Microorganims of the bovine rumen fluid biocatalyzed the reduction of nitro-compound substrates to yield the respective amines. This enzymatic process, using ruminal contents, has rarely been reported in associa- tion with the bioreduction of nitro groups. The biotransformation reactions catalyzed by this system were de- pendent of both the electronic characteristics and the area/volume of the nitro-substrates confirming the processes are enzymatic. The semi-preparative scale biotransformation went by in good yield showing the rumen fluid may be employed in the synthesis of amines under very mild conditions and, moreover, it may have application in the bioremediation of nitro-compounds
Metabolism of three different agro-pesticides widely used in Uruguay, the insecticides imidacloprid and thiamethoxam and the antiparasite nitroxinil, by bovine ruminal fluid, as supply of anaerobic microorganims, was studied. Complete ruminal fluid was incubated with each of the agrochemicals in different conditions, varying time, nutrients, and nitroethane supplementation as methanogenesis modificator. Only biotransformation was detected for nitroxinil in some of the studied variables. In the optimized condition only one product was generated and the chemical structure of this main metabolite was elucidated using combined spectroscopies evidencing a structural motive unrelated with the products of the corresponding mammal biotransformation results of reduction, and substitution processes. The ruminal generation of the metabolite was confirmed. In order to employ this anaerobic microbial system as potential bioremediator of agrochemical-contaminated soils, the toxicity, against mammal cells, and the mutagenicity, using Ames test, of the product of biotransformation were studied. The lack of toxic effects encouraged us to propose the ruminal system as a plausible system for agrochemicals bioremediation.
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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