Fungal biotransformation of benzo[f]quinoline, benzo[h]quinoline, and phenanthridine.
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.
Sutherland
John B
JB
National Center for Toxicological Research, Food and Drug Administration, Jefferson, AR 72079, USA. john.sutherland@fda.hhs.gov
Cross
E Lynn
EL
Heinze
Thomas M
TM
Freeman
James P
JP
Moody
Joanna D
JD
D001711:Biotransformation; D008956:Models, Chemical; D009089:Mucor / Q000737:chemistry / Q000254:growth & development / Q000378:metabolism*; D010617:Phenanthridines / Q000378:metabolism*; D011804:Quinolines / Q000378:metabolism*
D010617:Phenanthridines; D011804:Quinolines; C039107:benzo(h)quinoline; C039108:benzo(f)quinoline