Biphenyls metabolism

Bedard DL, ML Haberl, RJ May, MJ Brennan (1987) Evidence for novel mechanisms of polychlorinated biphenyl metabolism in Alcaligenes eutrophus H %50. Appl Environ Microbiol 53 1103-1112. 

S. Safe and O. Hutzinger, Polychlorinated Biphenyls Photolysis of 2,4,6,2, 6 Hexachlorobiphenyl, Nature232 (1971) 641-42 O. Hutzinger et al., Polychlorinated Biphenyls Metabolic Behavior of Pure Isomers in Pigeons, Rats, and Brook Trout, Science 178 (1972) 512-14 O. Hutzinger et al., Identification of Metabolic Dechlorination of Highly Chlorinated Biphenyl in Rabbits, Nature 252 (1974) 698-99. 

Following on his pioneering work from 1973, Focht and colleagues expanded their research to new bacterial strains and applications of these cultures. This work initially focused on the Acinetobacter P6 strain of Furukawa and utilized 14C-labeled PCBs to demonstrate the extent of mineralization that could be observed with Aroclors under conditions of biphenyl metabolism and bacterial inoculation of soils... 

Focht, D. D. Brunner, W. (1985). Kinetics of biphenyl and polychlorinated biphenyl metabolism in soil. Applied and Environmental Microbiology, 50, 1058-63. 

Hutzinger, O. Nash, D.M. Safe, S. DeFreitas, A.S.W. Norstrom, R.J. Wildish, D.J. Zitko, V, Polychlorinated biphenyls Metabolic behavior of pure isomers in pigeons, rats, and brook trout Science 1978, 178, 312-314. 

Degradation of DDT by Alcaligenes eutrophus strain A5 resulted in the formation of both ring-hydroxylated metabolites and 4-chlo-robenzoate (Nadeau et al. 1994). It was subsequently shown (Nadeau et al. 1998), however, that the phenolic compounds were artifacts produced by nonenzymatic reactions and do not lie on the pathway of degradation, and that cells of this strain grown with biphenyl metabolized DDT to the czs-2,3-dihydrodiol. 

Uhlik O, Strejcek M, Junkova P, Sanda M, Hroudova M, Vlcek C, Mackova M, Macek T. Matrix-assisted laser desorption ionization (MALDl)-time of flight mass spectrometry- and MALDl biotyper-based identification of cultured biphenyl-metabolizing bacteria from contaminated horseradish rhizosphere soil. Appl Environ Microbiol. 2011 77(19) 6858-66. doi 10.1128/ aem.05465-11. 

Borlakogln, J.T., Wilkins, J.P.G., and Walker, C.H. (1988). Polychlorinated biphenyls in sea birds—molecnlar features and metabolic interpretations. Marine Environmental Research 24, 15-19. 

Aislabie J, AD Davison, HL Boul, PD Franzmann, DR Jardine, P Karuso (1999) Isolation of Terrabacter sp. strain DDE-1, which metabolizes l,l-dichloro-2-2-bis(4-chlorophenyl)ethylene when induced with biphenyl. Appl Environ Microbiol 65 5607-5611. 

A cytochrome P450 has been purified from Saccharomyces cerevisiae that has benzo[a]pyrene hydroxylase activity (King et al. 1984), and metabolizes benzo[fl]pyrene to 3- and 9-hydroxybenzo[fl]pyrene and benzo[fl]pyrene-7,8-dihydrodiol (Wiseman and Woods 1979). The transformation of PAHs by Candida Upolytica produced predominantly monohydroxyl-ated products naphth-l-ol from naphthalene, 4-hydroxybiphenyl from biphenyl and 3- and 9-hydroxybenzo[fl]pyrene from benzo[fl]pyrene (Cerniglia and Crow 1981). The transformation of phenanthrene was demonstrated in a number of yeasts isolated from littoral sediments and of these, Trichosporumpenicillatum was the most active. In contrast, biotransformation of benz[fl]anthracene by Candida krusei and Rhodotorula minuta was much slower (MacGillivray and Shiaris 1993). 

Dodge RH, CE Cerniglia, DT Gibson (1979) Fungal metabolism of biphenyl. Biochem J 178 223-230. 

Golbeck JH, SA Albaugh, R Radmer (1983) Metabolism of biphenyl by Aspergillus toxicarius induction of hydroxylating activity and accumulation of water-soluble conjugates. J Bacteriol 156 49-57. 

Denef VJ, MA Patrauchan, C Florizone, J Park, TV Tsoi, W Verstraete, JM Tiedje, LD Eltis (2005) Growth substrate- and phase-specific expression of biphenyl, benzoate, and Cl metabolic pathways in Burkhold-eria xenovorans LB400. J Bacterial 187 7996-8005. 

Furukawa K, N Tomizuka, A Kamibayashi (1979) Effect of chlorine substitution on the bacterial metabolism of various polychlorinated biphenyls. Appl Environ Microbiol 38 301-310. 

Table I. Optical Purity of the Dihydrodiol Metabolites Formed in the Metabolism of Benzo[a]pyrene by Liver Microsomes from Untreated, Phenobarbital (PB)-, 3-Methylcholanthrene (3MC)-, and Polychlorinated Biphenyls (PCBs, Aroclor 1254)-Treated Rats...

Borlakoglu, J.T., J.P.G. Wilkins, C.H. Walker, and R.R. Dils. 1990. Polychlorinated biphenyls (PCBs) in fisheating seabirds. III. Molecular features and metabolic interpretations of PCB isomers and congeners in adipose tissues. Comp. Biochem. Physiol. 97C 173-177. 

Elskus, A.A., J J. Stegeman, J.W. Gooch, D.E. Black, and R.J. Pruell. 1994. Polychlorinated biphenyl congener distributions in winter flounder as related to gender, spawning site, and congener metabolism. Environ. Sci. Technol. 28 401-407. 

Sipes, I.G. and R.G. Schnellmann. 1987. Biotransformation of PCBs metabolic pathways and mechanisms. Pages 97-110 in S. Safe (ed.). Polychlorinated Biphenyls (PCBs) Mammalian and Environmental Toxicology. Environ. Toxin Ser. 1. Springer-Verlag, New York. 

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