scoposide C

• 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: scoposide C
• 英文别名: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl] (4aS,6aR,6aR,6bR,8aR,10S,12aR,14aR,14bS)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14,14a,14b-hexadecahydropicene-4a-carboxylate
• 化学式: C₆₉H₁₁₄O₃₄
• 分子量: 1487.64
• InChiKey: JOKACWDPCCFDPX-DDAXNDISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  103
• 可旋转键数：
  18
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.99
• 拓扑面积：
  531
• 氢给体数：
  19
• 氢受体数：
  34

反应信息

• 作为反应物：
  描述：

  scoposide C 在 水 、 potassium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 1.0h， 生成 3-O-β-D-glucopyranosyl-(1->4)-β-D-xylopyranosyl-(1->3)[-β-D-xylopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->2)]-α-L-arabinopyranosyl-olean-12-en-28-oic acid
  参考文献：
  名称：

  Antimicrobial Triterpenoid Glycosides from Cephalaria scoparia

  摘要：

  Five new oleanane-type triterpenoid glycosides (1-5), named scoposides A-E, along with one known bisdesmosidic triterpene glycoside, were isolated from the aerial parts of Cephalaria scoparia. Three prosapogenins (2a-4a) were also obtained after alkaline hydrolysis of the bisdesmosidic compounds 2-4. The structures of compounds 1-5 were determined by spectroscopic (ID and 2D NMR, HRESIMS) and chemical methods. The antimicrobial effects of compounds 1-5 were evaluated against a small panel of Gram-positive and Gram-negative bacteria.

  DOI：

  10.1021/np900724u

文献信息

• Antimicrobial Triterpenoid Glycosides from <i>Cephalaria scoparia</i>
  作者：Nazlı Böke Sarıkahya、Süheyla Kırmızıgül

  DOI：10.1021/np900724u

  日期：2010.5.28

  Five new oleanane-type triterpenoid glycosides (1-5), named scoposides A-E, along with one known bisdesmosidic triterpene glycoside, were isolated from the aerial parts of Cephalaria scoparia. Three prosapogenins (2a-4a) were also obtained after alkaline hydrolysis of the bisdesmosidic compounds 2-4. The structures of compounds 1-5 were determined by spectroscopic (ID and 2D NMR, HRESIMS) and chemical methods. The antimicrobial effects of compounds 1-5 were evaluated against a small panel of Gram-positive and Gram-negative bacteria.