Structural characterization of a novel glycoinositolphospholipid from the parasitic nematode, Ascaris suum.
A novel glycosphingolipid containing inositol phosphate as an acidic group has been demonstrated in whole tissues of the porcine roundworm, Ascaris suum. The thin layer chromatographic pattern of the total acidic glycolipid revealed the presence of several components, of which a major component (named AGL) with positive reactions toward both orcinol-sulfuric acid (sugar) and molybdate (phosphate) spray reagents was isolated and purified by the use of successive column chromatography on DEAE-Sephadex and silicic acid (latrobeads). From structural studies including compositional sugar analysis, hydrogen fluoride degradation, methylation analysis, periodate oxidation, proton magnetic resonance spectroscopy and fast atom bombardment mass spectrometry, the structure of AGL was deduced to be Gal alpha 1-2Ins(1-->)-P-Cer. Aliphatic constituents were lignoceric acid and its 2-hydroxy homologue as the principal fatty acids, and octadecasphinganine and branched heptadecasphinganine as the major sphingoids.
Sugita
M
M
Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University, Japan.
Mizunoma
T
T
Aoki
K
K
Dulaney
J T
JT
Inagaki
F
F
Suzuki
M
M
Suzuki
A
A
Ichikawa
S
S
Kushida
K
K
Ohta
S
S
Kurimoto
A
A
D000818:Animals; D017165:Ascaris suum / Q000737:chemistry*; D001894:Borohydrides / Q000737:chemistry; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002241:Carbohydrates / Q000032:analysis; D002849:Chromatography, Gas; D002855:Chromatography, Thin Layer; D005690:Galactose / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D006028:Glycosphingolipids / Q000032:analysis / Q000737:chemistry*; D006868:Hydrolysis; D007295:Inositol Phosphates / Q000032:analysis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D008968:Molecular Conformation; D008969:Molecular Sequence Data; D010084:Oxidation-Reduction; D010504:Periodic Acid / Q000737:chemistry; D016339:Spectrometry, Mass, Fast Atom Bombardment
D001894:Borohydrides; D002241:Carbohydrates; D006028:Glycosphingolipids; D007295:Inositol Phosphates; D010504:Periodic Acid; C025364:sodium borohydride; D005690:Galactose