Degradation of diphenyl ether herbicides by the lignin-degrading basidiomycete Coriolus versicolor

N. Hiratsuka, Hiroyuki Wariishi, H. Tanaka

Research output: Contribution to journalArticle

47 Citations (Scopus)

Abstract

Under ligninolytic conditions, the white-rot basidiomycete Coriolus versicolor metabolized chloronitrofen (2, 4, 6-trichloro-4′-nitrodiphenyl ether; CNP) and nitrofen (2, 4-dichloro-4′-nitrodiphenyl ether; NIP), which constitute the largest class of commercially produced diphenyl ether herbicides. The pathway of CNP degradation was elucidated by the identification of fungal metabolites upon addition of CNP and its metabolic intermediates. The metabolic pathway was initially branched to form four metabolites - 2, 4, 6-trichloro-3-hydroxy-4′-nitrodiphenyl ether, 2, 4-dichloro-6-hydroxy-4′-nitrodiphenyl ether, NIP, and 2, 4, 6-trichloro-4′-aminodiphenyl ether - indicating the involvement of hydroxylation, oxidative dechlorination, reductive dechlorination, and nitro-reduction. Of these reactions, hydroxylation was relatively major compared to the others. Extracellular ligninolytic enzymes such as lignin peroxidase, manganese peroxidase and laccase did not catalyze the oxidation of either CNP or NIP. Piperonyl butoxide, an inhibitor of cytochrome P450, suppressed fungal oxidation of CNP and NIP to their hydroxylated products. The inhibition resulted in increasing the amount of reductively dechlorinated and nitro-reduced products. These observations strongly suggest that basidiomycetes may possess a mechanism for a strict substrate recognition system and a corresponding metabolic response system to effectively degrade environmentally persistent aromatic compounds.

Original languageEnglish
Pages (from-to)563-571
Number of pages9
JournalApplied Microbiology and Biotechnology
Volume57
Issue number4
DOIs
Publication statusPublished - Nov 20 2001

Fingerprint

Basidiomycota
Lignin
Herbicides
Ethers
Degradation
Dechlorination
Hydroxylation
manganese peroxidase
Metabolites
Piperonyl Butoxide
Laccase
Oxidation
Aromatic compounds
Corrosion inhibitors
Metabolic Networks and Pathways
Cytochrome P-450 Enzyme System
Manganese
phenyl ether
4-nitrobiphenyl ether
Substrates

All Science Journal Classification (ASJC) codes

  • Biotechnology
  • Applied Microbiology and Biotechnology

Cite this

Degradation of diphenyl ether herbicides by the lignin-degrading basidiomycete Coriolus versicolor. / Hiratsuka, N.; Wariishi, Hiroyuki; Tanaka, H.

In: Applied Microbiology and Biotechnology, Vol. 57, No. 4, 20.11.2001, p. 563-571.

Research output: Contribution to journalArticle

@article{7c64acbd6a2e4b86920659affcbff464,
title = "Degradation of diphenyl ether herbicides by the lignin-degrading basidiomycete Coriolus versicolor",
abstract = "Under ligninolytic conditions, the white-rot basidiomycete Coriolus versicolor metabolized chloronitrofen (2, 4, 6-trichloro-4′-nitrodiphenyl ether; CNP) and nitrofen (2, 4-dichloro-4′-nitrodiphenyl ether; NIP), which constitute the largest class of commercially produced diphenyl ether herbicides. The pathway of CNP degradation was elucidated by the identification of fungal metabolites upon addition of CNP and its metabolic intermediates. The metabolic pathway was initially branched to form four metabolites - 2, 4, 6-trichloro-3-hydroxy-4′-nitrodiphenyl ether, 2, 4-dichloro-6-hydroxy-4′-nitrodiphenyl ether, NIP, and 2, 4, 6-trichloro-4′-aminodiphenyl ether - indicating the involvement of hydroxylation, oxidative dechlorination, reductive dechlorination, and nitro-reduction. Of these reactions, hydroxylation was relatively major compared to the others. Extracellular ligninolytic enzymes such as lignin peroxidase, manganese peroxidase and laccase did not catalyze the oxidation of either CNP or NIP. Piperonyl butoxide, an inhibitor of cytochrome P450, suppressed fungal oxidation of CNP and NIP to their hydroxylated products. The inhibition resulted in increasing the amount of reductively dechlorinated and nitro-reduced products. These observations strongly suggest that basidiomycetes may possess a mechanism for a strict substrate recognition system and a corresponding metabolic response system to effectively degrade environmentally persistent aromatic compounds.",
author = "N. Hiratsuka and Hiroyuki Wariishi and H. Tanaka",
year = "2001",
month = "11",
day = "20",
doi = "10.1007/s002530100789",
language = "English",
volume = "57",
pages = "563--571",
journal = "Applied Microbiology and Biotechnology",
issn = "0175-7598",
publisher = "Springer Verlag",
number = "4",

}

TY - JOUR

T1 - Degradation of diphenyl ether herbicides by the lignin-degrading basidiomycete Coriolus versicolor

AU - Hiratsuka, N.

AU - Wariishi, Hiroyuki

AU - Tanaka, H.

PY - 2001/11/20

Y1 - 2001/11/20

N2 - Under ligninolytic conditions, the white-rot basidiomycete Coriolus versicolor metabolized chloronitrofen (2, 4, 6-trichloro-4′-nitrodiphenyl ether; CNP) and nitrofen (2, 4-dichloro-4′-nitrodiphenyl ether; NIP), which constitute the largest class of commercially produced diphenyl ether herbicides. The pathway of CNP degradation was elucidated by the identification of fungal metabolites upon addition of CNP and its metabolic intermediates. The metabolic pathway was initially branched to form four metabolites - 2, 4, 6-trichloro-3-hydroxy-4′-nitrodiphenyl ether, 2, 4-dichloro-6-hydroxy-4′-nitrodiphenyl ether, NIP, and 2, 4, 6-trichloro-4′-aminodiphenyl ether - indicating the involvement of hydroxylation, oxidative dechlorination, reductive dechlorination, and nitro-reduction. Of these reactions, hydroxylation was relatively major compared to the others. Extracellular ligninolytic enzymes such as lignin peroxidase, manganese peroxidase and laccase did not catalyze the oxidation of either CNP or NIP. Piperonyl butoxide, an inhibitor of cytochrome P450, suppressed fungal oxidation of CNP and NIP to their hydroxylated products. The inhibition resulted in increasing the amount of reductively dechlorinated and nitro-reduced products. These observations strongly suggest that basidiomycetes may possess a mechanism for a strict substrate recognition system and a corresponding metabolic response system to effectively degrade environmentally persistent aromatic compounds.

AB - Under ligninolytic conditions, the white-rot basidiomycete Coriolus versicolor metabolized chloronitrofen (2, 4, 6-trichloro-4′-nitrodiphenyl ether; CNP) and nitrofen (2, 4-dichloro-4′-nitrodiphenyl ether; NIP), which constitute the largest class of commercially produced diphenyl ether herbicides. The pathway of CNP degradation was elucidated by the identification of fungal metabolites upon addition of CNP and its metabolic intermediates. The metabolic pathway was initially branched to form four metabolites - 2, 4, 6-trichloro-3-hydroxy-4′-nitrodiphenyl ether, 2, 4-dichloro-6-hydroxy-4′-nitrodiphenyl ether, NIP, and 2, 4, 6-trichloro-4′-aminodiphenyl ether - indicating the involvement of hydroxylation, oxidative dechlorination, reductive dechlorination, and nitro-reduction. Of these reactions, hydroxylation was relatively major compared to the others. Extracellular ligninolytic enzymes such as lignin peroxidase, manganese peroxidase and laccase did not catalyze the oxidation of either CNP or NIP. Piperonyl butoxide, an inhibitor of cytochrome P450, suppressed fungal oxidation of CNP and NIP to their hydroxylated products. The inhibition resulted in increasing the amount of reductively dechlorinated and nitro-reduced products. These observations strongly suggest that basidiomycetes may possess a mechanism for a strict substrate recognition system and a corresponding metabolic response system to effectively degrade environmentally persistent aromatic compounds.

UR - http://www.scopus.com/inward/record.url?scp=0034767657&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034767657&partnerID=8YFLogxK

U2 - 10.1007/s002530100789

DO - 10.1007/s002530100789

M3 - Article

VL - 57

SP - 563

EP - 571

JO - Applied Microbiology and Biotechnology

JF - Applied Microbiology and Biotechnology

SN - 0175-7598

IS - 4

ER -