Novel plasmalogalactosylalkylglycerol from equine brain.
A novel galactosylalkylglycerol modified with a long-chain cyclic acetal at the sugar moiety, 3-O-(4'6'-plasmalogalactosyl) 1-O-alkylglycerol, was isolated from equine brain. The presence of cyclic acetal linkage, its linked position, and the length of the acetal chain of the natural plasmalo lipid were determined by proton NMR spectroscopy and fast-atom bombardment;-mass spectrometry, as well as gas chromatography;-mass spectrometry and gas;-liquid chromatography. To identify the isomeric stereostructure of the natural product, the plasmalo derivative was chemically synthesized from 3-O-galactosyl 2-O-acyl 1-O-alkyl glyceride through acetalization after deacylation. As a result, the direction and position of the acetal chain of the natural plasmalo lipid were characterized as an "endo"-type 4',6'-O-acetal derivative linked to galactoside by comparison with the NMR data of the synthesized product. The chain lengths of alkyl and acetal groups were C(14) for the former and C(16) and C(18) for the latter, and those for the latter group were mostly similar to those of plasmalogalactosyl ceramide, which was previously isolated from equine brain.
Yachida
Y
Y
Departments of Chemistry, Sapporo Medical University School of Medicine, Chuo-Ku S1 W17, Sapporo 060-8556, Japan.
Kashiwagi
M
M
Mikami
T
T
Tsuchihashi
K
K
Daino
T
T
Akino
T
T
Gasa
S
S
D000818:Animals; D001923:Brain Chemistry; D002850:Chromatography, Gel; D005699:Galactosylceramides / Q000138:chemical synthesis / Q000302:isolation & purification; D006017:Glycolipids / Q000302:isolation & purification*; D006028:Glycosphingolipids / Q000138:chemical synthesis / Q000302:isolation & purification; D006736:Horses; D008055:Lipids / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism
D005699:Galactosylceramides; D006017:Glycolipids; D006028:Glycosphingolipids; D008055:Lipids