Formation of toxic 2-nonyl-p-benzoquinones from α-tertiary 4-nonylphenol isomers during microbial metabolism of technical nonylphenol

Environmental Science & Technology
Frederic L P GabrielHans-Peter E Kohler

Abstract

In many environmental compartments, microbial degradation of α-quaternary nonylphenols proceeds along an ipso-substitution pathway. It has been reported that technical nonylphenol contains, besides α-quaternary nonylphenols, minor amounts of various α-H, α-methyl substituted tertiary isomers. Here, we show that potentially toxic metabolites of such minor components are formed during ipso-degradation of technical nonylphenol by Sphingobium xenophagum Bayram, a strain isolated from activated sewage sludge. Small but significant amounts of nonylphenols were converted to the corresponding nonylhydroquinones, which in the presence of air oxygen oxidized to the corresponding nonyl-p-benzoquinones-yielding a complex mixture of potentially toxic metabolites. Through reduction with ascorbic acid and subsequent analysis by gas chromatography-mass spectrometry, we were able to characterize this unique metabolic fingerprint and to show that its components originated for the most part from α-tertiary nonylphenol isomers. Furthermore, our results indicate that the metabolites mixture also contained several α, β-dehydrogenated derivatives of nonyl-p-benzoquinones that originated by hydroxylation induced rearrangement, and subsequent ring and ...Continue Reading

References

Jan 1, 1992·Toxicology and Applied Pharmacology·T J MonksD G Graham
May 1, 1991·Environmental Health Perspectives·A M SotoC Sonnenschein
Jan 1, 1986·Contact Dermatitis·G W ReynoldsE Rodriguez
Feb 7, 1997·The Journal of Biological Chemistry·E J Routledge, J P Sumpter
Jan 30, 1999·Applied and Environmental Microbiology·T TangheW Verstraete
Apr 26, 2001·International Journal of Systematic and Evolutionary Microbiology·K FujiiS Kimura
Jul 21, 2004·Environmental Science & Technology·Bjoern ThieleKlaus Guenther
Mar 5, 2005·Applied and Environmental Microbiology·Frédéric L P GabrielHans-Peter E Kohler
Dec 13, 2005·Analytical and Bioanalytical Chemistry·Klaus GuentherBjoern Thiele
Sep 8, 2006·Environmental Science & Technology·Thomas G PreussHans Toni Ratte
Sep 16, 1966·Science·T Eisner, J Meinwald
Sep 20, 2008·Environmental Science & Technology·Frédéric L P GabrielHans-Peter E Kohler
Sep 20, 2008·Environmental Science & Technology·John Montgomery-BrownMartin Reinhard
Sep 9, 2009·Philosophical Transactions. Series A, Mathematical, Physical, and Engineering Sciences·Walter GigerHans-Peter E Kohler
Aug 10, 2011·Environmental Science & Technology·Jun ShanRong Ji

❮ Previous
Next ❯

Related Concepts

Related Feeds

Bioremediation (ASM)

Bioremediation is the treatment and removal of harmful pollutants or contaminants through the use of microorganisms. Discover the latest research here.