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Structural variation in the glycoinositolphospholipids of different strains ofTrypanosoma cruzi

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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 β-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 β-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.

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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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Authors and Affiliations

  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

    José O. Previato & Lucia Mendonça-Previato

  2. Fundação Oswaldo Cruz, Rio de Janeiro, RJ, Brasil

    João C. Carreira

  3. Laboratory for Molecular Structure, NIBSC, EN6 3QG, Herts, UK

    Christopher Jones

  4. CAMR, Porton Down, SP4 0JG, Salisbury, UK

    Robin Wait

Authors
  1. João C. Carreira
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  2. Christopher Jones
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  3. Robin Wait
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  4. José O. Previato
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  5. Lucia Mendonça-Previato
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Carreira, J.C., Jones, C., Wait, R. et al. Structural variation in the glycoinositolphospholipids of different strains ofTrypanosoma cruzi . Glycoconjugate J 13, 955–966 (1996). https://doi.org/10.1007/BF01053191

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  • DOI: https://doi.org/10.1007/BF01053191

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