Environmental Aromatic Nitro Compounds and their Bacterial Detoxification

Ohnishi, Yoshinari; Kinouchi, Takemi; Manabe, Yoshiki; Wakisaka, Kazumi

doi:10.1007/978-1-4613-3611-2_35

Cited by 12 publications

(11 citation statements)

References 16 publications

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“…When PAR is exposed to N02, mutagenic nitro derivatives are readily induced (31,40). Furthermore, we found I-NP in wastewater from oil-water separating tanks of gasoline stations (28).…”

Section: Discussionmentioning

confidence: 66%

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Biotransformation of 1‐Nitropyrene in Intestinal Anaerobic Bacteria

Kinouchi

Manabe

Wakisaka

et al. 1982

Microbiology and Immunology

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Mutagenic nitroaromatic compounds have recently been found in photocopies, urban atmosphere, automobile exhaust and wastewater. 1-Nitropyrene (I-NP) is readily formed when pyrene, ubiquitous in the environment, is exposed to nitrogen dioxide in the urban atmosphere or in automobile exhaust, and is highly mutagenic, inducing 449 hisr revertants/plate/nmol from Salmonella typhimurium strain T A98 in the absence of 89 fraction in the Salmonella-microsome test. It is possible to swallow sputum or some food containing I-NP and it would come into contact with the normal bacterial flora. We determined the I-NP nitroreductase activity in environmental and laboratory bacterial strains. We found that the mutagenicity of I-NP mixed with the feces of a healthy man or a culture of anaerobic bacteria was decreased. The product proved to be I-aminopyrene (I-AP), based on its fluorescence spectrum, its mass spectrum, and its characteristic thin layer chromatographic and high performance liquid chromatographic patterns. The I-NP nitroreductase activity of aerobic bacteria was low, but crude extracts from the anaerobic bacteria, i.e., Bacteroidesfragilis, B. thetaiotaomicron, B. oulgatus, Fusobacterium mortiferum, F. nucleatum, Clostridium perfringens, C. sporogenes, Bifidobacterium adolescentis, B. bifidum, Eubacterium lentum, E. limosum, andPeptostreptococcus anaerobius, all easily converted I-NP to I-AP and proportionally decreased the mutagenic activity of I-NP.A simple method for identifying chemical mutagens has been developed: the Ames test (I) measures back mutation in several specially constructed mutants of Salmonella typhimurium his-strains. A homogenate of rat liver 89 fraction is added to the Ames test to approximate mammalian metabolism.I-Nitropyrene (l-NP) is a nitroaromatic compound that is highly mutagenic in the Ames test. One nanomol of I-NP induces 484 hisr revertants/plate from S. typhimurium tester strain T A98 in the absence of 89 mix (21). Moreover, 1,8-dinitropyrene induces 72,900 hisr revertants/plate/nmol from strain TA98 (21). I-NP is more mutagenic than representative carcinogens and mutagens; for example, 2-nitronaphthalene and benzo(a)pyrene induce 8.7 and 121 hist revertants/plate/ nmol, respectively (20). I-NP is also carcinogenic in rats (26).I-NP has recently been detected in photocopies, airborne particles, automobile 993

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“…When PAR is exposed to N02, mutagenic nitro derivatives are readily induced (31,40). Furthermore, we found I-NP in wastewater from oil-water separating tanks of gasoline stations (28).…”

Section: Discussionmentioning

confidence: 66%

“…exhaust and wastewater (16,28,34,40). It is also readily formed by exposure of pyrene, always present in city air and automobile exhaust, to nitrogen dioxide (N0 2).…”

mentioning

confidence: 99%

Biotransformation of 1‐Nitropyrene in Intestinal Anaerobic Bacteria

Kinouchi

Manabe

Wakisaka

et al. 1982

Microbiology and Immunology

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“…Investigators should use the available technology to increase the level of sophistication of inhalation toxicology studies so that we can obtain a better understanding of the nature of environmental hazards. (Lee etal., 1980;Gibson etal., 1981;Schuetzle et al, 1981), photocopies (LOfroth et al, 1980;Rosenkranz et aI., 1980), wastewater from gasoline stations (Ohnishi et al, 1983;Manabe et al, 1984), and used crankcase oil (Manabe et al, 1984). They are direct-acting mutagens in the Ames Salmonella mutation test; I-NP, 1,3-diNP, 1,6-diNP, and 1,8-diNP produce 417; 65,500; 82,000; and 100,000 His+ revertants/plate/nmol, respectively, from strain TA98 in the absence of rat liver S9 mix (unpublished data).…”

Section: Discussionmentioning

confidence: 99%

Short-Term Bioassays in the Analysis of Complex Environmental Mixtures IV

1985

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“…We reported that 1-NP was converted to 1-AP when 1-NP was incubated with feces or intestinal bacteria (17,20,33). In the present study, taking notice of the enterohepatic circulation, we mixed the bile from the rats administered [3I-I]1-NP with the IC and determined the extent of binding to the IC, the mutagenicity of the bile and the metabolites in the reaction mixture.…”

Section: Discussionmentioning

confidence: 99%

“…In the hindgut and feces the population of obligate/facultative anaerobes reaches 1011 organisms per gram (8,28,29) and these bacteria can modify a wide range of environmental chemicals including food additives, carcinogens and mutagens, either directly or via enterohepatic circulation (9, 38). We measured the 1-NP nitroreductase (NRase) activity of a number of aerobic and anaerobic bacteria in vitro, and found while the activity of aerobic bacteria was low, the activity in anaerobic bacteria, especially those normally associated with the intestinal tract, was high (17,20,33). In addition, we isolated and purified four NRases from Bacteroides fragilis and reported that nitroreduction was a necessary step in metabolic activation of 1-NP (19,20).…”

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confidence: 99%