celangulin V | 139979-81-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: celangulin V
• 英文别名: angulatin A；Angulatin A；[(1S,2S,4S,5R,6S,7S,8S,9S,12R)-4,5-diacetyloxy-2,12-dihydroxy-2,10,10-trimethyl-8-(2-methylpropanoyloxy)-6-(2-methylpropanoyloxymethyl)-11-oxatricyclo[7.2.1.01,6]dodecan-7-yl] benzoate
• CAS: 139979-81-0
• 化学式: C₃₄H₄₆O₁₃
• 分子量: 662.731
• InChiKey: HAHJPPZGVANYSD-PNVCEFGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  47
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  181
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  1β,2β-diacetyloxy-8α,13-diisobutanoyloxy-6α-succinoyl-9-benzoyloxy-4α-hydroxy-β-dihydroagarofuran 、 celangulin V 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以63.6%的产率得到bis[(1S,2S,4S,5R,6S,7S,8S,9R,12R)-4,5-diacetyloxy-7-benzoyloxy-2-hydroxy-2,10,10-trimethyl-8-(2-methylpropanoyloxy)-6-(2-methylpropanoyloxymethyl)-11-oxatricyclo[7.2.1.01,6]dodecan-12-yl] butanedioate
  参考文献：
  名称：

  Synthesis and insecticidalactivity of novel dimers of celangulin-V and podophyllotoxin

  摘要：

  Celangulin-V（1）和鬼臼毒素（2）都是具有显著杀虫活性的天然化合物。以琥珀酸为连接剂合成了celangulin-V和鬼臼毒素的相同和非相同二聚体（3、4、5），并测试了它们对Mythimna separata三龄幼虫的杀虫活性。只有celangulin-V的相同二聚体（3）显示出一定的杀虫活性。

  DOI：

  10.1007/s10600-009-9396-9

文献信息

• Synthesis of 6β-([1-14C]propoxy)celangulin V
  作者：Zheng-Min Yang、Zhi-Qin Ji、Qing-Fu Ye、Wen-Jun Wu

  DOI：10.1002/jlcr.1493

  日期：2008.2

  Chinese bittersweet, Celastrus angulatus Max., is a widely distributed plant and is used as a traditional insecticide in China. Celangulin V (CA-V), one of the main insecticidal ingredients from the plant, has special insecticidal mechanism. A synthesized compound, 6β-propoxycelangulin V, exhibits more remarkable insecticidal activity against insect pests. In this study, the synthesis of a labeled

  中国苦甘菊Celastrus angulatus Max.是一种分布广泛的植物，在中国被用作传统的杀虫剂。Celangulin V (CA-V) 是植物中的主要杀虫成分之一，具有特殊的杀虫机制。合成的化合物 6β-丙氧基芹菜素 V 对害虫表现出更显着的杀虫活性。在这项研究中，标记版本的 CA-V 类似物 6β-([1-14C] 丙氧基) celangulin V 的合成是由 1-[1-14C] 丙醇和 CA-V 分两步完成的化学和放射化学纯度分别为 98.7% 和 99.9%。标记的化合物可用作放射性示踪剂来研究 CA-V 类似物的作用机制。版权所有 © 2008 John Wiley & Sons, Ltd.
• Preparation of Monoclonal Antibody against Celangulin V and Immunolocalization of Receptor in the Oriental Armyworm, <i>Mythimna separata</i> Walker (Lepidoptera:  Noctuidae)
  作者：Zhijun Qi、Xiaoping Xue、Wenjun Wu、Jiwen Zhang、Runya Yang

  DOI：10.1021/jf060890n

  日期：2006.10.1

  The botanical insecticide celangulin V (CA-V) is an insect digestive poison acting on midgut tissue of the target insect larvae. With the aim of localizing the receptor enacted by CA-V, monoclonal antibodies (MAbs) specific to the compound were developed. A hapten was synthesized by introducing a succinoyl into the CA-V structure and conjugated with three carrier proteins. From mice immunized with one conjugate, three MAbs were obtained with a potential capacity of detecting protein-bound residue forms of CA-V in the biological tissues. The oriental armyworm larvae ingested CA-V were examined by the technique of immuno-electron-microscopy (IEM) using the anti-CA-V MAb as the primary antibody and goat anti-mouse/ IgG labeled with colloidal gold as the secondary antibody. Electron micrographs of the armyworm midgut tissues showed that the CA-V was associated with the midgut epithelia of the insects. These results demonstrated the existence of a receptor enacted by CA-V on the midgut cells of the oriental armyworm larvae.
• Synthesis and insecticidalactivity of novel dimers of celangulin-V and podophyllotoxin
  作者：Zhang Ji-wen、Li Sheng-kun、Ji Zhi-qin、Hu Zhao-nong、Wu Wen-jun

  DOI：10.1007/s10600-009-9396-9

  日期：2009.7

  Celangulin-V (1) and podophyllotoxin (2) are both natural compounds with significant insecticidal activity. The identical and nonidentical dimers of celangulin-V and podophyllotoxin (3, 4, 5) were synthesized using succinic acid as the linker, and their insecticidal activities against 3rd instar larvae of Mythimna separata were tested. Only the identical dimer of celangulin-V (3) show some insecticidal activity.

  Celangulin-V（1）和鬼臼毒素（2）都是具有显著杀虫活性的天然化合物。以琥珀酸为连接剂合成了celangulin-V和鬼臼毒素的相同和非相同二聚体（3、4、5），并测试了它们对Mythimna separata三龄幼虫的杀虫活性。只有celangulin-V的相同二聚体（3）显示出一定的杀虫活性。