Structural elucidation of the neutral glycosphingolipids, mono-, di-, tri- and tetraglycosylceramides from the marine crab Erimacrus isenbeckii.
The neutral glycosphingolipids, mono-, di-, tri- and tetraglycosylceramides (GL-1, GL-2, GL-3, GL-4a and GL-4b), were identified from whole tissues of the marine crab Erimacrus isenbeckii by successive column chromatography with ion exchange Sephadex (QAE-Sephadex), magnesium silicate (Florisil) and silicic acid (Iatrobeads) resins. Through component analysis, sugar analysis, methylation studies, exoglycosidase cleavage, and various chromatographic and spectrometric techniques, their structures were proposed to be as follows: GL-1, Glcβ1-1Cer; GL-2, Manβ1-4Glcβ1-1Cer; GL-3, Galβ1-3Manβ1-4Glcβ1-1Cer; and GL-4a and GL-4b, Gal3Meα1-4Galβ1-3Manβ1-4Glcβ1-1Cer. The main molecular species of the aliphatic moiety in each purified glycolipid were 18:0, 22:0, 22:1-d14:1 (fatty acid-sphingoid) and 18:0-d16:1 for GL-1; 18:0-d16:1 and 22:1-d14:1, d16:1 for GL-2; 22:1, 24:1-d16:1 for GL-3; 22:1, 24:1-d16:1 for GL-4a; and h22:1, h24:1-d16:1 for GL-4b, respectively. By immunological detection, an arthro-series glycosphingolipid (At3Cer; GlcNAcβ1-3Manβ1-4Glcβ1-1Cer) was also detected as a minor component. The characteristic arthro-series glycosphingolipid has been observed in most animals belonging to the phylum Arthropoda.
Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University.
Koji
K
Kimura
Saki
S
Itonori
Chiho
C
Kajiwara
Noriyasu
N
Hada
Tadahiro
T
Takeda
Mutsumi
M
Sugita
D000818:Animals; D003386:Brachyura / Q000737:chemistry*; D002240:Carbohydrate Sequence; D002852:Chromatography, Ion Exchange / Q000379:methods; D002855:Chromatography, Thin Layer; D005227:Fatty Acids / Q000032:analysis; D005963:Glucosylceramides / Q000737:chemistry* / Q000302:isolation & purification; D006028:Glycosphingolipids / Q000737:chemistry* / Q000302:isolation & purification; D006868:Hydrolysis; D007475:Ion Exchange Resins; D017633:Magnesium Silicates; D013058:Mass Spectrometry; D008745:Methylation; D012824:Silicic Acid
D005227:Fatty Acids; D005963:Glucosylceramides; D006028:Glycosphingolipids; D007475:Ion Exchange Resins; D017633:Magnesium Silicates; C005013:Florisil; D012824:Silicic Acid