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Fungal biotransformation of benzo[f]quinoline, benzo[h]quinoline, and phenanthridine

  • Applied Microbial and Cell Physiology
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Abstract

Cultures of Umbelopsis ramanniana (=Mucor ramannianus) were grown in fluid Sabouraud medium for 3 days, dosed with 0.23 mM benzo[f]quinoline, benzo[h]quinoline, or phenanthridine (benzo[c]quinoline), and incubated for another 18 days. Cultures were extracted and metabolites (66–75% of the UV absorbance) were separated by high-performance liquid chromatography. They were identified by mass spectrometry and nuclear magnetic resonance spectroscopy. Benzo[f]quinoline was metabolized to benzo[f]quinoline trans-7,8-dihydrodiol, benzo[f]quinoline N-oxide, and 7-hydroxybenzo[f]quinoline, benzo[h]quinoline was metabolized to benzo[h]quinoline trans-5,6-dihydrodiol, benzo[h]quinoline trans-7,8-dihydrodiol, and 7-hydroxybenzo[h]quinoline, and phenanthridine was metabolized to phenanthridine N-oxide and phenanthridin-6(5H)-one. At least one of the metabolites produced from each compound was mutagenic and could not be considered detoxified.

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Acknowledgements

We thank C.E. Cerniglia and R.J. Turesky for helpful comments and thank M.D. Adjei and A.J. Williams for technical advice. This work was supported in part by an appointment (E.L.C.) to the Summer Student Research Program at the National Center for Toxicological Research administered by the Oak Ridge Institute for Science and Education through an interagency agreement between the United States Department of Energy and the United States Food and Drug Administration. The views presented in this article do not necessarily reflect those of the Food and Drug Administration.

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  1. National Center for Toxicological Research, Food and Drug Administration, Jefferson, AR 72079, USA

    John B. Sutherland, E. Lynn Cross, Thomas M. Heinze, James P. Freeman & Joanna D. Moody

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  1. John B. Sutherland
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  2. E. Lynn Cross
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  3. Thomas M. Heinze
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  4. James P. Freeman
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  5. Joanna D. Moody
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Correspondence to John B. Sutherland.

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Sutherland, J.B., Cross, E.L., Heinze, T.M. et al. Fungal biotransformation of benzo[f]quinoline, benzo[h]quinoline, and phenanthridine. Appl Microbiol Biotechnol 67, 405–411 (2005). https://doi.org/10.1007/s00253-004-1738-8

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  • DOI: https://doi.org/10.1007/s00253-004-1738-8

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