1-O-(β-D-glucopyranosyl)-(2S,3S,4R,8Z)-2-[(2'R)-2-hydroxyoctacosenoilamino]-8(Z)-octadecene-1,3,4-triol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: 1-O-(β-D-glucopyranosyl)-(2S,3S,4R,8Z)-2-[(2'R)-2-hydroxyoctacosenoilamino]-8(Z)-octadecene-1,3,4-triol
• 英文别名: Cerebroside B-3；(Z,2R)-N-[(Z,2S,3S,4R)-3,4-dihydroxy-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadec-8-en-2-yl]-2-hydroxyoctacos-19-enamide
• 化学式: C₅₂H₉₉NO₁₀
• 分子量: 898.359
• InChiKey: ROFBFXSSLSYVGV-LTPLXAISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.5
• 重原子数：
  63
• 可旋转键数：
  44
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  189
• 氢给体数：
  8
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-O-(β-D-glucopyranosyl)-(2S,3S,4R,8Z)-2-[(2'R)-2-hydroxyoctacosenoilamino]-8(Z)-octadecene-1,3,4-triol 在 盐酸 、 二硫化碳 、 碘 作用下， 以 水 为溶剂， 反应 66.0h， 生成 (2S,3S,4R)-2-amino-8,9-bis(methylsulfanyl)octadecane-1,3,4-triol
  参考文献：
  名称：

  Lipid metabolites with free-radical scavenging activity from Euphorbia helioscopia L.

  摘要：

  The methanolic extract of the plant Euphorbia helioscopia L. exhibited an interesting free-radical scavenging activity. From the aerial parts of Euphorbia helioscopia L. (Euphorbiaceae), a complex mixture of seven cerebrosides together with glucoclionasterol, a digalactosyldiacylglycerol and a diacylmonogalactosylglycerol were identified. The structures of the cerebrosides were characterized as 1-O-β-D-glucosides of phytosphingosines, which comprised (2S, 3S, 4E, 8E)-2-amino-4(E),8(E)-octadecadiene-1,3-diol, (2S, 3S, 4E, 8Z)-2-amino-4(E),8(Z)-octadecadiene-1,3-diol, (2S, 3S, 4R, 8Z)-2-amino-8(Z)-octadecene-1,3,4-triol as long chain bases with seven 2-hydroxy fatty acids of varying chain lengths (C16, C24:1, C26:1, C24, C26, C28:1) linked to the amino group. The glycosylglycerides were characterized as (2S)-2,3-O-di-(9,12,15-octadecatrienoyl)-glyceryl-6-O-(α-D-galactopyranosyl)-β-D-galactopyranoside and (2S)-2,3-O-di-(9,12,15-octadecatrienoyl)-glyceryl-1-O-β-D-galactopyranoside. The structures were established on the basis of spectroscopic data and chemical reactions.

  DOI：

  10.1016/j.chemphyslip.2014.03.001

文献信息

• Falsone, G.; Cateni, F.; Baumgartner, M., Zeitschrift fur Naturforschung, B: Chemical Sciences, 1994, vol. 49, # 1, p. 135 - 140
  作者：Falsone, G.、Cateni, F.、Baumgartner, M.、Lucchini, V.、Wagner, H.、Seligmann, O.

  DOI：——

  日期：——
• Lipid metabolites with free-radical scavenging activity from Euphorbia helioscopia L.
  作者：F. Cateni、J. Zilic、T. Altieri、M. Zacchigna、G. Procida、R. Gaggeri、D. Rossi、S. Collina

  DOI：10.1016/j.chemphyslip.2014.03.001

  日期：2014.7

  The methanolic extract of the plant Euphorbia helioscopia L. exhibited an interesting free-radical scavenging activity. From the aerial parts of Euphorbia helioscopia L. (Euphorbiaceae), a complex mixture of seven cerebrosides together with glucoclionasterol, a digalactosyldiacylglycerol and a diacylmonogalactosylglycerol were identified. The structures of the cerebrosides were characterized as 1-O-β-D-glucosides of phytosphingosines, which comprised (2S, 3S, 4E, 8E)-2-amino-4(E),8(E)-octadecadiene-1,3-diol, (2S, 3S, 4E, 8Z)-2-amino-4(E),8(Z)-octadecadiene-1,3-diol, (2S, 3S, 4R, 8Z)-2-amino-8(Z)-octadecene-1,3,4-triol as long chain bases with seven 2-hydroxy fatty acids of varying chain lengths (C16, C24:1, C26:1, C24, C26, C28:1) linked to the amino group. The glycosylglycerides were characterized as (2S)-2,3-O-di-(9,12,15-octadecatrienoyl)-glyceryl-6-O-(α-D-galactopyranosyl)-β-D-galactopyranoside and (2S)-2,3-O-di-(9,12,15-octadecatrienoyl)-glyceryl-1-O-β-D-galactopyranoside. The structures were established on the basis of spectroscopic data and chemical reactions.