New branches in the degradation pathway of monochlorocatechols by Aspergillus nidulans: a metabolomics analysis

J Hazard Mater. 2014 Mar 15;268:264-72. doi: 10.1016/j.jhazmat.2014.01.024. Epub 2014 Jan 25.

Abstract

A collective view of the degradation of monochlorocatechols in fungi is yet to be attained, though these compounds are recognised as key degradation intermediates of numerous chlorinated aromatic hydrocarbons, including monochlorophenols. In the present contribution we have analysed the degradation pathways of monochlorophenols in Aspergillus nidulans using essentially metabolomics. Degradation intermediates herein identified included those commonly reported (e.g. 3-chloro-cis,cis-muconate) but also compounds never reported before in fungi revealing for 4-chlorocatechol and for 3-chlorocatechol unknown degradation paths yielding 3-chlorodienelactone and catechol, respectively. A different 3-chlorocatechol degradation path led to accumulation of 2-chloromuconates (a potential dead-end), notwithstanding preliminary evidence of chloromuconolactones and protoanemonin simultaneous formation. In addition, some transformation intermediates, of which sulfate conjugates of mono-chlorophenols/chlorocatechols were the most common, were also identified. This study provides critical information for understanding the role of fungi in the degradation of chlorinated aromatic hydrocarbons; furthering their utility in the development of innovative bioremediation strategies.

Keywords: Aspergillus nidulans; Biodegradation; Chlorinated aromatic hydrocarbons; Metabolic pathway; Monochlorocatechols; Monochlorophenols.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aspergillus nidulans / growth & development
  • Aspergillus nidulans / metabolism*
  • Biodegradation, Environmental
  • Biotransformation
  • Catechols / chemistry
  • Catechols / isolation & purification*
  • Catechols / metabolism
  • Environmental Pollutants / chemistry
  • Environmental Pollutants / isolation & purification*
  • Environmental Pollutants / metabolism
  • Hydrocarbons, Chlorinated / chemistry
  • Hydrocarbons, Chlorinated / isolation & purification*
  • Hydrocarbons, Chlorinated / metabolism
  • Metabolic Networks and Pathways*
  • Metabolomics*
  • Molecular Structure
  • Mycelium / growth & development
  • Mycelium / metabolism

Substances

  • Catechols
  • Environmental Pollutants
  • Hydrocarbons, Chlorinated