11α-hydroxygedunin | 913092-21-4

• 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: 11α-hydroxygedunin
• 英文别名: 11alpha-Hydroxygedunin；[(1S,2R,4S,7S,8S,10R,11R,12S,17R,19R)-7-(furan-3-yl)-10-hydroxy-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.02,4.02,8.012,17]nonadec-13-en-19-yl] acetate
• CAS: 913092-21-4
• 化学式: C₂₈H₃₄O₈
• 分子量: 498.573
• InChiKey: CJCDIECVGAPJFT-BJEYKFBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  11α-hydroxygedunin 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以87%的产率得到7-deacetoxy-7α,11α-dihydroxygedunin
  参考文献：
  名称：

  Hydroxylated Gedunin Derivatives from Cedrela sinensis

  摘要：

  Four new limonoids, 11 alpha-hydroxygedunin ( 1), 11 beta-hydroxygedunin (2), 7-deacetoxy-7 alpha,11 alpha-dihydroxygedunin ( 3), and 7-deacetoxy-7 alpha, 11 beta-dihydroxygedunin (4), were isolated from the cortex of Cedrela sinensis, together with three known compounds, gedunin ( 5), 7-deacetoxy-7 alpha-hydroxygedunin ( 6), and 11-oxogedunin ( 7). The structures of 1-4 were determined by a combination of 2D NMR experiments and chemical methods and by X-ray crystallography of 1 and 2.

  DOI：

  10.1021/np068021f

文献信息

• Fluorinated and rearranged gedunin derivatives
  作者：Yukio Hitotsuyanagi、Kumiko Mitsui、Haruhiko Fukaya、Koichi Takeya

  DOI：10.1016/j.phytol.2012.04.011

  日期：2012.9

  When treated with (diethylamino)sulfur trifluoride (DAST), 11α-hydroxygedunin gave 11β-fluorogedunin and 9,11-didehydrogedunin, whereas deacetylgedunin afforded two skeletal rearranged products 6 and 7, in which the Me-30 had shifted from position 8 to position 7. Of those products, 11β-fluorogedunin and 6 were shown to be more cytotoxic than gedunin on P-388 leukemia cells.

  当用（二乙氨基）三氟化硫（DAST）处理时，11α-羟基葛根宁产生11β-氟葛根宁和9,11-二氢氢化葛宁素，而去乙酰基古丁宁提供两个骨架重排产物6和7，其中Me-30从位置8转移到位置7.在这些产品中，对P-388白血病细胞，11β-氟精蛋白和6的细胞毒性比精蛋白高。