J. Lipid Res.
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Originally published In Press as doi:10.1194/jlr.M400278-JLR200 on October 1, 2004

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Journal of Lipid Research, Vol. 45, 2317-2330, December 2004
Copyright © 2004 by American Society for Biochemistry and Molecular Biology

Structures and biological activity of phosphorylated dihydroceramides of Porphyromonas gingivalis

Frank C. Nichols1,*, Birgit Riep*,{dagger}, JiYoung Mun§, Martha D. Morton§, Mike T. Bojarski*, Floyd E. Dewhirst** and Michael B. Smith§

* Department of Periodontology, University of Connecticut School of Dental Medicine, 263 Farmington Avenue, Farmington, CT
{dagger} Department of Periodontology and Synoptic Dentistry, Charité University of Medicine Berlin, Augustenburger Platz 1, Berlin, Germany
§ Department of Chemistry, U3060 University of Connecticut, 55 North Eagleville Road, Storrs, CT
** Department of Molecular Genetics, Forsyth Institute, 140 The Fenway, Boston, MA

1 To whom correspondence should be addressed. e-mail: nichols{at}nso.uchc.edu

Porphyromonas 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 isoC17:0 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-1ß (IL-1ß)-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-1ß-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-1ß-treated fibroblasts and to produce marked alterations in cell morphology in culture.

Supplementary key words phosphoethanolamine ceramide • phosphoglycerol dihydroceramide • interleukin-1ß • prostaglandin E2 • gingival fibroblast • long-chain base • gas chromatography-mass spectrometry • electrospray MS/MS


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 J. Dent. Res.Home page
J. Zahlten, B. Riep, F.C. Nichols, C. Walter, B. Schmeck, J.-P. Bernimoulin, and S. Hippenstiel
Porphyromonas gingivalis Dihydroceramides Induce Apoptosis in Endothelial Cells
J. Dent. Res., July 1, 2007; 86(7): 635 - 640.
[Abstract] [Full Text] [PDF]

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 J. Lipid Res.Home page
F. C. Nichols, B. Riep, J. Mun, M. D. Morton, T. Kawai, F. E. Dewhirst, and M. B. Smith
Structures and biological activities of novel phosphatidylethanolamine lipids of Porphyromonas gingivalis
J. Lipid Res., April 1, 2006; 47(4): 844 - 853.
[Abstract] [Full Text] [PDF]


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