63(P35) 質量分析法によるキノコ類に含まれる複合脂質の構造解析(ポスター発表の部)

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As a part of our search for functional molecules in edible fungi, we report here the characterization and structural determination of complex lipids (1-6) including new type of glycosyl phosphosphingolipids in Hypsizigus marmoreus (Bunashimeji, a mushroom) and Pleurotus citrinopileatus (Nireouma, a mushroom) by B/E constant linked scan fast atom bombardment (FAB) mass spectrometry. The structures of complex lipids were determined to be O-(1,2-di-O-linoleoylglycero-3-phosphoryl)ethanolamine (1), (4E,8E)-N-2-hydroxyhexadecanoyl-1-O-β-glucopyranosyl-9-methyl-C18-sphinga-4,8-dienine (2), phosphodihexose N-(2-hydroxyoctadecanoyl)-4-hydroxy-C18-sphinganine (3), phosphodihexose N-(2-hydroxyhexadecanoyl)-4-hydroxy-C18-sphinganine (4), phosphodihexose N-(2-hydroxytetracosanoyl)-4-hydroxy-C18-sphinganine (5), and phosphodihexose N-(2-hydroxydocosanoyl)-4-hydroxy-C18-sphinganine (6). In particular, location of the double bonds in the long-chain base of 1 and in the fatty acid of 2 were clearly determined by the B/E constant linked scan method. The structure of cerebroside having a 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- H_2O]^+ 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. In the structural determination of 3-6, the ions of m/z 421 and 720 in the negative ion mode analyses are assigned to be characteristic of phosphodihexose and phytosphingosine containing phosphodihexose, respectively. This is a useful methodology for the structural determination of other unstable natural products such as lipids.
天然有機化合物討論会の論文
1996-09-02

63(P35) 質量分析法によるキノコ類に含まれる複合脂質の構造解析(ポスター発表の部)

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