title: Metabolism of 1,4-dinitro-2-methylpyrrole, a mutagen formed by a sorbic acid-nitrite reaction, by intestinal bacteria.
abstract: 1,4-Dinitro-2-methylpyrrole (DNMP), a mutagenic product formed by the interaction of two common food additives, sorbic acid and sodium nitrite, was transformed to 1-nitro-2-methyl-4-aminopyrrole (NMAP) by human fecal mixtures and various intestinal bacterial strains. Under anaerobic conditions the cell suspensions of Actinomyces, Bacteroides, Clostridium, Eubacterium, Fusobacterium, and Peptostreptococcus spp. demonstrated the nitroreduction activity. Under aerobic conditions, only Actinomyces and Bacteroides spp. showed activity, and this was at a decreased level. In cell suspensions of Bacteroides thetaiotaomicron VPI 5482, NAD(P)H and glucose accelerated the reduction rate, whereas dicoumarol and heat significantly inhibited the rate, and flavin adenine dinucleotide (FAD) and flavin mononucleotide (FMN) did not affect the rate. With cell-free preparations of the same strain, reduction required NAD(P)H as a cofactor in a dose-dependent fashion and was inactivated by air and heat.
authors.affiliation: Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg 24061-0212.
authors.forename: Y Z
authors.initials: YZ
authors.lastname: Shu
authors.forename: D G
authors.initials: DG
authors.lastname: Kingston
authors.forename: R L
authors.initials: RL
authors.lastname: Van Tassell
authors.forename: T D
authors.initials: TD
authors.lastname: Wilkins
mesh_terms: D001421:Bacteria, Anaerobic / Q000378:metabolism*; D001439:Bacteroides / Q000378:metabolism; D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D005243:Feces / Q000382:microbiology; D005260:Female; D006801:Humans; D007422:Intestines / Q000382:microbiology*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D009153:Mutagens / Q000378:metabolism*; D010084:Oxidation-Reduction; D011758:Pyrroles / Q000378:metabolism* / Q000633:toxicity; D012977:Sodium Nitrite / Q000378:metabolism*; D013011:Sorbic Acid / Q000378:metabolism*
chemical_list: D009153:Mutagens; D011758:Pyrroles; C068648:1-nitro-2-methyl-4-aminopyrrole; C028453:2-methyl-1,4-dinitropyrrole; D012977:Sodium Nitrite; D013011:Sorbic Acid