Initial Oxidation Products in the Metabolism of Pyrene, Anthracene, Fluorene, and Dibenzothiophene by the White Rot Fungus Pleurotus ostreatus.

Applied and Environmental Microbiology
L BezalelC E Cerniglia

Abstract

The initial metabolites in the degradation of pyrene, anthracene, fluorene, and dibenzothiophene by Pleurotus ostreatus were isolated by high-pressure liquid chromatography and characterized by UV-visible, gas-chromatographic, mass-spectrometric, and (sup1)H nuclear magnetic resonance spectral techniques. The metabolites from pyrene, dibenzothiophene, anthracene, and fluorene amounted to 45, 84, 64, and 96% of the total organic-solvent-extractable metabolites, respectively. Pyrene was metabolized predominantly to pyrene trans-4,5-dihydrodiol. Anthracene was metabolized predominantly to anthracene trans-1,2-dihydrodiol and 9,10-anthraquinone. In contrast, fluorene and dibenzothiophene were oxidized at the aliphatic bridges instead of the aromatic rings. Fluorene was oxidized to 9-fluorenol and 9-fluorenone; dibenzothiophene was oxidized to the sulfoxide and sulfone. Circular dichroism spectroscopy revealed that the major enantiomer of anthracene trans-1,2-dihydrodiol was predominantly in the S,S configuration and the major enantiomer of the pyrene trans-4,5-dihydrodiol was predominantly R,R. These results indicate that the white rot fungus P. ostreatus initially metabolizes polycyclic aromatic hydrocarbons by reactions similar t...Continue Reading

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Citations

May 29, 2010·Applied Microbiology and Biotechnology·Nomathemba Loice ChiguHiroyuki Wariishi
Jun 30, 2011·Applied Microbiology and Biotechnology·Jianqiao WangHirokazu Kawagishi
Aug 26, 2016·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·Steve C Mitchell, Rosemary H Waring
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Jul 4, 2003·Applied and Environmental Microbiology·Kari T SteffenMartin Hofrichter
Apr 17, 2013·Biotechnology and Applied Biochemistry·Hirofumi Ichinose
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Jul 1, 1997·Applied and Environmental Microbiology·L BezalelC E Cerniglia
Nov 5, 1997·Applied and Environmental Microbiology·U SackW Fritsche

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