Isolation and characterization of a novel phytosphingosine-containing GM2 ganglioside from mullet roe (Mugil cephalus).

The major ganglioside from the roe of striped mullet (Mugil cephalus) has been isolated and purified. Compositional analysis of this ganglioside revealed that it contained an equimolar ratio of the following residues: N-acetylneuraminic acid, N-acetylgalactosamine, galactose, glucose, and the long-chain base. Further structural studies by sequential enzymatic hydrolysis, permethylation analysis, and proton NMR spectroscopy indicated that the structure of the oligosaccharide moiety was identical to that of GM2 ganglioside from human brain: GalNAc beta 1----4Gal beta 1----4(3----2 alpha NeuAc)-Glc----ceramide. This ganglioside, however, differed from brain GM2 in its ceramide portion. The most striking differences are the presence of large amounts of C18 and C20 phytosphingosine (over 80% of the total long-chain bases) and the preponderance of monounsaturated alpha-hydroxy fatty acids (over 80%). Such a phytosphingosine-containing GM2 ganglioside has never been reported.