, Volume 40, Issue 1, pp 97-108

First online:

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

  • J. -F. RontaniAffiliated withLaboratoire de Microbiologie de Géochimie et d'Ecologie Marines (UMR 6117) Email author 
  • , S. ChristodoulouAffiliated withLaboratoire de Microbiologie de Géochimie et d'Ecologie Marines (UMR 6117)
  • , M. KoblizekAffiliated withInstitute of MicrobiologyInstitute of Physical Biology, University of South Bohemia

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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.