oleanolic acid hemidiglycolate

• 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: oleanolic acid hemidiglycolate
• 英文别名: Oleanolic acid 3-O-diglyorate；(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[2-(carboxymethoxy)acetyl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• 化学式: C₃₄H₅₂O₇
• 分子量: 572.783
• InChiKey: VMILUZTZBYEMRC-VGBCDPHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  41
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  二甘醇酐 、 齐墩果酸 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 12.0h， 以99%的产率得到oleanolic acid hemidiglycolate
  参考文献：
  名称：

  Synthesis and evaluation of potential complement inhibitory semisynthetic analogs of oleanolic acid

  摘要：

  A number of semisynthetic analogs of oleanolic acid have been synthesized and tested for their complement inhibitory, cytotoxic and apoptotic activities. Among these, compounds 10 and 17 exhibited complement inhibitory potency superior to oleanolic acid. Both have also shown a moderate improvement in in vitro therapeutic index (T.I.). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00314-5

文献信息

• Anti-AIDS Agents. 30. Anti-HIV Activity of Oleanolic Acid, Pomolic Acid, and Structurally Related Triterpenoids
  作者：Yoshiki Kashiwada、Hui-Kang Wang、Tsuneatsu Nagao、Susumu Kitanaka、Ichiro Yasuda、Toshihiro Fujioka、Takashi Yamagishi、L. Mark Cosentino、Mutsuo Kozuka、Hikaru Okabe、Yasumasa Ikeshiro、Chang-Qi Hu、Eric Yeh、Kuo-Hsiung Lee

  DOI：10.1021/np9800710

  日期：1998.9.1

  with an IC50 value of 21.8 microg/mL [therapeutic index (T. I.) 12.8]. Pomolic acid, isolated from R. woodsii and H. capitata, was also identified as an anti-HIV agent (EC50 1.4 microg/mL, T. I. 16.6). Although ursolic acid did show anti-HIV activity (EC50 2.0 microg/mL), it was slightly toxic (IC50 6.5 microg/mL, T. I. 3.3). A new triterpene (11) was also isolated from the CHCl3-soluble fraction of

  齐墩果酸（1）已从多种植物中鉴定为抗HIV成分，包括蔷薇木（叶子），甘蓝Prosopis glandulosa（叶子和嫩枝），杜鹃花（整个植物），蒲桃（叶子），Hyptis capitata（整个植物） ）和Ternstromia Gymnanthera（空中部分）。它抑制EC-1值为1.7 microg / mL的急性感染H9细胞中的HIV-1复制，并抑制IC50值为21.8 microg / mL的H9细胞生长[治疗指数（TI）12.8]。分离自伍兹木和人参中的波摩尔酸也被鉴定为抗HIV药物（EC50为1.4 microg / mL，TI 16.6）。尽管熊果酸确实显示出抗HIV活性（EC50为2.0微克/毫升），但毒性微弱（IC50为6.5微克/毫升，TI 3.3）。还从伍德氏木。的CHCl3可溶级分中分离出了新的三萜（11），尽管它没有显示抗HIV活性。通过光谱检查确定11的结构为
• Synthesis and evaluation of potential complement inhibitory semisynthetic analogs of oleanolic acid
  作者：Haregewein Assefa、Alison Nimrod、Larry Walker、Robert Sindelar

  DOI：10.1016/s0960-894x(99)00314-5

  日期：1999.7

  A number of semisynthetic analogs of oleanolic acid have been synthesized and tested for their complement inhibitory, cytotoxic and apoptotic activities. Among these, compounds 10 and 17 exhibited complement inhibitory potency superior to oleanolic acid. Both have also shown a moderate improvement in in vitro therapeutic index (T.I.). (C) 1999 Elsevier Science Ltd. All rights reserved.