Anaerobic biotransformation of roxarsone and related N-substituted phenylarsonic acids

Cortinas, I.; Field, J. A.; Kopplin, M.; Garbarino, J. R.; Gandolfi, A. J.; Sierra-Alvarez, R.

Abstract:

Large quantities of arsenic are introduced into the environment through land application of poultry litter containing the organoarsenical feed additive roxarsone (3-nitro-4-hydroxyphenylarsonic acid). The objective of this study was to evaluate the bioconversion of roxarsone and related N-substituted phenylarsonic acid derivatives under anaerobic conditions. The results demonstrate that roxarsone is rapidly transformed in the absence of oxygen to the corresponding aromatic amine, 4-hydroxy-3-aminophenylarsonic acid (HAPA). The formation of HAPA is attributable to the facile reduction of the nitro group. Electron-donating substrates, such as hydrogen gas, glucose, and lactate, stimulated the rate of nitro group reduction, indicating a microbial role. During long-term incubations, HAPA and the closely related 4-aminophenylarsonic acid (4-APA) were slowly biologically eliminated by up to 99% under methanogenic and sulfate-reducing conditions, whereas little or no removal occurred in heat-killed inoculum controls. Arsenite and, to a lesser extent, arsenate were observed as products of the degradation. Freely soluble forms of the inorganic arsenical species accounted for 19-28% of the amino-substituted phenylarsonic acids removed. This constitutes the first report of a biologically catalyzed rupture of the phenylarsonic group under anaerobic conditions. ?? 2006 American Chemical Society.

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Article

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70030534

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Cortinas, I.; Field, J. A.; Kopplin, M.; Garbarino, J. R.; Gandolfi, A. J.; Sierra-Alvarez, R.

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2957

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English

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Environmental Science and Technology

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Anaerobic biotransformation of roxarsone and related N-substituted phenylarsonic acids; 2006; Article; Journal; Environmental Science and Technology; Cortinas, I.; Field, J. A.; Kopplin, M.; Garbarino, J. R.; Gandolfi, A. J.; Sierra-Alvarez, R.