Anaerobic Biotransformation of Nitro-Compounds to Amines by Bovine Rumen Fluid

Rodríguez, Alfonso; Irazoqui, Ignacio; Álvarez, Guzmán; Cajarville, Cecilia; Repetto, José Luis; González, Mercedes; Cerecetto, Hugo

doi:10.4236/gsc.2011.13009

Cited by 3 publications

(3 citation statements)

References 23 publications

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“…Microbes of the bovine rumen fluid catalyzed the reduction of nitro compounds as substrates and yielded the respective amines. This enzymatic process, using ruminal contents, was rarely reported in case of bio-reduction of nitro groups [ 56 ]. Degradation or detoxification pathways include oxidation, reduction, hydrolysis, and conjugation.…”

Section: Discussionmentioning

confidence: 99%

Biotransformation of nitro aromatic amines in artificial alkaline habitat by pseudomonas DL17

Sarwade

Funde

2022

Environ Anal Health Toxicol

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Nitro-aromatics are listed in carcinogenic, teratogenic, and mutagenic compounds list. p- nitro-aniline is one of them used as a precursor of various chemical compounds in many industries like dyes, drugs, paints and several others. These are mostly given out as an effluent in rivers, lakes or open passage of land which exert several hazards to living creatures and environment. Some of the organic compounds are stable in alkaline condition and persist longer in environment. Very few reports are elaborating bio-remediation in alkaline condition using different hydrocarbons. This study was planned to elaborate mechanism of detoxification and searching the potential of decontamination of p-nitro-aniline in alkaline condition by experimental microbial strain. The bacterial strain pseudomonas DL17 was isolated from alkaline Lake Lonar, Buldana, (MS.) India; and employed in this experiment considering its indigenous property to tolerate the alkaline pH. It also showed resistance to p-nitro-aniline with its raising concentrations on testing after adaptation. The experimental microbial stain showed 100% biodegradation of (500 mg/L) p-nitro-aniline within 48h. On shaking incubator with 110 rpm and at 32 °C optimum temperature. The centrifugate obtained after spinning at 10,000 g by cold centrifuge was used for solvent extraction. Generally, ethyl acetate or DCM was used for solvent extraction. The estimation of residual remains of p-nitro aniline by 6h. intervals was carried after removal of flasks from shaking incubator and centrifugation. At the optimum temperature and pH experiments were carried after knowing the resistance to experimental contaminant range (100-400 mg/L) of p-nitro aniline one month and further extended to 500 mg/L for 15days more. The residual metabolites were purified by column chromatography and various spectrometric studies such as UV-Vis spectroscopy, HNMR, FTIR and GCMS revealed that p-Phenylenediamine, acetanilide, aniline, acetaminophen, catechol, p-bezoquinone, cis-cis muconate as a metabolites. On the basis of the metabolites isolated and characterized by different spectroscopic studies the bio-catalytic mechanism was deduced. The induced enzymes such as nitroreductase, catalase, peroxidase, acetanilide hydroxylase, super oxide dismutase, catechol 1, 2 dioxygenase, catechol 2, 3 dioxygenase has commercial importance in biochemical industries. Induction of such biotransformation enzymes and consumption of p-nitro aniline concentration in experiments makes sure that this microbial strain pseudomonas DL17 can be employed for decontamination of nitro aniline polluted sites as well as isolation of such metabolites characterized and enzymes studied.

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Section: Discussionmentioning

confidence: 99%

Biotransformation of nitro aromatic amines in artificial alkaline habitat by pseudomonas DL17

Sarwade

Funde

2022

Environ Anal Health Toxicol

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“…Additionally, the result was in concordance with our previous results where the nitro moiety was susceptible to be reduced in this biological conditions. 9 Probably, the slower kinetics of reduction of this N-oxide, indazole N 1 -oxide, and the ability of ruminal fluid to reduce nitro-aromatic systems 9 contribute to the generation of the isolated product 21.…”

Section: Scale-up Of Indazole N 1 -Oxide 6 Biotransformationmentioning

confidence: 99%

“…7,8 Additionally, we have recently described the ability of bovine ruminal fluid, in anaerobic conditions, to transform nitro-substrates into amines. 9 The stereo-electronic structural similarity between the nitro moiety and the heterocyclic N-oxide group (Figure 1) has led us to ask which behavior of the latter would be under the cow rumen biotransformer. The deoxygenation of N-oxide-containing aromatic heterocycles to the corresponding heterocycles is an important step in the preparation of new compounds, for example in the field of medicinal chemistry, toxicology, environmental sciences, and new materials.…”

Section: Introductionmentioning

confidence: 99%

Anaerobic Biotransformation ofN-oxide Containing Aromatic Heterocycles by Bovine Ruminal Fluid

Cerecetto¹,

Diaz-Viraqué²,

Irazoqui³

et al. 2013

Revista Virtual De Química

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Biotransformação Anaeróbia de Heterociclos Aromáticos Contendo N-óxido por Líquido Ruminal de Bovinos Resumo: Micro-organismos do fluido ruminal de bovinos foram estudados como biocatalizadores para a redução de diferentes heterociclos aromáticos contendo N-óxido, isto é, quinoxalina N 1 ,N 4-dióxido, fenazina N 5 ,N 10-dióxido, indazol N 1-óxido, benzofuroxano e furoxano. Em anaerobiose, os microorganismos biocatalisam a redução de alguns N-óxidos, dióxidos de quinoxalina e fenazina para se obter os heterociclos correspondentes, enquanto no caso do heterociclo benzofuroxano, ocorre abertura do anel, gerando a o-nitroanilina como único produto. Ao contrário, o furoxano não foi biotransformado nas condições estudadas. O indazol N 1-óxido foi biotransformado lenta e incompletamente ao indazol correspondente. Exceção foi observada apenas para um dos N 1-óxidos de indazol, que foi completamente convertido a um composto novo, diferente do indazol reduzido esperado. A biotransformação em escala semi-preparativa foi realizada e o novo produto obtido e identificado por métodos espectroscópicos.

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Effects of the methane-inhibitors Nitrophenol, 5-Nitrobenzimidazol and two new synthetic nitrocompounds on in vitro ruminal fermentation

Kheddouma

Arhab

Martín-García

et al. 2018

Biocatalysis and Agricultural Biotechnology

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Anaerobic Biotransformation of Nitro-Compounds to Amines by Bovine Rumen Fluid

Cited by 3 publications

References 23 publications

Biotransformation of nitro aromatic amines in artificial alkaline habitat by pseudomonas DL17

Biotransformation of nitro aromatic amines in artificial alkaline habitat by pseudomonas DL17

Anaerobic Biotransformation ofN-oxide Containing Aromatic Heterocycles by Bovine Ruminal Fluid

Effects of the methane-inhibitors Nitrophenol, 5-Nitrobenzimidazol and two new synthetic nitrocompounds on in vitro ruminal fermentation

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