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1.
Artículo en Inglés | MEDLINE | ID: mdl-33416934

RESUMEN

The hepatoprotective activity of heliomycin obtained from the culture broth of actinomycete AB5 against diethylnitrosamine (DEN)-induced hepatic cancer in Wistar rats was estimated. Heliomycin exhibited a significant decrease in the levels of alanine transaminase (ALT), aspartate transaminase (AST), and alkaline phosphatase (ALP) compared to the positive control. For instance, the heliomycin group after 20 weeks showed a significant decline in ALT, AST, and ALP values (70.75 ± 5.12, 140.25 ± 11.75, and 163.25 ± 18.66, respectively) compared to the positive control group (170.00 ± 9.55, 252.75 ± 12.33, and 278.00 ± 21.32, respectively). Additionally, the isolated compound showed a highly significant decrease in serum alpha-fetoprotein (AFP) levels. After 8, 16, and 20 weeks, the mean values of AFP in the heliomycin group revealed a highly significant decrease (33.62 ± 2.46, 30.00 ± 4.05, and 28.50 ± 2.64, respectively) compared to the positive control group (49.45 ± 3.03, 81.90 ± 6.70, and 90.75 ± 5.12, respectively). The histopathological investigation of liver sections supported the results of biochemical analysis. It was demonstrated that heliomycin showed histological improvement of hepatocytes and marked increase of nuclear pyknotic with clear cytoplasm, which is a sign of improving the apoptotic pathway of malignant cells. It also displayed marked fibrosis at most of the malignant cells and the development of some regenerative nodules. Heliomycin showed moderate immunoreactivity with alpha-fetoprotein (AFP), and proliferation cell nuclear antigen (PCNA) compared to the positive control group. To the best of our knowledge, this is the first study to report the anticancer activity of heliomycin against hepatocellular carcinoma in vivo.

2.
Mar Drugs ; 19(1)2021 Jan 08.
Artículo en Inglés | MEDLINE | ID: mdl-33429926

RESUMEN

Fish pathogens causing disease outbreaks represent a major threat to aquaculture industry and food security. The aim of the presented study is to develop safe and effective bioactive agents against two bacterial isolates: Aeromonas hydrophila and Pseudomonas fluorescens. We employed a broth microdilution method to investigate the antibacterial effect of biosynthesized silver nanoparticles (AgNPs); rutin, a natural flavonoid extracted from Ruta graveneoles; and heliomycin, a secondary metabolite produced by marine actinomycetes AB5, as monotherapeutic agents. Moreover, AgNPs in combination with rutin (AgNP + R) and heliomycin (AgNPs + H) were examined for their synergistic effect. The cytotoxic effect of individual bioactive compounds and in combination with AgNPs was investigated on epithelioma papulosum cyprini (EPC) fish cell lines. Individual treatment of AgNPs, rutin, and heliomycin exhibited a dose-dependent antimicrobial activity against A. hydrophila and P. fluorescens. Rutin minimum inhibitory concentration (MIC) showed the lowest cytotoxicity when tested on EPC cell lines, while heliomycin MIC was highly cytotoxic. Combined subtherapeutic doses of AgNPs + R and AgNPs + H displayed additive and synergistic effects against A. hydrophila and P. fluorescens, respectively, with improved results and relative safety profile. The study findings demonstrate that a combination of AgNPs and natural bioactive compounds may represent novel therapeutics fighting fish pathogens potentially affecting the fish farming industry.

3.
Antibiotics (Basel) ; 9(5)2020 May 14.
Artículo en Inglés | MEDLINE | ID: mdl-32422934

RESUMEN

New antibiotics are desperately needed to overcome the societal challenges being encountered with methicillin-resistant Staphylococcus aureus (MRSA). In this study, a new tetracene derivative, named Mersaquinone (1), and the known Tetracenomycin D (2), Resistoflavin (3) and Resistomycin (4) have been isolated from the organic extract of the marine Streptomyces sp. EG1. The strain was isolated from a sediment sample collected from the North Coast of the Mediterranean Sea of Egypt. The chemical structure of Mersaquinone (1) was assigned based upon data from a diversity of spectroscopic techniques including HRESIMS, IR, 1D and 2D NMR measurements. Mersaquinone (1) showed antibacterial activity against methicillin-resistant Staphylococcus aureus with a minimum inhibitory concentration of 3.36 µg/mL.

4.
Nat Prod Res ; 34(5): 613-620, 2020 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-30375885

RESUMEN

A new rotenoid named 12-O-methylrotenolol along with five known rotenoid and isoflavone metabolites were isolated from the seeds of Dalbergia lanceolaria subsp. paniculata, collected from Egypt. The structures of these compounds were identified by physical and spectroscopic data measurements ([α]D, UV, 1D- and 2D-NMR and MS). The methanol extract of the seeds exhibited strong antioxidant activity with IC50 value 0.7 µg/µl against DPPH radical, in respect to quercetin as antioxidant reference (IC50 1.5 µM), while the tested compounds from this extract showed weak activities with IC50 values ranged from 19.6 to 33.0 µM.


Asunto(s)
Antioxidantes/aislamiento & purificación , Dalbergia/química , Isoflavonas/aislamiento & purificación , Semillas/química , Antioxidantes/química , Compuestos de Bifenilo/antagonistas & inhibidores , Egipto , Concentración 50 Inhibidora , Isoflavonas/química , Estructura Molecular , Picratos/antagonistas & inhibidores , Extractos Vegetales/química
5.
Neurotox Res ; 37(1): 77-92, 2020 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-31332714

RESUMEN

Systemic administration of 3-nitropropionic acid (3-NPA) is commonly used to induce Huntington's disease (HD)-like symptoms in experimental animals. Here, the potential neuroprotective efficiency of rutin and selenium (RSe) co-administration on 3-NPA-induced HD-like symptoms model in mice was investigated. 3-NPA injection evoked severe alterations in redox status, as indicated via increased striatal malondialdehyde and nitric oxide levels, accompanied by a decrease in levels of antioxidant molecules including glutathione, glutathione peroxidase, glutathione reductase, superoxide dismutase, and catalase. Moreover, 3-NPA potentiated inflammatory status by enhancing the production of interleukin-1ß, tumor necrosis factor-α, and myeloperoxidase activity. Pro-apoptotic cascade was also recorded in the striatum as evidenced through upregulation of cleaved caspase-3 and Bax, and downregulation of Bcl-2. 3-NPA activated astrocytes as indicated by the upregulated glial fibrillary acidic protein and inhibited brain-derived neurotrophic factor. Furthermore, perturbations in cholinergic and monoaminergic systems were observed. RSe provided neuroprotective effects by preventing body weight loss, oxidative stress, neuroinflammation, and the apoptotic cascade. RSe inhibited the activation of astrocytes, increased brain-derived neurotrophic factor, and improved cholinergic and monoaminergic transmission following 3-NPA intoxication. Taken together, RSe co-administration may prevent or delay the progression of HD and its associated impairments through its antioxidant, anti-inflammatory, anti-apoptotic, and neuromodulatory effects.

6.
PLoS One ; 14(6): e0216737, 2019.
Artículo en Inglés | MEDLINE | ID: mdl-31194753

RESUMEN

Gastric ulcer is sores that form in the stomach mucosal layer because of erosion caused by high acid secretion and excessive use of non-steroidal anti-inflammatory drugs. Prodigiosins (PdGs) are red-pigmented secondary metabolites produced by bacteria, including actinomycetes. Butylcycloheptylprodigiosin (1) and undecylprodigiosin (2) were identified and isolated from a crude extract of the actinomycete RA2 isolated from the Red Sea Sponge Spheciospongia mastoidea. Chemical structure of 1 and 2 was determined by NMR and mass spectroscopy. Although their antioxidant and anti-inflammatory properties are known, their effect on gastric lesion is unknown. Therefore, this study aimed to investigate gastroprotective effects of PdGs against HCl/ethanol-induced gastric lesion in rats. Oral pretreatment with PdGs (100, 200, and 300 mg/kg) attenuated severity of HCl/ethanol-induced gastric mucosal injury, as evidenced by decreases in gastric lesion index scores, ulceration area, histopathologic abnormality, and neutrophil infiltration. These effects were comparable to those of omeprazole, a standard anti-gastric ulcer agent. HCl/ethanol-induced gastric erosions was associated with tremendous increases in lipid peroxidation, nitric oxide, and pro-inflammatory cytokines and mediators (myeloperoxidase, interleukin-1ß, tumor necrosis factor-α, and cyclooxygenase-2), and with significant decreases in enzymatic and non-enzymatic antioxidant activities. However, PdGs ameliorated gastric inflammation and oxidative stress by downregulating nuclear factor kappa B and inducible nitric oxide synthase expression and upregulating heme oxygenase-1 expression. PdGs prevented gastric mucosal apoptosis by downregulating Bax and caspase-3 expression and upregulating Bcl-2 expression, thereby increasing prostaglandin E2 production. Our results suggested that PdGs exerted gastroprotective effects by decreasing the levels of inflammatory mediators, apoptotic markers, and antioxidants.


Asunto(s)
Antiinflamatorios/farmacología , Antioxidantes/farmacología , Etanol/efectos adversos , Mucosa Gástrica/patología , Ácido Clorhídrico/efectos adversos , Poríferos/química , Prodigiosina/farmacología , Animales , Apoptosis/efectos de los fármacos , Citoprotección/efectos de los fármacos , Mucosa Gástrica/efectos de los fármacos , Mucosa Gástrica/metabolismo , Masculino , Estrés Oxidativo/efectos de los fármacos , Ratas , Ratas Wistar
7.
Nat Prod Res ; 32(12): 1369-1374, 2018 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-28669229

RESUMEN

The chemical investigation of the methylene chloride fraction of marine sponge Hyrtios erectus led to the isolation of the known oxysterol (2) along with a new alkyl benzoate compound identified by spectroscopic methods (NMR and MS) as 4'-methylheptyl benzoate (1), whilst the n-butanol fraction afforded the known indole 3-carbaldehyde and ß-carboline derivatives. Moreover, the hexane fraction was analysed by GC-MS for their fatty acids (FAs). A total of 17 FAs with chain lengths between 14 and 25 carbons were identified. Methyl-branched FAs are predominated suggesting the presence of bacterial symbionts in the H. erectus sponge. Furthermore, compounds 1 and 2 displayed significant cytotoxicity against breast adenocarcinoma (MCF-7) with IC50 values of 2.4 and 3.8 µM, respectively, since compound 2 was also shown to have potent cytotoxic effect against hepatocellular carcinoma cells (HepG 2) with IC50 value of 1.3 µM.


Asunto(s)
Antineoplásicos/farmacología , Benzoatos/química , Ácidos Grasos/farmacología , Poríferos/química , Animales , Antineoplásicos/química , Benzoatos/farmacología , Carbolinas/química , Ensayos de Selección de Medicamentos Antitumorales , Ácidos Grasos/química , Células Hep G2 , Humanos , Océano Índico , Concentración 50 Inhibidora , Células MCF-7 , Estructura Molecular , Oxiesteroles/química
8.
J Nat Med ; 71(3): 564-569, 2017 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-28378198

RESUMEN

A new ana-quinonoid tetracene metabolite, named sharkquinone (1), and the known SS-228R (2) have been isolated from the ethyl acetate extract of the culture of marine Streptomyces sp. EGY1. The strain was isolated from sediment sample collected from the Red Sea coast of Egypt. The structure of sharkquinone (1) was elucidated using detailed spectral (HRESI-MS, 1D and 2D NMR) analyses and quantum chemical calculations. This is the first report of the isolation of ana-quinonoid tetracene derivative from a natural source. Compound 1 showed the ability to overcome tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) resistance at a concentration of 10 µM in human gastric adenocarcinoma (AGS) cells.


Asunto(s)
Adenocarcinoma/metabolismo , Productos Biológicos/farmacología , Quinonas/farmacología , Neoplasias Gástricas/metabolismo , Streptomyces/química , Ligando Inductor de Apoptosis Relacionado con TNF/metabolismo , Organismos Acuáticos , Productos Biológicos/química , Productos Biológicos/aislamiento & purificación , Línea Celular Tumoral , Egipto , Humanos , Espectroscopía de Resonancia Magnética , Estructura Molecular , Naftacenos , Quinonas/química , Quinonas/aislamiento & purificación
9.
Oncol Rep ; 37(6): 3635-3642, 2017 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-28440502

RESUMEN

Tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) is a promising anticancer agent, as it can kill tumor cells selectively. In our search of bioactive natural products to overcome TRAIL-resistance, we isolated 47 actinomycete strains from different sediments and seawater samples collected from the Red Sea coast in Egypt and found four crude extracts (EGY1, EGY3, EGY24 and EGY34) displaying TRAIL sensitizing activity in the resistant breast cancer cell line MDA-MB-231. None of these crude extracts exhibited cytotoxic effect on normal mouse embryonic fibroblasts (MEF), with the exception of EGY34. Analysis of the signaling pathways underlying the sensitization of MDA-MB-231 cells to TRAIL-induced apoptosis, by western blotting, revealed that all crude extracts facilitated initiator caspase­8/-10 activation upon TRAIL stimulation, but that in addition, EGY3 and EGY34, alone, induced strong ER-stress activation, with the appearance of BiP in the cytosolic extracts. Our results pave the way to the discovery and the development of marine-derived drugs for cancer therapy.


Asunto(s)
Proliferación Celular/efectos de los fármacos , Mezclas Complejas/administración & dosificación , Resistencia a Antineoplásicos/efectos de los fármacos , Ligando Inductor de Apoptosis Relacionado con TNF/genética , Actinobacteria/química , Animales , Apoptosis/efectos de los fármacos , Organismos Acuáticos/química , Neoplasias de la Mama , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Mezclas Complejas/química , Femenino , Fibroblastos , Humanos , Ratones , Transducción de Señal/efectos de los fármacos , Ligando Inductor de Apoptosis Relacionado con TNF/antagonistas & inhibidores
10.
J Antibiot (Tokyo) ; 70(5): 601-606, 2017 May.
Artículo en Inglés | MEDLINE | ID: mdl-28074048

RESUMEN

Chemical investigations of the ethyl acetate extract of Streptomyces sp. IFM 11490 have led to the isolation of six new angucycline metabolites, named elmenols C-H (1-6), along with the previously reported elmonin (7) and elmenols A (8) and B (9). The known LS1924A (10), 6-deoxy-8-methylrabelomycin (11), tetrangulol methyl ether (12) and angucyclinone (13) were additionally identified. The structures of the isolated compounds were elucidated by means of spectroscopic methods including UV, IR, HRESIMS, and 1D and 2D NMR. Compounds 1-6 were evaluated for their abilities to overcome tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) resistance in human gastric adenocarcinoma (AGS) cells. Compounds 5 (10 µm) and 6 (50 µm) in combination with TRAIL showed moderate activity in sensitizing TRAIL-resistant AGS cells.


Asunto(s)
Adenocarcinoma/tratamiento farmacológico , Antraquinonas/farmacología , Antineoplásicos/farmacología , Neoplasias Gástricas/tratamiento farmacológico , Streptomyces/metabolismo , Adenocarcinoma/patología , Antraquinonas/química , Antraquinonas/aislamiento & purificación , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Línea Celular Tumoral , Resistencia a Antineoplásicos , Humanos , Análisis Espectral/métodos , Neoplasias Gástricas/patología , Ligando Inductor de Apoptosis Relacionado con TNF/farmacología
11.
Chem Pharm Bull (Tokyo) ; 64(7): 668-75, 2016 Jul 01.
Artículo en Inglés | MEDLINE | ID: mdl-26936155

RESUMEN

Natural products from actinomycetes are important and valuable sources for drug discovery and the development of biological tools. The present review describes our recent study on the isolation of new natural products mainly possessing heterocyclic and aromatic ring structures with biological effects on cancer-related cellular pathways such as tumor necrosis factor-α-related apoptosis-inducing ligand (TRAIL) and Wnt signaling.


Asunto(s)
Actinobacteria/química , Productos Biológicos/aislamiento & purificación , Productos Biológicos/farmacología , Compuestos Heterocíclicos/química , Compuestos Heterocíclicos/farmacología , Hidrocarburos Aromáticos/química , Hidrocarburos Aromáticos/farmacología , Metabolismo Secundario , Productos Biológicos/química , Productos Biológicos/metabolismo , Compuestos Heterocíclicos/aislamiento & purificación , Compuestos Heterocíclicos/metabolismo , Humanos , Hidrocarburos Aromáticos/aislamiento & purificación , Hidrocarburos Aromáticos/metabolismo , Ligando Inductor de Apoptosis Relacionado con TNF/antagonistas & inhibidores , Ligando Inductor de Apoptosis Relacionado con TNF/metabolismo , Vía de Señalización Wnt/efectos de los fármacos
12.
J Antibiot (Tokyo) ; 69(6): 446-50, 2016 06.
Artículo en Inglés | MEDLINE | ID: mdl-26669750

RESUMEN

Two new phenazine derivatives, aotaphenazine (1) and 5,10-dihydrophencomycin (2), were isolated from the ethyl acetate extract of Streptomyces sp. IFM 11694. In addition, the known 1-phenazinecarboxylic acid (3), phencomycin (4) and 1,6-phenazinedicarboxylic acid (5) were identified. The structures of the isolated compounds (1-5) were characterized by spectroscopic methods including NMR and mass spectrometry data. Compound 1 showed the ability to overcome tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) resistance at concentration of 12.5 µM. Aotaphenazine (1) enhanced the levels of apoptosis inducing proteins DR4, DR5, p53 and also decreased the levels of cell survival protein Bcl-2 in TRAIL-resistant human gastric adenocarcinoma (AGS) cells in a dose-dependent manner.


Asunto(s)
Adenocarcinoma/tratamiento farmacológico , Fenazinas/farmacología , Neoplasias Gástricas/tratamiento farmacológico , Streptomyces/metabolismo , Ligando Inductor de Apoptosis Relacionado con TNF/metabolismo , Adenocarcinoma/patología , Antineoplásicos/administración & dosificación , Antineoplásicos/aislamiento & purificación , Antineoplásicos/farmacología , Apoptosis/efectos de los fármacos , Línea Celular Tumoral , Relación Dosis-Respuesta a Droga , Resistencia a Antineoplásicos , Humanos , Espectroscopía de Resonancia Magnética/métodos , Espectrometría de Masas/métodos , Fenazinas/administración & dosificación , Fenazinas/aislamiento & purificación , Proteínas Proto-Oncogénicas c-bcl-2/metabolismo , Neoplasias Gástricas/patología
13.
J Nat Med ; 70(2): 266-70, 2016 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-26607379

RESUMEN

One new alkyl sulfonic acid derivative, sulfotanone (1), and the known panosialin wA (2) were isolated from the methanolic extract of mycelium of Streptomyces sp. 11694. The structure of the new compound (1) was established by a combination of spectroscopic techniques, including HRESIMS, IR, 1D and 2D NMR measurements. Compound 1 (40 µM) in combination with TRAIL showed synergistic activity in sensitizing TRAIL-resistance in human gastric adenocarcinoma cell lines.


Asunto(s)
Adenocarcinoma/tratamiento farmacológico , Antineoplásicos/uso terapéutico , Resistencia a Medicamentos/efectos de los fármacos , Neoplasias Gástricas/tratamiento farmacológico , Streptomyces/química , Ácidos Sulfónicos/uso terapéutico , Ligando Inductor de Apoptosis Relacionado con TNF/uso terapéutico , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Antineoplásicos/farmacología , Derivados del Benceno/aislamiento & purificación , Productos Biológicos/química , Productos Biológicos/aislamiento & purificación , Productos Biológicos/farmacología , Productos Biológicos/uso terapéutico , Línea Celular Tumoral , Sinergismo Farmacológico , Humanos , Espectroscopía de Resonancia Magnética , Estructura Molecular , Ácidos Sulfónicos/química , Ácidos Sulfónicos/aislamiento & purificación , Ácidos Sulfónicos/farmacología
14.
Nat Prod Res ; 28(19): 1549-56, 2014.
Artículo en Inglés | MEDLINE | ID: mdl-24934244

RESUMEN

This study attempts to elucidate the secondary metabolite profiles of Ficus lyrata leaves and fruits grown in Egypt. Non-targeted metabolite profiling via ultra performance liquid chromatography (UPLC)-qTOF-MS was used to identify various chemical classes in F. lyrata fruits and leaves (i.e. flavonoids, phenolic acids and fatty acids) analysed by chemometrics. A total of 72 metabolites were evaluated via a UPLC-qTOF-MS-based metabolomic study. Seventeen flavonoids were characterised and tentatively identified with the main constituents being catechins/procyanidins, O- and C-linked flavonoid glycosides. The major procyanidins were dimers and trimers comprising (epi)catechin and (epi)afzelechin units, whereas the predominant flavones were C-glycosides of luteolin and apigenin. Aside from these major flavonoid classes, a group of benzoic acids, caffeoylquinic acids, fatty acid and sphingolipids were also annotated. This study provides the most complete map for polyphenol distribution in F. lyrata leaves and fruits and the basis for future investigation of its fruits nutritional value or possible nutraceutical uses.


Asunto(s)
Ficus/química , Apigenina/análisis , Benzoatos/análisis , Biflavonoides/análisis , Catequina/análisis , Cromatografía Líquida de Alta Presión , Cromatografía Liquida , Egipto , Ácidos Grasos/química , Flavonas/análisis , Flavonoides/análisis , Frutas/química , Glicósidos/análisis , Estructura Molecular , Fenoles/análisis , Hojas de la Planta/química , Polifenoles/análisis , Proantocianidinas/análisis , Ácido Quínico/análogos & derivados , Ácido Quínico/análisis , Espectrometría de Masa por Ionización de Electrospray , Esfingolípidos/análisis
15.
Nat Prod Res ; 27(22): 2126-31, 2013.
Artículo en Inglés | MEDLINE | ID: mdl-23656313

RESUMEN

Chemical investigation of the marine Streptomyces sp. Eg25 led to the isolation of one new natural 2-aminophenoxazin-3-one-8-carboxylic acid methyl ester named maroxazinone (1) as well as the known compounds elloxazinone A (2), exfoliazone (3), carboxyexfoliazone (4), elloxazinone B (5) and venezueline D (6). The chemical structures of the isolated compounds were deduced from extensive studies of NMR ((1)H and (13)C NMR, (1)H-(1)H COSY, HMQC and HMBC) and mass spectra. The cytotoxic activities of the new maroxazinone (1) and venezueline D (6) against breast carcinoma cell line (MCF7), liver carcinoma cell line (HEPG2) and colon carcinoma cell line (HCT116) were investigated.


Asunto(s)
Alcaloides/aislamiento & purificación , Oxazinas/aislamiento & purificación , Streptomyces/química , Alcaloides/química , Ensayos de Selección de Medicamentos Antitumorales , Células HCT116 , Células Hep G2 , Humanos , Células MCF-7 , Estructura Molecular , Oxazinas/química
17.
J Antibiot (Tokyo) ; 64(11): 729-34, 2011 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-21934691

RESUMEN

Four new pyranonaphthoquinones (1-4) were isolated from the liquid culture of Streptomyces sp. IFM 11307. Additionally, one new phenazine derivative (5), along with the known phenazine-1,6-dicarboxylic acid (6) were identified. The chemical structure of compounds 1-6 was elucidated by 1D and 2D NMR spectroscopy together with CD spectral analysis. Compounds 1-4 significantly overcame tumor necrosis factor-related apoptosis-inducing ligand resistance in human gastric adenocarcinoma cell lines.


Asunto(s)
Alcaloides/farmacología , Factores Inmunológicos/farmacología , Naftoquinonas/farmacología , Fenazinas/farmacología , Streptomyces/metabolismo , Ligando Inductor de Apoptosis Relacionado con TNF/inmunología , Alcaloides/química , Alcaloides/aislamiento & purificación , Línea Celular Tumoral , Dicroismo Circular , Medios de Cultivo/química , Humanos , Factores Inmunológicos/química , Factores Inmunológicos/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Modelos Moleculares , Estructura Molecular , Naftoquinonas/química , Naftoquinonas/aislamiento & purificación , Fenazinas/química , Fenazinas/aislamiento & purificación , Ligando Inductor de Apoptosis Relacionado con TNF/metabolismo
18.
Chem Pharm Bull (Tokyo) ; 59(4): 508-10, 2011.
Artículo en Inglés | MEDLINE | ID: mdl-21467685

RESUMEN

A new phenazine derivative named izumiphenazine D (1), together with three known metabolites, 1-hydroxyphenazine (2), phenazine-1-carboxylic acid (3) and 6-hydroxyphenazine-1-carboxylic acid (4) has been isolated from the ethyl acetate extract of culture of Streptomyces sp. IFM 11204. The structure of 1 was established via spectroscopic methods, including 1D- and 2D-NMR measurements.


Asunto(s)
Óxidos/química , Quinolinas/química , Streptomyces/química , Línea Celular Tumoral , Humanos , Conformación Molecular , Óxidos/aislamiento & purificación , Óxidos/toxicidad , Quinolinas/aislamiento & purificación , Quinolinas/toxicidad , Ligando Inductor de Apoptosis Relacionado con TNF/farmacología
19.
J Antibiot (Tokyo) ; 64(3): 271-5, 2011 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-21304533

RESUMEN

Three new glycosylated phenazine derivatives, named izuminosides A-C (1-3) have been isolated from the ethyl acetate extract of Streptomyces sp. IFM 11260. The structures of the new compounds were determined on the basis of their spectral data. Compounds 1-3 were evaluated for their activity in overcoming tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) resistance in human gastric adenocarcinoma cells. Compounds 2 (10 µM) and 3 (60 µM) in combination with TRAIL showed synergistic activity in sensitizing TRAIL-resistance AGS cells.


Asunto(s)
Glicósidos/aislamiento & purificación , Fenazinas/aislamiento & purificación , Streptomyces/metabolismo , Adenocarcinoma/tratamiento farmacológico , Línea Celular Tumoral/efectos de los fármacos , Resistencia a Antineoplásicos , Glicósidos/química , Glicósidos/farmacología , Humanos , Fenazinas/química , Fenazinas/farmacología , Neoplasias Gástricas/tratamiento farmacológico
20.
J Nat Prod ; 73(12): 1999-2002, 2010 Dec 27.
Artículo en Inglés | MEDLINE | ID: mdl-21090727

RESUMEN

Three new phenazine derivatives, named izumiphenazines A-C (1-3), and the known phenazine-1,6-dicarboxylic acid (4) were isolated from Streptomyces sp. IFM 11204. The structures of the isolated compounds were elucidated by means of spectroscopic methods including UV, IR, HRESIMS, and 1D and 2D NMR. Compounds 1-3 were evaluated for their activity in overcoming TRAIL (TNF-related apoptosis-inducing ligand) resistance in human gastric adenocarcinoma cells. Compounds 2 (30 µM) and 3 (20 µM) in combination with TRAIL showed synergistic activity in sensitizing TRAIL-resistant AGS cells.


Asunto(s)
Fenazinas/aislamiento & purificación , Streptomyces/química , Ligando Inductor de Apoptosis Relacionado con TNF/efectos de los fármacos , Humanos , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Fenazinas/química , Fenazinas/farmacología , Células Tumorales Cultivadas
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