9,10-Phenanthrenedione biodegradation by a soil bacterium and identification of transformation products by LC/ESI-MS/MS

Robert A. Kanaly, Natsuko Hamamura

研究成果: ジャーナルへの寄稿記事

4 引用 (Scopus)

抄録

Transformation of 9,10-phenanthrenedione, a cytotoxic derivative of phenanthrene, was shown to occur by a soil bacterium belonging to the genus Sphingobium. Phenanthrene-grown cells of this strain were exposed to 50mgL-1 9,10-phenanthrenedione in liquid cultures, extracted, and extracts were analyzed by liquid chromatography electrospray ionization mass spectrometry in negative ionization mode. Full scan analyses of exposed cells over the range from m/z 50 to m/z 500 were compared to abiotic and biotic controls. Product and precursor ion scan mode analyses indicated that at least three aromatic ring-cleavage transformation products of 9,10-phenanthrenedione were present and structures for these products, corresponding to [M-H]-=271, [M-H]-=241, and [M-H]-=339 were proposed to be 4-(1-hydroxy-3,4-dioxo-2-naphthyl)-2-oxo-but-3-enoic acid, 2,2'-diphenic acid and 2-[(6-carboxy-2,3-dihydroxy-phenyl)-hydroxy-methyl]-5-oxo-hex-3-enedioic acid. The identity of 2,2'-diphenic acid was confirmed by comparison to an authentic standard and when the strain was exposed to 50mgL-1 2,2'-diphenic acid in separate assays, a transformation product with a similar mass spectrum as 9,10-phenanthrenedione-derived [M-H]-=339 was revealed. Based upon these results, pathways for the transformation of 9,10-phenanthrenedione by strain KK22 were proposed. Strain KK22 appeared unable to use 9,10-phenanthrenedione as a growth substrate under these conditions. This is the first report of potential biotransformation pathways of 9,10-phenanthrenedione by a bacterium.

元の言語英語
ページ(範囲)1442-1449
ページ数8
ジャーナルChemosphere
92
発行部数11
DOI
出版物ステータス出版済み - 9 1 2013

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Biodegradation
biodegradation
Bacteria
Soil
Soils
bacterium
Acids
acid
phenanthrene
soil
ionization
Electrospray ionization
Liquid chromatography
biotransformation
cleavage
Ionization
Mass spectrometry
liquid chromatography
Assays
Electrospray Ionization Mass Spectrometry

All Science Journal Classification (ASJC) codes

  • Environmental Engineering
  • Environmental Chemistry
  • Chemistry(all)
  • Pollution
  • Health, Toxicology and Mutagenesis

これを引用

9,10-Phenanthrenedione biodegradation by a soil bacterium and identification of transformation products by LC/ESI-MS/MS. / Kanaly, Robert A.; Hamamura, Natsuko.

:: Chemosphere, 巻 92, 番号 11, 01.09.2013, p. 1442-1449.

研究成果: ジャーナルへの寄稿記事

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abstract = "Transformation of 9,10-phenanthrenedione, a cytotoxic derivative of phenanthrene, was shown to occur by a soil bacterium belonging to the genus Sphingobium. Phenanthrene-grown cells of this strain were exposed to 50mgL-1 9,10-phenanthrenedione in liquid cultures, extracted, and extracts were analyzed by liquid chromatography electrospray ionization mass spectrometry in negative ionization mode. Full scan analyses of exposed cells over the range from m/z 50 to m/z 500 were compared to abiotic and biotic controls. Product and precursor ion scan mode analyses indicated that at least three aromatic ring-cleavage transformation products of 9,10-phenanthrenedione were present and structures for these products, corresponding to [M-H]-=271, [M-H]-=241, and [M-H]-=339 were proposed to be 4-(1-hydroxy-3,4-dioxo-2-naphthyl)-2-oxo-but-3-enoic acid, 2,2'-diphenic acid and 2-[(6-carboxy-2,3-dihydroxy-phenyl)-hydroxy-methyl]-5-oxo-hex-3-enedioic acid. The identity of 2,2'-diphenic acid was confirmed by comparison to an authentic standard and when the strain was exposed to 50mgL-1 2,2'-diphenic acid in separate assays, a transformation product with a similar mass spectrum as 9,10-phenanthrenedione-derived [M-H]-=339 was revealed. Based upon these results, pathways for the transformation of 9,10-phenanthrenedione by strain KK22 were proposed. Strain KK22 appeared unable to use 9,10-phenanthrenedione as a growth substrate under these conditions. This is the first report of potential biotransformation pathways of 9,10-phenanthrenedione by a bacterium.",
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AB - Transformation of 9,10-phenanthrenedione, a cytotoxic derivative of phenanthrene, was shown to occur by a soil bacterium belonging to the genus Sphingobium. Phenanthrene-grown cells of this strain were exposed to 50mgL-1 9,10-phenanthrenedione in liquid cultures, extracted, and extracts were analyzed by liquid chromatography electrospray ionization mass spectrometry in negative ionization mode. Full scan analyses of exposed cells over the range from m/z 50 to m/z 500 were compared to abiotic and biotic controls. Product and precursor ion scan mode analyses indicated that at least three aromatic ring-cleavage transformation products of 9,10-phenanthrenedione were present and structures for these products, corresponding to [M-H]-=271, [M-H]-=241, and [M-H]-=339 were proposed to be 4-(1-hydroxy-3,4-dioxo-2-naphthyl)-2-oxo-but-3-enoic acid, 2,2'-diphenic acid and 2-[(6-carboxy-2,3-dihydroxy-phenyl)-hydroxy-methyl]-5-oxo-hex-3-enedioic acid. The identity of 2,2'-diphenic acid was confirmed by comparison to an authentic standard and when the strain was exposed to 50mgL-1 2,2'-diphenic acid in separate assays, a transformation product with a similar mass spectrum as 9,10-phenanthrenedione-derived [M-H]-=339 was revealed. Based upon these results, pathways for the transformation of 9,10-phenanthrenedione by strain KK22 were proposed. Strain KK22 appeared unable to use 9,10-phenanthrenedione as a growth substrate under these conditions. This is the first report of potential biotransformation pathways of 9,10-phenanthrenedione by a bacterium.

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