3β,19α-dihydroxyurs-23-oxo-12-en-24,28-dioic 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: 3β,19α-dihydroxyurs-23-oxo-12-en-24,28-dioic acid
• 英文别名: ilexgenin A；IGA；NCGC00180415-03_C30H46O6_Urs-12-ene-24,28-dioic acid, 3,19-dihydroxy-, (3beta,5xi,9xi,18xi)-；(3S,4R,6aR,6bS,8aS,11R,12R,14bR)-3,12-dihydroxy-4,6a,6b,11,12,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,11,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylic acid
• 化学式: C₃₀H₄₆O₆
• 分子量: 502.692
• InChiKey: UIEGOKVPCRANSU-RIGHBNFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  36
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3β,19α-dihydroxyurs-23-oxo-12-en-24,28-dioic acid 在 sodium azide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.67h， 生成
  参考文献：
  名称：

  The first examples of ilexgenin A hybrids as a new class of multi-potent, anti-platelet agents

  摘要：

  Seventeen novel ilexgenin A hybrids (IA-aspirin) and (IA-NO), as donor hybrids (IA-NO will release NO in vivo and function as NO donor), were designed and synthesized in order to develop new multi-targeting agents for the treatment of platelet disorders. Their in vitro activities against ADP, AA and thrombin were evaluated. As a result, IA hybrids achieved substantial increases in the three tested pathways compared with IA. Encouragingly, the most potent hybrid compounds 6d and 14d displayed about 8-fold higher potency than aspirin, and 3-fold higher potency than the simultaneous administration of aspirin and IA in inhibiting ADP-induced aggregation with IC50 values of 0.15 mmol/L and 0.14 mmol/L, respectively. The results suggest these IA hybrids are good candidates for multi-target therapies, and especially, may be considered as promising ADP agonists. (C) 2013 Fei-Hua Wu and Jing-Yu Liang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.05.021
• 作为产物：
  描述：

  3β,19α-dihydroxyurs-12-en-24,28-dioic aicd 24-O-β-D-glucopyranosyl ster 在 盐酸 、 水 作用下， 反应 2.0h， 生成 可得然胶 、 3β,19α-dihydroxyurs-23-oxo-12-en-24,28-dioic acid
  参考文献：
  名称：

  Triterpenoides from the Leaves of Ilex pubescens and their Potential Xanthine Oxidase Inhibitory Activity

  摘要：

  从 Ilex pubescens 的叶子中分离出了一种新的三萜皂苷 Ilexsaponin B (1)，以及三种已知的三萜类化合物 2a、3b、19a、23-四羟基齐墩果酸 (2)、ilexgenin A (3) 和 ilexolide A (4)。通过紫外、红外、质谱、核磁共振光谱分析和化学降解，阐明了它们的化学结构。此外，还报告了所分离化合物的黄嘌呤氧化酶抑制活性。化合物 1 在试验中表现出中等程度的黄嘌呤氧化酶抑制活性，IC50 值为 26.01 μmol/L。

  DOI：

  10.14233/ajchem.2013.15024

文献信息

• The first examples of ilexgenin A hybrids as a new class of multi-potent, anti-platelet agents
  作者：Li-Ping Lin、Fei-Hua Wu、Jing-Yu Liang

  DOI：10.1016/j.cclet.2013.05.021

  日期：2013.8

  Seventeen novel ilexgenin A hybrids (IA-aspirin) and (IA-NO), as donor hybrids (IA-NO will release NO in vivo and function as NO donor), were designed and synthesized in order to develop new multi-targeting agents for the treatment of platelet disorders. Their in vitro activities against ADP, AA and thrombin were evaluated. As a result, IA hybrids achieved substantial increases in the three tested pathways compared with IA. Encouragingly, the most potent hybrid compounds 6d and 14d displayed about 8-fold higher potency than aspirin, and 3-fold higher potency than the simultaneous administration of aspirin and IA in inhibiting ADP-induced aggregation with IC50 values of 0.15 mmol/L and 0.14 mmol/L, respectively. The results suggest these IA hybrids are good candidates for multi-target therapies, and especially, may be considered as promising ADP agonists. (C) 2013 Fei-Hua Wu and Jing-Yu Liang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Triterpenoides from the Leaves of Ilex pubescens and their Potential Xanthine Oxidase Inhibitory Activity
  作者：Zhong-Liu Zhou、Zong-Cai Feng、Jing-Min Xia

  DOI：10.14233/ajchem.2013.15024

  日期：——

  A new triterpene saponin, ilexsaponin B (1), along with three known triterpenoides, 2a, 3b, 19a, 23-tetrahydroxy oleanolic acid (2), ilexgenin A (3) and ilexolide A (4) were isolated from the leaves of Ilex pubescens. Their chemical structures were elucidated on the basis of UV, IR, MS, NMR spectroscopic analyses coupled with chemical degradation. In addition, the xanthine oxidase inhibitory activity of the isolated compounds was reported. Compound 1 exhibited moderate xanthine oxidase inhibitory activity in the test with an IC50 value of 26.01 μmol/L.

  从 Ilex pubescens 的叶子中分离出了一种新的三萜皂苷 Ilexsaponin B (1)，以及三种已知的三萜类化合物 2a、3b、19a、23-四羟基齐墩果酸 (2)、ilexgenin A (3) 和 ilexolide A (4)。通过紫外、红外、质谱、核磁共振光谱分析和化学降解，阐明了它们的化学结构。此外，还报告了所分离化合物的黄嘌呤氧化酶抑制活性。化合物 1 在试验中表现出中等程度的黄嘌呤氧化酶抑制活性，IC50 值为 26.01 μmol/L。