3-sulfate of oleanolic 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: 3-sulfate of oleanolic acid
• 英文别名: oleanolic acid 3-O-sulfate；oleanolic acid 3-sulfate；oleanolic acid sulfate；(3beta)-3-(Sulfooxy)olean-12-en-28-oic Acid；(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10-sulfooxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• 化学式: C₃₀H₄₈O₆S
• 分子量: 536.774
• InChiKey: HPTCFCREEHCWMI-GTOFXWBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  37
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 3-sulfate of oleanolic acid 以 乙醚 为溶剂， 以45 mg的产率得到(4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-2,2,6a,6b,9,9,12a-Heptamethyl-10-sulfooxy-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid methyl ester
  参考文献：
  名称：

  Triterpene glycosides ofHedera helix III. Structure of the triterpene sulfates and their glycosides

  摘要：

  From the leaves of English ivy Hedera helix L. we have isolated the known 3-sulfates of oleanolic and echinocystic acids and their 28-O-alpha-L-rhamnopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-O-beta-D-glucopyranosyl esters and the new 3-sulfate of 28-O-beta-gentiobiosyl oleanolate - helicoside L-8a. The structures of the compounds isolated were deduced from the results of chemical transformations and NMR spectroscopy.

  DOI：

  10.1007/bf02238213
• 作为产物：
  描述：

  齐墩果酸 在 吡啶 、 硫酸 、 乙酸酐 作用下， 反应 0.5h， 生成 3-sulfate of oleanolic acid
  参考文献：
  名称：

  Selective inhibition of the interaction of C1q with immunoglobulins and the classical pathway of complement activation by steroids and triterpenoids sulfates

  摘要：

  Since undesirable activation of the complement system through the classical pathway is associated with tissue damage and other pathologic proinflammatory consequences at ischemia/reperfusion injury, autoimmune diseases, and rejection of allo-and xenografts, creation of selective inhibitors of the classical pathway leaving the alternative pathway intact is of great importance. Classical pathway is triggered by binding of its recognizing unit, protein Clq, to a number of targets like antibodies, pentraxins, apoptotic cells, and others. In order to obtain inhibitors blocking the first step of the classical cascade, synthesis of sulfates of steroids (Delta(5)-3 beta-hydroxycholenic, Delta(5)-3 beta-hydroxyetiocholenic, deoxycholic, and cholic acids) and triterpenoids (betulin, 20,29-dihydro-20,29-dichloromethylenbetulin, betulinic, Ursolic, and oleanolic acids) has been performed. Testing of the compounds in classical pathway inhibition assay has displayed derivatives of triterpenoid betulin (betulin disulfate and betulinic acid sulfate) to be the most potent inhibitors. Further studies of the two compounds established that their activity to inhibit the classical pathway had been due to their capability to block the interaction of Clq with antibodies. Betulin disulfate and betulinic acid sulfate have shown weak inhibition of the alternative route of activation, what makes them promising inhibitors for the selective suppression of the classical complement pathway at the earliest possible level as well as perspective agents for blocking the interaction of Clq with its other targets. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.03.002

文献信息

• Synthesis of triterpenoid sulfates using the SO3—dimethyl sulfoxide complex
  作者：V. I. Grishkovets

  DOI：10.1007/bf02238214

  日期：1999.1

  The 3-sulfates of oleanolic, echinocystic, and betulinic acids have been synthesized with the use of the SO3-dimethyl sulfoxide sulfating complex.
• Selective inhibition of the interaction of C1q with immunoglobulins and the classical pathway of complement activation by steroids and triterpenoids sulfates
  作者：Svetlana Bureeva、Julian Andia-Pravdivy、Andrey Symon、Anna Bichucher、Vera Moskaleva、Vladimir Popenko、Alexey Shpak、Vitaly Shvets、Leonid Kozlov、Alexander Kaplun

  DOI：10.1016/j.bmc.2007.03.002

  日期：2007.5

  Since undesirable activation of the complement system through the classical pathway is associated with tissue damage and other pathologic proinflammatory consequences at ischemia/reperfusion injury, autoimmune diseases, and rejection of allo-and xenografts, creation of selective inhibitors of the classical pathway leaving the alternative pathway intact is of great importance. Classical pathway is triggered by binding of its recognizing unit, protein Clq, to a number of targets like antibodies, pentraxins, apoptotic cells, and others. In order to obtain inhibitors blocking the first step of the classical cascade, synthesis of sulfates of steroids (Delta(5)-3 beta-hydroxycholenic, Delta(5)-3 beta-hydroxyetiocholenic, deoxycholic, and cholic acids) and triterpenoids (betulin, 20,29-dihydro-20,29-dichloromethylenbetulin, betulinic, Ursolic, and oleanolic acids) has been performed. Testing of the compounds in classical pathway inhibition assay has displayed derivatives of triterpenoid betulin (betulin disulfate and betulinic acid sulfate) to be the most potent inhibitors. Further studies of the two compounds established that their activity to inhibit the classical pathway had been due to their capability to block the interaction of Clq with antibodies. Betulin disulfate and betulinic acid sulfate have shown weak inhibition of the alternative route of activation, what makes them promising inhibitors for the selective suppression of the classical complement pathway at the earliest possible level as well as perspective agents for blocking the interaction of Clq with its other targets. (c) 2007 Elsevier Ltd. All rights reserved.
• Triterpene glycosides ofHedera helix III. Structure of the triterpene sulfates and their glycosides
  作者：V. I. Grishkovets、A. E. Kondratenko、A. S. Shashkov、V. Ya. Chirva

  DOI：10.1007/bf02238213

  日期：1999.1

  From the leaves of English ivy Hedera helix L. we have isolated the known 3-sulfates of oleanolic and echinocystic acids and their 28-O-alpha-L-rhamnopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-O-beta-D-glucopyranosyl esters and the new 3-sulfate of 28-O-beta-gentiobiosyl oleanolate - helicoside L-8a. The structures of the compounds isolated were deduced from the results of chemical transformations and NMR spectroscopy.