Skip to main content
Log in

Biodegradation of 4-nitroanisole by two Rhodococcus spp.

  • Article
  • Published:
Biodegradation Aims and scope Submit manuscript

Abstract

Two Rhodococcus strains, R. opacus strain AS2 and R. erythropolis strain AS3, that were able to use 4-nitroanisole as the sole source of carbon and energy, were isolated from environmental samples. The first step of the degradation involved the O-demethylation of 4-nitroanisole to 4-nitrophenol which accumulated transiently in the medium during growth. Oxygen uptake experiments indicated the transformation of 4-nitrophenol to 4-nitrocatechol and 1,2,4-trihydroxybenzene prior to ring cleavage and then subsequent mineralization. The nitro group was removed as nitrite, which accumulated in the medium in stoichiometric amounts. In R. opacus strain AS2 small amounts of hydroquinone were produced by a side reaction, but were not further degraded.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Alexander M (1994) Effect of chemical structure on biodegradation. In: Biodegradation and Bioremediation (pp 159–176). Academic Press, San Diego

    Google Scholar 

  • Bache R & Pfennig N (1981) Selective isolation of Acetobacterium woodii on methoxylated aromatic acids and determination of growth yields. Arch. Microbiol. 130: 255–261

    Google Scholar 

  • Bernhardt FH, Nastainczyk W & Seydewitz V (1977) Kinetic studies on a 4-methoxybenzoate O-demethylase from Pseudomonas putida. Eur. J. Biochem. 72: 107–115

    Google Scholar 

  • Bernhardt FH, Pachowsky H & Staudinger H (1975) A 4-methoxybenzoate O-demethylase from Pseudomonas putida: a new type of monooxygenase system. Eur. J. Biochem. 57: 241–256

    Google Scholar 

  • Cartwright NJ & Smith ARW (1967) Bacterial attack on phenolic ethers: an enzyme system demethylating vanillic acid. Biochem. J. 102: 826–841

    Google Scholar 

  • Duque E, Haidour A, Godoy F & Ramos JL (1993) Construction of a Pseudomonas hybrid strain that mineralizes 2,4,6-trinitrotoluene. J. Bacteriol. 175: 2278–2283

    Google Scholar 

  • Edelson J & McMullen JP (1977) O-Demethylation of p-nitroanisole by Escherichia coli. Stimulation by phenobarbital. Drug Metab. Dispos. 5: 185–190

    Google Scholar 

  • Frazer AC & Young LY (1986) Anaerobic C1 metabolism of the O-methyl-14C-labeled substituent of vanillate. Appl. Environ. Microbiol. 51: 84–87

    Google Scholar 

  • Groenewegen PEJ, Breeuwer P, vanHelvoort JMLM, Langenhoff AAM, deVries FP & deBont JAM (1992) Novel degradative pathway of 4-nitrobenzoate in Comamonas acidovorans NBA-10. J. Gen. Microbiol. 138: 1599–1605

    Google Scholar 

  • Haderlein SB & Schwarzenbach RP (1993) Adsorption of substituted nitrobenzenes and nitrophenols to mineral surfaces. Environ. Sci. Technol. 27: 316–326

    Google Scholar 

  • Haigler BE & Spain JC (1993) Biodegradation of 4-nitrotoluene by Pseudomonas sp. strain 4NT. Appl. Environ. Microbiol. 57: 3156–3162

    Google Scholar 

  • Haigler BE, Wallace WH & Spain JC (1994) Biodegradation of 2-nitrotoluene by Pseudomonas sp. strain JS42. Appl. Environ. Microbiol. 60: 3466–3469

    Google Scholar 

  • Harms H & Zehnder AJB (1994) Influence of substrate diffusion on degradation of dibenzofuran and 3-chlorodibenzofuran by attached and suspended bacteria. Appl. Environ. Microbiol. 60: 2736–2745

    Google Scholar 

  • Heudorf U & Peters M (1993) Umweltbelastung und Sanierungsverlauf nach dem Störfall in der Fa. Hoechst AG vom 22. 2. 1993. Forum Städte-Hygiene 44: 338–344

    Google Scholar 

  • Higson FK (1992) Microbial degradation of nitroaromatic compounds. Adv. Appl. Microbiol. 37: 1–19

    Google Scholar 

  • Jain RK, Dreisbach JH & Spain JC (1994) Biodegradation of p-nitrophenol via 1,2,4-benzenetriol by an Arthrobacter species. Appl. Environ. Microbiol. 60: 3030–3032

    Google Scholar 

  • Karlson U, Dwyer DF, Hooper SW, Moore ERB, Timmis KN & Eltis LD (1993) Two independently regulated cytochromes P-450 in a Rhodococcus rhodochrous strain that degrades 2-ethoxyphenol and 4-methoxybenzoate. J. Bacteriol. 175: 1467–1474

    Google Scholar 

  • Lenke H, Pieper DR, Bruhn C & Knackmuss H-J (1992) Degradation of 2,4-dinitrophenol by two Rhodococcus erythropolis strains, HL 24–1 and HL 24–2. Appl. Environ. Microbiol. 58: 2928–2932

    Google Scholar 

  • Marvin-Sikkema FD & deBont JAM (1994) Degradation of nitroaromatic compounds by microorganisms. Appl. Microbiol. Biotechnol. 42: 499–507

    Google Scholar 

  • Moir JWB, Baratta D, Richardson DJ & Ferguson SJ (1993) The purification of a cd 1-type nitrite reductase from, and the absence of a copper-type nitrite reductase from, the aerobic denitrifier thiosphaera pantotropha; the role of pseudoazurin as an electron donor. Eur. J. Biochem. 212: 377–385

    Google Scholar 

  • Nishino SF & Spain JC (1993) Degradation of nitrobenzene by a Pseudomonas pseudoalcaligenes. Appl. Environ. Microbiol. 59: 2520–2525

    Google Scholar 

  • Preuss A, Fimpel J & Diekert G (1993) Anaerobic transformation of 2,4,6-trinitrotoluene (TNT). Arch. Microbiol. 159: 345–353

    Google Scholar 

  • Phys-Williams W, Taylor SC & Williams PA (1993) A novel pathway for the catabolism of 4-nitrotoluene by Pseudomonas. J. Gen. Microbiol. 139: 1967–1972

    Google Scholar 

  • Schwarzenbach RP, Stierli R, Lanz K & Zeyer J (1988) Compound properties relevant for assessing the environmental partitioning of nitrophenols. Environ. Sci. Technol. 22: 83–92

    Google Scholar 

  • Spain JC, Wyss O & Gibson DT (1979) Enzymatic oxidation of p-nitrophenol. Biochem. Biophys. Res. Commun. 88: 634–641

    Google Scholar 

  • Spain JC & Gibson DT (1991) Pathway for biodegradation of p-nitrophenol in a Moraxella sp. Appl. Environ. Microbiol. 57: 812–819

    Google Scholar 

  • Spain JC (1995) Biodegradation of nitroaromatic compounds. Annu. Rev. Microbiol. 49: 523–555

    Google Scholar 

  • Spanggord RJ, Spain JC, Nishino SF & Mortelmans KE (1991) Biodegradation of 2,4-dinitrotoluene by a Pseudomonas sp. Appl. Environ. Microbiol. 57: 3200–3205

    Google Scholar 

  • Sutherland JB (1986) Demethylation of veratrole by cytochrome P-450 in Streptomyces setonii. Appl. Environ. Microbiol. 52: 98–100

    Google Scholar 

  • Wellens H (1990) Zur biologischen Abbaubarkeit mono-und disubstituierter Benzolderivate. Z. Wasser-Abwasser-Forsch. 23: 85–95

    Google Scholar 

  • Zeyer J & Kearney PC (1984) Degradation of o-nitrophenol and m-nitrophenol by a Pseudomonas putida. J. Agric. Food. Chem. 32: 238–242

    Google Scholar 

  • Zeyer J & Kocher HP (1988) Purification and characterization of a bacterial nitrophenol oxygenase which converts ortho-nitrophenol to catechol and nitrite. J. Bacteriol. 170: 1789–1794

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Schäfer, A., Harms, H. & Zehnder, A.J.B. Biodegradation of 4-nitroanisole by two Rhodococcus spp.. Biodegradation 7, 249–255 (1996). https://doi.org/10.1007/BF00058184

Download citation

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00058184

Key words

Navigation