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1.
Ecotoxicol Environ Saf ; 196: 110533, 2020 Jun 15.
Artigo em Inglês | MEDLINE | ID: mdl-32247241

RESUMO

1-naphthol (1-NAP) is the main metabolite of pesticide carbaryl and naphthalene, and is also a genotoxic and carcinogenic intermediate in the synthesis of organic compound, dyes, pigment and pharmaceutical industry. In this work, two novel haptens were designed and synthesized for developing a competitive indirect enzyme-linked immunosorbent assay (ciELISA) method for 1-NAP in urine samples. The assay showed a limit of detection of 2.21 ng/mL and working range from 4.02 ng/mL to 31.25 ng/mL for 1-NAP in optimized working buffer. The matrix effect of samples was eliminated via 15-fold dilution of optimized working buffer. Good average recoveries (102.4%-123.4%) with a coefficient of variation from 11.7% to 14.7% was obtained for spiked urine samples. Subsequent instrument verification test showed good correlation between the results of ciELISA and high-performance liquid chromatography. The developed ciELISA is a high-throughput tool to monitor 1-NAP in urine, which can provide technical support for the establishment of biological exposure level for the exposure to carbaryl, naphthalene and other related pollutants.


Assuntos
Anticorpos Monoclonais/química , Ensaio de Imunoadsorção Enzimática/métodos , Haptenos/química , Naftóis/urina , Resíduos de Praguicidas/urina , Anticorpos Monoclonais/imunologia , Carbaril/metabolismo , Exposição Ambiental/análise , Limite de Detecção , Naftalenos/metabolismo , Naftóis/imunologia , Resíduos de Praguicidas/imunologia , Resíduos de Praguicidas/metabolismo
2.
Ecotoxicol Environ Saf ; 192: 110254, 2020 Apr 01.
Artigo em Inglês | MEDLINE | ID: mdl-32007746

RESUMO

The direct interactions of bacterial membranes and polycyclic aromatic hydrocarbons (PAHs) strongly influence the biological processes, such as metabolic activity and uptake of substrates due to changes in membrane lipids. However, the elucidation of adaptation mechanisms as well as membrane phospholipid alterations in the presence of phenanthrene (PHE) from α-proteobacteria has not been fully explored. This study was conducted to define the degradation efficiency of PHE by Sphingopyxis soli strain KIT-001 in a newly isolated from Jeonju river sediments and to characterize lipid profiles in the presence of PHE in comparison to cells grown on glucose using quantitative lipidomic analysis. This strain was able to respectively utilize 1-hydroxy-2-naphthoic acid and salicylic acid as sole carbon source and approximately 90% of PHE (50 mg/L) was rapidly degraded via naphthalene route within 1 day incubation. In the cells grown on PHE, strain KIT-001 appeared to dynamically change profiles of metabolite and lipid in comparison to cells grown on glucose. The levels of primary metabolites, phosphatidylethanolamines (PE), and phosphatidic acids (PA) were significantly decreased, whereas the levels of phosphatidylcholines (PC) and phosphatidylglycerols (PG) were significantly increased. The adaptation mechanism of Sphingopyxis sp. regarded mainly the accumulation of bilayer forming lipids and anionic lipids to adapt more quickly under restricted nutrition and toxicity condition. Hence, these findings are conceivable that strain KIT-001 has a good adaptive ability and biodegradation for PHE through the alteration of phospholipids, and will be helpful for applications for effective bioremediation of PAHs-contaminated sites.


Assuntos
Fenantrenos/metabolismo , Fosfolipídeos/metabolismo , Sphingomonadaceae/metabolismo , Biodegradação Ambiental , Sedimentos Geológicos/microbiologia , Lipidômica , Metabolômica , Naftalenos/metabolismo , Naftóis/metabolismo , Fosfolipídeos/química , Ácido Salicílico/metabolismo , Sphingomonadaceae/isolamento & purificação
3.
Artigo em Inglês | MEDLINE | ID: mdl-31913782

RESUMO

A stain of Pseudomonas sp. Lphe-2, which could degrade phenanthrene as the main carbon and energy source, was isolated from the aerobic sludge of a coking plant. Then its biodegradation characteristics, whole genome sequence and biodegradation pathway were examined. The Lphe-2 strain exhibited broad-spectrum degradation activities for various polycyclic aromatic hydrocarbons (PAHs), including naphthalene (NAP), phenanthrene (PHE), and pyrene (PYR). Under the optimal conditions, the degradation efficiency of phenanthrene (100 mg/L) is 92.76% on the 7th day, and 2-carboxybenzaldehyde and 1-hydroxy-2-naphthoic acid are the major metabolites found in phenanthrene metabolism. Genomic analysis of Pseudomonas sp. Lphe-2 showed that a total of 3879 genes from the Lphe-2 strain were annotated based on the COG classification, and the genomic information was annotated to 185 metabolic pathways. Based on the intermediate metabolites detected by Gas Chromatography-Mass Spectrometer (GC-MS) and all potential phenanthrene-degrading genes identified by BLAST search, a phenanthrene biodegradation pathway of Lphe-2 strain was proposed. These results suggested that Lphe-2 strain has a good prospect in the bioremediation of PAHs pollution.


Assuntos
Genes Bacterianos , Fenantrenos/análise , Pseudomonas/metabolismo , Esgotos/microbiologia , Poluentes do Solo/análise , Biodegradação Ambiental , Cromatografia Gasosa-Espectrometria de Massas , Genômica , Redes e Vias Metabólicas/genética , Anotação de Sequência Molecular , Naftalenos/análise , Naftalenos/metabolismo , Fenantrenos/metabolismo , Pseudomonas/genética , Pirenos/análise , Pirenos/metabolismo , Poluentes do Solo/metabolismo
4.
Chem Biol Interact ; 315: 108905, 2020 Jan 05.
Artigo em Inglês | MEDLINE | ID: mdl-31765606

RESUMO

Mineral oils are widely applied in food production and processing and may contain polycyclic aromatic hydrocarbons (PAHs). The PAHs that may be present in mineral oils are typically alkylated, and have been barely studied. Metabolic oxidation of the aromatic ring is a key step to form DNA-reactive PAH metabolites, but may be less prominent for alkylated PAHs since alkyl substituents would facilitate side chain oxidation as an alternative. The current study investigates this hypothesis of preferential side chain oxidation at the cost of aromatic oxidation using naphthalene and a series of its alkyl substituted analogues as model compounds. The metabolism was assessed by measuring metabolite formation in rat and human liver microsomal incubations using UPLC and GC-MS/MS. The presence of an alkyl side chain markedly reduced aromatic oxidation for all alkyl-substituted naphthalenes that were converted. 1-n-Dodecyl-naphthalene was not metabolized under the experimental conditions applied. With rat liver microsomes for 1-methyl-, 2-methyl-, 1-ethyl-, and 2-ethyl- naphthalene, alkyl side chain oxidation was preferred over aromatic oxidation. With human liver microsomes this was the case for 2-methyl-, and 2-ethyl-naphthalene. It is concluded that addition of an alkyl substituent in naphthalene shifts metabolism in favor of alkyl side chain oxidation at the cost of aromatic ring oxidation. Furthermore, alkyl side chains of 6 or more carbon atoms appeared to seriously hamper and reduce overall metabolism, metabolic conversion being no longer observed with the C12 alkyl side chain. In summary, alkylation of PAHs likely reduces their chances of aromatic oxidation and bioactivation.


Assuntos
Alquilantes/metabolismo , Microssomos Hepáticos/metabolismo , Naftalenos/metabolismo , Alquilação/fisiologia , Animais , Cromatografia Gasosa/métodos , Cromatografia Líquida de Alta Pressão/métodos , Humanos , Oxirredução , Hidrocarbonetos Policíclicos Aromáticos/metabolismo , Ratos , Espectrometria de Massas em Tandem/métodos
5.
Chemosphere ; 243: 125389, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-31765893

RESUMO

The present study is aimed to isolate and identify polycyclic aromatic hydrocarbons (PAHs) degrading bacteria from brackish water and to assess the biodegradation efficiency against low and high molecular weight PAHs. Among 15 isolates, the isolate designated as RM effectively degraded 100 mg/L of phenanthrene (Phe) (67.0%), pyrene (Pyr) (63.0%), naphthalene (NaP) (60.0%), and benzo [a]pyrene (BaP) (58.0%) after 7 days of incubation. Carbon sources, pH, and salinity of the culture medium were optimized to enhance the growth and PAHs biodegradation of the isolate RM. Sucrose was found to be an excellent carbon source to enhance PAHs biodegradation (Phe, 75.0; Pyr, 68.5; NaP, 62.5; and BaP, 59.5%). Furthermore, the isolate showed enhanced degradation at pH 7.0 and 4% salinity. The isolate RM was identified as Halomonas sp. based on partial 16S rDNA gene sequence analysis. The results indicated that the isolate RM (i.e., Halomonas sp.) has the potential to be used in remediation of oil spills in the marine ecosystem.


Assuntos
Bactérias/metabolismo , Biodegradação Ambiental , Halomonas/isolamento & purificação , Hidrocarbonetos Policíclicos Aromáticos/metabolismo , Águas Salinas , Benzo(a)pireno/metabolismo , Ecossistema , Halomonas/metabolismo , Peso Molecular , Naftalenos/metabolismo , Pirenos/metabolismo
6.
Ecotoxicol Environ Saf ; 189: 109994, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31787385

RESUMO

The utilization of thermophilic hydrocarbon-degrading microorganisms is a suitable strategy for improving biodegradation of petroleum hydrocarbons and PAHs, as well as enhancing oil recovery from high-temperature reservoirs. In this study, the thermophilic strain Aeribacillus pallidus SL-1 was evaluated for the biodegradation of crude oil and PAHs at 60 °C. Strain SL-1 was found to preferentially degrade short-chain n-alkanes (

Assuntos
Bacillaceae/metabolismo , Biodegradação Ambiental , Hidrocarbonetos Policíclicos Aromáticos/metabolismo , Alcanos/metabolismo , Hidrocarbonetos/análise , Hidrocarbonetos/química , Hidrocarbonetos/metabolismo , Naftalenos/metabolismo , Petróleo/análise , Petróleo/metabolismo , Fenantrenos/metabolismo , Hidrocarbonetos Policíclicos Aromáticos/análise , Hidrocarbonetos Policíclicos Aromáticos/química , Pirenos/metabolismo , Temperatura
7.
Chemosphere ; 243: 125427, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-31778917

RESUMO

The quantization parameters, infrared and Raman spectra of 75 polychlorinated naphthalenes (PCNs) and 42 environmentally friendly CN-56 (CN-56: No. 56 PCN molecule; 1, 2, 3, 7, 8-PentaCN) molecules that are easier to degrade were first calculated via the density functional theory (DFT) method, and the structural characteristics of the molecules were analysed to obtain the substituent characteristics. The principal component analysis method was used to systematically analyse and summarize the effects of macroscopic substituent characteristics, microscopic quantitative parameters and spectral information on the biodegradability of PCNs and 42 environmentally friendly CN-56 molecules, and then the quantitative structure-activity relationship (QSAR), molecular docking and molecular dynamics simulation methods were used to further investigate the biodegradation mechanism from the perspective of molecules and protein receptors. The results showed that PCNs and new PCNs extracted 5 and 6 principal components from 21 kinds of original parameter indicators, respectively, which can effectively explain the original variable information. Besides that, electrostatic activity is the primary factor affecting the degradation of PCNs; reducing the para-substitution logarithm or increasing the total number of substituents and introducing electrostatic groups in the ortho or meta position of PCN molecules can design new PCN derivatives with higher degradability; enhancing the irradiation of Raman light or reducing the irradiation of infrared light properly can increase the biodegradation rate of PCN molecules.


Assuntos
Biodegradação Ambiental , Simulação de Acoplamento Molecular , Simulação de Dinâmica Molecular , Naftalenos/metabolismo , Análise de Componente Principal , Relação Quantitativa Estrutura-Atividade , Naftalenos/análise , Espectrofotometria Infravermelho , Análise Espectral Raman
8.
World J Microbiol Biotechnol ; 35(12): 186, 2019 Nov 14.
Artigo em Inglês | MEDLINE | ID: mdl-31728655

RESUMO

The pollution of aquatic environments by drugs is a problem for which scarce research has been conducted in regards of their removal. Amycolatopsis sp. Poz 14 presents the ability to biotransformation naphthalene at high efficiency, therefore, in this work this bacterium was proposed as an assimilator of naproxen and carbamazepine. Growth curves at different concentrations of naproxen and carbamazepine showed that Amycolatopsis sp. Poz 14 is able to utilize these drugs at a concentration of 50 mg L-1 as a source of carbon and energy. At higher concentrations, the bacterial growth was inhibited. The transformation kinetics of naproxen showed the total elimination of the compound in 18 days, but carbamazepine was only eliminated in 19.9%. The supplementation with cometabolites such as yeast extract and naphthalene (structure similar to naproxen) at 50 mg L-1, showed that the yeast extract shortened the naproxen elimination to 6 days and reached a higher global consumption rate compared to the naphthalene cometabolite. The biotransformation of carbamazepine was not improved by the addition of cometabolites. The partial sequencing of the genome of Amycolatopsis sp. Poz 14 detected genes encoding putative enzymes for the degradation of cyclic aromatic compounds and the activities of aromatic monooxygenase, catechol 1,2-dioxygenase and gentisate 1,2-dioxygenase exhibited their involving in the naproxen biodegradation. The HPLC-MS analysis detected the 5-methoxysalicylic acid at the end of the biotransformation kinetics. This work demonstrates that Amycolatopsis sp. Poz 14 utilizes naproxen and transforms it to 5-methoxysalicylic acid which is the initial compound for the catechol and gentisic acid metabolic pathway.


Assuntos
Actinomycetales/enzimologia , Actinomycetales/metabolismo , Redes e Vias Metabólicas , Naproxeno/metabolismo , Actinomycetales/efeitos dos fármacos , Actinomycetales/crescimento & desenvolvimento , Biodegradação Ambiental , Biotransformação , Carbamazepina/metabolismo , Carbamazepina/farmacologia , Carbono/metabolismo , Catecol 1,2-Dioxigenase , Catecóis , Dioxigenases , Poluição Ambiental , Gentisatos , Éteres de Hidroxibenzoatos/metabolismo , Cinética , Oxigenases de Função Mista , Naftalenos/metabolismo , Naproxeno/farmacologia , Salicilatos/metabolismo
9.
Int J Mol Sci ; 20(14)2019 Jul 11.
Artigo em Inglês | MEDLINE | ID: mdl-31373299

RESUMO

Polycyclic aromatic hydrocarbons (PAHs), such as naphthalene, are potential health risks due to their carcinogenic and mutagenic effects. Bacteria from the genus Rhodococcus are able to metabolise a wide variety of pollutants such as alkanes, aromatic compounds and halogenated hydrocarbons. A naphthalene dioxygenase from Rhodococcus sp. strain NCIMB12038 has been characterised for the first time, using electron paramagnetic resonance (EPR) spectroscopy and UV-Vis spectrophotometry. In the native state, the EPR spectrum of naphthalene 1,2-dioxygenase (NDO) is formed of the mononuclear high spin Fe(III) state contribution and the oxidised Rieske cluster is not visible as EPR-silent. In the presence of the reducing agent dithionite a signal derived from the reduction of the [2Fe-2S] unit is visible. The oxidation of the reduced NDO in the presence of O2-saturated naphthalene increased the intensity of the mononuclear contribution. A study of the "peroxide shunt", an alternative mechanism for the oxidation of substrate in the presence of H2O2, showed catalysis via the oxidation of mononuclear centre while the Rieske-type cluster is not involved in the process. Therefore, the ability of these enzymes to degrade recalcitrant aromatic compounds makes them suitable for bioremediative applications and synthetic purposes.


Assuntos
Biodegradação Ambiental , Dioxigenases/metabolismo , Poluentes Ambientais/metabolismo , Complexos Multienzimáticos/metabolismo , Naftalenos/metabolismo , Rhodococcus/enzimologia , Rhodococcus/metabolismo , Ditionita/química , Espectroscopia de Ressonância de Spin Eletrônica , Peróxido de Hidrogênio/química , Oxirredução
10.
J Agric Food Chem ; 67(49): 13487-13495, 2019 Dec 11.
Artigo em Inglês | MEDLINE | ID: mdl-31347368

RESUMO

The occurrence in Riesling wine of the potent odorant 1,1,6-trimethyl-1,2-dihydronaphthalene (TDN) is dependent upon vineyard and winemaking conditions, and TDN can have a prominent impact on the attributes of a wine after years in a bottle. As such, immediately assessing the impact of vineyard or winery treatments on future TDN formation requires forced creation of the aroma compound under non-wine-like conditions from other precursors. Here, we use a Box-Behnken approach and known TDN end points in commercial wines to optimize the conditions (pH, temperature, and time) of a "total TDN" hydrolytic assay for Riesling wine, which was intended to not interfere with yeast-derived formation pathways. The new assay (75 °C, pH 1.7, and 60 min) was used to determine the role of industry-relevant commercial yeasts as well as novel hybrid yeast strains on total TDN concentrations in young Riesling wines. While significant differences were observed between some yeasts, the impact of defoliation as a viticultural intervention outweighed yeast effects, suggesting that elevated TDN concentrations in wine are likely due to grape growing conditions and cannot be readily reduced or compensated for in the winery.


Assuntos
Naftalenos/análise , Naftalenos/metabolismo , Saccharomyces cerevisiae/metabolismo , Vinho/análise , Fermentação , Frutas/metabolismo , Frutas/microbiologia , Odorantes/análise , Vitis/metabolismo , Vitis/microbiologia
11.
Appl Microbiol Biotechnol ; 103(17): 7203-7215, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31256229

RESUMO

Since polycyclic aromatic hydrocarbons (PAHs) are mutagenic, teratogenic, and carcinogenic, they are of considerable environmental concern. A biotechnological approach to remove such compounds from polluted ecosystems could be based on the use of white-rot fungi (WRF). The potential of well-adapted indigenous Ganoderma strains to degrade PAHs remains underexplored. Seven native Ganoderma sp. strains with capacity to produce high levels of laccase enzymes and to degrade synthetic dyes were investigated for their degradation potential of PAHs. The crude enzymatic extracts produced by Ganoderma strains differentially degraded the PAHs assayed (naphthalene 34-73%, phenanthrene 9-67%, fluorene 11-64%). Ganoderma sp. UH-M was the most promising strain for the degradation of PAHs without the addition of redox mediators. The PAH oxidation performed by the extracellular enzymes produced more polar and soluble metabolites such as benzoic acid, catechol, phthalic and protocatechuic acids, allowing us to propose degradation pathways of these PAHs. This is the first study in which breakdown intermediates and degradation pathways of PAHs by a native strain of Ganoderma genus were determined. The treatment of PAHs with the biomass of this fungal strain enhanced the degradation of the three PAHs. The laccase enzymes played an important role in the degradation of these compounds; however, the role of peroxidases cannot be excluded. Ganoderma sp. UH-M is a promising candidate for the bioremediation of ecosystems polluted with PAHs.


Assuntos
Poluentes Ambientais/metabolismo , Ganoderma/metabolismo , Hidrocarbonetos Policíclicos Aromáticos/metabolismo , Biodegradação Ambiental , Fluorenos/metabolismo , Ganoderma/enzimologia , Lacase/metabolismo , Naftalenos/metabolismo , Oxirredução , Peroxidases/metabolismo , Fenantrenos/metabolismo
12.
J Pharmacol Sci ; 140(2): 193-196, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-31235271

RESUMO

We tested whether NNC 55-0396 (NNC), a T-type calcium channel (T-channel) blocker, reduces the brain injury caused by middle cerebral artery occlusion and reperfusion (MCAO/R) in mice. NNC, administered i.c.v. before the occlusion, greatly reduced the MCAO/R-induced brain infarct and neurological dysfunctions, although it, given toward the end of occlusion, was less effective. Systemic administration of NNC before the occlusion also attenuated the infarct and neurological dysfunctions. Our data imply that blood-brain-barrier-permeable T-channel blockers such as NNC are capable of reducing MCAO/R-induced brain damage, and that T-channels are involved in neuronal damage induced by ischemia rather than reperfusion.


Assuntos
Benzimidazóis/administração & dosagem , Lesões Encefálicas/etiologia , Lesões Encefálicas/prevenção & controle , Bloqueadores dos Canais de Cálcio/administração & dosagem , Ciclopropanos/administração & dosagem , Infarto da Artéria Cerebral Média/complicações , Naftalenos/administração & dosagem , Traumatismo por Reperfusão/complicações , Animais , Benzimidazóis/metabolismo , Barreira Hematoencefálica/metabolismo , Bloqueadores dos Canais de Cálcio/metabolismo , Canais de Cálcio Tipo T/fisiologia , Ciclopropanos/metabolismo , Infusões Intraventriculares , Infusões Parenterais , Masculino , Camundongos Endogâmicos , Naftalenos/metabolismo , Fatores de Tempo
13.
J Microbiol Biotechnol ; 29(9): 1412-1423, 2019 Sep 28.
Artigo em Inglês | MEDLINE | ID: mdl-31216791

RESUMO

The filamentous fungus Aspergillus tubingensis that belongs to the black Aspergillus section has the capacity to produce high-value metabolites, for instance, Naphtho-Gamma-Pyrones (NGPs). For these fungal secondary metabolites, numerous biological properties of industrial interest have been demonstrated, such as antimicrobial, antioxidant and anti-cancer capacities. It has been observed that these secondary metabolites production is linked with the fungal sporulation. The aim of this research was to apply environmental stresses to trigger the production of NGPs in liquid cultures with CYB (Czapek Dox Broth): osmotic and oxidative stresses. In addition, numerous parameters were tested during the experiments, such as pH value, incubation time, container geometry, and static and agitation conditions. Results demonstrate that the produced amount of NGPs can be enhanced by decreasing the water activity (aw) or by adding an oxidative stress factor. In conclusion, this study can contribute to our knowledge regarding A. tubingensis to present an effective method to increase NGPs's production, which may support the development of current industrial processes.


Assuntos
Aspergillus/metabolismo , Naftalenos/metabolismo , Pironas/metabolismo , Aspergillus/crescimento & desenvolvimento , Biomassa , Meios de Cultura , Concentração de Íons de Hidrogênio , Cinética , Estrutura Molecular , Naftalenos/química , Pressão Osmótica , Estresse Oxidativo , Pironas/química
14.
Int. microbiol ; 22(2): 217-225, jun. 2019. ilus, graf
Artigo em Inglês | IBECS | ID: ibc-184828

RESUMO

Biodegradation of polycyclic aromatic hydrocarbons (PAHs) using Pleurotus ostreatus was investigated in the current study along with the expression levels of laccase genes involved in biodegradation under variable conditions. Biodegradation of PAHs (naphthalene, anthracene, and 1,10-phenanthroline) was detected spectrophotometrically. Recorded data revealed that biodegradation of the tested PAHs was time dependent. Elevated level of naphthalene biodegradation (86.47%) was observed compared to anthracene (27.87%) and 1,10-phenanthroline (24.51%) within 3 days post incubation. Naphthalene was completely degraded within 5 days. Further incubation enhanced the biodegradation of both anthracene and 1,10-phenanthroline until reaches 93.69% and 92.00% biodegradation of the initial concentration within an incubation period of 11 and 14 days, respectively. Naphthalene was selected as a PAH model. HPLC and thin layer chromatography of naphthalene biodegradation products at time intervals proposed that naphthalene was first degraded to alpha- and ß-naphthol which was further metabolized to salicylic and benzoic acid. The metabolic pathway of naphthalene degradation by this fungus was elucidated based on the detected metabolites. The expression profile of six laccase isomers was evaluated using real-time PCR. The transcriptome of the fungal laccase isomers recorded higher levels of transcription under optimized fermentation conditions especially in presence of both naphthalene and Tween 80. The accumulation of such useful metabolites from the biodegradation of PAH pollutants recommended white rot fungus as a potential candidate for production of platform chemicals from PAH wastes


No disponible


Assuntos
Perfilação da Expressão Gênica , Lacase/biossíntese , Naftalenos/metabolismo , Pleurotus/enzimologia , Pleurotus/metabolismo , Biotransformação , Lacase/genética , Redes e Vias Metabólicas/genética , Hidrocarbonetos Policíclicos Aromáticos/metabolismo , Espectrofotometria , Fatores de Tempo
15.
J Agric Food Chem ; 67(24): 6819-6827, 2019 Jun 19.
Artigo em Inglês | MEDLINE | ID: mdl-31135148

RESUMO

Napropamide [ N, N-diethyl-2-(1-naphthalenyloxy)propenamide, NAP] is a highly efficient and broad-spectrum amide herbicide. Little is known about the bacterial catabolism of its different enantiomers. Here, we report the isolation of two NAP-degrading strains of Sphingobium sp., A1 and B2, and the different catabolic pathways of different enantiomers in these two strains. Strain A1 dioxygenated NAP at different positions of the naphthalene ring of different enantiomers, leading to the complete degradation of R-NAP while producing a dead-end product from S-NAP. Strain B2 cleaved the amido bonds of both enantiomers, but only the product from S-NAP could be further transformed to form α-naphthol and mineralize in strain B2. The degradation rates of R-NAP and S-NAP in the combination degradation by strains A1 and B2 were 24.8 and 7.5 times that in the single-strain degradation by strain B2 or A1, respectively, showing enhanced synergistic catabolism between strains A1 and B2. This study provides new insights into the enantioselective catabolic network of the chiral herbicide NAP in microorganisms.


Assuntos
Herbicidas/química , Herbicidas/metabolismo , Naftalenos/química , Naftalenos/metabolismo , Sphingomonadaceae/metabolismo , Biodegradação Ambiental , Sphingomonadaceae/química , Estereoisomerismo
16.
Microbiologyopen ; 8(9): e00855, 2019 09.
Artigo em Inglês | MEDLINE | ID: mdl-31119875

RESUMO

In this study, we compared the expression of CYP153, sodA, sodC, and recA genes and ROS generation in hydrocarbon-degrading Rhodococcus erythropolis in the presence of cyclohexane, naphthalene, and diesel fuel. The expression of cytochrome P450, sodA (encoding Fe/Mn superoxide dismutase), recA, and superoxide anion radical generation rate increased after the addition of all studied hydrocarbons. The peak of CYP153, sodA, and recA gene expression was registered in the presence of naphthalene. The same substrate upregulated the Cu/Zn superoxide dismutase gene, sodC. Cyclohexane generated the highest level of superoxide anion radical production. Hydrogen peroxide accumulated in the medium enriched with diesel fuel. Taken together, hydrocarbon biotransformation leads to oxidative stress and upregulation of antioxidant enzymes and CYP153 genes, and increases DNA reparation levels in R. erythropolis cells.


Assuntos
Cicloexanos/toxicidade , Gasolina/toxicidade , Regulação Bacteriana da Expressão Gênica/efeitos dos fármacos , Naftalenos/toxicidade , Estresse Oxidativo , Rhodococcus/efeitos dos fármacos , Rhodococcus/metabolismo , Proteínas de Bactérias/biossíntese , Proteínas de Bactérias/genética , Biotransformação , Cicloexanos/metabolismo , Perfilação da Expressão Gênica , Naftalenos/metabolismo , Espécies Reativas de Oxigênio/análise
17.
AAPS J ; 21(4): 63, 2019 05 15.
Artigo em Inglês | MEDLINE | ID: mdl-31093790

RESUMO

The number of new psychoactive substances (NPS) emerging on the illicit drug market has increased over the last decade. Halogenation of existing illicit drugs is a particular trend, with the purpose of both circumventing the law and altering the toxicodynamic and toxicokinetic profiles of the compounds. This study investigates the in vitro impact of JWH-122 ω-halogenation (fluoro, chloro, bromo and iodo) on the metabolism, apparent intrinsic hepatic clearance and analytical targets for detecting drug consumption. Metabolite profiling was conducted with pooled human liver microsomes, suspended rat hepatocytes and pooled human hepatocytes. The in vitro half-life was also determined in pooled human hepatocytes. All samples were analysed by liquid chromatography/high-resolution mass spectrometry. All compounds, except for JWH-122, showed high formation rates of phase I metabolites, predominantly ω-COOH and methylnaphthyl hydroxylation metabolites. Phase II metabolites were ω-O-glucuronides, methylnaphthyl O-glucuronides and ω-glutathione conjugates. The relative ion intensity of the glutathione conjugates increased with the ω-halogen size, with I-JWH-122 having the highest intensity. Stability studies gave a low half-life and a high intrinsic hepatic clearance for JWH-122 (1305 mL/min/kg) and MAM-2201 (1408 mL/min/kg). Cl-, Br- and I-JWH-122 showed increasing half-life with increasing ω-halogen size, with intrinsic clearance values of 235-502 mL/min/kg. The recommended analytical targets for consumption of JWH-122 or ω-halogenated JWH-122 analogues are the ω-COOH metabolites for unspecific profiling and the methylnaphthyl hydroxylated metabolites to distinguish the compounds. Furthermore, ω-halogenation with larger halogens appears to increase the intrinsic hepatic stability, thereby prolonging exposure and possibly the duration of action.


Assuntos
Agonistas de Receptores de Canabinoides/metabolismo , Hepatócitos/metabolismo , Indóis/metabolismo , Microssomos Hepáticos/metabolismo , Naftalenos/metabolismo , Animais , Halogenação , Humanos , Técnicas In Vitro , Indóis/química , Desentoxicação Metabólica Fase I , Desintoxicação Metabólica Fase II , Redes e Vias Metabólicas , Naftalenos/química , Ratos , Toxicocinética
18.
Metabolomics ; 15(5): 80, 2019 05 13.
Artigo em Inglês | MEDLINE | ID: mdl-31087208

RESUMO

INTRODUCTION: The demand to develop efficient and reliable analytical methods for the quality control of nutraceuticals is on the rise, together with an increase in the legal requirements for safe and consistent levels of its active principles. OBJECTIVE: To establish a reliable model for the quality control of widely used Senna preparations used as laxatives and assess its phyto-equivalency. METHODS: A comparative metabolomics approach via NMR and MS analyses was employed for the comprehensive measurement of metabolites and analyzed using chemometrics. RESULTS: Under optimized conditions, 30 metabolites were simultaneously identified and quantified including anthraquinones, bianthrones, acetophenones, flavonoid conjugates, naphthalenes, phenolics, and fatty acids. Principal component analysis (PCA) was used to define relative metabolite differences among Senna preparations. Furthermore, quantitative 1H NMR (qHNMR) was employed to assess absolute metabolites levels in preparations. Results revealed that 6-hydroxy musizin or tinnevellin were correlated with active metabolites levels, suggesting the use of either of these naphthalene glycosides as markers for official Senna drugs authentication. CONCLUSION: This study provides the first comparative metabolomics approach utilizing NMR and UPLC-MS to reveal for secondary metabolite compositional differences in Senna preparations that could readily be applied as a reliable quality control model for its analysis.


Assuntos
Metabolômica , Senosídeos/metabolismo , Acetofenonas/metabolismo , Antracenos/metabolismo , Antraquinonas/metabolismo , Flavonoides/metabolismo , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular , Naftalenos/metabolismo , Fenóis/metabolismo , Análise de Componente Principal , Controle de Qualidade , Senosídeos/química
19.
Microb Biotechnol ; 12(4): 662-676, 2019 07.
Artigo em Inglês | MEDLINE | ID: mdl-31087504

RESUMO

Polycyclic aromatic compounds (PAHs) are toxic compounds that are released in the environment as a consequence of industrial activities. The restoration of PAH-polluted sites considers the use of bacteria capable of degrading aromatic compounds to carbon dioxide and water. Here we characterize a new Xanthobacteraceae strain, Starkeya sp. strain N1B, previously isolated during enrichment under microaerophilic conditions, which is capable of using naphthalene crystals as the sole carbon source. The strain produced a structured biofilm when grown on naphthalene crystals, which had the shape of a half-sphere organized over the crystal. Scanning electron microscopy (SEM) and GC-MS analysis indicated that the biofilm was essentially made of cellulose, composed of several micron-long nanofibrils of 60 nm diameter. A cellulosic biofilm was also formed when the cells grew with glucose as the carbon source. Fourier transformed infrared spectroscopy (FTIR) confirmed that the polymer was type I cellulose in both cases, although the crystallinity of the material greatly depended on the carbon source used for growth. Using genome mining and mutant analysis, we identified the genetic complements required for the transformation of naphthalene into cellulose, which seemed to have been successively acquired through horizontal gene transfer. The capacity to develop the biofilm around the crystal was found to be dispensable for growth when naphthalene was used as the carbon source, suggesting that the function of this structure is more intricate than initially thought. This is the first example of the use of toxic aromatic hydrocarbons as the carbon source for bacterial cellulose production. Application of this capacity would allow the remediation of a PAH into such a value-added polymer with multiple biotechnological usages.


Assuntos
Alphaproteobacteria/metabolismo , Celulose/metabolismo , Nanoestruturas , Naftalenos/metabolismo , Alphaproteobacteria/crescimento & desenvolvimento , Carbono/metabolismo , Cromatografia Gasosa-Espectrometria de Massas , Microbiologia Industrial/métodos , Microscopia Eletrônica de Varredura
20.
Appl Microbiol Biotechnol ; 103(14): 5593-5605, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-31098686

RESUMO

The goal of the study was to compare the production of secondary metabolites by Aspergillus terreus ATCC 20542 under the conditions of submerged mono- and co-cultivation. The suggested experimental scheme encompassed a diverse set of co-culture initiation strategies differing mostly with respect to the development stage of tested fungal strains at the moment of their confrontation. Three species of filamentous fungi exhibiting distinct patterns of morphological evolution under submerged conditions, namely Penicillium rubens, Chaetomium globosum, and Mucor racemosus, were selected as the co-cultivation partners of A. terreus. The choice of the co-cultivated species and the approach of co-culture triggering noticeably influenced the levels of lovastatin (mevinolinic acid), (+)-geodin, asterric acid, and butyrolactone I in the broth. Even though the evaluated co-cultures did not lead to the increased titers of lovastatin relative to standard monocultures, the biosynthesis of the remaining three metabolites was either enhanced or inhibited depending on the experimental variant. The production of butyrolactone I turned out to be particularly affected by the presence of C. globosum. Interestingly, in the A. terreus/C. globosum co-cultures, the decrease of lovastatin concentration was recorded. According to the most probable scenario, lovastatin was in this case converted to monacolin J acid, a polyketide molecule that may be applied as a substrate for the synthesis of statin drugs. The study revealed that the spores of two distinct fungal species, namely A. terreus and C. globosum, co-agglomerate under submerged conditions to form pellets. Finally, the biosynthetic performance of co-cultures involving four fungal species was evaluated.


Assuntos
Aspergillus/metabolismo , Reatores Biológicos , Lovastatina/biossíntese , Metabolismo Secundário , Biomassa , Técnicas de Cocultura , Cinética , Técnicas Microbiológicas , Naftalenos/metabolismo , Penicillium/metabolismo , Esporos/fisiologia
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