ohioensin C

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: ohioensin C
• 英文别名: Ohioensin B；(1R,15S,23S)-6,9,11-trihydroxy-22-oxahexacyclo[10.10.2.02,7.08,24.015,23.016,21]tetracosa-2(7),3,5,8(24),9,11,16,18,20-nonaen-13-one
• 化学式: C₂₃H₁₆O₅
• 分子量: 372.377
• InChiKey: VYRXNKPPFHPOIN-BTPUUTEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ohioensin C 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以1.2 mg的产率得到1,4-di-O-methylohioensin B
  参考文献：
  名称：

  Ohioensins: novel benzonaphthoxanthenones from Polytrichum ohioense

  摘要：

  Ohioensins A (1), B (2), C (3), D (4), and E (5), containing the novel polycyclic skeleton of (7bbeta,12balpha,14calpha)-7b,12b,13,14c-tetrahydro-14H-benzo[c]naphtho[2,1,8-mna]xanthen-14-one, have been isolated from the moss Polytrichum ohioense (Polytrichaceae) following bioassay-directed fractionation. The structures and relative stereochemistry of ohioensins were established on the basis of spectral analysis (UV, IR, MS, 2D NMR, and CD), chemical correlation, and X-ray diffraction. These compounds showed cytotoxicity against 9PS murine leukemia and the human tumor cell lines A-549 lung carcinoma, MCF-7 breast adenocarcinoma, and HT-29 colon adenocarcinoma. The proposed biogenetic pathway to ohioensins involves o-hydroxycinnamate and hydroxylated phenanthrenes as the intermediates.

  DOI：

  10.1021/jo00054a019

文献信息

• Ohioensins: novel benzonaphthoxanthenones from Polytrichum ohioense
  作者：Guo Qiang Zheng、Ching Jer Chang、Thomas J. Stout、Jon Clardy、David K. Ho、John M. Cassady

  DOI：10.1021/jo00054a019

  日期：1993.1

  Ohioensins A (1), B (2), C (3), D (4), and E (5), containing the novel polycyclic skeleton of (7bbeta,12balpha,14calpha)-7b,12b,13,14c-tetrahydro-14H-benzo[c]naphtho[2,1,8-mna]xanthen-14-one, have been isolated from the moss Polytrichum ohioense (Polytrichaceae) following bioassay-directed fractionation. The structures and relative stereochemistry of ohioensins were established on the basis of spectral analysis (UV, IR, MS, 2D NMR, and CD), chemical correlation, and X-ray diffraction. These compounds showed cytotoxicity against 9PS murine leukemia and the human tumor cell lines A-549 lung carcinoma, MCF-7 breast adenocarcinoma, and HT-29 colon adenocarcinoma. The proposed biogenetic pathway to ohioensins involves o-hydroxycinnamate and hydroxylated phenanthrenes as the intermediates.