Naphthalene metabolites

Figure 1. Autoradiograc of thin layer chromatograErfiy plate showing solvent extractable naphthalene metabolites (A, B, C, D) produced by transformants Nah 1, Nah 25, Nah 28, B. megaterium, and B. subtilis. ...

Zinkham WH, Childs B. 1957. Effect of vitamin K and naphthalene metabolites on glutathione metabolism of erythrocytes from normal newborns and patients with naphthalene hemolytic anemia. Am J Dis Child 94 420-423. 

Simple naphthalene metabolites (146 and 147) were produced by Verticillium lamellicola [175] and (148) found in the fungus Scolecobasidiella avellanea. 

A number of LC tandem MS methods have been reported for OPAHs in environmental samples and biological fluids. Ramsauer et al. [48] and Andreoli et al. [49] describe LC—ESI—MS/MS methods for the determination of PAH metabolites in human urine. Andreoli et al. specifically targeted naphthalene metabolites for study for occupationally exposed workers, while Ramsauer et al. studied a broader range of hydroxylated PAHs in urine from smokers and nonsmokers. Levels of hydroxyl PAHs in smokers urine were also measured by Jacob, Wilson, and Benowitz [50] by LC—APCl—MS/MS however, this method utilized a derivitization step with pentafluorobenzyl bromide to increase sensitivity. LC—APCl—MS/ MS was employed by Fan et al. [51] to determine 1-hydroxypyrene and 3-hydroxybenzo[fl]pyrene in urine. 

AndreoU R, Manini P, Bergamaschi E, Mutti A, Franchini 1, Niessen WMA, et al. Determination of naphthalene metabolites in human urine by liquid chromatography-mass spectrometry with electrospray ionization. J Chromatogr A 1999 847(1—2) 9—17. 

Kelley I, JP Freeman, CE Cerniglia (1990) Identification of metabolites from degradation of naphthalene by a Mycobacterium sp. Biodegradation 1 283-290. 

Initially formed polar metabolites such as phenols and amines may be conjugated to water-soluble terminal metabolites that are excreted into the medium and function as an effective mechanism of detoxification. For example, pentachlorophenol and pentachlorothiophenol produced from pentachloronitrobenzene conjugated represented the major metabolites. Although the naphthalene dihydrodiol was the major metabolite produced from naphthalene, the further transformation... 

Collier TK, LC Thomas, DC Malins (1978) Influence of environmental temprature on disposition of dietary naphthalene in coho salmon (Oncorhynchus kisutch) isolation and identification of individual metabolites. Comp Biochem Physiol 61C 23-28. 

Naphth-l-ol is an established fungal metabolite of naphthalene and may play a role in the association of naphthalene with humic material (Burgos et al. 1996). 

The bacterial aerobic degradation of pyrene is initiated by the formation of cfi-pyrene-4,5-dihydrodiol. Analysis for this metabolite was used to demonstrate the biodegradability of pyrene in an environment in which there was continuous input of the substrate, when it was not possible to use any diminution in its concentration as evidence for biodegradation (Li et al. 1996). The corresponding metabolite from naphthalene—cfi-naphthalene-1,2-dihydrodiol—has been used to demonstrate biodegradation of naphthalene both in site-derived enrichment cultures and in leachate from the contaminated site (Wilson and Madsen 1996). 

Heitkamp MA, JP Freeman, CE Cerniglia (1987) Naphthalene biodegradation in environmental microcosms estimates of degradation rates and characterization of metabolites. Appl Environ Microbiol 53 129-136. 

Wilson MS, EL Madsen (1996) Field extraction of a transient intermediary metabolite indicative of real time in situ naphthalene biodegradation. Environ Sci Technol 30 2099-2103. 

Allen CCR, DR Boyd, H Dalton, ND Sharma, I Brannigan, NA Kerley, GN Sheldrake, SC Taylor (1995) Enantioselective bacterial biotransformation routes to cw-diol metabolites of monosubstituted benzenes, naphthalene and benzocycloalkenes of either absolute configuration. J Chem Soc Chem Commun 117-118. 

The presence of metabolites determined from laboratory experiments of degradation pathways. Examples inclnde (a) di-dihydrodiols of PAHs in a marine sediment (Li et al. 1996) and naphthalene in leachate from a contaminated site (Wilson and Madsen 1996),... 

Metabolites may also play a role in the association of the substrate with humic and fulvic acid components. Two illustrations are given (a) naphth-l-ol, an established fungal metabolite of naphthalene, may play a role in the association of naphthalene with humic material (Burgos et al. 1996) and (b) it has been shown that C-labeled metabolites of [9- C]-anthracene including 2-hydroxyanthracene-3-carboxylate and phthalate were not extractable from soil with acetone or dichloromethane, and required alkaline hydrolysis for their recovery (Richnow et al. 1998). 

A sulfate enrichment culture prepared from a contaminated site gave enrichment factors (e) of-1.1 for naphthalene and -0.9 for 2-methylnaphthalene (Griebler et al. 2004). These values combined with literature values from analogous laboratory experiments were used to quantify degradation of toluene, xylenes, and naphthalene at the site. Additional evidence for degradation of BTEX was derived from analyses of established metabolites produced by anaerobic degradation. 

Human activities have resulted in exposure of Antarctic fishes to petroleum-derived PAHs (McDonald et al. 1992). Fish captured near Palmer station on the Antarctic peninsula had induced EROD activities and elevated concentrations of biliary PAH metabolites of phenanthrene and naphthalene when compared to conspecifics from reference sites (McDonald et al. 1995). Artificial reefs consisting of oil and coal flyash stabilized with cement and lime in Florida waters near Vero Beach contained elevated PAH levels ranging from as high as 1.2 mg fluoranthene/kg and 0.25 mg naphthalene/kg. But there is negligible leaching because seawater is not an effective medium for removing PAHs from reef bricks or the ash (Frease and Windsor 1991). 

Table III. Accumulation and release of naphthalene and its metabolites in skin of rainbow trout...

Roubal et al. (8) applied TLC to the separation and identification of metabolites of l c-iabeled naphthalene administered to coho salmon fingerlings via intraperitoneal injection. 1-Naphthol, a dihydrodiol, mercapturic acid, 1-naphthyl glucuronic acid and a glycoside/sulfate fraction were identified in brain, liver, gall bladder, and muscle 1-naphthol, a dihydrodiol, and 1-naphthyl glucuronic acid were the only metabolites found in heart. 

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