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1.
Phytochemistry ; 194: 112969, 2022 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-34861538

RESUMEN

Phaeosphspirone, an undescribed polyketide with a unique 6/5/5/6-fused tetracyclic system, and two known analogues, herbarin and O-methylherbarin, were purified from the endophytic fungus Phaeosphaeriaceae sp. isolated from the desert plant Bassia dasyphylla. The connectivity and relative configuration of phaeosphspirone was elucidated by comprehensive HR-ESI-MS and NMR analysis together with a computer-assisted structure elucidation (CASE) method. A pair of enantiomers existing in phaeosphspirone were separated by HPLC chromatography after reacting with chiral reagents, from which the absolute configuration of phaeosphspirone was simultaneously determined based on Mosher's rule. This tandem strategy provides a useful approach for the separation and stereochemical determination of enantiomers possessing secondary hydroxyl groups. The structural feature of phaeosphspirone, herbarin and O-methylherbarin together with gene cluster analysis suggested their polyketide biosynthetic origin. Herbarin and O-methylherbarin exhibited moderate cytotoxicity against three cancer cell lines.


Asunto(s)
Ascomicetos , Policétidos , Cromatografía Líquida de Alta Presión , Espectroscopía de Resonancia Magnética
2.
Chin Herb Med ; 13(1): 98-104, 2021 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-36117764

RESUMEN

Objective: Peptidyl alkaloids, a series of important natural products can be assembled by fungal non-ribosomal peptide synthetases (NRPSs). However, many of the NRPSs associated gene clusters are silent under laboratory conditions, and the traditional chemical separation yields are low. In this study, we aim to discovery and efficiently prepare fungal peptidyl alkaloids assembled by fungal NRPSs. Methods: Bioinformatics analysis of gene cluster containing NRPSs from the genome of Penicillium thymicola, and heterologous expression of the putative gene cluster in Aspergillus nidulans were performed. Isolation, structural identification, and biological evaluation of the product from heterologous expression were carried out. Results: The putative tri-modular NRPS AncA was heterologous-expressed in A. nidulans to give anacine (1) with high yield, which showed moderate and selective cytotoxic activity against A549 cell line. Conclusion: Heterologous expression in A. nidulans is an efficient strategy for mining fungal peptidyl alkaloids.

3.
Chin J Nat Med ; 17(5): 394-400, 2019 May 20.
Artículo en Inglés | MEDLINE | ID: mdl-31171275

RESUMEN

Six novel monacolin analogs, monacolins V1-V6 (1-6), together with seven known ones (7-13), were isolated from the ethyl acetate extract of red yeast rice. Their structures and absolute configurations were determined by spectroscopic methods, especially 2D NMR (1H-1HCOSY, HSQC, HMBC, and NOESY/ROESY) and CD spectroscopic analyses as well as chemical derivation. Monacolins V2 (2) and V3 (3) represent the first examples of monacolins with 3-hydroxybutyrate substitute. The anti-inflammatory inhibitory activities against the lipopolysaccharide (LPS) induced NO production in BV-2 cells as well as antioxidant activities against rat liver microsomal lipid peroxidation were evaluated.


Asunto(s)
Productos Biológicos/química , Hidroxibutiratos/química , Naftalenos/química , Acetatos/química , Animales , Línea Celular Transformada , Hidroxibutiratos/aislamiento & purificación , Hidroxibutiratos/farmacología , Peroxidación de Lípido/efectos de los fármacos , Lipopolisacáridos/farmacología , Estructura Molecular , Naftalenos/aislamiento & purificación , Naftalenos/farmacología
4.
Mar Drugs ; 16(11)2018 Nov 16.
Artículo en Inglés | MEDLINE | ID: mdl-30453472

RESUMEN

Six new diphenyl ethers (1⁻6) along with eleven known analogs were isolated from the ethyl acetate extract of a marine-derived Aspergillus sydowii guided by LC-UV-MS. Their structures were unambiguously characterized by HRESIMS, NMR, as well as chemical derivatization. Compounds 1 and 2 are rare diphenyl ether glycosides containing d-ribose. The absolute configuration of the sugar moieties in compounds 1⁻3 was determined by a LC-MS method. All the compounds were evaluated for their cytotoxicities against eight cancer cell lines, including 4T1, U937, PC3, HL-60, HT-29, A549, NCI-H460, and K562, and compounds 1, 5, 6, and 8⁻11 were found to exhibit selective cytotoxicity against different cancer cell lines.


Asunto(s)
Antineoplásicos/farmacología , Organismos Acuáticos/química , Aspergillus/química , Éteres Fenílicos/farmacología , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Línea Celular Tumoral , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Espectroscopía de Resonancia Magnética , Estructura Molecular , Éteres Fenílicos/química , Éteres Fenílicos/aislamiento & purificación , Espectrometría de Masa por Ionización de Electrospray
5.
Mar Drugs ; 16(10)2018 Oct 01.
Artículo en Inglés | MEDLINE | ID: mdl-30275353

RESUMEN

By treating with histone-deacetylase inhibitor valproate sodium, three new heterdimeric tetrahydroxanthone⁻chromanone lactones chrysoxanthones A⁻C (1⁻3), along with 17 known compounds were isolated from a sponge-associated Penicillium chrysogenum HLS111. The planar structures of chrysoxanthones A⁻C were elucidated by means of spectroscopic analyses, including MS, 1D, and 2D NMR. Their absolute configurations were established by electronic circular dichroism (ECD) calculations. Chrysoxanthones A⁻C exhibited moderate antibacterial activities against Bacillus subtilis with minimum inhibitory concentration (MIC) values of 5⁻10 µg/mL.


Asunto(s)
Antibacterianos/química , Inhibidores de Histona Desacetilasas/farmacología , Penicillium chrysogenum/química , Penicillium chrysogenum/efectos de los fármacos , Poríferos/química , Xantonas/química , Animales , Antibacterianos/farmacología , Bacillus subtilis/efectos de los fármacos , Pruebas de Sensibilidad Microbiana/métodos , Poríferos/efectos de los fármacos , Ácido Valproico/farmacología , Xantonas/farmacología
6.
J Hazard Mater ; 274: 53-62, 2014 Jun 15.
Artículo en Inglés | MEDLINE | ID: mdl-24762701

RESUMEN

Sulfur dioxide from flue gas was converted into sulfate after the absorption of alkaline solutions. Haloalkaliphilic microorganisms have been used in reducing sulfate to decrease expenses and avoid sulfide inhibition. The effects of different COD/SO4(2-) ratios and hydraulic retention times (HRTs) on the sulfate removal efficiency and bacterial community were investigated in model experiments. Ethanol showed better performance as an electron donor than lactate. The optimum COD/SO4(2-) ratio and HRT were 4.0 and 18 h, respectively, with respective sulfate removal efficiency and rate of 97.8 ± 1.11% and 6.26 ± 0.0710 g/Ld. Sulfide concentrations reached 1,603 ± 3.38 mg/L. Based on denaturing gradient gel electrophoresis analysis of 16S rDNA, the major sulfate-reducing bacterium (SRB) was Desulfonatronovibrio sp., which was only detected at a COD/SO4(2-) ratio of 4.0 using ethanol as an electron donor. Different HRTs had no significant effect on the band corresponding to this species. PCR results show that methane-producing archaea (MPA) were from the acetoclastic methanogenic family Methanosarcinaceae. Quantitative real-time PCR did not demonstrate any significant competition between SRB and MPA. The findings of this study indicate that sulfate reduction, nitrate reduction, and sulfide oxidization may occur in the same bioreactor.


Asunto(s)
Bacterias/metabolismo , Reactores Biológicos , Methanosarcinaceae/metabolismo , Sulfatos/metabolismo , Bacterias/clasificación , Bacterias/genética , Análisis de la Demanda Biológica de Oxígeno , ADN de Archaea/genética , ADN Bacteriano/genética , ADN Ribosómico , Methanosarcinaceae/genética , Nitratos/metabolismo , Sulfuros/metabolismo
7.
Bioresour Technol ; 153: 216-22, 2014 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-24368270

RESUMEN

Effects of NO3(-)/SO4(2-) ratio on denitrification and sulfate removal efficiency were investigated in model experiments applying haloalkaliphilic bioreactor. The reduction of both substrates performed well at different NO3(-)/SO4(2-) ratios ranging from 17.6 to l.5. The removal rates of nitrate and sulfate were 6 and 1.39kgm(-3)d(-1), respectively, at NO3(-)/SO4(2-) ratio 3.0, while sulfide concentration reached up to 703gm(-3). The major sulfate-reducing and denitrifying bacteria were Desulfonatronovibrio sp. and Halomonas campisalis, respectively. Decrease in NO3(-)/SO4(2-) ratio led to obvious changes in bacterial community. Although the sulfate reducers became dominant, the population of denitrifying ones also increased as it was demonstrated by analysis of PCR-amplified 16S rDNA fragments, which suggested that SRB and DB coexisted well in bioreactor.


Asunto(s)
Álcalis/farmacología , Reactores Biológicos/microbiología , Halógenos/farmacología , Nitratos/farmacología , Sulfatos/farmacología , Bacterias/efectos de los fármacos , Bacterias/genética , Bacterias/crecimiento & desarrollo , Biodiversidad , Electroforesis en Gel de Gradiente Desnaturalizante , Desnitrificación/efectos de los fármacos , Etanol/metabolismo , Ácidos Grasos Volátiles/metabolismo , Lactatos/metabolismo , Datos de Secuencia Molecular , Oxidación-Reducción/efectos de los fármacos , Filogenia , ARN Ribosómico 16S/genética , Sulfatos/aislamiento & purificación , Sulfuros/farmacología , Eliminación de Residuos Líquidos
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