Acidic Glycolipids from Marine Annelida (Lugworm, Tylorhynchus heterochaetus) : Occurrence of Methylinositol Phosphate-Containing Sphingolipids

  • SUGITA Mutsumi
    Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University
  • AOKI Kazuhiro
    Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University
  • DULANEY John T.
    Department of Medicine, Division of Nephrology, The University of Tennessee
  • SUZUKI Minoru
    Department of Membrane Biochemistry, The Tokyo Metropolitan Institute of Medical Science
  • SUZUKI Akemi
    Department of Membrane Biochemistry, The Tokyo Metropolitan Institute of Medical Science
  • NISHIZAWA Naoko
    Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University
  • SAKATA Ayako
    Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University

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Other Title
  • イトメ, <I>Tylorhynchus heterochaetus</I> (環形動物) の酸性糖脂質 : メチルイノシトールリン酸を含有したスフィンゴ脂質の存在
  • イトメ Tylorhynchus heterochaetus カンケイ ドウブ

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Abstract

Two novel series of glycosphingolipids containing inositolphosphate or methylinositolphosphate as an acidic group were found present in whole tissues of the lugworm, Tylorhynchus heterochaetus. The thin layer chromatographic pattern of the total acidic glycolipid revealed the presence of several components with positive reactions toward molybdate (phosphate) and/or both molybdate and orcinol-sulfuric acid (sugar) spray reagents. Three components (AGL01, AGL1 and AGL21) were isolated and purified by successive column chromatography on two ion exchange Sephadexes and silicic acid (Iatrobeads). From structural studies including compositional sugar analysis, hydrogen fluoride degradation, boron tribromide demethylation, methylation analysis and fast atom bombardment, their structures were deduced to be as follows : AGL01, InsMe (1→) -P-Cer; AGL1, Fuc-InsMe (1→) -P-Cer; and AGL21, Ins (1→) -P-Cer. The ceramide moieties of the inositollipids consisted mainly of C16 : 0 and C18 : 0 fatty acids and dihydroxy- (C18 : 1 and C18 : 0) sphingoids for AGL21, and 2-hydroxylated C16 : 0 and C18 : 0 fatty acids and trihydroxy- (C18 : 0) sphingoid for AGL01 and AGL1.<BR>In addition, their thin layer chromatographic behavior and the results of compositional anal-ysis indicated presence of at least four more inositollipids to possibly be Man-InsMe-P-Cer (AGL22), Fuc-Ins-P-Cer (AGL3), Man-Ins-P-Cer (AGL4) and Man (Fuc-) Ins-P-Cer (AGL5).

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