Formation of hydride-Meisenheimer complexes of picric acid (2,4, 6-trinitrophenol) and 2,4-dinitrophenol during mineralization of picric acid by Nocardioides sp. strain CB 22-2

Appl Environ Microbiol. 1999 Apr;65(4):1372-7. doi: 10.1128/AEM.65.4.1372-1377.1999.

Abstract

There are only a few examples of microbial conversion of picric acid (2,4,6-trinitrophenol). None of the organisms that have been described previously is able to use this compound as a sole source of carbon, nitrogen, and energy at high rates. In this study we isolated and characterized a strain, strain CB 22-2, that was able to use picric acid as a sole source of carbon and energy at concentrations up to 40 mM and at rates of 1.6 mmol. h(-1). g (dry weight) of cells(-1) in continuous cultures and 920 micromol. h(-1). g (dry weight) of cells(-1) in flasks. In addition, this strain was able to use picric acid as a sole source of nitrogen at comparable rates in a nitrogen-free medium. Biochemical characterization and 16S ribosomal DNA analysis revealed that strain CB 22-2 is a Nocardioides sp. strain. High-pressure liquid chromatography and UV-visible light data, the low residual chemical oxygen demand, and the stoichiometric release of 2.9 +/- 0.1 mol of nitrite per mol of picric acid provided strong evidence that complete mineralization of picric acid occurred. During transformation, the metabolites detected in the culture supernatant were the [H-]-Meisenheimer complexes of picric acid and 2,4-dinitrophenol (H--DNP), as well as 2,4-dinitrophenol. Experiments performed with crude extracts revealed that H--DNP formation indeed is a physiologically relevant step in picric acid metabolism.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 2,4-Dinitrophenol / chemistry
  • 2,4-Dinitrophenol / metabolism
  • Actinomycetales / classification
  • Actinomycetales / isolation & purification*
  • Actinomycetales / metabolism*
  • Biodegradation, Environmental
  • Chromatography, High Pressure Liquid
  • DNA, Ribosomal / genetics
  • Magnetic Resonance Spectroscopy
  • Picrates / metabolism*
  • RNA, Ribosomal, 16S / genetics
  • Soil Microbiology

Substances

  • DNA, Ribosomal
  • Picrates
  • RNA, Ribosomal, 16S
  • picric acid
  • 2,4-Dinitrophenol