(-)-(4S,5S,10R,20R)-12,18-dihydroxyabieta-8,11,13-trien-20-aldehyde 18,20-methyl acetal | 1255526-07-8

• 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: (-)-(4S,5S,10R,20R)-12,18-dihydroxyabieta-8,11,13-trien-20-aldehyde 18,20-methyl acetal
• 英文别名: (-)-(4S,5S,10R,20R)-12,18-dihydroxyabieta-8,11,13-trien-20-aldehyde18,20-methyl acetal；(1R,10S,11S,14R)-14-methoxy-11-methyl-5-propan-2-yl-13-oxatetracyclo[9.3.3.01,10.02,7]heptadeca-2,4,6-trien-4-ol
• CAS: 1255526-07-8
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: UBQQOJDZHPQINO-BQJUDKOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲醇 、 (4S,5S,10R)-12,18-dihydroxyabieta-8,11,13-trien-20-aldehyde 18,20-hemiacetal 反应 24.0h， 生成 (-)-(4S,5S,10R,20R)-12,18-dihydroxyabieta-8,11,13-trien-20-aldehyde 18,20-methyl acetal 、 (-)-(4S,5S,10R,20S)-12,18-dihydroxyabieta-8,11,13-trien-20-aldehyde 18,20-methyl acetal
  参考文献：
  名称：

  Abietane and C₂₀-Norabietane Diterpenes from the Stem Bark of Fraxinus sieboldiana and Their Biological Activities

  摘要：

  Fourteen new abietane (1-14) and seven new C-20-norabietane (15-21) diterpenes, together with five known analogues, have been isolated from the stem bark of Fraxinus sieboldiana. Their structures were elucidated by spectroscopic data analysis. In the in vitro assays, at 10(-5) M, compounds 8, 16, and 22 showed inhibitory activity against the release of beta-glucuronidase in rat polymorphonuclear leukocytes induced by platelet-activating factor, with 59.7 +/- 4.8%, 56.1 +/- 5.6%, and 65.9 +/- 3.1% inhibition, respectively. Compound 23 was active against H5N1 avian influenza virus with an IC50 value of 4.8 mu M. Compounds 3 and 5 exhibited selective cytotoxic activities against A2780 (IC50 1.7 mu M) and A549 (IC50 6.0 mu M), respectively.

  DOI：

  10.1021/np100583u

文献信息

• Abietane and C₂₀-Norabietane Diterpenes from the Stem Bark of <i>Fraxinus sieboldiana</i> and Their Biological Activities
  作者：Sheng Lin、Yanling Zhang、Mingtao Liu、Sen Yang、Maoluo Gan、Jiachen Zi、Weixia Song、Xiaona Fan、Sujuan Wang、Yang Liu、Yongchun Yang、Xiaoguang Chen、Ying Guo、Wenjie Wang、Jiangong Shi

  DOI：10.1021/np100583u

  日期：2010.11.29

  Fourteen new abietane (1-14) and seven new C-20-norabietane (15-21) diterpenes, together with five known analogues, have been isolated from the stem bark of Fraxinus sieboldiana. Their structures were elucidated by spectroscopic data analysis. In the in vitro assays, at 10(-5) M, compounds 8, 16, and 22 showed inhibitory activity against the release of beta-glucuronidase in rat polymorphonuclear leukocytes induced by platelet-activating factor, with 59.7 +/- 4.8%, 56.1 +/- 5.6%, and 65.9 +/- 3.1% inhibition, respectively. Compound 23 was active against H5N1 avian influenza virus with an IC50 value of 4.8 mu M. Compounds 3 and 5 exhibited selective cytotoxic activities against A2780 (IC50 1.7 mu M) and A549 (IC50 6.0 mu M), respectively.