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Subterminal hydroxylation of lauric acid by microsomes from a marine fish

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Lipids

Abstract

Microsomes from the liver of sea bass (Dicentrarchus labrax) were shown to hydroxylate lauric acid at subterminal positions. The cytochrome P-450 system converted lauric acid to several mono-hydroxylated metabolites including ω-1 hydroxylaurate, which was the major metabolite (44% of total products). In addition, ω-2, ω-3, ω-4 and a small amount (2.3%) of ω hydroxylaurates were found. Reaction products were identified using thin-layer chromatography (TLC) and gas chromatography/mass spectrometry (GC/MS). Oxidation reactions were dependent upon O2 and NADPH, and did not occur with boiled microsomes or in the presence of a mixture of CO/O2. Hydroxylation proceeded linearly up to 20 min at 28°C for protein concentrations below 380 μg. Treatment of fish with benzo(α)pyrene (BP) (20 mg/kg) drastically increased xenobiotic metabolism (ECOD, EROD and BPMO activities), but no difference in laurate hydroxylase activity was observed between untreated and treated fish. Starvation strongly enhanced laurate hydroxylase activity, and resumption of feeding reduced by half this increase of activity. In all of the experiments we did not observe any modification of the regioselectivity of lauric acid hydroxylation by this microsomal in-chain hydroxylating system. We suggest that cytochrome P-450 enzymes involved in lauric acid and xenobiotics metabolism are regulated independently.

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Abbreviations

BP:

benzo(α)pyrene

BPMO:

benzo(α)pyrene monooxygenase

ECOD:

7-ethoxycoumarinO-de-ethylase

EROD:

7-ethoxyresorufinO-de-ethylase

GC/MS:

gas chromatography/mass spectrometry

LAH:

lauric acid hydroxylase

RP-HPLC:

reverse phase high-performance liquid chromatography

TLC:

thin-layer chromatography

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Author notes

  1. Philippe Pflieger (Recipient of a Rhone-Poulenc Agrochimie Fellowship)

    Present address: Hofmann-La Roche Laboratories, Bau Labor 216, CH-4002, Basel, Switzerland

Authors and Affiliations

  1. Laboratoire de Biotransformation et de Cancérogénèse, Faculté de Médecine de Nice, F-06034, Nice-Cedex

    Philippe Lemaire & Marc Lafaurie

  2. Laboratoire de Chimie Bio-organique, Université Louis Pasteur-CNRS, UA 1386, F-67048, Strasbourg-Cedex, France

    Philippe Pflieger (Recipient of a Rhone-Poulenc Agrochimie Fellowship) & Charles Mioskowski

  3. Département d'Enzymologie Cellulaire et moléculaire, Institut de Biologie Moléculaire des Plantes, 28 rue Goethe, UPR 406, F-67083, Strasbourg-cedex, France

    Daniel Weissbart, Francis Durst & Jean-Pierre Salaün

Authors
  1. Philippe Lemaire
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  2. Marc Lafaurie
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  3. Daniel Weissbart
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  4. Francis Durst
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  7. Jean-Pierre Salaün
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Lemaire, P., Lafaurie, M., Weissbart, D. et al. Subterminal hydroxylation of lauric acid by microsomes from a marine fish. Lipids 27, 187–191 (1992). https://doi.org/10.1007/BF02536176

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  • DOI: https://doi.org/10.1007/BF02536176

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