Structures and biological activity of phosphorylated dihydroceramides of Porphyromonas gingivalis

Frank C. Nichols, Birgit Riep, Ji Young Mun, Martha D. Morton, Mike T. Bojarski, Floyd E. Dewhirst, Michael B. Smith

Research output: Contribution to journalArticlepeer-review

56 Scopus citations


Porphyromanas gingivalis, a recognized periodontal pathogen, synthesizes free ceramides as well as other phosphorylated ceramide lipids. The purpose of this study was to separate complex lipids of P. gingivalis by high-performance liquid chromatography (HPLC) and determine the structures and biological activities of the major ceramide classes. Using gas chromatography-mass spectrometry, electrospray tandem mass spectrometry (ESI-MS/MS) and NMR analyses, three major classes of dihydroceramides were identified in specific HPLC fractions, with all classes containing the same dihydroceramide base structures (3-OH isoC17:10 in amide linkage to saturated long-chain bases of 17, 18, or 19 carbons). The free dihydroceramide class recovered in HPLC fractions 7-8 revealed little biological activity. HPLC fraction 20 dihydroceramides, substituted with 1-O-phosphoglycerol and isoC15:0 linked to the hydroxyl of 3-OH isoC17:0, significantly potentiated interleukin-1β (IL-1β) (-mediated prostaglandin secretion and produced marked alterations in fibroblast morphology. HPLC fraction 28 dihydroceramides, substituted with 1-O-phosphoethanolamine, demonstrated little capacity to potentiate IL-1β-mediated prostaglandin secretion. The novel phosphorylated dihydroceramides synthesized by P. gingivalis demonstrate varying biological activities based on the phosphorylated head group substitution and/or the addition of esterified fatty acid. These results also demonstrate the strong virulence capacity of phosphoglycerol dihydroceramides of P. gingivalis to promote inflammatory factor secretion from IL-1 β-treated fibroblasts and to produce marked alterations in cell morphology in culture.

Original languageEnglish (US)
Pages (from-to)2317-2330
Number of pages14
JournalJournal of Lipid Research
Issue number12
StatePublished - Dec 2004
Externally publishedYes


  • Electrospray MS/MS
  • Gas chromatography-mass spectrometry
  • Gingival fibroblast
  • Interleukin-1β
  • Long-chain base
  • Phosphoethanolamine ceramide
  • Phosphoglycerol dihydroceramide
  • Prostaglandin E

ASJC Scopus subject areas

  • Biochemistry
  • Endocrinology
  • Cell Biology


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