taccabulin A

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: taccabulin A
• 英文别名: 1-(3-hydroxy-4-methoxyphenyl)-3-(2,4,6-trimethoxyphenyl)-propan-1-one；1-(3-Hydroxy-4-methoxyphenyl)-3-(2,4,6-trimethoxyphenyl)propan-1-one；1-(3-hydroxy-4-methoxyphenyl)-3-(2,4,6-trimethoxyphenyl)propan-1-one
• 化学式: C₁₉H₂₂O₆
• 分子量: 346.38
• InChiKey: GCROVFAGFAHOEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-甲氧基-3-羟基苯乙酮 在 4-二甲氨基吡啶 、 [Rh(acac)(CO)2] 、 potassium carbonate 、 三乙胺 、 三氟乙酸 、 diisopropylammonium trifluoroacetate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 46.0h， 生成 taccabulin A
  参考文献：
  名称：

  水杨醛与乙烯基酮的Rh催化脱羰基加成：牛角菌素A–E的合成

  摘要：

  开发了水杨醛与乙烯基酮进行Rh催化的羰基脱羰加成反应，以高收率合成邻羟基二氢查耳酮。该方案被应用于天然产物他卡布林家族的合成。

  DOI：

  10.1002/ejoc.201901314

文献信息

• Selective oxidation of benzylic alcohols by laccase from white-rot mushroom Tricholoma giganteum AGHP: Total synthesis of taccabulin A, taccabulin D and taccabulin E
  作者：Amardeep R. Jadhao、Helina Patel、Kisan M. Kodam、Akshaya Gupte、Suresh B. Waghmode

  DOI：10.1016/j.tet.2022.133114

  日期：2022.12

  green and selective oxidation of benzylic alcohols to corresponding aldehydes using laccase enzyme, produced by mushroom Tricholoma giganteum AGHP in presence of TEMPO as a mediator under mild and environmentally friendly reaction conditions with excellent yield (up to 95%) in 8–24 h. The applicability of this methodology has been extended to various substrates and in the total synthesis of anticancer agents

  使用漆酶将苄醇绿色选择性氧化为相应的醛，由蘑菇Tricholoma giganteum AGHP 在 TEMPO 存在下作为介质在温和和环境友好的反应条件下产生，在 8-24 小时内具有优异的产率（高达 95％）。这种方法的适用性已扩展到各种底物和抗癌剂、天然二氢查耳酮 taccabulin A、taccabulin D 和 taccabulin E 的全合成。
• The Bat Flower: A Source of Microtubule-Destabilizing and -Stabilizing Compounds with Synergistic Antiproliferative Actions
  作者：April L. Risinger、Jiangnan Peng、Cristina C. Rohena、Hector R. Aguilar、Doug E. Frantz、Susan L. Mooberry

  DOI：10.1021/np4005079

  日期：2013.10.25

  The biosynthesis of secondary metabolites provides higher plants with mechanisms of defense against microbes, insects, and herbivores. One common cellular target of these molecules is the highly conserved microtubule cytoskeleton, and microtubule-targeting compounds with insecticidal, antifungal, nematicidal, and anticancer activities have been identified from plants. A new retro-dihydrochalcone, taccabulin A, with microtubule-destabilizing activity has been identified from the roots and rhizomes of Tacca species. This finding is notable because the microtubule-stabilizing taccalonolides are also isolated from these sources. This is the first report of an organism producing compounds with both microtubule-stabilizing and -destabilizing activities. A two-step chemical synthesis of taccabulin A was performed. Mechanistic studies showed that taccabulin A binds within the colchicine site on tubulin and has synergistic antiproliferative effects against cancer cells when combined with a taccalonolide, which binds to a different site on tubulin. Taccabulin A is effective in cells that are resistant to many other plant-derived compounds. The discovery of a natural source that contains both microtubule-stabilizing and -destabilizing small molecules is unprecedented and suggests that the synergistic action of these compounds was exploited by nature long before it was discovered in the laboratory.