ligerin | 1401999-49-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ligerin
• 英文别名: Ligerin；4-[(1R,2S,3S,4R)-4-(chloromethyl)-4-hydroxy-2-methoxy-3-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]cyclohexyl]oxy-4-oxobutanoic acid
• CAS: 1401999-49-2
• 化学式: C₂₀H₃₁ClO₇
• 分子量: 418.915
• InChiKey: FKTJAQKUCINAIF-JNYDFHNISA-N

物化性质

• 沸点：
  557.5±50.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  烟曲霉素 在 吡啶 、 4-二甲氨基吡啶 、 溶剂黄146 、 lithium chloride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 44.0h， 生成 ligerin
  参考文献：
  名称：

  Ligerin，一种来自海洋的青霉菌株的抗增殖氯化倍半萜素

  摘要：

  从海洋衍生的青霉属青霉属菌株中分离出一种新的烟曲霉素的氯化倍半萜类化合物Ligerin（1）以及已知的化合物青霉酸（2），奥西诺尔和奥数酸。通过对包括IR，UV和HRESIMS在内的光谱数据的解释，以及对一维和二维NMR光谱分析以及X射线分析的分析，可以确定化学结构，从而确定绝对构型。Ligerin（1）对骨肉瘤细胞系表现出强大的抑制活性。这是首次从海洋来源的青霉菌株中分离出烟曲霉素类似物。

  DOI：

  10.1021/np3007364

文献信息

• Synthesis and antiproliferative activity of ligerin and new fumagillin analogs against osteosarcoma
  作者：Elodie Blanchet、Marieke Vansteelandt、Ronan Le Bot、Maxim Egorov、Yann Guitton、Yves François Pouchus、Olivier Grovel

  DOI：10.1016/j.ejmech.2014.04.012

  日期：2014.5

  Ligerin (1) is a natural chlorinated merosesquiterpenoid related to fumagillin (2) exhibiting a selective antiproliferative activity against osteosarcoma cell lines and an in vivo antitumor activity in a murine model. Semisynthesis of ligerin analogs was performed in order to study the effects of the C3-spiroepoxide substitution by a halogenated moiety together with the modulation of the C6 chain. Results showed that all derivatives exhibited an in vitro antiproliferative activity against osteosarcoma cell lines and that chlorohydrin compounds were equally or more active than their spiroepoxy analogs. Among semisynthetic analogs, the parent compound 1 was the best candidate for further studies since it exhibited higher or equivalent activity compared to TNP470 (3) against SaOS2 and MG63 human osteosarcoma cells with a four times weaker toxicity against HFF2 human fibroblasts. Quantitative videomicroscopy analysis was conducted and allowed a better understanding of the mechanism of its antiproliferative activity. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Ligerin, an Antiproliferative Chlorinated Sesquiterpenoid from a Marine-Derived <i>Penicillium</i> Strain
  作者：Marieke Vansteelandt、Elodie Blanchet、Maxim Egorov、Fabien Petit、Loïc Toupet、Arnaud Bondon、Fabrice Monteau、Bruno Le Bizec、Olivier P. Thomas、Yves François Pouchus、Ronan Le Bot、Olivier Grovel

  DOI：10.1021/np3007364

  日期：2013.2.22

  A new chlorinated sesquiterpenoid analogue of fumagillin, ligerin (1), was isolated from a marine-derived strain of Penicillium, belonging to the subgenus Penicillium, along with the known compounds penicillic acid (2), orcinol, and orsellinic acid. Chemical structures were established by an interpretation of spectroscopic data including IR, UV, and HRESIMS, together with analyses of 1D and 2D NMR

  从海洋衍生的青霉属青霉属菌株中分离出一种新的烟曲霉素的氯化倍半萜类化合物Ligerin（1）以及已知的化合物青霉酸（2），奥西诺尔和奥数酸。通过对包括IR，UV和HRESIMS在内的光谱数据的解释，以及对一维和二维NMR光谱分析以及X射线分析的分析，可以确定化学结构，从而确定绝对构型。Ligerin（1）对骨肉瘤细胞系表现出强大的抑制活性。这是首次从海洋来源的青霉菌株中分离出烟曲霉素类似物。