, Honokiol pretreatment ameliorated ATO-induced myocardial apoptosis, cardiac dysfunction, and cardiac remodeling. Collectively, these results indicated that Honokiol provide a protection against ATO-induced cardiotoxicity by reducing mitochondrial damage. In addition, given that Honokiol has shown considerable suppressive effects on leukemia cells, our data also imply that ATO and Honokiol combination may possibly be a superior avenue in leukemia therapy.


Asunto(s)
Apoptosis/efectos de los fármacos , Trióxido de Arsénico/toxicidad , Compuestos de Bifenilo/farmacología , Cardiotoxicidad/prevención & control , Lignanos/farmacología , Animales , Compuestos de Bifenilo/aislamiento & purificación , Cardiotoxicidad/etiología , Lignanos/aislamiento & purificación , Magnolia/química , Masculino , Ratones , Ratones Endogámicos BALB C , Ratones Endogámicos C57BL , Mitocondrias/efectos de los fármacos , Miocitos Cardíacos/efectos de los fármacos , Miocitos Cardíacos/patología , Estrés Oxidativo/efectos de los fármacos , Especies Reactivas de Oxígeno/metabolismo
3.
J Ethnopharmacol ; 289: 115061, 2022 May 10.
Artículo en Inglés | MEDLINE | ID: mdl-35114342

RESUMEN

ETHNOPHARMACOLOGICAL RELEVANCE: Flos Magnoliae (the dried flower buds of Magnolia biondii Pamp, FM) is a known herbal traditional medicine used for the symptomatic relief of nasal congestion and rhinorrhea caused by rhinitis and sinusitis. Magnolol, a neolignan from the magnolia family, is a secondary metabolite known to have anti-allergic and anti-inflammatory effects. However, the underlying mechanisms and therapeutic effect of magnolol in the treatment of allergic rhinitis (AR) remain elusive. AIMS OF THE STUDY: Anoctamin 1 (ANO1), a calcium-activated anion channel, mediates mucus and electrolyte secretion in nasal airway epithelial cells, whereas calcium release-activated calcium channel protein 1 (ORAI1) participates in the activation of T-lymphocytes and mast cells. The aim of our study is to understand the mechanisms of action of magnolol against AR, i.e., whether it acts through the modulation of ANO1 and ORAI1 channels that are expressed in nasal epithelial cells and T-lymphocytes, respectively. MATERIALS AND METHODS: Whole-cell patch clamp was used to record the activity of ORAI1 and ANO1 ion channels in ORAI1 or ANO1 overexpressed HEK293T cells, while the Ussing chamber apparatus was used to measure electrolyte transport via the epithelium, in Calu-3 cells cultured in an air-liquid interface. Additionally, calcium imaging of Jurkat T-lymphocytes was used to assess changes in the intracellular calcium concentration. Magnolol toxicity was assessed using the CCK-8 assay, and its effect on T-lymphocyte proliferation was measured by labeling human primary T-lymphocytes with carboxyfluorescein succinimidyl ester. Finally, OVA-induced Balb/c mice were employed to evaluate the effect of magnolol on nasal symptoms, as well as cytokine and eosinophil infiltration in AR. RESULTS: Magnolol inhibits ORAI1 and ANO1 channels in a concentration-dependent manner. Magnolol (30 µM) inhibits anti-CD3 induced cellular proliferation and production of IL-2 via ORAI1 channels in T-lymphocytes. Further, ATP-induced electrolyte transport mediated by ANO1 channels is significantly inhibited by magnolol in IL-4 sensitized Calu-3 cells. Notably, 300 µM magnolol significantly attenuates cytokine and eosinophil infiltration, thus alleviating AR symptoms in mice OVA-induced AR. CONCLUSION: Magnolol may be a promising therapeutic agent for the treatment and prevention of AR.


Asunto(s)
Antialérgicos/farmacología , Compuestos de Bifenilo/farmacología , Lignanos/farmacología , Magnolia/química , Rinitis Alérgica/tratamiento farmacológico , Animales , Anoctamina-1/antagonistas & inhibidores , Antialérgicos/administración & dosificación , Antialérgicos/aislamiento & purificación , Compuestos de Bifenilo/administración & dosificación , Compuestos de Bifenilo/aislamiento & purificación , Línea Celular Tumoral , Citocinas/metabolismo , Modelos Animales de Enfermedad , Relación Dosis-Respuesta a Droga , Femenino , Flores , Células HEK293 , Humanos , Lignanos/administración & dosificación , Lignanos/aislamiento & purificación , Ratones , Ratones Endogámicos BALB C , Proteínas de Neoplasias/antagonistas & inhibidores , Proteína ORAI1/antagonistas & inhibidores , Ovalbúmina , Técnicas de Placa-Clamp
4.
J Ethnopharmacol ; 289: 115023, 2022 May 10.
Artículo en Inglés | MEDLINE | ID: mdl-35074454

RESUMEN

ETHNOPHARMACOLOGICAL RELEVANCE: Magnolia officinalis constitutes a traditional Korean medicine used for the treatment of atopic dermatitis, and honokiol is an active diphenyl compound present in Magnolia officinalis. AIM OF THE STUDY: The aim of the study was to investigate the therapeutic effects of honokiol on atopic dermatitis in vivo. MATERIALS AND METHODS: The therapeutic effects of honokiol were evaluated in a 2,4-dinitrochlorobenzene (DNCB)-induced atopic dermatitis model. RESULTS: Administration of honokiol (10 mg/kg) significantly suppressed mast cell accumulation and inflammation induced by DNCB in skin tissues. Moreover, DNCB-induced increases in serum immunoglobulin E levels were reversed by honokiol treatment. In addition, DNCB-induced elevation of inflammatory cytokines (interleukin (IL)-4, IL-13, IL-17, and interferon-γ) in the skin and lymph nodes was significantly ameliorated by honokiol administration. Furthermore, the increase in lymph nodes sizes induced by DNCB treatment was reduced by honokiol administration. CONCLUSION: DNCB-induced atopic responses in the ears and lymph nodes were significantly suppressed by honokiol treatment. These results suggested that honokiol is a potential therapeutic agent for atopic dermatitis.


Asunto(s)
Compuestos de Bifenilo/farmacología , Dermatitis Atópica/tratamiento farmacológico , Lignanos/farmacología , Magnolia/química , Animales , Compuestos de Bifenilo/aislamiento & purificación , Citocinas/metabolismo , Dermatitis Atópica/patología , Dinitroclorobenceno , Inmunoglobulina E/sangre , Inflamación/tratamiento farmacológico , Inflamación/patología , Lignanos/aislamiento & purificación , Masculino , Mastocitos/efectos de los fármacos , Mastocitos/metabolismo , Ratones , Ratones Endogámicos BALB C
5.
Biomed Chromatogr ; 35(11): e5203, 2021 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-34145610

RESUMEN

An accurate and sensitive UPLC-MS/MS method was developed and validated for the simultaneous estimation of the newly developed combination of sacubitril and valsartan and the co-administered drugs nebivolol, chlorthalidone and esomeprazole in human plasma. Solid-phase extraction was conducted for the purification and extraction of the drugs from human plasma. Chromatographic separation was carried out on an Agilent SB-C18 (1.8 µm, 2.1 × 50 mm) column using losartan as internal standard. Isocratic elution was applied using acetonitrile-0.1% formic acid in water (85: 15, v/v) as mobile phase. Detection was carried out using a triple-quadrupole tandem mass spectrometer using multiple reaction monitoring, at positive mode at m/z 412.23 → 266.19 for sacubitril, m/z 436.29 → 235.19 for valsartan, m/z 405.8 → 150.98 for nebivolol, m/z 346.09 → 198 for esomeprazole and a selected combination of two fragments m/z 423.19 → 207.14 and 423.19 → 192.2 for losartan (internal standard), and in negative ionization mode at m/z 337.02 → 190.12 for chlorthalidone. The method was linear over the concentration ranges 30-2,000 ng/ml for sacubitril, 70-2,000 ng/ml for valsartan, esomeprazole and chlorthalidone and 70-5,000 pg/ml for nebivolol. The developed method is sensitive and selective and could be applied for dose adjustment, bioavailability and drug-drug interaction studies.


Asunto(s)
Aminobutiratos/sangre , Compuestos de Bifenilo/sangre , Cromatografía Líquida de Alta Presión/métodos , Extracción en Fase Sólida/métodos , Espectrometría de Masas en Tándem/métodos , Valsartán/sangre , Aminobutiratos/administración & dosificación , Aminobutiratos/aislamiento & purificación , Compuestos de Bifenilo/administración & dosificación , Compuestos de Bifenilo/aislamiento & purificación , Clortalidona/administración & dosificación , Clortalidona/sangre , Clortalidona/aislamiento & purificación , Combinación de Medicamentos , Estabilidad de Medicamentos , Esomeprazol/administración & dosificación , Esomeprazol/sangre , Esomeprazol/aislamiento & purificación , Humanos , Límite de Detección , Modelos Lineales , Nebivolol/administración & dosificación , Nebivolol/sangre , Nebivolol/aislamiento & purificación , Reproducibilidad de los Resultados , Valsartán/administración & dosificación , Valsartán/aislamiento & purificación
6.
Chem Biodivers ; 18(5): e2100079, 2021 May.
Artículo en Inglés | MEDLINE | ID: mdl-33821531

RESUMEN

Eight natural biphenyl-type phytoalexins exhibiting antifungal effect were isolated from the leaves of Sorbus pohuashanensis, which invaded by Alternaria tenuissi, and their growth inhibition rate towards A. tenuissi were 50.3 %, 54.0 %, 66.4 %, 58.8 %, 48.5 %, 51.0 %, 33.3 %, and 37.0 %, respectively. In vivo activity assay verified the protective effect of these natural biphenyls on tobacco leaves. The observation of mycelial morphology revealed that these compounds possessed adverse effects on mycelial growth of A. tenuissi. Subsequently, the most potent active compounds, 3',4',5'-trimethoxy[1,1'-biphenyl]-4-ol (3) and 3,4,4',5-tetramethoxy-1,1'-biphenyl (4), were conducted to the further antifungal evaluation and showed significant activity against the other four crop pathogens, Fusarium graminearum, Helminthosporium maydis, Sclerotinia sclerotiorum, and Exserohilum turcicum. Further, the structure-activity relationships and biosynthesis of these compounds were speculated in this work.


Asunto(s)
Alternaria/efectos de los fármacos , Antifúngicos/farmacología , Compuestos de Bifenilo/farmacología , Sorbus/química , Alternaria/crecimiento & desarrollo , Alternaria/patogenicidad , Antifúngicos/química , Antifúngicos/aislamiento & purificación , Ascomicetos/efectos de los fármacos , Ascomicetos/patogenicidad , Compuestos de Bifenilo/química , Compuestos de Bifenilo/aislamiento & purificación , Bipolaris/efectos de los fármacos , Bipolaris/patogenicidad , Fusarium/efectos de los fármacos , Fusarium/patogenicidad , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Extractos Vegetales , Hojas de la Planta/química
7.
Bioorg Med Chem Lett ; 43: 128045, 2021 07 01.
Artículo en Inglés | MEDLINE | ID: mdl-33865968

RESUMEN

Inhibiting myocardial fibrosis can help prevent cardiovascular diseases, including heart failure. Magnolol (Mag), a natural component of Magnoliae officinalis, has been reported to inhibit fibrosis. However, the mechanism of Mag activity and its effects on myocardial fibrosis remain unclear. Here, we investigated the involvement of ALDH2, an endogenous protective agent against myocardial fibrosis, in the Mag-mediated inhibition of cardiac fibroblast proliferation and collagen synthesis. We found that Mag significantly inhibited cardiac fibroblast proliferation and collagen synthesis, based on the results of MTT, EdU and western blot assays. Moreover, molecular docking, molecular dynamics simulation and surface plasmon resonance (SPR) assays showed that Mag could bind directly and stably to ALDH2. Further analysis of the mechanism of these effects indicated that treatment with Mag dose-dependently enhanced ALDH2 activity without altering protein expression. Mag could enhance the activity of recombinant human ALDH2 proteins with a half-maximal effective concentration of 5.79 × 10-5 M. In addition, ALDH2 activation via Alda-1 inhibited cardiac fibroblast proliferation and collagen synthesis, while ALDH2 inhibition via daidzin partially blocked the suppressive effects of Mag. In summary, Mag may act as a natural ALDH2 agonist and inhibit cardiac fibroblast proliferation and collagen synthesis.


Asunto(s)
Aldehído Deshidrogenasa Mitocondrial/antagonistas & inhibidores , Compuestos de Bifenilo/farmacología , Colágeno/antagonistas & inhibidores , Fibroblastos/efectos de los fármacos , Lignanos/farmacología , Miocitos Cardíacos/efectos de los fármacos , Aldehído Deshidrogenasa Mitocondrial/metabolismo , Compuestos de Bifenilo/química , Compuestos de Bifenilo/aislamiento & purificación , Proliferación Celular/efectos de los fármacos , Colágeno/biosíntesis , Relación Dosis-Respuesta a Droga , Fibroblastos/metabolismo , Humanos , Lignanos/química , Lignanos/aislamiento & purificación , Magnolia/química , Estructura Molecular , Miocitos Cardíacos/metabolismo , Relación Estructura-Actividad
8.
J Sep Sci ; 44(7): 1345-1352, 2021 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-33400375

RESUMEN

The lack of suitable chromatographic purification methods makes it a challenge to effectively isolate the chemical components of traditional Tibetan medicines. Ribes himalense is a rarely studied Tibetan medicine, reputed to have free radical-scavenging effects. In the present work, we utilized it as a model herb to highlight an approach for the separation of 1,1-diphenyl-2-picrylhydrazyl inhibitors via medium-pressure chromatography and two-dimensional reversed-phase/reversed-phase interaction liquid chromatography under the guidance of an online high-performance liquid chromatography-1,1-diphenyl-2-picrylhydrazyl assay. Finally, we obtained two free radical inhibitors (>95% purity) from the R. himalense extract. This is the first report of the rapid isolation of these free radical inhibitors from R. himalense. This method can be useful in quality standard assessment and further pharmacological activity research, and may be used as a reference for the composition research of various natural products.


Asunto(s)
Compuestos de Bifenilo/aislamiento & purificación , Picratos/aislamiento & purificación , Extractos Vegetales/aislamiento & purificación , Ribes/química , Compuestos de Bifenilo/química , Cromatografía Líquida de Alta Presión , Cromatografía de Fase Inversa , Picratos/química , Extractos Vegetales/química
9.
Nat Prod Res ; 35(13): 2137-2144, 2021 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-31512485

RESUMEN

One new xanthone, (±) garciesculenxanthone C (1), two new biphenyls, garciesculenbiphenyls A (2) and B (3), together with two known compounds, doitungbiphenyl B (4) and morusignin D (5), were isolated from Garcinia esculenta. The structures of new compounds were elucidated by spectroscopic analysis, and the absolute configuration of (±) garciesculenxanthone C (1) was assigned by a modified Mosher's method. All isolates were evaluated for their antistaphylococcal activities against Staphylococcus aureus Newman, USA300 LAC, USA400 MW2, and Mu50 strains. Among these, (±) garciesculenxanthone C (1) showed the best antistaphylococcal activity, and its effect was determined to be bactericidal by time-kill experiment.


Asunto(s)
Antibacterianos/farmacología , Compuestos de Bifenilo/aislamiento & purificación , Compuestos de Bifenilo/farmacología , Garcinia/química , Prenilación , Staphylococcus aureus/efectos de los fármacos , Xantonas/aislamiento & purificación , Xantonas/farmacología , Antibacterianos/química , Compuestos de Bifenilo/química , Espectroscopía de Resonancia Magnética con Carbono-13 , Pruebas de Sensibilidad Microbiana , Estereoisomerismo , Xantonas/química
10.
Nat Prod Rep ; 38(4): 822-842, 2021 04 28.
Artículo en Inglés | MEDLINE | ID: mdl-33141135

RESUMEN

Covering: 2007 to 2020 Selaginellins are a small group of pigments exclusively found in the ancient genus Selaginella. Since the first report of selaginellin from S. sinensis in 2007, more than 110 selaginellins with diverse polyphenolic skeletons have been reported. This review provides extensive coverage of the selaginellins discovered from 2007 to 2020, including 61 natural ones and 52 synthetic analogues. The isolation, chemical structures, plausible biosynthetic pathways, bioactivity, and total synthesis of these selaginellins have been summarized for the first time, and this highlights the fact that the vast uninvestigated Selaginella species may serve as a potential treasure trove of chemically diverse selaginellins waiting to be discovered.


Asunto(s)
Compuestos de Bifenilo/aislamiento & purificación , Ciclohexanonas/aislamiento & purificación , Selaginellaceae/química , Compuestos de Bifenilo/síntesis química , Compuestos de Bifenilo/química , Compuestos de Bifenilo/farmacología , Ciclohexanonas/síntesis química , Ciclohexanonas/química , Ciclohexanonas/farmacología , Humanos
11.
Fitoterapia ; 146: 104708, 2020 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-32827694

RESUMEN

Patchouli is a tropical medicinal and spice crop with high economic value, and the endophytic microorganism is also one of its important components and can provide new active compounds with medicinal use. In the present study, four new biphenyl compounds named 3-O-demethylaltenuisol (1), (-)-dialtenuisol (5) and (+)-dialtenuisol (6), and altertoxin VII (9), as well as six known related compounds, were isolated from the patchouli (Pogostemon cablin) endophytic fungus Alternaria sp. PfuH1. The structures of the new compounds were elucidated from spectroscopic data, ECD spectra analysis, and ECD calculations. Compounds 5 and 6 are a pair of dimeric axially chiral enantiomers. Compounds 2, 4, and 9 showed antibacterial activities against S. agalactiae with MIC values of 9.3, 85.3, and 17.3 µg/mL, respectively, and compound 4 also showed weak antibacterial activity against E. coli with MIC value of 128 µg/mL.


Asunto(s)
Alternaria/química , Antibacterianos/farmacología , Compuestos de Bifenilo/farmacología , Pogostemon/microbiología , Antibacterianos/aislamiento & purificación , Compuestos de Bifenilo/aislamiento & purificación , Línea Celular Tumoral , China , Endófitos/química , Escherichia coli/efectos de los fármacos , Flores/microbiología , Humanos , Pruebas de Sensibilidad Microbiana , Estructura Molecular
12.
J Gen Appl Microbiol ; 66(5): 273-278, 2020 Nov 30.
Artículo en Inglés | MEDLINE | ID: mdl-32669511

RESUMEN

An Indonesian soil fungus, Talaromyces pinophilus BioMCC-f.T.3979 was cultured to find novel scaffolds of Plasmodium falciparum dihydroorotate dehydrogenase (PfDHODH) inhibitors. We obtained altenusin (1), which inhibits PfDHODH, with an IC50 value of 5.9 µM, along with other metabolites: mitorubrinol (2) and mitorubrinic acid (3). Compounds 1 and 2 inhibited PfDHODH but displayed no activity against the human orthologue. They also inhibited P. falciparum 3D7 cell growth in vitro. Compound 3 showed little PfDHODH inhibitory activity or cell growth inhibitory activity.


Asunto(s)
Antimaláricos/farmacología , Oxidorreductasas actuantes sobre Donantes de Grupo CH-CH/antagonistas & inhibidores , Plasmodium falciparum/efectos de los fármacos , Proteínas Protozoarias/antagonistas & inhibidores , Talaromyces/química , Antimaláricos/química , Antimaláricos/aislamiento & purificación , Benzoatos/química , Benzoatos/aislamiento & purificación , Benzoatos/farmacología , Compuestos de Bifenilo/química , Compuestos de Bifenilo/aislamiento & purificación , Compuestos de Bifenilo/farmacología , Línea Celular , Supervivencia Celular/efectos de los fármacos , Dihidroorotato Deshidrogenasa , Inhibidores Enzimáticos/química , Inhibidores Enzimáticos/aislamiento & purificación , Inhibidores Enzimáticos/farmacología , Humanos , Plasmodium falciparum/enzimología , Plasmodium falciparum/crecimiento & desarrollo , Microbiología del Suelo , Especificidad de la Especie
13.
J Chromatogr A ; 1625: 461238, 2020 Aug 16.
Artículo en Inglés | MEDLINE | ID: mdl-32709314

RESUMEN

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


Asunto(s)
Compuestos de Bifenilo/sangre , Cromatografía Líquida de Alta Presión/métodos , Lignanos/sangre , Metacrilatos/química , Polietilenglicoles/química , Animales , Compuestos de Bifenilo/aislamiento & purificación , Compuestos de Bifenilo/normas , Cromatografía Líquida de Alta Presión/normas , Congelación , Interacciones Hidrofóbicas e Hidrofílicas , Lignanos/aislamiento & purificación , Lignanos/normas , Control de Calidad , Ratas , Reproducibilidad de los Resultados , Extracción en Fase Sólida
14.
PLoS One ; 15(2): e0226901, 2020.
Artículo en Inglés | MEDLINE | ID: mdl-32084140

RESUMEN

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


Asunto(s)
Compuestos de Bifenilo/aislamiento & purificación , Ciclooctanos/aislamiento & purificación , Frutas/química , Lignanos/aislamiento & purificación , Extractos Vegetales/química , Schisandra/metabolismo , Hidrólisis , Líquidos Iónicos/química , Campos Magnéticos , Microondas , Agua/química
15.
J Antibiot (Tokyo) ; 73(5): 283-289, 2020 05.
Artículo en Inglés | MEDLINE | ID: mdl-31949315

RESUMEN

Eight new fasamycin-type polyketides, streptovertimycins A-H (1-8), were isolated from soil-derived Streptomyces morookaense SC1169 cultivated on wheat grains. Their structures were established by extensive spectroscopic analysis and theoretical computations of ECD spectra. Compounds 1-8 have a fasamycin-type pentacyclic structure featuring a 15-O-methyl group. They exhibited potent activity against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus faecium (VRE) with MIC values in the range of 0.63-5.0 µg/ml. The activity profile provided new insights into the structure-activity relationships of fasamycin-type antibiotics.


Asunto(s)
Antibacterianos/farmacología , Compuestos de Bifenilo/farmacología , Hidrocarburos Policíclicos Aromáticos/farmacología , Policétidos/farmacología , Streptomyces/metabolismo , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Compuestos de Bifenilo/química , Compuestos de Bifenilo/aislamiento & purificación , Staphylococcus aureus Resistente a Meticilina/efectos de los fármacos , Pruebas de Sensibilidad Microbiana , Hidrocarburos Policíclicos Aromáticos/química , Hidrocarburos Policíclicos Aromáticos/aislamiento & purificación , Policétidos/química , Policétidos/aislamiento & purificación , Microbiología del Suelo , Relación Estructura-Actividad , Enterococos Resistentes a la Vancomicina/efectos de los fármacos
16.
Chem Biodivers ; 17(2): e1900609, 2020 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-31916412

RESUMEN

The fruit of Crataegus dahurica Koehne was used to treat the disease of infantile indigestion and dyspepsia as an ethnic medicine and food. As a continuous work on finding the active constituents from the edible herbs, four new biphenyl derivatives (1-4), together with two known compounds (5 and 6), were obtained from the petroleum ether fraction of the fruits of C. dahurica. Their structures were determined by the extensive 1D and 2D NMR spectra and HR-MS spectrometry. Furthermore, the anti-inflammatory activities of all the isolated compounds were investigated, in which compound 4 showed moderately inhibitory effects on NO production in RAW264.7 cells without inducing cytotoxicity.


Asunto(s)
Antiinflamatorios/química , Crataegus/química , Animales , Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/farmacología , Compuestos de Bifenilo/química , Compuestos de Bifenilo/aislamiento & purificación , Compuestos de Bifenilo/farmacología , Supervivencia Celular/efectos de los fármacos , Crataegus/metabolismo , Frutas/química , Frutas/metabolismo , Lipopolisacáridos/toxicidad , Macrófagos/citología , Macrófagos/efectos de los fármacos , Macrófagos/metabolismo , Espectroscopía de Resonancia Magnética , Ratones , Conformación Molecular , Óxido Nítrico/metabolismo , Células RAW 264.7
17.
Bioorg Chem ; 94: 103469, 2020 01.
Artículo en Inglés | MEDLINE | ID: mdl-31787345

RESUMEN

Obovatol, a novel lignan isolated from the leaf and stem bark of Magnolia obovata Thunb exhibits many important biological activities. To discover natural-product-based potential fungicides with novel structural skeletons, a series of Mannich base derivatives were prepared by the C-4-aminomethylated modification of obovatol and all synthesized compounds were evaluated for antifungal activities in vitro against several phytopathogenic fungi using the spore germination method and the mycelium growth rate method. Furthermore, their structures were also characterized by 1H NMR, 13C NMR, and HR-MS, and compound 2k was further analyzed by single-crystal X-ray diffraction. Among all of the derivatives, compounds 2b (IC50 = 28.68 µg/mL) and 2g (IC50 = 16.90 µg/mL) demonstrated greater inhibition of Botrytis cinerea spore germination than two positive controls, hymexazol and difenoconazole. Compounds 2c, 2f, and 2g displayed potent mycelial growth inhibition of B. cinerea with an average inhibition rate (AIR) of >90% at a concentration of 100 µg/mL. Additionally, the structure-activity relationships (SARs) suggested that the introduction of a diethylamino, pyrrolyl, 1-methyl-piperazinyl or 1-ethyl-piperazinyl groups on the C-4 position of obovatol may be more likely to yield potential antifungal compounds than the introduction of 4-phenyl-piperazinyl or 4-phenyl-piperidinyl groups.


Asunto(s)
Antifúngicos/farmacología , Compuestos de Bifenilo/farmacología , Botrytis/efectos de los fármacos , Lignanos/química , Bases de Mannich/farmacología , Éteres Fenílicos/farmacología , Antifúngicos/química , Antifúngicos/aislamiento & purificación , Compuestos de Bifenilo/química , Compuestos de Bifenilo/aislamiento & purificación , Relación Dosis-Respuesta a Droga , Bases de Mannich/química , Bases de Mannich/aislamiento & purificación , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Éteres Fenílicos/química , Éteres Fenílicos/aislamiento & purificación , Relación Estructura-Actividad
18.
PLoS One ; 14(7): e0218974, 2019.
Artículo en Inglés | MEDLINE | ID: mdl-31287826

RESUMEN

The extracts of seven Lavandulae species (Lavandula stoechas, Lavandula lanata, Lavandula viridis, Lavandula angustifolia "Rosea", Lavandula angustifolia "Afropurpurea", Lavandula angustifolia and one unknown) were analyzed using the reversed-phase-high performance liquid chromatography-diode array detection (RP-HPLC-DAD) with gradient elution technique to obtain the chromatographic fingerprint profiles. The HPLC analysis was performed using the Kinetex RP18 chromatographic column and eluent consisting of methanol-water-0.1% formic acid (5-100% (v/v)) at 30 °C with the run time of 60 min. and the detection wavelength 280 nm. The chromatograms were preliminary processed with the smoothing, noise reduction, background subtraction and alignment using the SpecAlign program (version 2.4.1). The presence of selected standards (apigenin, myricetin, luteolin, luteolin 7-glucoside, chlorogenic acid, caffeic acid, ferulic acid) in the extracts was confirmed. The chemical similarity between studied plants was evaluated using the Cluster Analysis (Pearson correlation coefficient, r, and Euclidean) and PCA. The preliminary antioxidant activity of studied extracts was evaluated based on the total phenolic content (Folin-Ciocalteu method), ferric ion reducing antioxidant parameter (FRAP) and α,α-diphenyl-ß-picrylhydrazyl (DPPH) free radical scavenging method using the spectrophotometric technique.


Asunto(s)
Antioxidantes/química , Depuradores de Radicales Libres/química , Lavandula/química , Extractos Vegetales/química , Apigenina/química , Apigenina/aislamiento & purificación , Compuestos de Bifenilo/química , Compuestos de Bifenilo/aislamiento & purificación , Ácidos Cafeicos/química , Ácidos Cafeicos/aislamiento & purificación , Cromatografía Líquida de Alta Presión , Cromatografía de Fase Inversa , Flavonoides/química , Flavonoides/aislamiento & purificación , Fenoles/química , Fenoles/aislamiento & purificación , Picratos/química , Especificidad de la Especie
19.
Microb Pathog ; 132: 66-72, 2019 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-31028863

RESUMEN

Biosurfactants are surface-active compounds that display a range of physiological functions. The present study investigated the antioxidant, antimicrobial, and anti-adhesive or anti-biofilm potential of biosurfactants isolated from Bacillus subtilis VSG4 and Bacillus licheniformis VS16. The antioxidant activity of the biosurfactants was studied in vitro using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and hydroxyl radicals. At 5 mg/mL of the biosurfactant concentration, the scavenging of DPPH and hydroxyl radicals was found to be between 69.1-73.5% and 63.3-69.8%, respectively. The biosurfactants also displayed significant antibacterial activities against both Gram-positive and Gram-negative bacteria. The anti-adhesive activities of the biosurfactants were evaluated against Staphylococcus aureus ATCC 29523, Salmonella typhimurium ATCC 19430, and Bacillus cereus ATCC 11778. The biosurfactants exhibited anti-adhesive activity, even at concentrations of 3-5 mg/mL. Moreover, both biosurfactants displayed notable anti-biofilm activities with a biofilm eradication percentage ranging from 63.9 to 80.03% for VSG4 biosurfactant, and from 61.1-68.4% for VS16 biosurfactant. Furthermore, VSG4 biosurfactant exhibited emulsification and surface tension stability over a wide range of pH (4-10) and temperature up to 100 °C. These results show that VSG4 and VS16 biosurfactants can be potentially used as natural antioxidants, antimicrobials, and/or anti-adhesive agents for food and biomedical applications.


Asunto(s)
Antibacterianos/farmacología , Antioxidantes/farmacología , Bacillus licheniformis/metabolismo , Bacillus subtilis/metabolismo , Adhesión Bacteriana/efectos de los fármacos , Biopelículas/efectos de los fármacos , Tensoactivos/farmacología , Antibacterianos/aislamiento & purificación , Antioxidantes/aislamiento & purificación , Compuestos de Bifenilo/aislamiento & purificación , Bacterias Gramnegativas/efectos de los fármacos , Bacterias Grampositivas/efectos de los fármacos , Concentración de Iones de Hidrógeno , Radical Hidroxilo/aislamiento & purificación , Picratos/aislamiento & purificación , Tensoactivos/aislamiento & purificación , Temperatura
20.
Molecules ; 24(7)2019 Apr 02.
Artículo en Inglés | MEDLINE | ID: mdl-30986967

RESUMEN

We aimed to purify polyphenols from distiller's grain extract using macroporous resins and to identify its polyphenolic components. The influence of operational parameters on purification efficiency was investigated. The polyphenolic composition was analyzed by ultra-performance liquid chromatography tandem mass spectrometry (UPLC-MS/MS) and then quantified by UPLC-MS using authenticated standards. The results showed that the optimal purifying conditions were D101 resin with a dosage of 3 g, four hours adsorption, three hours desorption time, and 60% ethanol as the eluent, producing the highest purification rate of 51%. The purified distiller's grain extract exhibited stronger antioxidant activity than the unpurified extracts, which was assessed using DPPH and ABTS methods (IC50 DPPH = 34.03 and 16.21 µg/mL, respectively; IC50 ABTS = 20.31 and 5.73 µg/mL, respectively). UPLC-MS results indicated that (-)-epicatechin is the major compound found in distiller's grain extract which was quantified as 562.7 µg/g extract, followed by ferulic acid (518.2 µg/g), p-hydroxybenzoic acid (417.7 µg/g), caffeic acid (217.1 µg/g), syringic acid (158.0 µg/g) and quercetin (147.8 µg/g). Two compounds, vanillic acid (66.5 µg/g) and gallic acid (41.4 µg/g), were found in lower concentrations. The findings of this study suggest that purification of polyphenolic compounds from distiller's grain by macroporous resins is feasible, providing a new and effective method for the secondary use of distiller's grain resources.


Asunto(s)
Polifenoles/aislamiento & purificación , Resinas de Plantas/química , Benzotiazoles/química , Benzotiazoles/aislamiento & purificación , Compuestos de Bifenilo/química , Compuestos de Bifenilo/aislamiento & purificación , Ácidos Cafeicos/química , Ácidos Cafeicos/aislamiento & purificación , Cromatografía Liquida , Ácidos Cumáricos/química , Ácidos Cumáricos/aislamiento & purificación , Ácido Gálico/análogos & derivados , Ácido Gálico/química , Ácido Gálico/aislamiento & purificación , Hidroxibenzoatos/química , Hidroxibenzoatos/aislamiento & purificación , Picratos/química , Picratos/aislamiento & purificación , Polifenoles/química , Quercetina/química , Quercetina/aislamiento & purificación , Ácidos Sulfónicos/química , Ácidos Sulfónicos/aislamiento & purificación , Espectrometría de Masas en Tándem , Ácido Vanílico/química , Ácido Vanílico/aislamiento & purificación
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