The polar lipids from the hydrocarbon using and biosurfactant-producing bacterium Alcanivorax borkumensis were isolated and identified by mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy. The biosurfactant produced by this species is an anionic glucose lipid with a tetrameric oxyacyl side chain. The glycolipids extracted from the cell wall consist of this biosurfactant N-terminally esterified with glycine. Ten different derivatives of this lipid type were identified and their structures elucidated by MSMS. They vary by the chain length of one or two of the four L-hydroxy fatty acids (C6, C8 and C10) and by the location of these different fatty acids within the molecule. All compounds are reported here for the first time. In addition to these glycolipids, three different phosphatidylglycerols were identified. While these lipids were found in all strains of A. borkumensis, the relative abundances of the different lipids vary between the strains.

tandem mass spectrometry, glycolipid; biosurfactant, N-(glucopyranosyl-tetra(oxyacyl))-glycine, isobaric compound, Alcanivorax borkumensis

• Compound ID: 13383
  

  b-D-Glcp-(1-3)-3HODco-(1-3)-3HODco-(1-3)-3HODco-(1-3)-3HODco-(1-1)-Gly

  Show graphically

  Show legend Show as text

  Structure type: monomer ; 916 [M-H]-, 940 [M+Na]+
  Compound class: glycolipid
  Reference(s) to other database(s): GTC:G50859CR
  
   
  
  Alcanivorax borkumensis SK2 DSM11573
  CSDB ID 45541 (all data & tools)