25-methoxymogrol | 1342294-19-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 25-methoxymogrol
• 英文别名: (3S,8S,9R,10R,11R,13R,14S,17R)-17-[(2R,5R)-5-hydroxy-6-methoxy-6-methylheptan-2-yl]-4,4,9,13,14-pentamethyl-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,11-diol
• CAS: 1342294-19-2
• 化学式: C₃₁H₅₄O₄
• 分子量: 490.767
• InChiKey: MNFZTFFLVOXBSX-CXQKDEFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲醇 、 mogrol 在 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成 3β-hydroxy-25-dehydroxy-24-oxomogrol 、 25-methoxymogrol
  参考文献：
  名称：

  Potential AMPK activators of cucurbitane triterpenoids from Siraitia grosvenorii Swingle

  摘要：

  AMP-activated kinase (AMPK) as a key controller in the regulation of whole-body energy homeostasis, plays an important role in protecting the body from metabolic diseases. Recently, improved glucose, lipid utility and increased insulin sensitivity were observed on several diabetic rodent models treated with crude mogrosides isolated from the fruit of Siraitia grosvenorii Swingle, but the precise active compounds responsible for the anti-diabetic activity of this plant have not been clearly identified. In our current work, acid hydrolysis of crude mogrosides provided five new cucurbitane triterpenoids (1-4, 8), along with three known ones (5-7). The main aglycone mogrol (7) and compounds 4 and 8 were found to be potent AMPK activators in the HepG2 cell line. This result suggested AMPK activation by the mogroside aglycones 7 and 8 was proved to contribute at least partially to the anti-hyperglycemic and anti-lipidemic properties in vivo of S. grosvenorii. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.030

文献信息

• Potential AMPK activators of cucurbitane triterpenoids from Siraitia grosvenorii Swingle
  作者：Xu-bing Chen、Jing-jing Zhuang、Jun-hua Liu、Min Lei、Lei Ma、Jing Chen、Xu Shen、Li-hong Hu

  DOI：10.1016/j.bmc.2011.08.030

  日期：2011.10

  AMP-activated kinase (AMPK) as a key controller in the regulation of whole-body energy homeostasis, plays an important role in protecting the body from metabolic diseases. Recently, improved glucose, lipid utility and increased insulin sensitivity were observed on several diabetic rodent models treated with crude mogrosides isolated from the fruit of Siraitia grosvenorii Swingle, but the precise active compounds responsible for the anti-diabetic activity of this plant have not been clearly identified. In our current work, acid hydrolysis of crude mogrosides provided five new cucurbitane triterpenoids (1-4, 8), along with three known ones (5-7). The main aglycone mogrol (7) and compounds 4 and 8 were found to be potent AMPK activators in the HepG2 cell line. This result suggested AMPK activation by the mogroside aglycones 7 and 8 was proved to contribute at least partially to the anti-hyperglycemic and anti-lipidemic properties in vivo of S. grosvenorii. (C) 2011 Elsevier Ltd. All rights reserved.