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Regiospecific enzymatic oxygenation of cis-vaccenic acid during aerobic senescence of the halophilic purple sulfur bacterium Thiohalocapsa halophila

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Lipids

Abstract

A regiospecific oxygenation of the allylic carbon 10 of cis-vaccenic acid has been observed in senescent cells of the halophilic purple sulfur bacterium Thiohalocapsa halophila incubated under aerobic conditions in darkness. The results obtained strongly suggest that these enzymatic processes involve the initial dioxygenase-mediated formation of 10-hydroperoxyoctadec-cis-11-enoic acid, which is not accumulated in the cells of T. halophila owing to its high cytotoxic properties. Deuterium labeling and GC-MS analyses enabled us to demonstrate that subsequent enzymatic conversions of this allylic hydroperoxide involved reduction, cleavage, isomerization, and saturation reactions. Some of the specific oxidation products thus formed could constitute potential T. halophila biomarkers.

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Abbreviations

BSTFA:

bis(trimethylsilyl) trifluoroacetamide

DMDS:

dimethyl disulfide

TMS:

trimethylsilyl

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Authors and Affiliations

  1. Laboratoire d’Océanographie et de Biogéochimie (UMR 6535), Centre d’Océanologie de Marseille (OSU), campus de Luminy case 901, 13288, Marseille, France

    Daphné Marchand, Vincent Grossi & Jean-François Rontani

  2. Laboratoire de Microbiologie, IMEP, 13397, Marseille, France

    Agnès Hirschler-Rea

Authors
  1. Daphné Marchand
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  2. Vincent Grossi
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  3. Agnès Hirschler-Rea
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  4. Jean-François Rontani
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Correspondence to Jean-François Rontani.

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Marchand, D., Grossi, V., Hirschler-Rea, A. et al. Regiospecific enzymatic oxygenation of cis-vaccenic acid during aerobic senescence of the halophilic purple sulfur bacterium Thiohalocapsa halophila . Lipids 37, 541–548 (2002). https://doi.org/10.1007/s11745-002-0930-2

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  • DOI: https://doi.org/10.1007/s11745-002-0930-2

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