Fate of naphthenic hydrocarbons in the bile of rainbow trout (<i>Salmo gairdneri</i>)

Hellou, Jocelyne; Banoub, Joseph; Ryan, A J

doi:10.1002/etc.5620081005

Cited by 10 publications

(6 citation statements)

References 23 publications

(16 reference statements)

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“…The metabolism of PAHs proceeds in two stages. Oxidation products are formed in the first stage, and these compounds further react to form various conjugates such as glu-coronides, sulphates, or amino acid or glutathione derivatives (Hellou et al, 1989;Hellou and Upshall, 1995). These more polar derivatives can then be eliminated from the organisms through the gall bladder bile (Hellou and Payne, 1987).…”

Section: Metabolismmentioning

confidence: 99%

Contamination of Fish and Shellfish Following Oil Spill Incidents

Law

Hellou

1999

Environ Geosci

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ABSTRACT• Accidents and spillages are an inevitable consequence of the worldwide transport of crude oil and refined petroleum products by sea. The number of major spills occurring each year has decreased since the 1970s, but spillages and operational discharges from tankers nonetheless constitute a significant input of oil to the marine environment. The rapid uptake of oil and polycyclic aromatic hydrocarbons (PAHs) by exposed fish and shellfish, resulting from large oil spillages in coastal waters, poses a potential threat to human consumers of fish and shellfish and also affects the marketability of catches. In this article, the processes influencing uptake and retention of PAHs in fish and shellfish are outlined by drawing on the experience gained from previous incidents. This includes particular reference to three recent major oil spills from tankers in the United Kingdom and the United States, those involving the Exxon Valdez, Braer, and Sea Empress, and to the resulting contamination of local stocks. A more uniform approach to oil spill monitoring would aid comparisons between spills and would help interpret the kinetics and dynamics of released hydrocarbons in future cases. Currently, no statutory limits or guideline values have been established for PAHs in edible tissues of fish or shellfish, whether derived from oil or combustion sources.

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Section: Metabolismmentioning

confidence: 99%

Contamination of Fish and Shellfish Following Oil Spill Incidents

Law

Hellou

1999

Environ Geosci

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“…A typical conjugation reaction is with glucuronic acid to form glucuronides in the liver. These are transported to the gall bladder for later elimination [11]. In this study, gall bladder bile, obtained from fish orally exposed in the laboratory to individual PACs representing tri‐, tetra‐, and penta‐cyclic aromatic hydrocarbons and heteroaromatic compounds, was analyzed, without pretreatment, by high‐performance liquid chromatography (HPLC) with fluorescence (F) and ultraviolet (UV) detection.…”

Section: Introductionmentioning

confidence: 99%

Separation and characterization of gall bladder bile metabolites from speckled trout, Salvelinus fontinalis, exposed to individual polycyclic aromatic compounds

Leonard

Hellou

2001

Enviro Toxic and Chemistry

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Speckled trout, Salvelinus fontinalis, were orally exposed to individual polycyclic aromatic compounds (PACs) represented by benzo[a]pyrene, carbazole, chrysene, dibenzofuran, dibenzothiophene, fluorene, phenanthrene, and pyrene. Fish were sacrificed 7 d after exposure and the gall bladder removed for bile analysis. High pressure liquid chromatography (HPLC) with fluorescence (F) and ultraviolet (UV) detection was used to determine the presence of PAC derivatives in the bile without pretreatment. Glucuronide conjugates were predominant in all exposures with variable amounts (0-53%) of phenols and starting material. Identification of compounds was confirmed by selective extraction of less polar nonconjugated PACs and enzymatic hydrolysis of water-soluble material. This was followed by HPLC and/or gas chromatography-mass spectrometry (GCMS) characterization of the produced phenols. Total metabolite levels varied widely among compounds.

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“…(Hellou et al 1989). A temperature program starting at 50 or 100°C for 1 min and then increasing to 250°C at S°C/min was employed for DHPG and resorcinol, respectively.…”

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confidence: 99%

“…Resorcinol was acetylated and detected by GC-MS (Hellou et al 1989). The DHPG preparative solution (1 mg/mL, 25 mL) was acidified to pH 2.0 with concentrated HCl and the clear acidified liquid was extracted for 24 h in an oscillating (100 rpm) separatory funnel containing 50 mL of ethyl acetate.…”

mentioning

confidence: 99%

“…The DHPG preparative solution (1 mg/mL, 25 mL) was acidified to pH 2.0 with concentrated HCl and the clear acidified liquid was extracted for 24 h in an oscillating (100 rpm) separatory funnel containing 50 mL of ethyl acetate. The organic phase was evaporated to dryness and acetylated in acetic anhydride and pyridine at room temperature for 12 h; the products were compared with the authentic acetylated standards by GC-MS (Hellou et al 1989;Hellou and Payne 1987). Resorcinol was detected by TLC (Randerath 1963), in the solvent system benzene : dioxane : acetic acid (60:36:4), and by uv spectrophotometry (Shimadzu UV-260 recording spectrophotometer) (Armstrong and Patel 1993;Patel et al 1990).…”

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confidence: 99%

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Abiotic conversion of dihydrophloroglucinol to resorcinol

Armstrong¹,

Patel²

1993

Can. J. Microbiol.

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Chemical conversion of a dihydrophloroglucinol preparation (a mixture of the tautomers 1,3,5-trihydroxy-1,3-cyclohexadiene, 1,3-dioxo-5-hydroxycyclohexane, and 3,5-dihydroxy-3-cyclohexene-1-one) to resorcinol occurred during a 24-h extraction of an acidic (pH 2.0) aqueous dihydrophloroglucinol preparation into ethyl acetate. This conversion did not occur at neutral pH, nor did phloroglucinol (1,3,5-trihydroxybenzene)-induced or succinate-induced Penicillium simplicissimum enzyme extracts convert the dihydrophloroglucinol preparation to resorcinol at pH values of 5.5–8.0. The chemical structure of the dihydrophloroglucinol preparation was determined by gas chromatography - mass spectrometry, high resolution 13C and 1H nuclear magnetic resonance, Fourier-transformed infrared spectrometry, and ultraviolet spectrophotometry. Resorcinol (1,2-dihydroxybenzene) was detected by gas chromatography - mass spectrometry or thin-layer chromatography and ultraviolet spectrophotometry. A chemical mechanism for the conversion of the dihydrophloroglucinol preparation to resorcinol is proposed.Key words: dihydrophloroglucinol, chemical conversion, resorcinol.

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Fate of naphthenic hydrocarbons in the bile of rainbow trout (Salmo gairdneri)

Cited by 10 publications

References 23 publications

Contamination of Fish and Shellfish Following Oil Spill Incidents

Contamination of Fish and Shellfish Following Oil Spill Incidents

Separation and characterization of gall bladder bile metabolites from speckled trout, Salvelinus fontinalis, exposed to individual polycyclic aromatic compounds

Abiotic conversion of dihydrophloroglucinol to resorcinol

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