(2S,3R,4E,8E)-2-(hexadecanoylamino)-4,8-octadecadien-1,3-diol | 141980-53-2

• 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: (2S,3R,4E,8E)-2-(hexadecanoylamino)-4,8-octadecadien-1,3-diol
• 英文别名: N-hexadecanoylsphinga-(4E,8E)-dienine；N-[(2S,3R,4E,8E)-1,3-dihydroxyoctadeca-4,8-dien-2-yl]hexadecanamide
• CAS: 141980-53-2
• 化学式: C₃₄H₆₅NO₃
• 分子量: 535.895
• InChiKey: GMWIWVUTMCBDSP-ILAZMTIGSA-N

物化性质

• 熔点：
  96-98 °C(Solv: chloroform (67-66-3); methanol (67-56-1))
• 沸点：
  675.2±55.0 °C(Predicted)
• 密度：
  0.926±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  38
• 可旋转键数：
  29
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (2S,3R,4E,8E)-2-(hexadecanoylamino)-4,8-octadecadien-1,3-diol 生成 Acetic acid (2E,6E)-(R)-1-((S)-2-acetoxy-1-hexadecanoylamino-ethyl)-hexadeca-2,6-dienyl ester
  参考文献：
  名称：

  摘要：

  Sphingolipids and glycolipids including previously unknown (2S,3S,4R)-1,3,4-trihydroxy-2-(2-(R)-hydroxyoctadecanoylamino)octadec-8E-ene, (2S,3R)-1,3-dihydroxy-2-octadecanoylamino-4E,8E-hexadecadiene, and (2-hydroxy-3-hexadecyloxypropyl)-alpha-L-fucopyranoside were isolated from soft corals collected on the shelf near the Andaman Islands (Indian Ocean). The structures of all compounds were established by spectroscopic methods and chemical analyses. The lipids possessed antibacterial activity against Bacillus subtilis, Bacillus pumilus, Escherichia coli, and Pseudomonas aeruginosa and antifungal activity against Aspergillus niger, Rhizopus oryzae, and Candida albicans.

  DOI：

  10.1023/a:1026089612129
• 作为产物：
  描述：

  棕榈酸酐 、 trans-4,trans-8-sphingadienine 以 甲醇 为溶剂， 反应 22.0h， 以1 mg的产率得到(2S,3R,4E,8E)-2-(hexadecanoylamino)-4,8-octadecadien-1,3-diol
  参考文献：
  名称：

  Neurite Outgrowth and Morphological Changes Induced by 8-trans Unsaturation of Sphingadienine in kCer Molecular Species

  摘要：

  魔芋酸二酰胺（kCer）由具有特征性shingoid碱基和脂肪酸的植物型分子种类组成，通过化酶去葡萄糖化从魔芋葡糖鞘氨醇GlcCer制备而成。kCer激活semaforin 3A（Sema3A）信号通路，诱导崩塌反应介导蛋白2（CRMP2）的磷酸化。这导致PC12细胞中神经突起生长受抑制，剩余长神经突起形态发生变化。特定的kCer分子种类是否能与Sema3A受体（神经丝蛋白1，Nrp1）结合并激活Sema3A信号通路目前尚不清楚。在这里，我们使用内葡糖鞘氨醇酶I介导的去葡萄糖化制备了kCer分子种类，并检查了在神经生长因子（NGF）预处理的细胞中神经突起生长和崩塌反应介导蛋白2的磷酸化。kCer的鞘二烯醇8-反式不饱和对于Sema3A类似信号通路的激活至关重要。相反，kCer分子种类的鞘二烯醇8-顺式不饱和对Sema3A类似激活没有影响，并导致剩余短神经突起的神经突起抑制。此外，脂肪酸的α-羟基化与kCer分子种类的Sema3A类似活性无关。这些结果表明，鞘二烯醇8-反式或8-顺式异构化决定了Nrp1配体结合位点的特定相互作用。

  DOI：

  10.3390/ijms20092116

文献信息

• Substrate specificity, kinetic properties and inhibition by fumonisin B1 of ceramide synthase isoforms from Arabidopsis
  作者：Kyle D. Luttgeharm、Edgar B. Cahoon、Jonathan E. Markham

  DOI：10.1042/bj20150824

  日期：2016.3.1

  Ceramides are organizing components of sphingolipids in the eukaryotic cell. Three ceramide synthase isoforms are found in Arabidopsis thaliana each with specific substrate preferences and sensitivity to inhibitors and activators.

  神经酰胺是真核细胞中鞘磷脂的组织成分。拟南芥中有三种神经酰胺合成酶异构体，每种异构体都有特定的底物偏好以及对抑制剂和激活剂的敏感性。
• Neurite Outgrowth and Morphological Changes Induced by 8-trans Unsaturation of Sphingadienine in kCer Molecular Species
  作者：Seigo Usuki、Noriko Tamura、Tomohiro Tamura、Kunikazu Tanji、Daisuke Mikami、Katsuyuki Mukai、Yasuyuki Igarashi

  DOI：10.3390/ijms20092116

  日期：——

  Konjac ceramide (kCer), which consists of plant-type molecular species of characteristic shingoid bases and fatty acids, is prepared from konjac glucosylceramide GlcCer by chemoenzymatical deglucosylation. kCer activates the semaphorin 3A (Sema3A) signaling pathway, inducing collapsin response mediator protein 2 (CRMP2) phosphorylation. This results in neurite outgrowth inhibition and morphological changes in remaining long neurites in PC12 cells. Whether a specific molecular species of kCer can bind to the Sema3A receptor (Neuropilin1, Nrp1) and activate the Sema3A signaling pathway remains unknown. Here, we prepared kCer molecular species using endoglycoceramidase I-mediated deglucosylation and examined neurite outgrowth and phosphorylation of collapsin response mediator protein 2 in nerve growth factor (NGF)-primed cells. The 8-trans unsaturation of sphingadienine of kCer was essential for Sema3A-like signaling pathway activation. Conversely, 8-cis unsaturation of kCer molecular species had no effect on Sema3A-like activation, and neurite outgrowth inhibition resulted in remaining short neurites. In addition, α-hydroxylation of fatty acids was not associated with the Sema3A-like activity of the kCer molecular species. These results suggest that 8-trans or 8-cis isomerization of sphingadienine determines the specific interactions at the ligand-binding site of Nrp1.

  魔芋酸二酰胺（kCer）由具有特征性shingoid碱基和脂肪酸的植物型分子种类组成，通过化酶去葡萄糖化从魔芋葡糖鞘氨醇GlcCer制备而成。kCer激活semaforin 3A（Sema3A）信号通路，诱导崩塌反应介导蛋白2（CRMP2）的磷酸化。这导致PC12细胞中神经突起生长受抑制，剩余长神经突起形态发生变化。特定的kCer分子种类是否能与Sema3A受体（神经丝蛋白1，Nrp1）结合并激活Sema3A信号通路目前尚不清楚。在这里，我们使用内葡糖鞘氨醇酶I介导的去葡萄糖化制备了kCer分子种类，并检查了在神经生长因子（NGF）预处理的细胞中神经突起生长和崩塌反应介导蛋白2的磷酸化。kCer的鞘二烯醇8-反式不饱和对于Sema3A类似信号通路的激活至关重要。相反，kCer分子种类的鞘二烯醇8-顺式不饱和对Sema3A类似激活没有影响，并导致剩余短神经突起的神经突起抑制。此外，脂肪酸的α-羟基化与kCer分子种类的Sema3A类似活性无关。这些结果表明，鞘二烯醇8-反式或8-顺式异构化决定了Nrp1配体结合位点的特定相互作用。
• ——
  作者：A. S. Dmitrenok、P. Radhika、V. Anjaneyulu、C. Subrahmanyam、P. V. Subba Rao、P. S. Dmitrenok、V. M. Boguslavsky

  DOI：10.1023/a:1026089612129

  日期：——

  Sphingolipids and glycolipids including previously unknown (2S,3S,4R)-1,3,4-trihydroxy-2-(2-(R)-hydroxyoctadecanoylamino)octadec-8E-ene, (2S,3R)-1,3-dihydroxy-2-octadecanoylamino-4E,8E-hexadecadiene, and (2-hydroxy-3-hexadecyloxypropyl)-alpha-L-fucopyranoside were isolated from soft corals collected on the shelf near the Andaman Islands (Indian Ocean). The structures of all compounds were established by spectroscopic methods and chemical analyses. The lipids possessed antibacterial activity against Bacillus subtilis, Bacillus pumilus, Escherichia coli, and Pseudomonas aeruginosa and antifungal activity against Aspergillus niger, Rhizopus oryzae, and Candida albicans.