ophiobolin H | 90108-64-8

• 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: ophiobolin H
• 英文别名: (1S,3R,6R,7S,9E,13S,15R,16S)-3,15-dimethyl-6-[(2S,3Z)-6-methylhepta-3,5-dien-2-yl]-12-oxatetracyclo[8.5.1.03,7.013,16]hexadec-9-ene-13,15-diol
• CAS: 90108-64-8
• 化学式: C₂₅H₃₈O₃
• 分子量: 386.575
• InChiKey: IBUCSLMTZXQXRS-CNKIPQCUSA-N

物化性质

• 沸点：
  520.9±50.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ophiobolin K 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以0.8 mg的产率得到ophiobolin H
  参考文献：
  名称：

  Cytotoxic sesterterpenes, 6-epi-ophiobolin G and 6-epi-ophiobolin N, from marine derived fungus Emericella variecolor GF10

  摘要：

  Two new sesterterpenes, 6-epi-ophiobolin G (1) and 6-epi-ophiobolin N (3), and six known ophiobolins were isolated from the extracts of the fungus, Emericella variecolor GF10, which was separated from marine sediment. The planar structures of the new compounds were deduced from analysis of the 2D NMR spectra, and the stereochemistry was determined by extensive examination of the NOESY spectrum. Additionally, the configuration of the C-6 proton in ophiobolin G (2) was revised from alpha to beta, and the unsolved stereochemistry of ophiobolin H (4) was determined by its physicochemical evidence and the chemical correlation with ophiobolin K (8). Ophiobolin K (8) showed cytotoxic activity against various tumor cell lines, including adriamycin-resistant mouse leukemia cells (P388), with IC50 of 0.27-0.65 muM. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.021