Isolation and identification of xenobiotic aryl hydrocarbon receptor ligands in dyeing wastewater

Pei Hsin Chou, Saburo Matsui, Kentaro Misaki, Tomonari Matsuda

Research output: Contribution to journalArticlepeer-review

49 Citations (Scopus)


Dyeing wastewater collected in Kyoto city, Japan, was investigated for the occurrence of aryl hydrocarbon receptor (AhR) ligands by using an AhR-responsive reporter gene assay. Concentrated extracts of wastewater samples elicited a dose-dependent increase in AhR ligand activity, and several hydrophobic HPLC fractions of the extracts were highly effective in inducing AhR ligand activity. Three potential AhR ligands were isolated from these fractions and identified to be Disperse Red 92, Disperse Yellow 64, and 3′-hydroxybenzo[b] quinophthalone by using HPLC and LC-MS/MS. Disperse Red 92, which has also been detected in the treated effluent from a sewage plant receiving the wastewater, is an anthraquinone disperse dye showing weak AhR binding affinity in the assay. Disperse Yellow 64 and 3′-hydroxybenzo[b]quinophthalone are quinoline disperse dyes capable of activating the AhR at nanomolar concentrations. In particular, Disperse Yellow 64 is a highly potent AhR ligand that was 3 times more effective in inducing AhR ligand activity than β-naphthoflavone in the assay. Quinoline disperse dyes are suggested to be a new class of xenobiotic AhR ligands which pose a danger to aquatic biota and human health.

Original languageEnglish
Pages (from-to)652-657
Number of pages6
JournalEnvironmental Science and Technology
Issue number2
Publication statusPublished - 2007 Jan 15

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Environmental Chemistry


Dive into the research topics of 'Isolation and identification of xenobiotic aryl hydrocarbon receptor ligands in dyeing wastewater'. Together they form a unique fingerprint.

Cite this