3α-hydroxytaraxer-14-en-28-oic acid

• 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: 3α-hydroxytaraxer-14-en-28-oic acid
• 英文别名: 3β-hydroxytaraxer-14-en-28-oic acid；3α-hydroxy-14-taraxeren-28-acid；isoaleuritolic acid；(4aS,6aR,6bR,8aR,10R,12aR,14aS,14bS)-10-hydroxy-2,2,6b,9,9,12a,14a-heptamethyl-1,3,4,5,6a,7,8,8a,10,11,12,13,14,14b-tetradecahydropicene-4a-carboxylic acid
• 化学式: C₃₀H₄₈O₃
• 分子量: 456.709
• InChiKey: BHHPRAFMEFGOLZ-KRKYDRBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  33
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3α-hydroxytaraxer-14-en-28-oic acid 在 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 0.5h， 以11 mg的产率得到
  参考文献：
  名称：

  Anti-HIV and NO production inhibition activities of epi-aleuritolic acid derivatives

  摘要：

  Fifteen epi-aleuritolic acid derivatives were synthesized and evaluated for anti-HIV activity in 293 T cells and NO production inhibition activity. Of the derivatives, 1, 2, 3, 4, 11, and 13 showed relatively potent anti-HIV activity with EC50 values ranging from 5.80 to 13.30M. The most potent compound, 3-2,2-dimethylsuccinic acyl epi-aleuritolic acid (11), displayed significant anti-HIV activity with an EC50 value of 5.80M. Compounds 1, 3, 4, and 11 showed NO inhibition activity, with IC50 values ranging from 3.40 to 7.10M and compound 1 inhibited NO production with an IC50 value of 3.40M.

  DOI：

  10.1080/10286020.2013.787990
• 作为产物：
  描述：

  3α-(3'',4''-dihydroxy-trans-cinnamoyloxy)-D-friedoolean-14-en-28-oic acid 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以3 mg的产率得到3α-hydroxytaraxer-14-en-28-oic acid
  参考文献：
  名称：

  Isotamarixen - A New Antioxidant and Prolyl Endopeptidase-Inhibiting Triterpenoid fromTamarix hispida

  摘要：

  从Tamarix hispida Willd.的地上部分中分离出一种新的五环三萜类化合物3α-(3′′,4′′-二羟基-反式-肉桂酰氧基)-D-弗里多烷-14-烯-28-酸（1）以及两种已知化合物鼠李素（2）和异鼠李素（3）。化合物1是一种强效抗氧化剂。此外，化合物1-3对脯氨酰内肽酶（PEP）显示出显著的抑制活性。

  DOI：

  10.1055/s-2004-815458

文献信息

• Isotamarixen - A New Antioxidant and Prolyl Endopeptidase-Inhibiting Triterpenoid from<i>Tamarix hispida</i>
  作者：Sultanova, Nurgul、Makhmoor, Talat、Yasin, Amsha、Abilov、Omurkamzinova、Atta-ur-Rahman、Choudhary, M. Iqbal

  DOI：10.1055/s-2004-815458

  日期：2004.1

  A new pentacyclic triterpenoid, 3α-(3′′,4′′-dihydroxy-trans-cinnamoyloxy)-D-friedoolean-14-en-28-oic acid (1) has been isolated along with two known compounds, rhamnocitrin (2) and isorhamnetin (3) from the aerial parts of Tamarix hispida Willd. Compound 1 was found to be a potent antioxidant. In addition, compounds 1 - 3 showed significant inhibitory activity against prolylendopeptidase (PEP).

  从Tamarix hispida Willd.的地上部分中分离出一种新的五环三萜类化合物3α-(3′′,4′′-二羟基-反式-肉桂酰氧基)-D-弗里多烷-14-烯-28-酸（1）以及两种已知化合物鼠李素（2）和异鼠李素（3）。化合物1是一种强效抗氧化剂。此外，化合物1-3对脯氨酰内肽酶（PEP）显示出显著的抑制活性。
• Anti-HIV and NO production inhibition activities of epi-aleuritolic acid derivatives
  作者：Jia-Bao Liu、Ying Zhang、Bao-Song Cui、Ying-Li Cao、Shao-Peng Yuan、Ying Guo、Qi Hou、Shuai Li

  DOI：10.1080/10286020.2013.787990

  日期：2013.5

  Fifteen epi-aleuritolic acid derivatives were synthesized and evaluated for anti-HIV activity in 293 T cells and NO production inhibition activity. Of the derivatives, 1, 2, 3, 4, 11, and 13 showed relatively potent anti-HIV activity with EC50 values ranging from 5.80 to 13.30M. The most potent compound, 3-2,2-dimethylsuccinic acyl epi-aleuritolic acid (11), displayed significant anti-HIV activity with an EC50 value of 5.80M. Compounds 1, 3, 4, and 11 showed NO inhibition activity, with IC50 values ranging from 3.40 to 7.10M and compound 1 inhibited NO production with an IC50 value of 3.40M.