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1.
Chem Biodivers ; : e202401547, 2024 Aug 13.
Artículo en Inglés | MEDLINE | ID: mdl-39136586

RESUMEN

The fungus Phialomyces macrosporus was cultured using the One Strain Many Compounds (OSMAC) strategies to evaluate its metabolome. Variations in the nutrient culture media, culture regime, and cultivation parameters can significantly influence fungal extract quantity and chemical diversity. This study aimed to explore the mycobolome of P. macrosporus in five different culture media and two different cultivation conditions using NMR-based metabolomics. Principal component analysis (PCA) of 1H NMR spectra revealed clear differentiation between these samples, highlighting the rice dextrose agar medium (RDA) and potato dextrose broth (PDB) as standard complex media for conducting a fungal metabolite screening program.

2.
J Nat Prod ; 85(9): 2236-2250, 2022 09 23.
Artículo en Inglés | MEDLINE | ID: mdl-36098709

RESUMEN

This Review provides a critical analysis of the literature covering the naturally occurring partially reduced perylenequinones (PQs) from fungi without carbon substituents (which can be named class A perylenequinones) and discusses their structures, stereochemistry, biosynthesis, and biological activities as appropriate. Perylenequinones are natural pigments with a perylene skeleton produced by certain fungi, aphids, some plants, and animal species. These compounds display several biological activities, e.g., antimicrobial, anti-HIV, photosensitizers, cytotoxic, and phytotoxic. It describes 36 fungal PQs and cites 81 references, covering from 1956 to August 2022.


Asunto(s)
Hongos , Perileno , Pigmentos Biológicos , Quinonas , Animales , Hongos/química , Perileno/análogos & derivados , Perileno/química , Perileno/farmacología , Fármacos Fotosensibilizantes , Pigmentos Biológicos/biosíntesis , Pigmentos Biológicos/química , Pigmentos Biológicos/aislamiento & purificación , Pigmentos Biológicos/farmacología , Quinonas/química , Quinonas/farmacología
3.
J Nat Prod ; 84(8): 2157-2164, 2021 08 27.
Artículo en Inglés | MEDLINE | ID: mdl-34283606

RESUMEN

Four new chromenones, kielmeyerones A-D (1-4), were obtained from the roots of Kielmeyera reticulata. Their structures were elucidated based on spectroscopic data (NMR and HRESIMS) interpretation. The pharmacological activity of kielmeyerone A (1), the major compound, was evaluated using in vitro and in vivo inflammation and pain models. During in vitro screening, 1, at noncytotoxic concentrations (0.097-1.56 µM), inhibited NO production by J774 macrophages stimulated with LPS and IFN-γ. In the complete Freund's adjuvant-induced inflammation model in mice, 1 (12.5-50 mg/kg) inhibited paw edema, demonstrating an anti-inflammatory effect. Additionally, 1 (12.5-50 mg/kg) induced a dose-dependent antinociceptive effect in the late phase of the formalin test, a profile similar to those of nonsteroidal anti-inflammatory drugs. Mice treated with 1 (100 mg/kg) did not show motor performance alterations using a rota-rod test. Thus, the present study has characterized new chromenones from Kielmeyera reticulata and has provided evidence of the anti-inflammatory and antinociceptive properties of one of these, kielmeyerone A (1).


Asunto(s)
Analgésicos/farmacología , Antiinflamatorios/farmacología , Magnoliopsida/química , Analgésicos/aislamiento & purificación , Animales , Antiinflamatorios/aislamiento & purificación , Brasil , Línea Celular , Edema/inducido químicamente , Edema/tratamiento farmacológico , Inflamación/inducido químicamente , Inflamación/tratamiento farmacológico , Macrófagos/efectos de los fármacos , Masculino , Ratones , Estructura Molecular , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Raíces de Plantas/química
4.
Br J Haematol ; 192(5): 922-931, 2021 03.
Artículo en Inglés | MEDLINE | ID: mdl-33476407

RESUMEN

Sickle cell anaemia (SCA) is a debilitating genetic haemoglobinopathy predominantly affecting the disenfranchised strata of society in Africa and the Americas. The most common pharmacological treatment for this disease is the administration of hydroxycarbamide (HC) for which questions remain regarding its mechanism of action, efficacy and long-term toxicity specifically in paediatric individuals. A multiplatform metabolomics approach was used to assess the metabolome of plasma samples from a population of children and adolescents with SCA with and without HC treatment along with non-SCA individuals. Fifty-three metabolites were identified by ultra-high performance liquid chromatography coupled to high-resolution mass spectrometry (UHPLC-HRMS) and 1 H nuclear magnetic resonance (NMR) with a predominance of membrane lipids, amino acids and organic acids. The partial least-squares discriminant analysis (PLS-DA) analysis allowed a clear discrimination between the different studied groups, revealing clear effects of the HC treatment in the patients' metabolome including rescue of specific metabolites to control levels. Increased creatine/creatinine levels under HC treatment suggests a possible increase in the arginine pool and increased NO synthesis, supporting existing models for HC action in SCA. The metabolomics results extend the current knowledge on the models for SCA pathophysiology including impairment of Lands' cycle and increased synthesis of sphingosine 1-phosphate. Putative novel biomarkers are suggested.


Asunto(s)
Anemia de Células Falciformes/sangre , Antidrepanocíticos/uso terapéutico , Hidroxiurea/uso terapéutico , Metabolómica , Ácidos/sangre , Síndrome Torácico Agudo/etiología , Adolescente , Aminoácidos/sangre , Anemia de Células Falciformes/complicaciones , Anemia de Células Falciformes/tratamiento farmacológico , Antidrepanocíticos/farmacología , Arteriopatías Oclusivas/etiología , Biomarcadores , Butiratos/sangre , Niño , Cromatografía Líquida de Alta Presión , Creatina/sangre , Creatinina/sangre , Femenino , Humanos , Hidroxiurea/farmacología , Lisofosfolípidos/sangre , Masculino , Espectrometría de Masas , Lípidos de la Membrana/sangre , Modelos Biológicos , Resonancia Magnética Nuclear Biomolecular , Esfingosina/análogos & derivados , Esfingosina/sangre
5.
Nat Prod Res ; 31(14): 1647-1654, 2017 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-28278657

RESUMEN

The alpha-D-glucans are worldwide acknowledged as powerful immune system stimulants found in several sources; however, the fungal-derived sources appear to respond with higher activity. The present study has investigated polysaccharide production in Moniliophthora perniciosa. The dry biomass was subjected to thermal treatment in alkaline solution after fermentation. The biopolymers dissolved in this solution were precipitated after three volumes of absolute ethanol were added to the supernatant. The pure polysaccharide MPS1 was obtained through molecular exclusion chromatography using the Sephacryl S-200 column. The HPLC-RI analysis showed that MPS1 was a glucose homopolysaccharide. Nuclear magnetic resonance (NMR) spectra indicated the α-form as the anomeric carbon configuration in glucose residue. The structure of the polysaccharide was further confirmed as (1→4)-α-D-glucan through the chemical shift of C4. The molecular weight of MPS1 was 31.0 kDa.


Asunto(s)
Agaricales/química , Polisacáridos/aislamiento & purificación , Cromatografía en Gel/métodos , Fermentación , Glucanos , Isomerismo , Espectroscopía de Resonancia Magnética/métodos , Estructura Molecular , Peso Molecular , Polisacáridos/química
6.
Carbohydr Polym ; 105: 293-9, 2014 May 25.
Artículo en Inglés | MEDLINE | ID: mdl-24708983

RESUMEN

ß-d-glucans are polymers of d-glucose monomers found in the cell walls of many bacteria, plants, fungi and yeasts. A variety of ß-d-glucans differing in structures have been isolated from various sources and their biological activity to be regulated by various structural factors, such as the primary structure, molecular weight, solubility, and conformation. This study investigated the effect of extraction time and temperature on the yield of ß-d-glucan produced by Rhodotorulamucilaginosa. A statistical Doehlert design was applied to determine the important effects and interactions of these independent variables on the yield of ß-d-glucan, the dependent variable. Significant models were obtained. The best yield was of 25% obtained after 128min of extraction in a temperature of 72°C. The polysaccharides were characterized as (1⟶3)-ß-d-glucan by methods spectroscopic (FT-IR, (1)HNMR and (13)CNMR). In addition, the antinociceptive effect was evaluated using different experimental tests (acetic acid-induced writhing test, formalin test and tail immersion test). The (1⟶3)-ß-d-glucan showed a potent peripheral antinociceptive effect, possibly by the inhibition of inflammatory mediators.


Asunto(s)
Analgésicos/química , Analgésicos/uso terapéutico , Dolor/tratamiento farmacológico , Rhodotorula/química , beta-Glucanos/química , beta-Glucanos/uso terapéutico , Analgésicos/aislamiento & purificación , Animales , Fraccionamiento Químico , Espectroscopía de Resonancia Magnética , Masculino , Ratones , Espectroscopía Infrarroja por Transformada de Fourier , beta-Glucanos/aislamiento & purificación
7.
An Acad Bras Cienc ; 85(2): 487-96, 2013.
Artículo en Inglés | MEDLINE | ID: mdl-23780307

RESUMEN

The chemical reactions carried out by microorganisms have been used as a tool in modern chemistry. This paper reports the production of mycophenolic acid and a new phthalide by the endophytic fungus Penicillium crustosum obtained from coffee seeds. The fungus was cultivated in a liquid medium for a period of seven days and after that the culture medium was divided into four treatments: A, B, C and D, to which different organic substances were added. Treatment A was maintained as the control to evaluate the occurrence of biotransformation. Organic acids were added to the culture media of treatments B (ferulic and quinic acids) and C [cinnamic and 3,4-(methylenedioxy) cinnamic acids], and caffeine was added in the treatment D. All these organic compounds were dissolved in DMSO, and the fermentation was maintained for more 13 days, totalizing 20 days. Mycophenolic acid was isolated from the culture with no added acids (treatment A). Mycophenolic acid and a new phthalide, 5-hydroxy-7-methoxy-4-methylphthalide were isolated from treatments B and C, and mycophenolic acid and caffeine (added to the culture medium) were isolated from treatment D. The structures were determined by NMR techniques and confirmed by MS and MS/MS techniques.


Asunto(s)
Benzofuranos/metabolismo , Ácido Micofenólico/biosíntesis , Penicillium/metabolismo , Benzofuranos/química , Biotransformación , Café/microbiología , Medios de Cultivo , Espectroscopía de Resonancia Magnética , Ácido Micofenólico/química , Espectrometría de Masas en Tándem , Factores de Tiempo
8.
An Acad Bras Cienc ; 84(2): 495-508, 2012 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-22652760

RESUMEN

The genus Leuconostoc belongs to a group of lactic acid bacteria usually isolated from fermented vegetables, which includes species involved in the production of exopolysaccharides (EPS). These biopolymers possess considerable commercial potential. Because of the wide variety of industrial applications of EPS, this study aimed to produce and characterize the native exopolysaccharide strain Leuconostoc pseudomesenteroides R2, which was isolated from cabbage collected in a semi-arid region of Bahia. We employed the following conditions for the production of EPS: 10.7% sucrose, pH 8.2, without agitation and incubation at 28ºC for 30 hours. The fermentation broth was treated with ethanol and generated two types of polysaccharide substances (EPS I and EPS II). The identification of EPS I and EPS II was conducted using FT-IR, (1)H, (13)C and DEPT-135 NMR spectra. The two substances were identified as linear dextran α polysaccharides (1 → 6) which indicated different characteristics with respect to thermal analysis and density of free packaging, viscosity and time of solubilization. Both dextrans are of low density, possess high thermal stability and exhibited the behavior characteristic of pseudoplastic polymers.


Asunto(s)
Brassica/microbiología , Leuconostoc/metabolismo , Polisacáridos Bacterianos/biosíntesis , Fermentación , Espectroscopía de Resonancia Magnética , Polisacáridos Bacterianos/aislamiento & purificación , Viscosidad
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