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Structural analysis of neutral glycosphingolipids from Ascaris suum adults (Nematoda: Ascaridida)

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Abstract

The neutral glycosphingolipid fraction from adults of the pig parasitic nematode, Ascaris suum, was resolved into four components on thin-layer chromatography. The high-performance liquid chromatography-isolated components were structurally analysed by: methylation analysis; exoglycosidase cleavage; gas-liquid chromatography/mass spectrometry; liquid secondary-ion mass spectrometry; and, in particular, matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Their chemical structures were determined as: Glc(β1-1)ceramide, Man(β1-4)Glc(β1-1)ceramide, GlcNAc(β1-3)Man(β1-4)Glc(β1-1)ceramide and Gal(α1-3)GalNAc(β1-4)GlcNAc(β1-3)Man(β1-4)Glc(β1-1)ceramide; and were characterized as belonging to the arthro-series of protostomial glycosphingolipids. No glycosphingolipid component corresponding to ceramide tetrasaccharide was detected during these analyses. The ceramide composition of the parent glycosphingolipids was dominated by the 2-(R)-hydroxy C24:0 fatty acid, cerebronic acid, and C17 sphingoid-bases: 15-methylhexadecasphing-4-enine and 15-methylhexadecaphinganine in approximately equal proportions. The component ceramide monohexoside was characterized by an additional 15-methylhexadecaphytosphingosine. Abbreviations: CDH, ceramide dihexoside; Cer, ceramide; CMH, ceramide monohexoside; CPH, ceramide pentahexoside; CTH, ceramide trihexoside; CTetH, ceramide tetrahexoside; Hex, hexose; HexNAc, N-acetylhexosamine; HPTLC, high-performance thin-layer chromatography; LSIMS, liquid secondary-ion mass spectrometry; MALDI-TOF-MS, matrix-assisted laser desorption/ionization time-of-flight mass spectrometry; N-, Nz- and A-glyco(sphingo)lipids, neutral, neutralzwitterionic and acidic glyco(sphingo)lipids, respectively

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Authors and Affiliations

  1. Institute of Biochemistry, University of Giessen, Friedrichstrasse 24, D-35392, Giessen, Germany

    Gunter Lochnit, Roger D Dennis & Rudolf Geyer

  2. Division of Immunochemistry, Center for Medicine and Biosciences, Research Center Borstel, D-23845, Borstel, Germany

    Ulrich Zahringer

Authors
  1. Gunter Lochnit
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  2. Roger D Dennis
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  3. Ulrich Zahringer
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  4. Rudolf Geyer
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Lochnit, G., Dennis, R.D., Zahringer, U. et al. Structural analysis of neutral glycosphingolipids from Ascaris suum adults (Nematoda: Ascaridida). Glycoconj J 14, 389–399 (1997). https://doi.org/10.1023/A:1018530914067

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