Novel plasmalogalactosylalkylglycerol from equine brain

• Main Authors: Youichi Yachida, Motoi Kashiwagi, Takeshi Mikami, Keiko Tsuchihashi, Takumi Daino, Toyoaki Akino, Shinsei Gasa
• Format: Article
• Language: English
• Published: Elsevier 1999-12-01
• Series: Journal of Lipid Research
• Subjects: plasmaloglycolipid; acetalization; galactosyl glycerol; NMR; fatty aldehyde
• Online Access: http://www.sciencedirect.com/science/article/pii/S0022227520321027

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 C14 for the former and C16 and C18 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., M. Kashiwagi, T. Mikami, K. Tsuchihashi, T. Daino, T. Akino, and S. Gasa. Novel plasmalogalactosylalkylglycerol from equine brain.