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1.
Ecotoxicol Environ Saf ; 208: 111621, 2021 Jan 15.
Artigo em Inglês | MEDLINE | ID: mdl-33396141

RESUMO

The study explored the polycyclic aromatic hydrocarbon tolerance of indigenous biosurfactant producing microorganisms. Three bacterial species were isolated from crude oil contaminated sites of Haldia, West Bengal. The three species were screened for biosurfactant production and identified by 16S rRNA sequencing as Brevundimonas sp. IITISM 11, Pseudomonas sp. IITISM 19 and Pseudomonas sp. IITISM 24. The strains showed emulsification activities of 51%, 57% and 63%, respectively. The purified biosurfactants were characterised using FT-IR, GC-MS and NMR spectroscopy and found to have structural similarities to glycolipopeptides, cyclic lipopeptides and glycolipids. The biosurfactants produced were found to be stable under a wide range of temperature (0-100 °C), pH (4-12) and salinity (up to 20% NaCl). Moreover, the strains displayed tolerance to high concentrations (275 mg/L) of anthracene and fluorene and showed a good amount of cell surface hydrophobicity with different hydrocarbons. The study reports the production and characterisation of biosurfactant by Brevundimonas sp. for the first time. Additionally, the kinetic parameters of the bacterial strains grown on up to 300 mg/L concentration of anthracene and fluorene, ranged between 0.0131 and 0.0156 µmax (h-1), while the Ks(mg/L) ranged between 59.28 and 102.66 for Monod's Model. For Haldane-Andrew's model, µmax (h-1) varied between 0.0168 and 0.0198. The inhibition constant was highest for Pseudomonas sp. IITISM 19 on anthracene and Brevundimonas sp. IITISM 11 on fluorene. The findings of the study suggest that indigenous biosurfactant producing strains have tolerance to high PAH concentrations and can be exploited for bioremediation purposes.


Assuntos
Antracenos/metabolismo , Biodegradação Ambiental , Fluorenos/metabolismo , Tensoativos/metabolismo , Antracenos/química , Bactérias/metabolismo , Fluorenos/química , Glicolipídeos , Hidrocarbonetos/metabolismo , Cinética , Petróleo/metabolismo , Hidrocarbonetos Policíclicos Aromáticos/metabolismo , Pseudomonas/metabolismo , RNA Ribossômico 16S/metabolismo , Espectroscopia de Infravermelho com Transformada de Fourier , Tensoativos/química
2.
Ecotoxicol Environ Saf ; 208: 111619, 2021 Jan 15.
Artigo em Inglês | MEDLINE | ID: mdl-33396139

RESUMO

Fluorene, a low molecular weight polycyclic aromatic hydrocarbon (PAH), is of immense environmental interest because of its carcinogenicity, teratogenicity, mutagenicity, toxicity and persistence to microbial degradation. Existentially, there is paucity of information on PAH degradation by fungi isolated from marine environment. Therefore, this study investigated fluorene degradation efficiency of marine derived filamentous fungus, Mucor irregularis strain bpo1 (GenBank Accession Number: MK373020). Response Surface Methodology (RSM) using Box-Behnken Design (BBD) was successfully deployed in the optimization of process parameters (pH-7, temperature-32.5 °C, substrate concentration-100 mg L-1 and dry weight-2 g) resulting in 81.50% fluorene degradation on 5th day. The design and regression model were found to be statistically significant, adequate and appropriate with p < 0.0001, F value= 202.39, and predicted coefficient of determination (R2 =0.9991). Optimization of the vital constituents of the mineral salt medium (MSM) used for the study using RSM-Central Composite Design (CCD) resulted in 79.80% fluorene degradation rate. Enhanced fluorene degradation efficiency (82.50%) was recorded when the optimized process variables were subjected to growth-linked validation experiments. The enzyme activities revealed 87%, 59% and 31% induction of laccase, manganese peroxidase and lignin peroxidase respectively. Four metabolites; 9H-fluoren-9-one, benzene-1,2-dicarboxylic acid, 2-hydroxybenzoic acid and phenol obtained after the experiment were characterized and confirmed with GC-MS analysis. The findings revealed the promising potentials of M. irregularis in PAH degradation and by extension green remediation technology.


Assuntos
Fluorenos/metabolismo , Modelos Teóricos , Mucor/metabolismo , Biodegradação Ambiental , Biomassa , Fluorenos/análise , Lacase/metabolismo , Mucor/crescimento & desenvolvimento , Mucor/isolamento & purificação , Peroxidases/metabolismo , Água do Mar/microbiologia
3.
Chemosphere ; 260: 127622, 2020 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-32673875

RESUMO

In this study, fluorene (FL), FL-1-carboxylic acid (FC-1), and FL-9-carboxylic acid (FC-9) were investigated to understand their acute toxicity by measuring inhibitory effects on hatching rates and developmental processes of zebrafish embryos (Danio rerio). For exposure concentrations up to 3000 µg/L, FC-1 alone showed acute toxicity at 1458 µg/L for LC50 value. FC-1 caused yolk sac and spinal deformities, and pericardial edema. Molecular studies were undertaken to understand FC-1 toxicity examining 61 genes after exposure to 5 µM (equivalent to LC20 value of FC-1) in embryos. In the FC-1-treated embryos, the expression of the cyp7a1 gene, involved in bile acid biosynthesis, was dramatically decreased, while the expression of the Il-1ß gene involved in inflammation was remarkably increased. In addition to these findings, in FC-1-treated embryos, the expression of nppa gene related to the differentiation of the myocardium was 3-fold increased. On the other hand, cyp1a, cyp3a, ugt1a1, abcc4, mdr1, and sult1st1 responsible for detoxification of xenobiotics were upregulated in FC-9-treated embryos. Taken together, carboxylation on carbon 1 of FL increased acute toxicity in zebrafish embryos, and its toxicity might be related to morphological changes with modification of normal biological functions and lowered defense ability.


Assuntos
Fluorenos/toxicidade , Poluentes Químicos da Água/toxicidade , Animais , Ácidos Carboxílicos/metabolismo , Embrião não Mamífero/efeitos dos fármacos , Fluorenos/metabolismo , Peixe-Zebra/metabolismo
4.
Aquat Toxicol ; 226: 105565, 2020 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-32682195

RESUMO

Pyrene (PYR) and fluorene (FLU) are among the sixteen priority Polycyclic Aromatic Hydrocarbons (PAH) of the United States Environmental Protection Agency and are both frequently detected in contaminated sites. Due to the importance of bivalve mollusks in biomonitoring programs and the scarce information on the biotransformation system in these organisms, the aim of this study was to investigate the effect of PYR and FLU at the transcriptional level and the enzymatic activities of some biotransformation systems in the Pacific oyster Crassostrea gigas, and to evaluate the histological effects in their soft tissues. Oysters C. gigas were exposed for 24 h and 96 h to PYR (0.25 and 0.5 µM) and FLU (0.6 and 1.2 µM). After exposure, transcript levels of cytochrome P450 coding genes (CYP1-like, CYP2-like, CYP2AU2, CYP356A1, CYP17α-like), glutathione S tranferase genes (omega GSTO-like and microsomal, MGST-like) and sulfotransferase gene (SULT-like), and the activity of ethoxyresorufin O-deethylase (EROD), Glutathione S-transferase (GST) and microssomal GST (MGST) were evaluated in gills. Histologic changes were also evaluated after the exposure period. PYR and FLU bioconcentrated in oyster soft tissues. The half-life time of PYR in water was lower than fluorene, which is in accordance to the higher lipophilicity and bioconcentration of the former. EROD activity was below the limit of detection in all oysters exposed for 96 h to PYR and FLU. The reproductive stage of the oysters exposed to PYR was post-spawn. Exposure to PYR caused tubular atrophy in digestive diverticula, but had no effect on transcript levels of biotransformation genes. However, the organisms exposed for 96 h to PYR 0.5 µM showed higher MGST activity, suggesting a protective role against oxidative stress in gills of oysters under higher levels of PYR in the tissues. Increased number of mucous cells in mantle were observed in oysters exposed to the higher FLU concentration, suggesting a defense mechanisms. Oysters exposed for 24 h to FLU 1.2 µM were in the ripe stage of gonadal development and showed higher transcript levels of CYP2AU2, GSTO-like and SULT-like genes, suggesting a role in the FLU biotransformation. In addition, after 96 h of exposure to FLU there was a significant increase of mucous cells in the mantle of oysters but no effect was observed on the EROD, total GST and MGST activities. These results suggest that PAH have different effects on transcript levels of biotransformation genes and enzyme activities, however these differences could also be related to the reproductive stage.


Assuntos
Crassostrea/efeitos dos fármacos , Fluorenos/toxicidade , Pirenos/toxicidade , Poluentes Químicos da Água/toxicidade , Animais , Biotransformação/efeitos dos fármacos , Crassostrea/metabolismo , Citocromo P-450 CYP1A1/metabolismo , Sistema Enzimático do Citocromo P-450/metabolismo , Fluorenos/metabolismo , Brânquias/efeitos dos fármacos , Brânquias/metabolismo , Glutationa Transferase/metabolismo , Estresse Oxidativo/efeitos dos fármacos , Pirenos/metabolismo , Poluentes Químicos da Água/metabolismo
5.
Occup Environ Med ; 77(7): 488-495, 2020 07.
Artigo em Inglês | MEDLINE | ID: mdl-32385190

RESUMO

OBJECTIVES: Exposure to high-molecular-weight polycyclic aromatic hydrocarbons (PAHs) may cause cancer in chimney sweeps and creosote-exposed workers, however, knowledge about exposure to low-molecular-weight PAHs in relation to cancer risk is limited. In this study, we aimed to investigate occupational exposure to the low-molecular-weight PAHs phenanthrene and fluorene in relation to different cancer biomarkers. METHODS: We recruited 151 chimney sweeps, 19 creosote-exposed workers and 152 unexposed workers (controls), all men. We measured monohydroxylated metabolites of phenanthrene and fluorene in urine using liquid chromatography coupled to tandem mass spectrometry. We measured, in peripheral blood, the cancer biomarkers telomere length and mitochondrial DNA copy number using quantitative PCR; and DNA methylation of F2RL3 and AHRR using pyrosequencing. RESULTS: Median PAH metabolite concentrations were higher among chimney sweeps (up to 3 times) and creosote-exposed workers (up to 353 times), compared with controls (p<0.001; adjusted for age and smoking). ∑OH-fluorene (sum of 2-hydroxyfluorene and 3-hydroxyfluorene) showed inverse associations with percentage DNA methylation of F2RL3 and AHRR in chimney sweeps (B (95% CI)=-2.7 (-3.9 to -1.5) for F2RL3_cg03636183, and -7.1 (-9.6 to -4.7) for AHRR_cg05575921: adjusted for age and smoking), but not in creosote-exposed workers. In addition, ∑OH-fluorene showed a 42% mediation effect on the inverse association between being a chimney sweep and DNA methylation of AHRR CpG2. CONCLUSIONS: Chimney sweeps and creosote-exposed workers were occupationally exposed to low-molecular-weight PAHs. Increasing fluorene exposure, among chimney sweeps, was associated with lower DNA methylation of F2RL3 and AHRR, markers for increased lung cancer risk. These findings warrant further investigation of fluorene exposure and toxicity.


Assuntos
Epigênese Genética , Fluorenos/efeitos adversos , Exposição Ocupacional/efeitos adversos , Hidrocarbonetos Policíclicos Aromáticos/efeitos adversos , Adulto , Idoso , Biomarcadores Tumorais/sangue , Creosoto/efeitos adversos , Estudos Transversais , Metilação de DNA , DNA Mitocondrial , Fluorenos/metabolismo , Fluorenos/urina , Humanos , Neoplasias Pulmonares/genética , Masculino , Pessoa de Meia-Idade , Exposição Ocupacional/análise , Fenantrenos/metabolismo , Fenantrenos/urina , Hidrocarbonetos Policíclicos Aromáticos/metabolismo , Homeostase do Telômero
6.
Chemosphere ; 250: 126332, 2020 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-32234626

RESUMO

Vermiremediation, which uses earthworms to remediate polluted soils, is an expanding technology in recently years. Surfactants have been widely used in bioremediation and other remediation technologies. However, the roles of surfactants in vermiremediation have been rarely studied. In this paper, an investigation of the effects of Tween-80 and rhamnolipid surfactant on the fluoranthene fraction distribution, vermiaccumulation, and removal during vermiremediation was conducted. Both Tween-80 and rhamnolipid improved the proportion of the desorbed fraction, bound residual fluoranthene, and correspondingly, proportions of the non-desorbed fraction were reduced. The vermiaccumulation of fluoranthene was significantly elevated by 35-64.1% and 34.5-44.2% by the Tween-80 and rhamnolipid, respectively. The vermiaccumulation of fluoranthene is positively correlated with the proportion of desorbed fraction of fluoranthene. Moreover, Tween-80 and rhamnolipid enhanced the removal of fluoranthene from contaminated soil during vermiremediation by 43.6-189.2% and 14.7-45.6%, respectively. The enhanced removal of fluoranthene was attributed to stimulated microbial degradation and increased vermiaccumulation resulting from the desorption ability of surfactants and earthworm activity. However, the total amount of fluoranthene that accumulated in earthworms was approximately 4-10% of the initial amount in the treatments, which suggested that microbial degradation rather than direct uptake contributed to the fluoranthene removal. The study suggests that the use of surfactants to enhance the efficiency of vermiremediation of polycyclic aromatic hydrocarbons (PAHs) contaminated soils might be feasible, and that surfactants-enhanced vermiremediation is an alternative strategies for treat PAHs contaminated soils.


Assuntos
Biodegradação Ambiental , Fluorenos/metabolismo , Oligoquetos/metabolismo , Poluentes do Solo/metabolismo , Tensoativos/química , Animais , Glicolipídeos , Hidrocarbonetos Policíclicos Aromáticos/análise , Polissorbatos , Solo , Microbiologia do Solo , Poluentes do Solo/análise , Tensoativos/metabolismo
7.
Chemosphere ; 251: 126318, 2020 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-32143076

RESUMO

Exposure of endocrine disrupting chemicals (EDCs) is closely related to induction of obesity, nonalcoholic fatty liver disease (NAFLD) and other lipid-metabolism diseases. Herein, we compared the effects of three EDCs exposure (triclosan, bisphenol A and fluorene-9-bisphenol) on lipid metabolism in zebrfish (Danio rerio). The differential lipid-metabolism disorders were analyzed in depth through RNA-Seq and qRT-PCR, as well as assessment of the relationship between lipid disorder and RNA methylation. Histopathological observation along with varying physiological and biochemical indexes all identified that triclosan and bisphenol A induced liver fat accumulation in acute and chronic exposure. RNA-Seq analysis showed that triclosan exposure disrupted multiple physiological processes including drug metabolism, sucrose metabolism, fat metabolism and bile secretion. The dysregulation of lipid-metabolism related genes indicated that liver steatosis in triclosan and BPA-exposed zebrafish resulted from increased fatty acid synthetase, and uptake and suppression of ß-oxidation. Besides, the dysregulation of pro-inflammatory genes and endoplasmic reticulum stress showed that triclosan and bisphenol A exposure not only induced occurrence of NAFLD, but also promoted progression of hepatic inflammation. However, no significant effect on lipid metabolism was observed in fluorene-9-bisphenol-exposed treatment although the larval phenotypic malformation was found compared to the control group. Moreover, EDCs exposure led to decreased global m6A level and abnormal expression of m6A modulators in larvae. Especially, the expression of demethylase FTO (fat mass and obesity-associated protein) was significantly increased in triclosan-exposure treatment. These findings are conductive for us to deeply understand the underlying molecular mechanisms regarding the obesity and NAFLD from EDCs exposure.


Assuntos
Compostos Benzidrílicos/toxicidade , Disruptores Endócrinos/toxicidade , Metabolismo dos Lipídeos/efeitos dos fármacos , Fenóis/toxicidade , Peixe-Zebra/fisiologia , Animais , Disruptores Endócrinos/metabolismo , Fluorenos/metabolismo , Larva/efeitos dos fármacos , Lipídeos , Hepatopatia Gordurosa não Alcoólica , Obesidade , RNA-Seq , Triclosan/metabolismo , Peixe-Zebra/metabolismo
8.
J Appl Microbiol ; 129(3): 554-564, 2020 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-32162457

RESUMO

AIMS: To increase the biodegradation of phenanthrene (PHE), pyrene (PYR) and fluoranthene (FLU) through mixed cultures of polycyclic aromatic hydrocarbon (PAH)-degrading bacteria, using modified repeated batch fermentation. METHODS AND RESULTS: Novel bacterial strains of Pseudomonas putida, Pseudomonas sp. and Ralstonia eutropha were cultivated and the biodegradation and conversion of mixed PAH to medium-chain-length polyhydroxyalkanoates (MCL-PHA) was determined. The highest degradation of PAH (100%) and PHA production (50·0%) was obtained in medium containing 30 mmol l-1 of mixed PAH after three cycles of repeated batch fermentation. The concentration of PAH in the reactor was increased from 30 to 90 mmol l-1 with repeated additions of PAH, and bacteria were able to produce PHA at 40% of cell dry mass. The MCL-PHA were identified by gas chromatography/mass spectroscopy, with the 3-hydroxydecanoate (3-HD) monomer higher than 75 mol.%. CONCLUSIONS: This study demonstrated that the biodegradation of PHE, PYR and FLU was enhanced by modified repeated batch fermentation using a mixed culture of bacteria. In addition, this fermentation strategy also increased the production of PHA, with an increase in monomer composition. SIGNIFICANCE AND IMPACT OF THE STUDY: This was the first study to describe the enhancement of the degradation of mixed solutions of PHE, PYR and FLU, and PHA production, using novel mixed bacterial cultures and modified repeated batch fermentation. The MCL-PHA formed had uniquely high 3-HD content.


Assuntos
Bactérias/metabolismo , Hidrocarbonetos Policíclicos Aromáticos/metabolismo , Poli-Hidroxialcanoatos/biossíntese , Bactérias/classificação , Técnicas de Cultura Celular por Lotes , Biodegradação Ambiental , Fermentação , Fluorenos/metabolismo , Fenantrenos/metabolismo , Hidrocarbonetos Policíclicos Aromáticos/química , Pirenos/metabolismo
9.
Amino Acids ; 52(2): 199-211, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31520286

RESUMO

The polyamine (PA) metabolism is involved in cell proliferation and differentiation. Increased cellular PA levels are observed in different types of cancers. Products of PA oxidation induce apoptosis in cancer cells. These observations open a perspective to exploit the enzymes of PA catabolism as a target for anticancer drug design. The substances capable to enhance PA oxidation may become potential anticancer agents. The goal of our study was to explore how the mode of ligand binding with a PA catabolic enzyme is associated with its stimulatory or inhibitory effect upon PA oxidation. Murine N1-acetylpolyamine oxidase (5LFO) crystalline structure was used for molecular docking with ligands of various chemical structures. In vitro experiments were carried out to evaluate the action of the tested compounds upon PA oxidative deamination in a cell-free test system from rat liver. Two amino acid residues (Aps211 and Tyr204) in the structure of 5LFO were found to be significant for binding with the tested compounds. 19 out of 51 screened compounds were activators and 17 were inhibitors of oxidative deamination of PA. Taken together, these results enabled to construct a recognition model with characteristic descriptors depicting activators and inhibitors. The general tendency indicated that a strong interaction with Asp211 or Tyr204 was rather typical for activators. The understanding of how the structure determines the binding mode of compounds with PA catabolic enzyme may help in explanation of their structure-activity relationship and thus promote structure-based drug design.


Assuntos
Poliaminas/química , Poliaminas/metabolismo , Compostos de Anilina/química , Compostos de Anilina/metabolismo , Animais , Apoptose , Fluorenos/química , Fluorenos/metabolismo , Ligantes , Fígado/enzimologia , Simulação de Acoplamento Molecular , Oxirredução , Oxirredutases atuantes sobre Doadores de Grupo CH-NH/química , Oxirredutases atuantes sobre Doadores de Grupo CH-NH/genética , Oxirredutases atuantes sobre Doadores de Grupo CH-NH/metabolismo , Piridinas/química , Piridinas/metabolismo , Ratos , Ratos Sprague-Dawley , Relação Estrutura-Atividade
10.
Environ Mol Mutagen ; 61(2): 235-245, 2020 02.
Artigo em Inglês | MEDLINE | ID: mdl-31490564

RESUMO

Carcinogenic aromatic amines such as 4-aminobiphenyl (ABP) and 2-aminofluorene (AF) require metabolic activation to form electrophilic intermediates that mutate DNA leading to carcinogenesis. Bioactivation of these carcinogens includes N-hydroxylation catalyzed by CYP1A2 followed by O-acetylation catalyzed by arylamine N-acetyltransferase 2 (NAT2). To better understand the role of NAT2 genetic polymorphism in ABP- and AF-induced mutagenesis and DNA damage, nucleotide excision repair-deficient (UV5) Chinese hamster ovary (CHO) cells were stably transfected with human CYP1A2 and either NAT2*4 (rapid acetylator) or NAT2*5B (slow acetylator) alleles. ABP and AF both caused significantly (P < 0.001) greater mutagenesis measured at the hypoxanthine phosphoribosyl transferase (hprt) locus in the UV5/CYP1A2/NAT2*4 acetylator cell line compared to the UV5, UV5/CYP1A2, and UV5/CYP1A2/NAT2*5B cell lines. ABP- and AF-induced hprt mutant cDNAs were sequenced and over 80% of the single-base substitutions were at G:C base pairs. DNA damage also was quantified by γH2AX in-cell western assays and by identification and quantification of the two predominant DNA adducts, N-(deoxyguanosin-8-yl)-4-aminobiphenyl (dG-C8-ABP) and N-(deoxyguanosin-8-yl)-2-aminofluorene (dG-C8-AF) by liquid chromatography-mass spectrometry. DNA damage and adduct levels were dose-dependent, correlated highly with levels of hprt mutants, and were significantly (P < 0.0001) greater in the UV5/CYP1A2/NAT2*4 rapid acetylator cell line following treatment with ABP or AF as compared to all other cell lines. Our findings provide further clarity on the importance of O-acetylation in CHO mutagenesis assays for aromatic amines. They provide evidence that NAT2 genetic polymorphism modifies aromatic amine-induced DNA damage and mutagenesis that should be considered in human risk assessments following aromatic amine exposures. Environ. Mol. Mutagen. 61:235-245, 2020. © 2019 Wiley Periodicals, Inc.


Assuntos
Compostos de Aminobifenil/metabolismo , Arilamina N-Acetiltransferase/genética , Carcinógenos/metabolismo , Fluorenos/metabolismo , Polimorfismo Genético , Acetilação , Compostos de Aminobifenil/toxicidade , Animais , Arilamina N-Acetiltransferase/metabolismo , Células CHO , Carcinógenos/toxicidade , Cricetinae , Cricetulus , Dano ao DNA/efeitos dos fármacos , Fluorenos/toxicidade , Humanos , Mutagênese/efeitos dos fármacos , Testes de Mutagenicidade
11.
Environ Geochem Health ; 42(8): 2485-2494, 2020 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31264041

RESUMO

Polycyclic aromatic hydrocarbons (PAHs) have been a major concern because of their carcinogenicity, mutagenicity, teratogenicity and wide distribution in the environment. Over 90% of PAHs in the environment exist on soil surface/sediment. Benzo[a]pyrene (BaP) is one of the predominant PAHs in soil. Thus, it is critically important to understand the patterns of BaP accumulation and transformation peculiarities in soil for the risk assessment. The studies were conducted in model experiment with Haplic Chernozem spiked with various doses of BaP (20, 200, 400 and 800 µg kg-1) equivalent to 1, 10, 20 and 40 levels of maximum permissible concentrations. The unique properties of Haplic Chernozem were studied allow to accumulate and transform BaP as well as barley plants ability to absorb of some BaP concentration. Extraction of BaP from the soil was carried out by the saponification method. The qualitative and quantitative determination of BaP and other polycyclic aromatic hydrocarbons (PAHs) was performed by high-performance liquid chromatography with fluorescence detection (Agilent 1260 Germany, 2014). BaP accumulation in soil depended on the applied BaP concentrations in Haplic Chernozem. Studying the features of PAHs transformation in the soil of a model experiment 1 year after the compound application showed the BaP content in the soil decreased up to 11-40%. Two years after the BaP application the content in the soil decreased up to 15-44% from the initial BaP content in the soil. The percentage of BaP concentration reduction in Haplic Chernozem increased with an increase in the dose of the applied xenobiotic. An increase in the dose of the applied pollutant to the soil of the model experiment contributed to an increase in all PAHs, which indicated a rapid BaP transformation in Haplic Chernozem. The PAHs content in the soils of model experiment in the first year of the research formed the following descending series: pyrene > chrysene > fluoranthene > phenanthrene. In the second year of research the phenanthrene content became higher than the fluoranthene content. The content of these compounds exceeded 20% of the total PAHs content in the soil samples in the first and second years of the model experiment. The features of PAHs accumulation and transformation in soils under artificial pollution showed the degradation of large-nuclear PAHs, starting from 5-ring polyarenes, and their structural reorganization into the less-nuclear polyarenes, such as 4-, 3-, and 2-ring PAHs. During the 2 years of the model experiment the BaP concentration in the soil decreased up to 15-44% from the initial BaP content in the soil.


Assuntos
Benzo(a)pireno/metabolismo , Poluentes do Solo/metabolismo , Benzo(a)pireno/química , Biodegradação Ambiental , Crisenos/química , Crisenos/metabolismo , Fluorenos/química , Fluorenos/metabolismo , Hordeum/metabolismo , Fenantrenos/química , Fenantrenos/metabolismo , Hidrocarbonetos Policíclicos Aromáticos/química , Hidrocarbonetos Policíclicos Aromáticos/metabolismo , Pirenos/química , Pirenos/metabolismo , Federação Russa , Solo/química , Poluentes do Solo/química
12.
Sci Total Environ ; 688: 935-943, 2019 Oct 20.
Artigo em Inglês | MEDLINE | ID: mdl-31726575

RESUMO

Phytohormones are crucial endogenous modulators that regulate and integrate plant growth and responses to various environmental pollutants, including the uptake of pollutants into the plant. However, possible links between endogenous phytohormone pathways and pollutant accumulation are unclear. Here we describe the fluoranthene uptake, plant growth, and superoxide dismutase (SOD), catalase (CAT), peroxidase (POD), and glutathione S-transferase (GST) activities in relation to different endogenous phytohormones and different levels in Arabidopsis thaliana. Three phytohormone inhibitors-N-1-naphthyl-phthalamic acid (NPA), daminozide (DZ), and silver nitrate (SN)-were used to regulate endogenous auxin, gibberellin, and ethylene levels, respectively. Fluoranthene inhibited plant growth and root proliferation while increasing GST and SOD activity. The three inhibitors reduced fluoranthene levels in Arabidopsis by either affecting plant growth or modulating antioxidant enzyme activity. NPA reduced plant growth and increased CAT activity. SN promoted plant growth and increased POD and CAT activity, whereas DZ increased POD activity.


Assuntos
Arabidopsis/fisiologia , Fluorenos/metabolismo , Reguladores de Crescimento de Planta/metabolismo , Catalase/metabolismo , Glutationa Transferase/metabolismo , Peroxidase/metabolismo , Superóxido Dismutase/metabolismo
13.
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
14.
Food Chem ; 297: 124977, 2019 Nov 01.
Artigo em Inglês | MEDLINE | ID: mdl-31253260

RESUMO

Polycyclic aromatic hydrocarbons (PAHs) are primarily produced during the incomplete combustion of organic matter. PAHs are suspected endocrine disruptors and possible carcinogenic materials. The major sources of human exposure to PAHs are inhaled fumes and food. The aim of this study was to provide an alternative drying method to mitigate PAH formation in dried red peppers. We prepared dried red pepper samples using air-drying and heat pump-assisted drying methods, and measured the concentrations of four PAHs (PAH4), benzo[a] anthracene (B[a]A), chrysene (CHR), benzo[b]fluoranthene (B[b]F), and benzo[a]pyrene (B[a]P), in the resulting pepper samples. The PAH concentrations ranged from 3.61 to 18.0 µg/kg and from 2.22 to 8.35 µg/kg in the air-dried and heat pump-dried pepper samples, respectively. Overall, the results have shown that dried peppers contain PAH4, that the drying conditions for these contaminants should be optimized for mitigating the PAH formation in dried red peppers.


Assuntos
Capsicum/química , Hidrocarbonetos Policíclicos Aromáticos/metabolismo , Antracenos/análise , Antracenos/metabolismo , Benzo(a)pireno/análise , Benzo(a)pireno/metabolismo , Carcinógenos/análise , Carcinógenos/metabolismo , Crisenos/análise , Crisenos/metabolismo , Dessecação , Fluorenos/análise , Fluorenos/metabolismo , Temperatura Alta , Hidrocarbonetos Policíclicos Aromáticos/análise
15.
Bioresour Technol ; 284: 115-120, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-30927648

RESUMO

Polycyclic aromatic hydrocarbons (PAHs) are highly recalcitrant compounds and difficult to degrade. Therefore in this work, using a bioremediation approach, mixed bacterial cultures (ASPF) was developed and enriched from polluted marine sediments capable of degrading 400 mg/L of phenanthrene and fluoranthene in Bushnell Hass medium. ASPF consists of 22 bacterial genera dominated by Azoarcus and Chelativorans. The biostimulation effect of three water soluble fertilizers (NPK, urea, and ammonium sulfate) showed that NPK and ammonium sulfate have enhanced the degradation, whereas urea has decreased their degradation. ASPF was also able to degrade phenanthrene and fluoranthene in the presence of petroleum hydrocarbons. But degradation was found to decrease in the presence of pathway intermediates (phthalic acid and catechol) due to enzymatic feedback inhibition. Optimum degradation of both PAHs was observed under room temperature, suggesting the practical applicability of ASPF.


Assuntos
Bactérias/metabolismo , Fluorenos/metabolismo , Fenantrenos/metabolismo , Fertilizantes , Petróleo/metabolismo , Hidrocarbonetos Policíclicos Aromáticos/metabolismo
16.
Appl Biochem Biotechnol ; 188(4): 1168-1184, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-30854608

RESUMO

The intensive production of polycyclic aromatic hydrocarbons by anthropogenic activities is a serious environmental problem. Therefore, new bioremediation methods are required to avoid widespread contamination. In this work, Serratia sp. AC-11 strain isolated from a tropical peat was selected for immobilization into chitosan beads, which were employed in the biodegradation of fluoranthene. The sizes of the produced beads were relatively uniform with an average diameter of 3 mm. The material was characterized by SEM and FT-IR, confirming the cells immobilization and the protective barrier formed by the chitosan surrounding the biomass. The immobilized bacteria were able to degrade 56% of fluoranthene (the initial concentration was 100 mg L-1) in just 1 day at twice the degradation rate achieved by free-living cells. Furthermore, the immobilized bacteria showed excellent removal during five reuse cycles, from 76% to 59% of biodegradation. These results showed the potential of this approach for remediation of contaminated sites.


Assuntos
Quitosana/química , Fluorenos/metabolismo , Serratia/metabolismo , Biodegradação Ambiental , Espectroscopia de Infravermelho com Transformada de Fourier
17.
Mar Drugs ; 17(3)2019 Mar 04.
Artigo em Inglês | MEDLINE | ID: mdl-30836614

RESUMO

Diazobenzofluorene-containing atypical angucyclines exhibit promising biological activities. Here we report the inactivation of an amidotransferase-encoding gene flsN3 in Micromonospora rosaria SCSIO N160, a producer of fluostatins. Bioinformatics analysis indicated that FlsN3 was involved in the diazo formation. Chemical investigation of the flsN3-inactivation mutant resulted in the isolation of a variety of angucycline aromatic polyketides, including four racemic aminobenzo[b]fluorenes stealthins D⁻G (9⁻12) harboring a stealthin C-like core skeleton with an acetone or butanone-like side chain. Their structures were elucidated on the basis of nuclear magnetic resonance (NMR) spectroscopic data and X-ray diffraction analysis. A plausible mechanism for the formation of stealthins D⁻G (9⁻12) was proposed. These results suggested a functional role of FlsN3 in the formation/modification of N⁻N bond-containing fluostatins.


Assuntos
Organismos Aquáticos/metabolismo , Proteínas de Bactérias/metabolismo , Fluorenos/isolamento & purificação , Micromonospora/metabolismo , Transaminases/metabolismo , Proteínas de Bactérias/genética , Vias Biossintéticas , Biologia Computacional , Cristalografia por Raios X , Fluorenos/química , Fluorenos/metabolismo , Compostos Heterocíclicos de 4 ou mais Anéis/química , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Nitrogênio/química , Streptomyces , Transaminases/genética
18.
Chemosphere ; 223: 140-147, 2019 May.
Artigo em Inglês | MEDLINE | ID: mdl-30772593

RESUMO

A strain KL (Klebsiella sp.), with a high polycyclic aromatic hydrocarbons (PAHs) degradation efficiency, was isolated and purified. Immobilization of strain KL using a boric acid-CaCl2 cross-linking method based on polyvinyl alcohol (PVA)-sodium alginate (SA)-nano alumina (ALNPs) composite was investigated for removal of phenanthrene (PHE), fluoranthene (FLA), and pyrene (PYR) in soil washing effluent. The concentration of PVA, SA, and ALNPs in immobilized beads had significant effects on the physicochemical properties and biodegradation performance. When beads had a PVA, SA, and ALNPs content of 10% (w/v), 0.8% (w/v), and 0.7% (w/v), and the initial biomass dosage was 10% (v/v), the biodegradation efficiency and mass transfer performance of the immobilized beads were optimal with the specific surface area of 13.3971 m2/g. Scanning electron microscopy (SEM) showed that the surface of immobilized beads was dense. The growth and adhesion of cells inside the beads were adequate, and pores of the beads were abundant and irregularly staggered. The immobilization method was successfully applied to the treatment of the three PAHs in soil washing effluent. Adsorption of beads contributed to PAHs removal in the initial stage of degradation. Higher residual concentrations of Tween 80 in the soil washing effluent have toxic effects on strain KL growth and reduce the PAHs degradation capacity. Tween 80 of 2500 mg/L was proper conditions for PAHs biodegradation efficiency. Compared to freely suspended KL cells, the removal rates of PHE, FLA, and PYR using the immobilization method on the 30th day were increased by 15.91%, 17.07%, and 19.08%, respectively.


Assuntos
Biodegradação Ambiental , Klebsiella/metabolismo , Hidrocarbonetos Policíclicos Aromáticos/metabolismo , Solo/química , Adsorção , Fluorenos/metabolismo , Klebsiella/isolamento & purificação , Fenantrenos/metabolismo , Polissorbatos , Pirenos/metabolismo , Poluentes do Solo/metabolismo
19.
ACS Chem Biol ; 14(3): 390-396, 2019 03 15.
Artigo em Inglês | MEDLINE | ID: mdl-30735344

RESUMO

The ability to non-invasively monitor membrane potential dynamics in excitable cells like neurons and cardiomyocytes promises to revolutionize our understanding of the physiology and pathology of the brain and heart. Here, we report the design, synthesis, and application of a new class of fluorescent voltage indicators that make use of a fluorene-based molecular wire as a voltage-sensing domain to provide fast and sensitive measurements of membrane potential in both mammalian neurons and human-derived cardiomyocytes. We show that the best of the new probes, fluorene VoltageFluor 2 (fVF 2), readily reports on action potentials in mammalian neurons, detects perturbations to the cardiac action potential waveform in human induced pluripotent stem cell-derived cardiomyocytes, shows a substantial decrease in phototoxicity compared to existing molecular wire-based indicators, and can monitor cardiac action potentials for extended periods of time. Together, our results demonstrate the generalizability of a molecular wire approach to voltage sensing and highlight the utility of fVF 2 for interrogating membrane potential dynamics.


Assuntos
Potenciais de Ação/fisiologia , Fluorenos/síntese química , Corantes Fluorescentes/síntese química , Miócitos Cardíacos/metabolismo , Neurônios/metabolismo , Membrana Celular , Permeabilidade da Membrana Celular , Transporte de Elétrons , Fluorenos/metabolismo , Corantes Fluorescentes/metabolismo , Células HEK293 , Humanos , Células-Tronco Pluripotentes Induzidas , Cinética , Estrutura Molecular , Imagem Óptica/métodos , Relação Estrutura-Atividade
20.
Biochemistry ; 58(8): 1120-1130, 2019 02 26.
Artigo em Inglês | MEDLINE | ID: mdl-30661358

RESUMO

The glycan moiety of glycoproteins plays key roles in various biological processes. However, there are few versatile methods for releasing, separating, and recovering monomeric reducing N-glycans for further functional analysis. In this study, we developed a new method to achieve the release, separation, and recovery of monomeric reducing N-glycans using enzyme E (Pronase E) combined with 9-chloromethyl chloroformate (Fmoc-Cl) and glycosylasparaginase (GA). Ovalbumin, ribonuclease B, ginkgo, and pine nut glycoproteins were used as materials and sequentially enzymatically hydrolyzed with Pronase E, derivatized with Fmoc-Cl, and enzymatically hydrolyzed with GA. The products produced by this method were then detected by electrospray ionization mass spectrometry, high-performance liquid chromatography (HPLC), and online hydrophilic interaction chromatography (HILIC-MS) separation. The results showed that all N-glycans with essentially one amino acid obtained with Pronase E were labeled with Fmoc-Cl and could be efficiently separated and detected via HPLC and HILIC-MS. Finally, the isolated Asn-glycan derivatives were digested with GA, enabling the recovery of all monomeric reducing N-glycans modified by core α-1,3 fucose. This method was simple, inexpensive, and broadly applicable and could therefore be quite important for analysis of the structure-function relationships of glycans.


Assuntos
Aspartilglucosilaminase/metabolismo , Fluorenos/metabolismo , Glicoproteínas/metabolismo , Polissacarídeos/química , Polissacarídeos/metabolismo , Pronase/metabolismo , Ginkgo biloba/metabolismo , Ovalbumina/metabolismo , Polissacarídeos/isolamento & purificação , Espectrometria de Massas por Ionização por Electrospray
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