Naphthalene, metabolization

Cerniglia CE, DT Gibson, C van Baalen (1982) Naphthalene metabolism by diatoms isolated from the Kachemak Bay region of Alaska. J Gen Microbiol 128 987-990. 

Patel TR, EA Barnsley (1980) Naphthalene metabolism by pseudomonads purification and properties of... 

If PAH-degrading microorganisms use broad-specificity enzymes or common pathways to transform multiple PAHs, then inducers for the metabolism of one PAH substrate might co-induce the transformation of a range of PAHs. Preliminary evidence indicated that the transformation of naphthalene, phenanthrene, fluoranthene, and pyrene by Pseudomonas saccharophila P15 was stimulated by salicylate [132], a known inducer of naphthalene metabolism in pseudomonads [43]. However, Chen and Aitken [181] reported in more detail the inducing effects of salicylate on the transformation of various HMW PAHs by Pseudomonas saccharophila P15 isolated from contaminated soil, including... 

Barnsley, E. A. (1976a). Naphthalene metabolism by pseudomonads The oxidation of 1,2-dihydroxynaphthalene to 2-hydroxychromene-2-carboxylic acid and the formation of 2 -hydroxybenzalpyruvate. Biochemistry and Biophysics Research Communications, 72, 1116-21. 

Several naphthalene-degrading Pseudomonas spp. were able to metabolize monochloro-naphthalene, but the chloronaphthalene did not support growth [34], as an example of cometabolism. Ihe cometabolism of monochloro-naphthalene is dependent on the normal enzymes of naphthalene metabolism, which are induced during the process. 

Lewis DF, Ito Y, Lake BG (2009) Molecular modelling of CYP2F substrates comparison of naphthalene metabolism by human, rat and mouse CYP2F subfamily enzymes. Drug Metab Drug Interact 24 229-257... 

Gorsline, J., and W.N. Holmes. 1981. Effects of petroleum on adrenocortical activity and on hepatic naphthalene-metabolizing activity in mallard ducks. Archives of Environmental Contamination and Toxicology 10 765-777. 

Some green algae are able to use aromatic sulfonic acids (Figure 2.4a) (Soeder et al. 1987) and aliphatic sulfonic acids (Figure 2.4b) (Biedlingmeier and Schmidt 1983) as sources of sulfur. Cultures of Scenedesmus obliquus under conditions of sulfate limitation metabolized naphthalene-l-sulfonate to l-hydroxy-naphthalene-2-sulfonate and the gluco-side of naphth-l-ol (Kneifel et al. 1997). These results are consistent with formation of a 1,2-epoxide followed by an NIH shift. 

Salicylate is an intermediate in the metabolism of PAHs including naphthalene and phen-anthrene, and its degradation involves oxidation to catechol. The hydroxylase (monooxygenase) has been extensively studied (references in White-Stevens and Kamin 1972) and in the presence of an analog that does not serve as a substrate, NADH is oxidized with the production of H2O2 (White-Stevens and Kamin 1972). This uncoupling is characteristic of flavoenzymes and is exemplified also by the chlorophenol hydroxylase from an Azotobacter sp. that is noted later. 

Eaton RW, PJ Chapman (1992) Bacterial metabolism of naphthalene construction and use of recombinant bacteria to study ring cleavage of 1,2-dihydroxy naphthalene and subsequent reactions. J Bacteriol 174 7542-7554. 

Zhang X, LY Young (1997) Carboxylation as an initial reaction in the anaerobic metabolism of naphthalene and phenanthrene by sulfidogenic consortia. Appl Environ Microbiol 63 4759-4764. 

FIGU RE 8.1 Alternative pathways for the oxidative metabolism of naphthalene by (a) bacteria and (b) fungi. 

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). 

Allen CC, DR Boyd, Ml Larkin, KA Reid, ND Sharma, K Wilson (1997) Metabolism of naphthalene, 1-naphthol, indene, and indole by Rhodococcus sp. strain NCIMB 12038. Appl Environ Microbiol 63 151-155. 

Annweiler E, W Michaelis, RU Meckenstock (2002) Identical ring cleavage products during anaerobic degradation of naphthalene, 2-methylnaphthalene, and tetralin indicate a new metabolic pathway. Appl Environ Microbiol 68 853-858. 

Barnsley EA (1976) Role and regulation of the ortho and meta pathways of catechol metabolism in pseudomonads metabolizing naphthalene and salicylate. J Bacteriol 125 404-408. 

Cerniglia CE, JR Althus, EE Evans, JP Freeman, RK Mitchum, SK Yang (1983) Stereochemistry and evidence for an arene oxide-NIH shift pathway in the fungal metabolism of naphthalene. Chem-Biol Interactions 44 119-132. 

Cerniglia CE, RL Herbert, PJ Szaniszlo, DT Gibson (1978) Fungal metabolism of naphthalene. Arch Microbiol 117 135-143. 

Pinphanichakarn P (2006) Novel intermediates of acenaphthylene degradation by Rhizobium sp. strain CU-Al evidence for naphthalene-1-8-dicarboxylic acid metabolism. Appl Environ Microbiol 72 6034-6039. 

Dihydroxybiphenyl 1,2-dioxygenase from the naphthalene sulfonate-degrading Sphin-gomonas sp. strain BN6 metabolized 3-chlorocatechol by extradiol fission between the 1- and 6-positions (distal fission) (Riegert et al. 1998)... 

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