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Structural characterization of a novel mono-sulfated gangliotriaosylceramide containing a 3-O-sulfatedN-acetylgalactosamine from rat kidney

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Abstract

A novel mono-sulfated glycosphingolipid based on the gangliotriaose core structure was isolated from rat kidney. The isolation procedure involved extraction of lipids with chloroform/methanol, mild alkaline methanolysis, column chromatographies with anion exchangers and silica beads. The structure was characterized by compositional analysis, FTIR spectroscopy, methylation analysis,1H-NMR spectroscopy and negative-ion liquid secondary ion mass spectrometry (LSIMS) using the intact glycolipid and its desulfation product. The two dimensional chemical shift correlated spectroscopy provided information on the sugar sequence as well as anomeric configurations, and indicated the presence of a 3-O-sulfatedN-acetylgalactosamine within the molecule. Negative-ion LSIMS with high- and low-energy collision-induced dissociation defined the sugar sequence and ceramide composition, confirming the presence of a sulfatedN-acetylgalactosamine at the non-reducing terminus. From these results, the complete structure was proposed to be HSO3-3GalNAcβ1-4Galβ1-4Glcβ1-1Cer (Gg3Cer III3-sulfate, SM2b).

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Authors and Affiliations

  1. Department of Biochemistry, Teikyo University School of Medicine, Kaga 2-11-1, Itabashi-ku, 173, Tokyo, Japan

    Keiko Tadano-Aritomi & Ineo Ishizuka

  2. Shimadzu Corporation, Nakagyo-ku, 604, Kyoto, Japan

    Harumi Kubo

  3. Shimadzu Techno-Research, Inc., Nakagyo-ku, 604, Kyoto, Japan

    Philip Ireland

  4. Laboratory for Biomedical Analysis, Tokyo Medical and Dental University, Bunkyo-ku, 113, Tokyo, Japan

    Takeshi Kasama

  5. Department of Biochemistry, Faculty of Medicine, Tokyo Medical and Dental University, Bunkyo-ku, 113, Tokyo, Japan

    Shizuo Handa

Authors
  1. Keiko Tadano-Aritomi
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  2. Harumi Kubo
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  3. Philip Ireland
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  4. Takeshi Kasama
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  5. Shizuo Handa
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  6. Ineo Ishizuka
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Additional information

Abbreviations: Abbreviations for sulfated glycolipids [17] follow the modifications of the nomenclature system of Svennerholm for gangliosides [37], and the designation of the other glycosphingolipids follows the IUPAC-IUB recommendations [38]. Cer, ceramide; LacCer, lactosylceramide, Galβ1-4Glcβ1-1Cer; Gg3Cer, gangliotriaosylceramide, GalNAcβ1-4Galβ1-4Glcβ1-1Cer; Gg4Cer, gangliotetraosylceramide, Galβ1-3GalNAcβ1-4Galβ1-4Glcβ1-1Cer; iGb4Cer, isoglobotetraosylceramide, GalNAcβ1-3Galβ1-3Galβ1-4Glcβ1-1Cer; Gb4Cer, globotetraosylceramide, GalNAcβ1-3Galβ1-4Galβ1-4Glcβ1-1Cer; SM4s, galactosylceramide sulfate, GalCer I3-sulfate; SM3, lactosylceramide sulfate, LacCer II3-sulfate; SM2a, Gg3Cer II3-sulfate; SM2b, Gg3Cer III3-sulfate; SB2, Gg3Cer II3,III3-bis-sulfate; SM1a, Gg4Cer II3-sulfate; SM1b, Gg4Cer IV3-sulfate; SB1a, Gg4Cer II3,IV3-bissulfate; GLC, gas-liquid chromatography; GC-MS, gas chromatography-mass spectrometry; DQF, double quantum filtered; COSY, chemical-shift-correlated spectroscopy; LSIMS, liquid secondary ion mass spectrometry; CID, collision-induced dissociation; MS/MS, tandem mass spectrometry.

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Tadano-Aritomi, K., Kubo, H., Ireland, P. et al. Structural characterization of a novel mono-sulfated gangliotriaosylceramide containing a 3-O-sulfatedN-acetylgalactosamine from rat kidney. Glycoconjugate J 13, 285–293 (1996). https://doi.org/10.1007/BF00731503

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  • DOI: https://doi.org/10.1007/BF00731503

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