Anaerobic metabolism of 1-amino-2-naphthol-based azo dyes (Sudan dyes) by human intestinal microflora

Appl Environ Microbiol. 2007 Dec;73(23):7759-62. doi: 10.1128/AEM.01410-07. Epub 2007 Oct 12.

Abstract

The rates of metabolism of Sudan I and II and Para Red by human intestinal microflora were high compared to those of Sudan III and IV under anaerobic conditions. Metabolites of the dyes were identified as aniline, 2,4-dimethylaniline, o-toluidine, and 4-nitroaniline through high-performance liquid chromatography and liquid chromatography electrospray ionization tandem mass spectrometry analyses. These data indicate that human intestinal bacteria are able to reduce Sudan dyes to form potentially carcinogenic aromatic amines.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Anaerobiosis
  • Aniline Compounds / chemistry
  • Aniline Compounds / metabolism
  • Azo Compounds / chemistry
  • Azo Compounds / metabolism*
  • Bacteria / metabolism*
  • Chromatography, High Pressure Liquid
  • Humans
  • Intestines / microbiology*
  • Molecular Structure
  • Naphthols / chemistry
  • Naphthols / metabolism*
  • Spectrometry, Mass, Electrospray Ionization
  • Tandem Mass Spectrometry
  • Toluidines / chemistry
  • Toluidines / metabolism

Substances

  • Aniline Compounds
  • Azo Compounds
  • Naphthols
  • Toluidines
  • 4-nitroaniline
  • 2,4-xylidine
  • 1-phenylazo-2-naphthol
  • sudan red
  • 2-toluidine
  • 1-amino-2-naphthol
  • sudan III
  • aniline