2beta,3alpha-Epitaondiol | 863548-84-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2beta,3alpha-Epitaondiol
• 英文别名: (1S,2R,11R,14S,15R,18S,20R)-1,8,11,15,19,19-hexamethyl-10-oxapentacyclo[12.8.0.02,11.04,9.015,20]docosa-4(9),5,7-triene-6,18-diol
• CAS: 863548-84-9
• 化学式: C₂₇H₄₀O₃
• 分子量: 412.613
• InChiKey: LRMHPGVONLYGQD-XFNQIGALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  30
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2beta,3alpha-Epitaondiol 、 乙酸酐 在 吡啶 作用下， 反应 24.0h， 生成 2β,3α-epitaondiol diacetate
  参考文献：
  名称：

  Neurotoxic Meroditerpenoids from the Tropical Marine Brown Alga Stypopodium flabelliforme

  摘要：

  Brine shrimp toxicity and TLC analysis guided the isolation of five new and biologically active meroditerpenoids [2 beta,3 alpha-epitaondiol (1), flabellinol (2), flabellinone (3), stypotriolaldehyde (4), and stypohydroperoxide (5)] along with five known compounds from the marine brown alga Stypopodium. flabelliforme collected in Papua New Guinea. The planar structures of compounds 1-5 were determined by extensive spectroscopic analysis (1D and 2D NMR, LRMS, HRMS, IR, and UV), while relative configuration was determined by 1D and 2D NOE experiments. X-ray crystallography confirmed the relative configuration of 2 beta,3 alpha-epitaondiol (1), and the modified Mosher's ester method was used to establish its absolute configuration. All of the new metabolites were moderately toxic to murine neuro2a cells (LC50 2-25 mu M), and three [2 beta,3 alpha-epitaondiol (1), flabellinol (2), and flabellinone (3)] possessed potent sodium channel blocking activity. Stypotriolaldehyde (4) had a biphasic effect on the concentration of intracellular Ca2+ in rat cerebellar granule neurons (CGN). The previously known compound, stypoldione (6), also modulated intracellular calcium concentration and was cytotoxic in CGN. Metabolites 2 beta,3 alpha-epitaondiol (1), flabellinol (2), and flabellinone (3) displayed moderate cytotoxicity to the NCI-H460 human lung cancer cell line.

  DOI：

  10.1021/np050051f