Biodegradation

, Volume 22, Issue 1, pp 1–11 | Cite as

Fe-superoxide dismutase and 2-hydroxy-1,4-benzoquinone reductase preclude the auto-oxidation step in 4-aminophenol metabolism by Burkholderia sp. strain AK-5

  • Shinji Takenaka
  • Jyun Koshiya
  • Susumu Okugawa
  • Akiko Takata
  • Shuichiro Murakami
  • Kenji Aoki
Original Paper

Abstract

Burkholderia sp. strain AK-5 converts 4-aminophenol to maleylacetic acid via 1,2,4-trihydroxybenzene, which is unstable in vitro and non-enzymatically auto-oxidized to 2-hydroxy-1,4-benzoquinone. Crude extract of strain AK-5 retarded the auto-oxidation and reduced the substrate analogue, 2,6-dimethoxy-1,4-benzoquinone, in the presence of NADH. The two enzymes responsible were purified to homogeneity. The deduced amino acid sequence of the enzyme that inhibited the auto-oxidation showed a high level of identity to sequences of iron-containing superoxide dismutases (Fe-SODs) and contained a conserved metal-ion-binding site; the purified enzyme showed superoxide dismutase activity and contained 1 mol of Fe per mol of enzyme, identifying it as Fe-SOD. Among three type SODs tested, Fe-SOD purified here inhibited the auto-oxidation most efficiently. The other purified enzyme showed a broad substrate specificity toward benzoquinones, including 2-hydroxy-1,4-benzoquinone, converting them to the corresponding 1,4-benzenediols; the enzyme was identified as 2-hydroxy-1,4-benzoquinone reductase. The deduced amino acid sequence did not show a high level of identity to that of benzoquinone reductases from bacteria and fungi that degrade chlorinated phenols or nitrophenols. The indirect role of Fe-SOD in 1,2,4-trihydroxybenzene metabolism is probably to scavenge and detoxify reactive species that promote the auto-oxidation of 1,2,4-trihydroxybenzene in vivo. The direct role of benzoquinone reductase would be to convert the auto-oxidation product back to 1,2,4-trihydroxybenzene. These two enzymes together with 1,2,4-trihydroxybenzene 1,2-dioxygenase convert 1,2,4-trihydroxybenzene to maleylacetic acid.

Keywords

4-Aminophenol Burkholderia 1,2,4-Trihydroxybenzene 2-Hydroxy-1,4-benzoquinone reductase Fe-superoxide dismutase 

Abbreviations

SOD

Superoxide dismutase

Fe-SOD

Fe-containing superoxide dismutase

Benzoquinone reductase

2-Hydroxy-1,4-benzoquinone reductase

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Copyright information

© Springer Science+Business Media B.V. 2010

Authors and Affiliations

  • Shinji Takenaka
    • 1
  • Jyun Koshiya
    • 1
  • Susumu Okugawa
    • 1
  • Akiko Takata
    • 1
  • Shuichiro Murakami
    • 2
  • Kenji Aoki
    • 3
  1. 1.Department of Applied Biological Chemistry, Graduate School of Agricultural ScienceKobe UniversityKobeJapan
  2. 2.Department of Bioscience, Biotechnology and Agrochemistry, Faculty of AgricultureMeiji UniversityKawasakiJapan
  3. 3.Department of Nutritional Management, Faculty of Nutritional ScienceSagami Women’s UniversitySagamiharaJapan

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