(2R,17Z)-N-{(1S,2S,3R,7Z)-1-[(β-D-glucopyranosyloxy)methyl]-2,3-dihydroxyheptadec-7-en-1-yl}-2-hydroxyhexacos-17-enamide

• 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: (2R,17Z)-N-{(1S,2S,3R,7Z)-1-[(β-D-glucopyranosyloxy)methyl]-2,3-dihydroxyheptadec-7-en-1-yl}-2-hydroxyhexacos-17-enamide
• 英文别名: 1-O-(β-D-glucopyranosyl)-(2S,3S,4R,8Z)-2-[(2'R)-2'-hydroxyhexacosenoilamino]-8(Z)-octadecene-1,3,4-triol；Cerebroside B-2；(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-hydroxyhexacos-17-enamide
• 化学式: C₅₀H₉₅NO₁₀
• 分子量: 870.305
• InChiKey: UVFYANYUVOLGBR-CYARAHIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.4
• 重原子数：
  61
• 可旋转键数：
  42
• 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：

  (2R,17Z)-N-{(1S,2S,3R,7Z)-1-[(β-D-glucopyranosyloxy)methyl]-2,3-dihydroxyheptadec-7-en-1-yl}-2-hydroxyhexacos-17-enamide 在 盐酸 、 碘 作用下， 以 二硫化碳 为溶剂， 反应 58.0h， 生成
  参考文献：
  名称：

  Falsone, G.; Cateni, F.; Baumgartner, M., Zeitschrift fur Naturforschung, B: Chemical Sciences, 1994, vol. 49, # 1, p. 135 - 140

  摘要：

  DOI：

文献信息

• Preliminary biological assay on cerebroside mixture from Euphorbia nicaeensis All. Isolation and structure determination of five glucocerebrosides
  作者：F. Cateni、J. Zilic、G. Falsone、F. Hollan、F. Frausin、V. Scarcia

  DOI：10.1016/s0014-827x(03)00137-x

  日期：2003.9

  Preliminary studies of in vitro cytostatic activity on less polar fraction of the MeOH extract of the plant Euphorbia nicaeensis All., carried out on KB cells, have evinced a relatively low ability of extract to inhibit cell growth. Successive, five glucocerebrosides were isolated from the cerebroside molecular species obtained from this extract using normal and reversed phase column 'flash-chromatography'. The structures of these cerebrosides were determined on the basis of chemical and spectroscopic evidences. Mass spectrometry of dimethyl disulfide derivatives was useful for the determination of the double-bond positions in the long-chain bases.
• 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.