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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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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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