Seven neutral glycosphingolipids were isolated and purified from the lamp shell,
Lingula unguis by successive column chromatography on ion exchange Sephadex (QAE-Sephadex), magnesium silicate (Florisil) and silicic acid (Iatrobeads). Their chemical structures were characterized as Glcβ1-1ceramide (CMS
1, CMS
2 and CMS
3), Manβ1-4Glcβ1-1ceramide (MlOse
2Cer, CDS), Manα1-3Manβ1-4Glcβ1-1ceramide (MlOse
3Cer, CTS), GlcNAcβ1-2Manα1-3Manβ1-4Glcβ1-1ceramide (MlOse
4Cer, CQS) and GlcNAcβ1-4GlcNAcβ1-2Manα1-3Manβ1-4Glcβ1-1ceramide (IV
4βGlcNAc-MlOse
4Cer, CPS) by compositional analysis, methylation analysis, exoglycosidase cleavage, gas-liquid chromatography, gas chromatograph-mass spectrometry and matrix-assisted laser desorption ionization time-of-flight mass spectrometry. Aliphatic constituents of CDS, CTS, CQS and CPS were virtually the same, with C16:0 and C18:0, and their 2-hydroxy homologues as the fatty acids, and octadecasphinga-4,8,10-trienine as the sole sphingoid. However, the ceramide compositions of CMS
1, CMS
2 and CMS
3 differed from those of the other four glycolipids. The fatty acid composition of CMS
1 consisted completely of C16:0, C17:0 and C18:0 acids, but both CMS
2 and CMS
3 contained instead of their 2-hydroxy homologues. The sphingoid components of CMS
1 and CMS
2 were octadecasphinga-4-enine and octadecasphinga-4,8,10-trienine, but that of CMS
3 was entirely trihydroxysphingoid, 4-hydroxyoctadecasphiganine.
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