Degradation of Phenanthrene and Anthracene by Cell Suspensions of<i>Mycobacterium</i>sp. Strain PYR-1

DOI Web Site 7 Citations
  • Joanna D. Moody
    <!--label omitted: 1-->Division of Microbiology,1
  • James P. Freeman
    <!--label omitted: 2-->Division of Chemistry,2 and
  • Daniel R. Doerge
    <!--label omitted: 3-->Division of Biochemical Toxicology,3 National Center for Toxicological Research, U.S. Food and Drug Administration, Jefferson, Arkansas 72079
  • Carl E. Cerniglia
    <!--label omitted: 1-->Division of Microbiology,1

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<jats:title>ABSTRACT</jats:title><jats:p>Cultures of<jats:italic>Mycobacterium</jats:italic>sp. strain PYR-1 were dosed with anthracene or phenanthrene and after 14 days of incubation had degraded 92 and 90% of the added anthracene and phenanthrene, respectively. The metabolites were extracted and identified by UV-visible light absorption, high-pressure liquid chromatography retention times, mass spectrometry,<jats:sup>1</jats:sup>H and<jats:sup>13</jats:sup>C nuclear magnetic resonance spectrometry, and comparison to authentic compounds and literature data. Neutral-pH ethyl acetate extracts from anthracene-incubated cells showed four metabolites, identified as<jats:italic>cis</jats:italic>-1,2-dihydroxy-1,2-dihydroanthracene, 6,7-benzocoumarin, 1-methoxy-2-hydroxyanthracene, and 9,10-anthraquinone. A novel anthracene ring fission product was isolated from acidified culture media and was identified as 3-(2-carboxyvinyl)naphthalene-2-carboxylic acid. 6,7-Benzocoumarin was also found in that extract. When<jats:italic>Mycobacterium</jats:italic>sp. strain PYR-1 was grown in the presence of phenanthrene, three neutral metabolites were identified as<jats:italic>cis</jats:italic>- and<jats:italic>trans</jats:italic>-9,10-dihydroxy-9,10-dihydrophenanthrene and<jats:italic>cis</jats:italic>-3,4-dihydroxy-3,4-dihydrophenanthrene. Phenanthrene ring fission products, isolated from acid extracts, were identified as 2,2′-diphenic acid, 1-hydroxynaphthoic acid, and phthalic acid. The data point to the existence, next to already known routes for both gram-negative and gram-positive bacteria, of alternative pathways that might be due to the presence of different dioxygenases or to a relaxed specificity of the same dioxygenase for initial attack on polycyclic aromatic hydrocarbons.</jats:p>

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