Document Detail

Structural characterization of a novel class of glycophosphosphingolipids from the protozoan Leptomonas samueli.
MedLine Citation:
PMID:  1447177     Owner:  NLM     Status:  MEDLINE    
Aqueous phenol extraction of the lower trypanosomatid Leptomonas samueli released into the aqueous layer a chloroform/methanol/water-soluble glycophosphosphingolipid fraction. Alkaline degradation and purification by gel filtration chromatography resulted in a tetrasaccharide (phosphatidylinositol (PI)-oligosaccharide A), and a pentasaccharide (PI-oligosaccharide B), each containing 2 mol of 2-aminoethylphosphonate and 1 mol of phosphate. Nuclear magnetic resonance spectroscopy and fast atom bombardment-mass spectrometry suggested that the structure of PI-oligosaccharide A is [formula: see text] and that of PI-oligosaccharide B is as shown. [formula: see text] Both compounds contain an inositol unit linked to ceramide via a phosphodiester bridge. The major aliphatic components of the ceramide portion are stearic acid, lignoceric acid, and C20-phytosphingosine. These novel glycolipids fall within the glycosylated phosphatidylinositol (GPI) family, since they contain the core structure Man alpha (1-->4)GlcNH2 alpha (1-->6)myo-inositol-1-PO4, which is also found in the glycoinositolphospholipids and lipophosphoglycan of Leishmania spp., the L. major promastigote surface protease, the glycosylphosphatidylinositol anchor of Trypanosoma brucei variant surface glycoprotein, and the lipopeptidophosphoglycan of Trypanosoma cruzi. The glycophosphosphingolipids of Leptomonas have features in common with the glycolipids of both Leishmania and T. cruzi, resembling the former by the alpha (1-->3) linkage of mannose to the GPI core, while the 2-aminoethylphosphonate substituent on O-6 of glucosamine and the presence of ceramide in place of glycerol lipids is more reminiscent of T. cruzi. Thus these data lend some support to the hypothesis that both T. cruzi and Leishmania evolved from a Leptomonas-like ancestor.
J O Previato; L Mendonça-Previato; C Jones; R Wait; B Fournet
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of biological chemistry     Volume:  267     ISSN:  0021-9258     ISO Abbreviation:  J. Biol. Chem.     Publication Date:  1992 Dec 
Date Detail:
Created Date:  1992-12-30     Completed Date:  1992-12-30     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  2985121R     Medline TA:  J Biol Chem     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  24279-86     Citation Subset:  IM    
Departamento de Microbiologia Geral, Universidade Federal do Rio de Janeiro, Brazil.
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MeSH Terms
Carbohydrate Conformation
Carbohydrate Sequence
Chromatography, Gel
Glycosphingolipids / chemistry*,  isolation & purification
Inositol Phosphates / analysis
Magnetic Resonance Spectroscopy
Molecular Sequence Data
Oligosaccharides / chemistry*,  isolation & purification
Spectrometry, Mass, Fast Atom Bombardment
Trypanosomatina / chemistry*
Reg. No./Substance:
0/Glycosphingolipids; 0/Inositol Phosphates; 0/Oligosaccharides

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