The location of double bonds in a cerebroside from edible fungi (mushroom) estimated by B/E linked scan fast atom bombardment mass spectrometry

The structure of a cerebroside isolated from Hypsizigus marmoreus (mushroom, Bunashimeji) was determined to be (4E, 8E)-N-2-hydroxyhexadecanoyl-1-O-β-glucopyranosyl-9-methyl-C18-sphinga-4,8-dienine (1) by positive and negative ion mode fast atom bombardment (FAB) mass spectrometry using the B/E constant linked scan method. In particular, the location of the double bonds in the long-chain base was determined by the method. The structure of cerebrosides having the long-chain base of 9-methyl-C18-sphinga-4,8-dienine could be determined in general by the presence of characteristic fragment ions of [C19-sphingadienine + H − H2O]+ at m/z 276 and [C19-sphingadienine + H]+ at m/z 294, and the fatty acid carbon number could be calculated from the characteristic fragment ion of [ceramide − 180]+ ([MH − GlcOH − 180]+) in positive ion mode FAB mass spectrometry. Compound 1 was isolated for the first time from Hypsizigus marmoreus in the present study.

[1]  Jeanette Adams,et al.  Structure determination of sphingolipids by mass spectrometry , 1993 .

[2]  Y. Ohashi,et al.  Fast-atom-bombardment chemistry of sulfatide (3-sulfogalactosylceramide) , 1991, Carbohydrate research.

[3]  G. Kawai Molecular species of cerebrosides in fruiting bodies of Lentinus edodes and their biological activity. , 1989, Biochimica et biophysica acta.

[4]  J. W. Klein,et al.  Phospholipid dependence of calcium ion effects on electrophoretic mobilities of liposomes. , 1987, Chemistry and physics of lipids.

[5]  Y. Banno,et al.  Cerebroside of the dimorphic human pathogen, Candida albicans. , 1987, Chemistry and physics of lipids.

[6]  G. Kawai PC25 CHEMICAL INDUCTION OF FRUITING IN THE BASIDIOMYCETE SCHIZOPHYLLUM COMMUNE , 1988 .

[7]  K. Mori,et al.  Synthesis and Biological Activity of the Isomers and Analogs of (4E, 8E, 2S, 3R, 2'R)-N-2'-Hydroxyhexadecanoyl-9-methyl-4, 8-sphingadienine, the Ceramide Portion of the Fruiting-inducing Cerebroside in a Basidiomycete Schizophyllum commune , 1986 .

[8]  Y. Ikeda,et al.  Structure of biologically active and inactive cerebrosides prepared from Schizophyllum commune. , 1985, Journal of lipid research.

[9]  Y. Ikeda,et al.  Chemistry and functional moiety of a fruiting-inducing cerebroside in Schizophyllum commune , 1983 .

[10]  K. Karlsson,et al.  Characterization of cerebroside (monoglycosylceramide) from the sea anemone, Metridium senile. Identification of the major long-chain base as an unusual dienic base with a methyl branch at a double bond. , 1979, Biochimica et biophysica acta.

[11]  G. Marino,et al.  A new cerebroside from Fusicoccum amygdali Del. , 1979, Biochimica et biophysica acta.