Structure activity characterization of Bordetella petrii lipid A, from environment to human isolates

Biochimie. 2016 Jan;120:87-95. doi: 10.1016/j.biochi.2015.07.006. Epub 2015 Jul 8.


Bordetella petrii, a facultative anaerobic species, is the only known member of the Bordetella genus with environmental origin. However it was also recently isolated from humans. The structures of the B. petrii lipid A moieties of the endotoxins were characterized here for the first time for an environmental strain and compared to that of human isolates. Characterization was achieved using chemical analyses, gas chromatography-mass spectrometry, and Matrix Assisted Laser Desorption Ionisation mass spectrometry. The analyses revealed that the different lipid A structures contain a common bisphosphorylated β-(1→6)-linked d-glucosamine disaccharide with hydroxytetradecanoic acid in amide as well at the C-3' in ester linkages. Similar to Bordetella pertussis and Bordetella bronchiseptica lipids A, the hydroxytetradecanoic acid at the C-2' position was substituted by tetradecanoic acid. Unlike B. pertussis, the hydroxytetradecanoic acid at the C-2 position was substituted with either 12:0 or 14:0 and/or their 2-OH forms. Depending on the environmental or human origin the structures differed in the length and degree of fatty acid acylation and impacted the IL-6 and TNF-α inflammatory responses tested. In one isolate we showed the presence at the C-3 position of the short-chain 10:0(3-OH), which according to our previous analyses is more characteristic of the human pathogens in the genus like B. pertussis and Bordetella parapertussis.

Keywords: Bordetella; Bordetella petrii; Endotoxin; Lipid A; Structure–activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bordetella / chemistry*
  • Bordetella / isolation & purification
  • Cell Line, Tumor
  • Female
  • Humans
  • Interleukin-6 / biosynthesis*
  • Lipid A* / chemistry
  • Lipid A* / isolation & purification
  • Lipid A* / toxicity
  • Male
  • Mass Spectrometry
  • Monocytes / metabolism*
  • Structure-Activity Relationship
  • Tumor Necrosis Factor-alpha / biosynthesis*


  • IL6 protein, human
  • Interleukin-6
  • Lipid A
  • Tumor Necrosis Factor-alpha