tomentosin | 33649-15-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: tomentosin
• 英文别名: xanthalongin；(3aR,7S,8aR)-7-methyl-3-methylidene-6-(3-oxobutyl)-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one
• CAS: 33649-15-9
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: AVFIYMSJDDGDBQ-CUOATXAZSA-N

物化性质

• 熔点：
  121-122 °C(Solv: methanol (67-56-1))
• 沸点：
  416.2±45.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)
• 溶解度：
  溶于 DMSO (50 mg/ml)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tomentosin 在 叠氮基三甲基硅烷 、 copper(II) sulfate 、 溶剂黄146 、 sodium ascorbate 、 四亚甲基二胺 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 60.0h， 生成
  参考文献：
  名称：

  Synthesis of novel 1,2,3-triazole-substituted tomentosins

  摘要：

  摘要：从tomentosin中获得了一系列含1,2,3-三唑的tomentosin骨架。合成涉及将三甲基硅氮化物进行迈克尔加成反应，作用于天然倍半萜内酯tomentosin的α-亚甲基-γ-内酯功能上，得到了两个非对映异构体2和3，通过柱层析法容易分离。这些化合物经历了铜催化的Huisgen 1,3-双极环加成反应与各种末端炔烃，得到了化合物4a-h和5a-h，收率较高。

  DOI：

  10.1515/znb-2018-0225

文献信息

• Synthesis of novel spiro-isoxazoline and spiro-isoxazolidine derivatives of tomentosin
  作者：Mohamed Zaki、Abdelouahd Oukhrib、Mohamed Akssira、Sabine Berteina-Raboin

  DOI：10.1039/c6ra25869g

  日期：——

  A series of novel enantiomerically pure spiro-isoxazolidines and spiro-isoxazolines were synthesized regioselectively by 1,3-dipolar cycloaddition using respectively two dipoles, nitrones and nitrile oxides, on the exocyclic double bond of the B ring of tomentosin (α-methylene-γ-butyrolactone), a sesquiterpene lactone extracted from Dittrichia viscosa.

  通过1,3-偶极环加成反应，分别在绒毛膜球蛋白B环（α-亚甲基-γ -丁内酯），一种从粘菌（Dittrichia viscosa）中提取的倍半萜烯内酯。
• Design, Synthesis, and Biological Evaluation of Novel Tomentosin Derivatives in NMDA-Induced Excitotoxicity
  作者：Mohamed Zaki、Mohammed Loubidi、Tuğçe Bilgiç、Derviş Birim、Mohamed Akssira、Taner Dagcı、Sabine Berteina-Raboin、Luciano Saso、Mostafa Khouili、Güliz Armagan

  DOI：10.3390/ph15040421

  日期：——

  N-methyl-D-aspartate (NMDA) receptor stimulation may lead to excitotoxicity, which triggers neuronal death in brain disorders. In addition to current clinical therapeutic approaches, treatment strategies by phytochemicals or their derivatives are under investigation for neurodegenerative diseases. In the present study, novel amino and 1,2,3-triazole derivatives of tomentosin were prepared and tested for their protective and anti-apoptotic effects in NMDA-induced excitotoxicity. Amino-tomentosin derivatives were generated through a diastereoselective conjugate addition of several secondary amines to the α-methylene-γ-butyrolactone function, while the 1,2,3-triazolo-tomentosin was prepared by a regioselective Michael-type addition carried out in the presence of trimethylsilyl azide (TMSN3) and the α-methylene-γ-lactone function. The intermediate key thus obtained underwent 1,3-dipolar Huisgen cycloaddition using a wide range of terminal alkynes. The possible effects of the derivatives on cell viability and free-radical production following NMDA treatment were measured by Water-Soluble Tetrazolium Salts (WST-1) and Dichlorofluorescein Diacetate (DCF-DA) assays, respectively. The alterations in apoptosis-related proteins were examined by Western blot technique. Our study provides evidence that synthesized triazolo- and amino-tomentosin derivatives show neuroprotective effects by increasing cellular viability, decreasing ROS production, and increasing the Bcl-2/Bax ratio in NMDA-induced excitotoxicity. The findings highlight particularly 2e, 2g, and 6d as potential regulators and neuroprotective agents in NMDA overactivation.

  N-甲基-D-天门冬氨酸（NMDA）受体刺激可能导致兴奋毒性，在脑部疾病中触发神经元死亡。除了当前的临床治疗方法外，植物化学物质或其衍生物的治疗策略正在研究中用于神经退行性疾病。在本研究中，制备了新型的天门冬素氨基和1,2,3-三唑衍生物，并测试了它们在NMDA诱导的兴奋毒性中的保护和抗凋亡作用。通过二对映选择性的缩合加成，将多种次级胺与α-亚甲基-γ-丁内酯功能基结合，生成了氨基天门冬素衍生物，而1,2,3-三唑基天门冬素则通过在三甲基硅基偶氮甲烷（TMSN3）和α-亚甲基-γ-内酯功能的存在下进行区域选择性的Michael加成制备。因此获得的中间体经历了1,3-偶极环加成，使用广泛的末端炔烃。通过水溶性四唑盐（WST-1）和二氯荧光二乙酸酯（DCF-DA）试验测量了衍生物对NMDA处理后细胞存活率和自由基产生的可能影响。使用Western blot技术检查了与凋亡相关的蛋白质的变化。我们的研究证明，合成的三唑基和氨基天门冬素衍生物通过增加细胞存活率，降低ROS产生，并在NMDA诱导的兴奋毒性中增加Bcl-2/Bax比率，显示出神经保护作用。发现特别是2e、2g和6d作为NMDA过度活化的潜在调节剂和神经保护剂。
• LANZETTA, ROSA;LAMA, GIUSEPPE;MAURIELLO, GIACOMO;PARRILLI, MICHELANGELO;R+, PHYTOCHEMISTRY, 30,(1991) N, C. 1121-1124
  作者：LANZETTA, ROSA、LAMA, GIUSEPPE、MAURIELLO, GIACOMO、PARRILLI, MICHELANGELO、R+

  DOI：——

  日期：——
• Ichthyotoxic sesquiterpenes and xanthanolides from Dittrichia graveolens
  作者：Rosa Lanzetta、Giuseppe Lama、Giacomo Mauriello、Michelangelo Parrilli、Rocco Racioppi、Guido Sodano

  DOI：10.1016/s0031-9422(00)95185-9

  日期：1991.1

  The ichthyotoxicity of Dittrichia graveolens was found to be due to the major sesquiterpenes 12-carboxyeudesma-3,11(13)-diene and tomentosin. In addition, seven structurally related sesquiterpenes and two new xanthanolides were isolated and their structures elucidated.
• [EN] COMPOSITIONS AND METHODS FOR TREATING A SKIN DISORDER<br/>[FR] COMPOSITIONS ET MÉTHODES DE TRAITEMENTS D'UNE AFFECTION CUTANÉE
  申请人：ABRHAM GALYA

  公开号：WO2012090194A2

  公开（公告）日：2012-07-05

  The present invention discloses compositions, methods and kits for treating topical disorders, some of which are associated with a viral infections, the composition comprising at least one of a plant extract comprising at least one of tomentosin and inuviscolide, tomentosin, inuviscolide, a plant cell culture extract comprising at least one of tomentosin and inuviscolide and an Inula viscosa extract and a pharmaceutically acceptable carrier.