Fungal metabolism of 3-nitrofluoranthene.
We investigated the metabolism of 3-nitrofluoranthene by filamentous fungus, Cunninghamella elegans ATCC 36112. Cunninghamella elegans metabolized about 72% of the 3-nitro[3,4-14C]fluoranthene added during 144 h of incubation to 2 major metabolites. These metabolites were separated by reversed-phase high-performance liquid chromatography and identified as 3-nitrofluoranthene-8-sulfate and 3-nitrofluoranthene-9-sulfate by 1H nuclear magnetic resonance, UV-visible, and mass spectral techniques. These results, in conjunction with previous studies on the fungal metabolism of fluoranthene, indicate that the nitro substituent at the C-3 position of fluoranthene sterically hinders epoxidation and shifts metabolism to the C-8 and C-9 positions. Since the phenolic microsomal metabolites of 3-nitrofluoranthene are mutagenic, the formation of sulfate conjugates of 8- and 9-hydroxy-3-nitrofluoranthene by C. elegans suggests that the fungal metabolic pathways may be beneficial for detoxification of this ubiquitous pollutant.
Pothuluri
J V
JV
Food and Drug Administration, National Center for Toxicological Research, Jefferson, Arksansas 72079.
Evans
F E
FE
Heinze
T M
TM
Cerniglia
C E
CE
D002273:Carcinogens / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D004785:Environmental Pollutants / Q000378:metabolism; D005449:Fluorenes / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D009090:Mucorales / Q000378:metabolism*; D009153:Mutagens / Q000378:metabolism*
D002273:Carcinogens; D004785:Environmental Pollutants; D005449:Fluorenes; D009153:Mutagens; C087717:3-nitrofluoranthene-8-sulfate; C087718:3-nitrofluoranthene-9-sulfate; C033643:3-nitrofluoranthene