Structural variation in the glycoinositolphospholipids of different strains ofTrypanosoma cruzi |
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Authors: | João C Carreira Christopher Jones Robin Wait José O Previato Lucia Mendonça-Previato |
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Institution: | (1) Instituto de Microbiologia, Centro de Ciências da Saúde, Bloco I, Universidade Federal do Rio de Janeiro, 21 944 970, Cidade Universitária, Rio de Janeiro, RJ, Brasil;(2) Fundação Oswaldo Cruz, Rio de Janeiro, RJ, Brasil;(3) Laboratory for Molecular Structure, NIBSC, EN6 3QG, Herts, UK;(4) CAMR, Porton Down, SP4 0JG Salisbury, UK |
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Abstract: | The structures of the glycoinositolphospholipids (GIPLs) from five strains of the protozoan parasiteTrypanosoma cruzi have been determined. Two series of structures were identified, all but one containing the same Man4(AEP)GlcN-Ins-PO4 core. Series 1 oligosaccharides are substituted at the third mannose distal to inositol (Man 3) by ethanolamine-phosphate or 2-aminoethylphosphonic acid, as are some glycosyl-phosphatidylinositol-protein anchors ofT. cruzi. The core can be further substituted by terminal (1–3)-linked -galactofuranose units. In contrast, Series 2 oligosaccharides do not have additional phosphorus-containing groups attached to Man 3, the latter being substituted instead by a single side chain unit of -galactofuranose. Series 1 oligosaccharides are present in all strains (G, G-645, Tulahuen CL, and Y) whereas Series 2 structures are present mainly in CL and Y strains. The lipid moiety in the GIPLs from the G, G-645 and Tulahuen strains is predominantly ceramide, as reported for the Y strain, whilst that from the CL strain is a mixture of ceramide and alkylacylglycerol species. The lipid moiety of the GIPLs, and probably also the phosphoinositol-oligosaccharide structures may play an important immunomodulatory role in infection byT. cruzi.Abbreviations GIPL
glycoinositolphospholipid
- LPPG
lipopeptidophosphoglycan
- GPI
glycosylphosphatidylinositol
- AEP
2-aminoethylphosphonic acid
- PI
phosphoinositol
- GC
gas-liquid chromatography
- MS
mass spectrometry
- FAB
fast atom bombardment
- NMR
nuclear magnetic resonance
- DQF-COSY
double quantum-filtered correlation spectroscopy
- TOCSY
total correlation spectroscopy
- ROESY
rotating frame nuclear Overhauser enhancement spectroscopy
- EtNP
ethanolaminephosphate
- HMQC
heteronuclear multiple quantum coherence
- Man
mannose
- Galf
galactofuranose
- GlcN
glucosamine
- Ins
inositol
- InsP
inositolphosphate
- Man 3
third mannose distal to inositol
- NOE
nuclear Overhauser effect
- M+H]+
protonated molecule
- M–H]–
deprotonated molecule
- RMM
relative molecular mass (monoisotopic) |
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Keywords: | Trypanosoma cruzi glycoinositolphospholipids nuclear magnetic resonance FAB-mass spectrometry |
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