Phosphonoglycolipids in Marine Crustacean: Structural Characterization of Two Novel Phosphonocerebrosides, from the Crab, Erimacrus isenbeckii.

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  • KIMURA Koji
    Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University
  • ITONORI Saki
    Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University
  • HADA Noriyasu
    Department of Pharmacognosy and Phytochemistry, Kyoritsu Collge of Pharmacy
  • ITASAKA Osamu
    Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University
  • DULANEY John T.
    Department of Medicine, Division of Nephrology, The University of Tennessee
  • TAKEDA Tadahiro
    Department of Pharmacognosy and Phytochemistry, Kyoritsu Collge of Pharmacy
  • SUGITA Mutsumi
    Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University

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Two novel phosphonoglycolipids, named PnGC1 and PnGC2 were isolated from the marine crab, Erimacrus isenbeckii by successive column chromatography on ion exchange Sephadex (DEAE- and QAE-Sephadex) and silicic acid (Iatrobeads). Their chemical structures were characterized as phosphonocerebrosides, 4’-O-(2-aminoethylphosphonyl) Glcpβ1-1 ceramide for PnGC1 and 4’-O-(N-methyl-2-aminoethylphosphonyl) Glcpβ1-1 ceramide for PnGC2 by IR, MALDI-TOF MS, 1H-NMR, GC and GC-MS analyses of the water-soluble products after acid hydrolysis, and methylation of the product of hydrogen fluoride degradation. In both phosphonocerebrosides, the ceramide moieties were composed of tetradeca-4-sphingenine as the sole sphingoid, and stearic, arachidic, behenic and docosamonoenoic acids as the major fatty acids.

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