(2S,3S,4R,8Z)-2-amino-1,3,4-trihydroxy-8-octadecene | 218786-92-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2S,3S,4R,8Z)-2-amino-1,3,4-trihydroxy-8-octadecene
• 英文别名: (2S,3S,4R,8Z)-2-amino-8(Z)-octadecene-1,3,4-triol；2-amino-1,3,4-trihydroxy-8-octadecene；4-hydroxy-cis-8-sphingenine；t18:1(c8)；4-Hydroxy-8cis-sphingenine；(Z,2S,3S,4R)-2-aminooctadec-8-ene-1,3,4-triol
• CAS: 218786-92-6
• 化学式: C₁₈H₃₇NO₃
• 分子量: 315.497
• InChiKey: CQKNELOTFUSOTP-OGAXSGQXSA-N

物化性质

• 沸点：
  484.0±45.0 °C(Predicted)
• 密度：
  0.996±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  86.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,8Z)-2-amino-1,3,4-trihydroxy-8-octadecene 在 吡啶 、 碘 作用下， 以 二硫化碳 为溶剂， 反应 48.0h， 生成 [(2S,3S,4R)-2-acetamido-3,4-diacetyloxy-8,9-bis(methylsulfanyl)octadecyl] acetate
  参考文献：
  名称：

  Cerebrosides and a Monoacylmonogalactosylglycerol from Clinacanthus nutans

  摘要：

  从坚果蕨（Clinacanthus nutans）叶片中分离出了由九种脑苷脂和一种单酰基半乳糖甘油组成的混合物。这些脑苷脂的结构被表征为植物鞘氨醇的 1-O-β-<小>D-葡萄糖苷，由一个共同的长链基团 (2S,3S,4R,8Z)-2-氨基-8(Z)-十八烯-1,3,4-三醇和九个不同链长（C16、C18、C20-26）的 2-羟基脂肪酸组成，与氨基相连。这种糖基甘油的特征是(2S)-1-O-亚麻酰基-3-O-β-<小>D-吡喃半乳糖基甘油。这些结构是根据光谱数据和化学反应确定的。

  DOI：

  10.1248/cpb.52.27
• 作为产物：
  描述：

  甲醇 、 (R)-N-((2S,3S,4R,Z)-3,4-dihydroxy-1-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)octadec-8-en-2-yl)-2-hydroxydocosanamide 在 盐酸 作用下， 反应 12.0h， 生成 methyl 2-hydroxydocosanoate 、 甲基 Β-D-吡喃葡萄糖苷 、 (2S,3S,4R,8Z)-2-amino-1,3,4-trihydroxy-8-octadecene
  参考文献：
  名称：

  Preliminary biological assay on cerebroside mixture from Euphorbia nicaeensis All. Isolation and structure determination of five glucocerebrosides

  摘要：

  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.

  DOI：

  10.1016/s0014-827x(03)00137-x

文献信息

• Development of an LC–MS/MS Method for the Analysis of Free Sphingoid Bases Using 4-Fluoro-7-nitrobenzofurazan (NBD-F)
  作者：Toshiki Ishikawa、Hiroyuki Imai、Kawai-Yamada Maki

  DOI：10.1007/s11745-013-3871-6

  日期：2014.3

  species of free sphingoid bases present in plant sphingolipids were separated and quantified for the first time; a complete baseline resolution was achieved for cis‐8 and trans‐8 isomers of sphingoid bases by reversed phase HPLC on a C18 column. The extraction and derivatization procedures and LC–MS/MS method can facilitate the progress of the studies for seeking the active components of sphingoid bases

  鞘氨醇碱基的分子种类用荧光氨基试剂4-氟-7-硝基苯并呋喃（NBD-F）标记。通过高度选择性和灵敏的液相色谱-电喷雾电离串联质谱（LC-ESI-MS / MS）技术对NBD鞘氨醇碱基进行了分析，该技术能够可靠地检测几种fmol的衍生物。用NBD-F衍生化了植物样品中的脂质提取物，首次分离并定量了植物鞘脂中存在的所有9种游离鞘氨醇碱基；通过在C 18上进行反相HPLC可以实现鞘氨醇碱基的顺式8和反式8异构体的完整基线分离柱。提取和衍生化步骤以及LC-MS / MS方法可以促进研究寻找鞘氨醇碱类物种的活性成分以应对生物学挑战的研究进展。
• 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.
• Sphingolipids with neuritogenic activity from Euphorbia sororia
  作者：Wei-Ku Zhang、Jie-Kun Xu、Xiao-Qi Zhang、Xin-Sheng Yao、Wen-Cai Ye

  DOI：10.1016/j.chemphyslip.2007.04.008

  日期：2007.8

  Two groups of sphingolipids 1 and 2 were isolated from the aerial parts of Euphorbia sororia. On the basis of spectroscopic data, chemical methods and GC-MS analysis, the structures of 1 and 2 were characterized as 1-O-beta-D-glucopyranosyl-(2S, 3S,4R, 8Z)-2- [(2'R)-2'-hydroxydocosanoyl similar to hex acosanoyl, octacosanoyl amino] 1,3,4-octadecanetriol-8-ene and (2S,3S,4R, 8E)-2-[(2'R)-2'-hydroxyeicosanoyl similar to hexacosanoyl amino] 1,3,4-octadecanetriol-8-ene, respectively. Both of them exhibited marked neuritogenic activity on the rat pheochromocytoma PC 12 cell line. (c) 2007 Elsevier Ireland Ltd. All rights reserved.
• Cerebrosides with antiproliferative activity from Euphorbia peplis L.
  作者：Francesca Cateni、Jelena Zilic、Marina Zacchigna、Giuseppe Procida

  DOI：10.1016/j.fitote.2009.08.022

  日期：2010.3

  Two new cerebrosides have been isolated from the whole plants of Euphorbia peplis L. The structures were established by FT-IR spectroscopy, FAB MS, EI-MS, ESI-MS, 1D and 2D NMR spectroscopy.The structures of the cerebrosides were characterized as 1-O-beta-D-glycosides of phytosphingosines, which comprised a common long-chain base, (2S, 3S, 4R, 8Z)-2-amino-8 (Z)-octadecene-1,3,4-triol with 2-hydroxy fatty acids of varying chain lengths (C25, C22) linked to the amino group. The isolated compounds were shown to possess significant antiproliferative properties against cultured human tumor cell lines KB and IMR-32. (C) 2009 Elsevier B.V. All rights reserved.
• 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.