[(1S,3aR,5R,5aR,8aR,9S,9aR)-1,5,8a-三甲基-2,8-二氧代-3a,4,5,5a,9,9a-六氢-1H-薁并[6,5-b]呋喃-9-基] 乙酸酯 | 36505-53-0

• 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
• 中文名称: [(1S,3aR,5R,5aR,8aR,9S,9aR)-1,5,8a-三甲基-2,8-二氧代-3a,4,5,5a,9,9a-六氢-1H-薁并[6,5-b]呋喃-9-基] 乙酸酯
• 中文别名: [(1S,3aR,5R,5aR,8aR,9S,9aR)-1,5,8a-三甲基-2,8-二氧代-3a,4,5,5a,9,9a-六氢-1H-薁并[6,5-b]呋喃-9-基]乙酸酯
• 英文名称: arnicolide A
• 英文别名: 6-O-acetyl-11α,13-dihydrohelenalin；11α,13-dihydrohelenanlin acetate；11α,13-dihydrohelenalin acetate；11α,13-dihydrohelenalinacetate；acetyldihydrohelenalin；O-Acetyl-dihydrohelenalin；[(1S,3aR,5R,5aR,8aR,9S,9aR)-1,5,8a-trimethyl-2,8-dioxo-3a,4,5,5a,9,9a-hexahydro-1H-azuleno[6,5-b]furan-9-yl] acetate
• CAS: 36505-53-0
• 化学式: C₁₇H₂₂O₅
• 分子量: 306.359
• InChiKey: NEIIKBWBBCJSQU-HESYKRBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  reduced glutathione 、 [(1S,3aR,5R,5aR,8aR,9S,9aR)-1,5,8a-三甲基-2,8-二氧代-3a,4,5,5a,9,9a-六氢-1H-薁并[6,5-b]呋喃-9-基] 乙酸酯 以 乙醇 、 水 为溶剂， 生成 2β-S-glutathionyl-2,3,11α,13-tetrahydrohelenalin acetate
  参考文献：
  名称：

  Helenanolide type sesquiterpene lactones. Part 5: The role of glutathione addition under physiological conditions

  摘要：

  Sesquiterpene lactones (STLs) are known to exert most of their numerous biological activities through inhibition of enzymes and other functional proteins by forming covalent bonds with free cysteine residues in these macromolecules. The question arises how these drugs can alkylate such vital target structures instead of being quickly deactivated by reaction with the cysteine group of glutathione (GSH) which is present in high concentrations in all cells. We have measured in this study the pH dependent kinetics of GSH addition to the cyclopentenone and alpha-methylene-gamma-lactone group of helenanolide type sesquiterpene lactones using UV-spectrophotometry. The reaction with GSH at physiological pH proceeds very quickly but is reversible so that a fraction of STL molecules-will always be available for reaction with protein targets. In agreement with these chemical data, helenalin-monoand -bis-glutathionyl adducts were demonstrated to inhibit the nuclear transcription factor NF-kappa B at concentrations similar to the free sesquiterpene lactone. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00234-5
• 作为产物：
  描述：

  (1S,3aR,5R,5aR,8aR,9S,9aS)-9-羟基-1,5,8a-三甲基-3a,4,5,5a,9,9a-六氢-1H-薁并[7,6-D]呋喃-2,8-二酮 生成 [(1S,3aR,5R,5aR,8aR,9S,9aR)-1,5,8a-三甲基-2,8-二氧代-3a,4,5,5a,9,9a-六氢-1H-薁并[6,5-b]呋喃-9-基] 乙酸酯
  参考文献：
  名称：

  Helenalin. III. Reduction and Dehydrogenation

  摘要：

  DOI：

  10.1021/ja01175a089

文献信息

• On the Stability of Sesquiterpene Lactones in the Officinal Arnica Tincture of the German Pharmacopoeia¹
  作者：Thomas J. Schmidt、Uwe Matthiesen、Günter Willuhn

  DOI：10.1055/s-2000-8635

  日期：2000.10

  An investigation of sesquiterpene lactone content in Arnica tincture (German Pharmacopoeia) after storage for three years at different temperatures (+ 4, + 25 and + 30 °C) was carried out by GC and GC-MS analysis. A decrease (13, 32 and 37 %, respectively) in the content of the main active compounds in this preparation, 11α,13-dihydrohelenalin esters, correlating with storage temperature was found. This change was shown to be caused by addition of ethanol to the cyclopentenone structure of these molecules leading to 2-ethoxy-2,3,11,13-tetrahydrohelenalin derivatives.

  通过气相色谱和气相色谱-质谱分析，对山金车酊（德国药典）在不同温度（+4、+25和+30°C）下存放三年后的倍半萜内酯含量进行了调查。研究发现，该制剂中主要活性成分11α,13-二氢海伦宁酯的含量分别下降了13%、32%和37%，这与存放温度有关。这种变化是由于在这些分子的环戊烯酮结构中添加了乙醇，导致形成2-乙氧基-2,3,11,13-四氢海伦宁衍生物。
• Helenalin. III. Reduction and Dehydrogenation
  作者：Roger. Adams、Werner. Herz

  DOI：10.1021/ja01175a089

  日期：1949.7
• Helenanolide type sesquiterpene lactones. Part 5: The role of glutathione addition under physiological conditions
  作者：Thomas J Schmidt、Guido Lyß、Heike L Pahl、Irmgard Merfort

  DOI：10.1016/s0968-0896(99)00234-5

  日期：1999.12

  Sesquiterpene lactones (STLs) are known to exert most of their numerous biological activities through inhibition of enzymes and other functional proteins by forming covalent bonds with free cysteine residues in these macromolecules. The question arises how these drugs can alkylate such vital target structures instead of being quickly deactivated by reaction with the cysteine group of glutathione (GSH) which is present in high concentrations in all cells. We have measured in this study the pH dependent kinetics of GSH addition to the cyclopentenone and alpha-methylene-gamma-lactone group of helenanolide type sesquiterpene lactones using UV-spectrophotometry. The reaction with GSH at physiological pH proceeds very quickly but is reversible so that a fraction of STL molecules-will always be available for reaction with protein targets. In agreement with these chemical data, helenalin-monoand -bis-glutathionyl adducts were demonstrated to inhibit the nuclear transcription factor NF-kappa B at concentrations similar to the free sesquiterpene lactone. (C) 1999 Elsevier Science Ltd. All rights reserved.