Metabolism of 2, 6-dimethylnaphthalene in starry flounder (Platichthys stellatus) exposed to naphthalene and p-cresol

Gruger, Edward H.; Schnell, Jerome V.; Fraser, P. S.; Brown, Donald W.; Malins, Donald C.

doi:10.1016/0166-445x(81)90005-9

Cited by 24 publications

(11 citation statements)

References 22 publications

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“…Many of the individual AH metabolites found in hydrolysed fish bile (table 5) were typical of metabolites that have been reported in laboratory studies (Roubal et al , Gruger et al 1981, LaVoie et al 1981. However, we identified two phenanthrols rather than the 1,2-dihydroxy-1,2-dihydrophenanthrene (phenanthrene dihydrodiol) reported by Solbakken and Palmork (1 981) as the major primary metabolite (>95%) of phenanthrene in flounder.…”

Section: Discussionsupporting

confidence: 59%

“…2,6-Dimethyl-3-naphthol, 6-methyl-2-naphthalenemethanol and trans-3,4-dihydroxy-3,4dihydro-2,6-dimethylnaphthalene were prepared in our laboratories (Gruger et al 1981 was prepared (listed in order of g.1.c. Phenanthrene-9-carboxaldehyde, 9-fluorenylmethanol, 9( 1 OH)-anthracenone, 9,10-anthraquinone, anthracene-9-carboxaldehyde, 9,lO-phenanthraquinone and 9-anthracenemethanol were purchased from Fluka Chemical (Hauppauge, NY, USA).…”

Section: Chemicals and Reference Standardmentioning

confidence: 99%

“…For example, recent studies in Puget Sound, WA, USA have linked certain idiopathic liver lesions, including neoplasms, in bottom-dwelling fish to aromatic hydrocarbons (AH) associated with the sediments . dihydrodiols and phenols) (Roubal et al 1977, Gruger et al 1981, Varanasi and Gmur 1981, but current routine analyses for AH do not assay for metabolites or other polar compounds. It is well established that AH taken up by the fish are readily converted to metabolites (e.g.…”

Section: Introductionmentioning

confidence: 99%

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Determination of metabolites of xenobiotics in the bile of fish from polluted waterways

et al. 1984

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An h.p.l.c.-fluorescence technique was used to estimate relative concentrations of metabolites of xenobiotics in bile of 103 English sole (Parophrys vetulus) from both polluted and minimally polluted (reference) sites in Puget Sound, WA. Fish from polluted sites had concentrations of xenobiotics in bile with naphthalene-, phenanthrene- and benzo[a]pyrene-like fluorescence that averaged 9, 14 and 19 times, respectively, those of fish from reference sites. Within a polluted site, fish with liver lesions had significantly higher bile concentrations of xenobiotics with benzo[a]pyrene-like fluorescence than did fish without liver lesions. Individual metabolites of fluorene, phenanthrene, anthracene, biphenyl and dimethylnaphthalene were determined by g.l.c.-mass spectrometry in extracts of hydrolysed bile of three English sole from polluted waterways; concentrations ranged from 90 to 19000 ng/g, wet wt. Other xenobiotics were tentatively identified, but not quantified.

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Section: Discussionsupporting

confidence: 59%

Section: Chemicals and Reference Standardmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Determination of metabolites of xenobiotics in the bile of fish from polluted waterways

et al. 1984

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“…Longer studies are needed to test these possibilities and to investigate whether uptake and depuration rates can be altered to even greater extents by induction or inhibition of other biochemical systems in fish. Furthermore, a variety of complex effluents and defined chemical mixtures will have t o be tested to better understand the environmental fates of complex chemical mixtures [4,6,14,22].…”

Section: Discussionmentioning

confidence: 99%

Anthracene Bioconcentration in Rainbow Trout During Single-Compound and Complex-Mixture Exposures

Linder¹,

Bergman²,

Meyer³

1985

Environ Toxicol Chem

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Rainbow trout were exposed for 72 h to ['4C]anthracene alone and [I4C]anthracene in an oil shale retort water. Tissue levels of ['4C]anthracene were analyzed at 24, 48 and 72 h to determine non-steady-state bicconcentration factors (BCFs), and uptake and depuration rates were calculated from anthracene disappearance in exposure waters and metabolite appearance in depuration waters. Uptake rates (14.6 to 16.9 h-I) were similar to previously reported values; however, depuration rates (0.00158 to 0.00188 h-I) were very low. Consequently, measured non-steadystate BCFs after 72 h (9, OOO to 9,200) for anthracene were higher than expected, probably because fish were not fed and had low excretion rates. Measured and estimated anthracene BCFs were lower in retort water exposures than in single-compound exposures because of slower uptake and faster depuration. We attribute slower uptake during retort water exposures to either decreased bioavailability of anthracene or rate-limiting transport of contaminants from uptake sites to storage and processing sites. Induction of mixed-function oxidases may have increased depuration from fish exposed to retort water. We conclude that bioconcentration of individual compounds from complex chemical mixtures may be difficult to predict based on single-compound kinetics.

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“…untersuchung(GRUGER et al; KOBAYASHI et al 1976 KOBAYASHI et al ,1977; LECH; STATHAM and LECII) sowiedeneigenen Befunden wird ein prinzipiellerAnal~.sengang vorgesc-hlagen (GRAHL) : Gewinnnng der erforderlichen Rlenge an Fischgalle Bonservierung und EnteiweiBung Vorfraktionierung durch Flussigextraktion oder andere Verfahren Bubfraktioniernng durch chromatographische Verfalireii i Differenzieriing der Xenobiotika bzw. typischer Metabolite von anderen Galleinhaltsstoffen, erforderlichenfalls durch Anwendung der enzpmatischen bzw.…”

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Zur Analytik von Chlorphenoxyalkansäuren und Chlorphenolen. Teil 2: Nachweis von Chlorphenoxyalkansäuren und Chlorphenolen in der Fischgalle

Grahl¹,

Hermenau²

1984

Acta hydrochim. hydrobiol.

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S"um/nary: The bile liquid is preserved with ethanol and the protein is precipitated. Prefractionating is done by liquid-liquid Pxtraction by chloroform and ethyl aceta.t,e. The extra& are eo-1 nmn-chromatographically separated on Florisil and subsequently detect,ed by t hin-layer chromatography. For determining the identit,g of substances, the penta fluorobenzyl derivatives are prepared and chromatographed under the same conditions. Detection is carried out. with the aid of aiiinioiiiacal silver nitrate reagency and ultraviolet irradiat,ion. The highly polar conjugates of chlorophenoxyalkane acids and chlorophenols which are present in the bile are cracked by acid hydrolysis and then cleaned by re-extraction. I n this way, 2, 4-D, MCPA, MCPP, 2,4-dichlorophenol and 2-methyl-4-chlorophenol were detected from Salmo gnirdneri. 6 ... 21 d after t,he application of t,he herbicides in the catchment area their concentration in the fish bile amounted to about 200 mgil, 90 O;,, of them having been conjiipat,es. Thus, the biliary excretion of xenobiotic substances offers an important new aspect of biomonitoring by means of fish tests, especially in the raiige of subacute and chronic toxicity.

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Metabolism of 2, 6-dimethylnaphthalene in starry flounder (Platichthys stellatus) exposed to naphthalene and p-cresol

Cited by 24 publications

References 22 publications

Determination of metabolites of xenobiotics in the bile of fish from polluted waterways

Determination of metabolites of xenobiotics in the bile of fish from polluted waterways

Anthracene Bioconcentration in Rainbow Trout During Single-Compound and Complex-Mixture Exposures

Zur Analytik von Chlorphenoxyalkansäuren und Chlorphenolen. Teil 2: Nachweis von Chlorphenoxyalkansäuren und Chlorphenolen in der Fischgalle

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