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GC-MS structural characterization of fatty acids from marine aerobic anoxygenic phototrophic bacteria

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Lipids

Abstract

The FA composition of 12 strains of marine aerobic anoxygenic phototrophic bacteria belonging to the genera Erythrobacter, Roseobacter, and Citromicrobium was investigated. GC-MS analyses of different types of derivatives were performed to determine the structures of the main FA present in these organisms. All the analyzed strains contained the relatively rare 11-methyloctadec-12-enoic acid, and three contained 12-methyl-octadec-11-enoic acid, which has apparently never been reported before. High amounts of the very unusual octadeca-5,11-dienoic acid were present in 9 of the 12 strains analyzed. A FA containing a furan ring was detected in three strains. Analytical data indicated that this FA was 10,13-epoxy-11-methyloctadeca-10,12-dienoic acid. A very interesting enzymatic peroxidation of the allylic carbon 10 of cis-vaccenic acid was observed in three strains. Deuterium labeling and GC-MS analyses enabled us to demonstrate that this enzymatic process involves the initial dioxygenase-mediated formation of 10-hydroperoxyoctadec-11(cis)-enoic acid, which is then isomerized to 10-hydroperoxyoctadec-11(trans)-enoic acid and converted to the corresponding hydroxy-acids and oxoacids. Different biosynthetic pathways were proposed for these different compounds.

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Abbreviations

AAP:

aerobic anoxygenic phototrophs

Bchl:

bacteriochlorophyll

BSTFA:

bis(trimethylsily)trifluoroacetamide

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Authors and Affiliations

  1. Laboratoire de Microbiologie de Géochimie et d'Ecologie Marines (UMR 6117), 13288, Marseille, France

    J. -F. Rontani & S. Christodoulou

  2. Institute of Microbiology, 379 81, Trebon, Czech Republic

    M. Koblizek

  3. Institute of Physical Biology, University of South Bohemia, Nove Hrady, Czech Republic

    M. Koblizek

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  1. J. -F. Rontani
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  2. S. Christodoulou
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  3. M. Koblizek
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Correspondence to J. -F. Rontani.

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Rontani, J.F., Christodoulou, S. & Koblizek, M. GC-MS structural characterization of fatty acids from marine aerobic anoxygenic phototrophic bacteria. Lipids 40, 97–108 (2005). https://doi.org/10.1007/s11745-005-1364-6

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