Document Detail

Structures and biological activity of phosphorylated dihydroceramides of Porphyromonas gingivalis.
MedLine Citation:
PMID:  15466368     Owner:  NLM     Status:  MEDLINE    
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 isoC(17:0) 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 isoC(15:0) linked to the hydroxyl of 3-OH isoC(17:0), significantly potentiated interleukin-1beta (IL-1beta)-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-1beta-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-1beta-treated fibroblasts and to produce marked alterations in cell morphology in culture.
Frank C Nichols; Birgit Riep; JiYoung Mun; Martha D Morton; Mike T Bojarski; Floyd E Dewhirst; Michael B Smith
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2004-10-01
Journal Detail:
Title:  Journal of lipid research     Volume:  45     ISSN:  0022-2275     ISO Abbreviation:  J. Lipid Res.     Publication Date:  2004 Dec 
Date Detail:
Created Date:  2004-11-19     Completed Date:  2005-04-22     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0376606     Medline TA:  J Lipid Res     Country:  United States    
Other Details:
Languages:  eng     Pagination:  2317-30     Citation Subset:  IM    
Department of Periodontology, University of Connecticut School of Dental Medicine, 263 Farmington Avenue, Farmington, CT, USA.
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MeSH Terms
Ceramides / chemistry,  metabolism*
Fibroblasts / metabolism
Gingiva / cytology,  metabolism
Porphyromonas gingivalis / metabolism*
Spectrometry, Mass, Electrospray Ionization
Reg. No./Substance:
0/Ceramides; 0/dihydroceramide

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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