endiandrin B | 1140478-56-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 环丁烷木脂素
• 英文名称: endiandrin B
• 英文别名: 8β,8'β-dimethyl-7α,7'α-bis(3-methoxy-4-hydroxyphenyl)cyclobutane；4-[(1R,2S,3R,4S)-2-(4-hydroxy-3-methoxyphenyl)-3,4-dimethylcyclobutyl]-2-methoxyphenol
• CAS: 1140478-56-3
• 化学式: C₂₀H₂₄O₄
• 分子量: 328.408
• InChiKey: QDBUCXMBHJMGCN-JARDSOJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 endiandrin B 以 甲醇 、 乙醚 为溶剂， 以74%的产率得到cis-1,2-Di-(3,4-dimethoxyphenyl)-anti-cis-3,4-dimethylcyclobutane
  参考文献：
  名称：

  Isolation, structure elucidation and cytotoxic evaluation of endiandrin B from the Australian rainforest plant Endiandra anthropophagorum

  摘要：

  Chemical investigations of the DCM extract from the roots of Endiandra anthropophagorum resulted in the isolation of a new cyclobutane lignan endiandrin B (1), together with the known natural products, endiandrin A (2), and (-)-dihydroguaiaretic acid (3). The structure of 1 was determined by extensive spectroscopic analyses, and confirmed by single crystal X-ray crystallography. Methylation of 1 using diazomethane afforded the previously reported natural product, cinbalansan (4). All compounds were evaluated for their cytotoxicity towards human lung carcinoma cells (A549) using high-content screening. (-)-Dihydroguaiaretic acid (3) was found to be the most potent cytotoxin against the A549 lung carcinoma cell line, with an IC50 value of 7.49 mu M. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.12.030

文献信息

• Isolation, structure elucidation and cytotoxic evaluation of endiandrin B from the Australian rainforest plant Endiandra anthropophagorum
  作者：Rohan A. Davis、Emma C. Barnes、James Longden、Vicky M. Avery、Peter C. Healy

  DOI：10.1016/j.bmc.2008.12.030

  日期：2009.2

  Chemical investigations of the DCM extract from the roots of Endiandra anthropophagorum resulted in the isolation of a new cyclobutane lignan endiandrin B (1), together with the known natural products, endiandrin A (2), and (-)-dihydroguaiaretic acid (3). The structure of 1 was determined by extensive spectroscopic analyses, and confirmed by single crystal X-ray crystallography. Methylation of 1 using diazomethane afforded the previously reported natural product, cinbalansan (4). All compounds were evaluated for their cytotoxicity towards human lung carcinoma cells (A549) using high-content screening. (-)-Dihydroguaiaretic acid (3) was found to be the most potent cytotoxin against the A549 lung carcinoma cell line, with an IC50 value of 7.49 mu M. (C) 2008 Elsevier Ltd. All rights reserved.