11S-jalapinolic acid 11-O-β-D-glucopyranosyl-(1->4)-O-(3-O-tigloyl)-β-D-glucopyranosyl-(1->3)-O-(2-O-2S-methylbutyryl)-α-L-rhamnopyranosyl-(1->2)-[O-β-D-glucopyranosyl-(1->3)]-O-β-D-glucopyranosyl-(1->2)-β-D-quinovopyranoside | 1341223-52-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 11S-jalapinolic acid 11-O-β-D-glucopyranosyl-(1->4)-O-(3-O-tigloyl)-β-D-glucopyranosyl-(1->3)-O-(2-O-2S-methylbutyryl)-α-L-rhamnopyranosyl-(1->2)-[O-β-D-glucopyranosyl-(1->3)]-O-β-D-glucopyranosyl-(1->2)-β-D-quinovopyranoside
• 英文别名: calysolin IV；[(2S,3R,4R,5S,6S)-5-hydroxy-4-[(2S,3R,4R,5R,6R)-3-hydroxy-6-(hydroxymethyl)-4-[(E)-2-methylbut-2-enoyl]oxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-methyl-2-[[(1S,3S,5R,6S,7S,8R,20S,22R,24R,25S,26S,27R,29S,31R,32R,33R)-6,7,25,26,32-pentahydroxy-5,31-bis(hydroxymethyl)-24-methyl-10-oxo-20-pentyl-2,4,9,21,23,28,30-heptaoxatetracyclo[27.3.1.03,8.022,27]tritriacontan-33-yl]oxy]oxan-3-yl] (2S)-2-methylbutanoate
• CAS: 1341223-52-6
• 化学式: C₆₂H₁₀₄O₃₂
• 分子量: 1361.49
• InChiKey: NOCFVQPNEPRIJG-TYUKJMIASA-N

物化性质

• 熔点：
  170-175 °C
• 沸点：
  1328.0±65.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  94
• 可旋转键数：
  21
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  473
• 氢给体数：
  14
• 氢受体数：
  32

反应信息

• 作为反应物：
  描述：

  11S-jalapinolic acid 11-O-β-D-glucopyranosyl-(1->4)-O-(3-O-tigloyl)-β-D-glucopyranosyl-(1->3)-O-(2-O-2S-methylbutyryl)-α-L-rhamnopyranosyl-(1->2)-[O-β-D-glucopyranosyl-(1->3)]-O-β-D-glucopyranosyl-(1->2)-β-D-quinovopyranoside 在 potassium hydroxide 、 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 生成 惕格酸 、 (S)-(+)-2-甲基丁酸 、 calysolic acid D
  参考文献：
  名称：

  Calysolins I–IV, Resin Glycosides from Calystegia soldanella

  摘要：

  Four new resin glycosides having intramolecular cyclic ester structures (jalapins), named calysolins I-IV (1-4), were isolated from the methanol extract of leaves, stems, and roots of Calystegia soldanella, along with one known jalapin (5) derivative. The structures of 1-4 were determined on the basis of spectroscopic data and chemical evidence. They fall into two types, one having a 22-membered ring (1 and 4) and the other with a 27-membered ring (2 and 3). The sugar moieties of 1-4 were partially acylated by some organic acids. Compound 4 is the first example of a hexaglycoside of jalapin.

  DOI：

  10.1021/np2006378

文献信息

• Calysolins I–IV, Resin Glycosides from Calystegia soldanella
  作者：Ayako Takigawa、Haruka Muto、Kiyotaka Kabata、Masafumi Okawa、Junei Kinjo、Hitoshi Yoshimitsu、Toshihiro Nohara、Masateru Ono

  DOI：10.1021/np2006378

  日期：2011.11.28

  Four new resin glycosides having intramolecular cyclic ester structures (jalapins), named calysolins I-IV (1-4), were isolated from the methanol extract of leaves, stems, and roots of Calystegia soldanella, along with one known jalapin (5) derivative. The structures of 1-4 were determined on the basis of spectroscopic data and chemical evidence. They fall into two types, one having a 22-membered ring (1 and 4) and the other with a 27-membered ring (2 and 3). The sugar moieties of 1-4 were partially acylated by some organic acids. Compound 4 is the first example of a hexaglycoside of jalapin.