RESUMO
Four new α-pyrone derivatives, nodulisporipyrones A-D (1-4), were isolated from the extract of an endolichenic fungal strain Nodulisporium sp. (65-12-7-1) that was fermented with rice. The structures of 1-4 were elucidated by extensive spectroscopic analysis, and the absolute configurations were determined by modified Mosher's method and electronic circular dichroism experiments. Their antimicrobial activities against Staphylococcus aureus 209P, Escherichia coli ATCC0111, Aspergillus niger R330, and Candida albicans FIM709 were evaluated using a paper disk diffusion method. Nodulisporipyrones A-D (1-4) are the first α-pyrone derivatives from Nodulisporium fungi.
Assuntos
Pironas/isolamento & purificação , Xylariales/química , Aspergillus niger/efeitos dos fármacos , Candida albicans/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Escherichia coli/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Oryza/metabolismo , Pironas/química , Pironas/farmacologia , Staphylococcus aureus/efeitos dos fármacosRESUMO
Pericoterpenoid A (1), a new cadinane-type sesquiterpene, was isolated from an endolichenic fungal strain Periconia sp. (No. 19-4-2-1). Its structure was characterized by analyzing the spectroscopic data (IR, MS, 1D- and 2D-NMR). The antimicrobial activity against Escherichia coli, Staphylococcus aureus, Aspergillus niger, and Candida albicans was evaluated. Pericoterpenoid A showed moderate antimicrobial activity against A. niger and weak activity against C. albicans. This is the first report of the presence of cadinane-type sesquiterpene in Periconia sp.
Assuntos
Ascomicetos/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Aspergillus niger/efeitos dos fármacos , Candida albicans/efeitos dos fármacos , Escherichia coli/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Sesquiterpenos Policíclicos , Sesquiterpenos/química , Staphylococcus aureus/efeitos dos fármacosRESUMO
Tacrolimus is an important immunosuppressant produced by microbial fermentation. In this study, a modified nanoscale polymeric adsorbent, Ag+-exchanged resin, was prepared and studied for the preparative separation and purification of tacrolimus from fermentation broth of Streptomyces tsukubaensis. The performance and absorption characteristics of the modified nanoscale polymeric adsorbent namely Ag-NPS was evaluated. Notably, Ag-NPS resin displayed the pronounced separation capacities for tacrolimus and its equilibrium adsorption data was well-fitted to the Langmuir isotherm. Moreover, the dynamic adsorption and desorption tests was carried out to obtain the operational parameters for further purification of tacrolimus. Finally, tacrolimus and the two major impurities, ascomycin and dihydrotacrolimus, were separated well in the scale-up purification process. The purity and recovery of tacrolimus was recorded to be 99.12±0.25% and 90.41±2.05%. In conclusion, this method displayed a high potential for separation and purification of tacrolimus and other unsaturated bioactive compounds in high yield from the fermentation broth.
Assuntos
Streptomyces , Tacrolimo , Adsorção , Fermentação , ImunossupressoresRESUMO
The actinomycete strain FIM06-0036 was isolated from marine sponge sample collected from the East China Sea and identified as Verrucosispora sp. based upon the results of 16S rRNA sequence analysis. One new alkaloid, 2-ethylhexyl 1H-imidazole-4-carboxylate (1), together with a known alkaloid butyl 1H-imidazole-4-carboxylate (2) was obtained from the fermentation products of this strain, the structures of compounds 1 and 2 were determined by their detailed analysis of 1 D, 2 D NMR and HR-ESI-MS data, along with literature data analysis. Compounds 1 and 2 were evaluated for their antimicrobial activity with MIC (minimum inhibitory concentration) values ranging from 8 to 256 µg · mL-1 against Helicobacter pylori, Klebsiella Pneumonia, Staphylococcus aureus and Enterococcus faecalis.
Assuntos
Alcaloides , Anti-Infecciosos , Micromonosporaceae , Alcaloides/farmacologia , Antibacterianos/farmacologia , Testes de Sensibilidade Microbiana , Micromonosporaceae/genética , RNA Ribossômico 16S/genéticaRESUMO
Using the draft genome sequence of Verrucosispora sp. FIM060022, we have identified a new desferrioxamine-like siderophore, FW0622. This is the first chemically characterized siderophore obtained from Verrucosispora. The structure was elucidated by extensive spectral analyses. The biosynthetic pathway of FW0622 was proposed to occur via the non-ribosomal peptide synthetase (NRPS)-independent (NIS) synthetase pathway based on the putative biosynthetic siderophore gene cluster in FIM060022. The results demonstrate that marine-derived Verrucosispora species deserve recognition as an important source of new natural products. Furthermore, this study verified that genome mining is an effective way to identify compounds that may be overlooked by traditional methods.
Assuntos
Anti-Infecciosos/farmacologia , Micromonosporaceae/genética , Sideróforos/química , Sideróforos/metabolismo , Anti-Infecciosos/química , Vias Biossintéticas , Genoma Bacteriano , Genômica , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Micromonosporaceae/metabolismo , Estrutura Molecular , Família Multigênica , Peptídeo Sintases/genética , Peptídeo Sintases/metabolismo , Metabolismo Secundário/genética , Sideróforos/genética , Sideróforos/farmacologiaRESUMO
Chemical investigation of a marine-derived actinomycete strain Verrucosispora sp. FIM06025 isolated from a marine sponge sample collected from the East China Sea, resulted in the discovery of two new alkaloids, (2-(hydroxymethyl)-3-(2-(hydroxymethyl)-3-methylaziridin-1-yl) (2-hydroxyphenyl) methanone (1) and 2-(1-hydroxyethyl)-3,4-dihydrobenzo [f] [1,4]oxazepin-5(2H)-one (2). The structures of compounds 1 and 2 were determined by the detailed analysis of 1D, 2D NMR and HR-TOF-MS data, along with literature data analysis. The bioefficacy investigations revealed that compound 1 exhibited a broad spectrum of antimicrobial activity with MIC (minimum inhibitory concentration) values ranging from 3.4 to 200 µg·mL-1 against H. pylori, P. aeroginosa, A. baumanniiin, E. coli and K. pneumonia, S. aureus, C. albicans and E. faecium, however, compound 2, up to 200 µg/mL, displayed no antibacterial activity against these bacteria.
Assuntos
Actinobacteria/química , Alcaloides/isolamento & purificação , Anti-Infecciosos/isolamento & purificação , Actinobacteria/metabolismo , Alcaloides/farmacologia , Animais , Anti-Infecciosos/farmacologia , Bactérias/efeitos dos fármacos , China , Fungos/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Poríferos/microbiologia , Análise EspectralRESUMO
Chemical investigation of a marine-derived actinomycete strain Micromonospora sp. FIM05328 isolated from a soil sample collected from the East China Sea, resulted in the discovery of a new 26-membered polyene macrolactam metabolite FW05328-1 (1), together with a known polyene with pyridone ring compound aurodox (2). The structures of compounds 1 and 2 were determined by the detailed analysis of 1D, 2D NMR and HR-TOF-MS data, along with literature data analysis. 1 and 2 exhibited excellent antiproliferative activities against KYSE30, KYSE180 and EC109 human tumour cell lines, but displayed no antibacterial activities against bacteria or fungi were tested.
Assuntos
Antineoplásicos/isolamento & purificação , Micromonospora/química , Polienos/química , Actinobacteria/metabolismo , Antibacterianos , Antineoplásicos/química , Antineoplásicos/farmacologia , Linhagem Celular Tumoral , China , Humanos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Polienos/isolamento & purificaçãoRESUMO
One new dihydroisocoumarin, pericocin A (1), one new chromone, pericocin B (2), and two new α-pyrone derivatives, pericocins C-D (3-4), together with two known compounds, 3-(2-oxo-2H-pyran-6-yl)propanoic acid (5) and (E)-3-(2-oxo-2H-pyran-6-yl)acrylic acid (6), were isolated from the culture of the endolichenic fungus Periconia sp.. Their structures were elucidated by spectroscopic methods. All these compounds are derived from the polyketone biosynthetic pathway. Compound 1 was obtained as a mixture of enantiomers. The antimicrobial activity of compounds 1-5 was tested against Escherichia coli, Staphylococcus aureus, Aspergillus niger, and Candida albicans. Compounds 1-5 showed moderate antimicrobial activity against A. niger and weak activity against C. albicans.