Characterization of a new phosphonocerebroside, N-methyl-2-aminoethylphosphonylglucosylceramide, from the antarctic krill, Euphausia superba.
A novel phosphonglycosphingolipid was purified from the whole tissue of the antarctic krill, Euphausia superba by successive column chromatography on DEAE- and QAE-Sephadex and silicic acid (Iatrobeads). The structure was elucidated by means of IR, FAB-MS, 1H-NMR, GC and GC-MS analyses of the water-soluble products after complete and partial acid hydrolysis, and methylation analysis of a product of hydrogen fluoride degradation; it was identified to be a phosphonocerebroside, 6'-O-(N-methyl-2-aminoethylphosphonyl)Glcp beta 1----1ceramide. The ceramide moiety was composed of tetradecasphingenine and octadecasphingatriene as the main sphingoids, and monounsaturated C22- and C24-acids and their 2-hydroxy homologues as the major fatty acids.
Itonori
S
S
Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University, Japan.
Kamemura
K
K
Narushima
K
K
Sonku
N
N
Itasaka
O
O
Hori
T
T
Sugita
M
M
D000818:Animals; D002554:Cerebrosides / Q000737:chemistry* / Q000302:isolation & purification; D002849:Chromatography, Gas; D002853:Chromatography, Liquid; D002855:Chromatography, Thin Layer; D003445:Crustacea / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D005963:Glucosylceramides / Q000737:chemistry*; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D010766:Phosphorylation; D013055:Spectrophotometry, Infrared
D002554:Cerebrosides; D005963:Glucosylceramides; C067578:N-methyl-2-aminoethylphosphonylglucosylceramide