16,22-O-diacetyl-21-O-angeloyltheasapogenol E 3-O-[β-D-galactopyranosyl(1->2)][β-D-glucopyranosyl(1->2)-α-L-arabinopyranosyl(1->3)]-β-D-glucopyranosiduronic acid | 316157-15-0

• 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: 16,22-O-diacetyl-21-O-angeloyltheasapogenol E 3-O-[β-D-galactopyranosyl(1->2)][β-D-glucopyranosyl(1->2)-α-L-arabinopyranosyl(1->3)]-β-D-glucopyranosiduronic acid
• 英文别名: assamsaponin F；(2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8,9-diacetyloxy-4-formyl-8a-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(Z)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3-hydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
• CAS: 316157-15-0
• 化学式: C₆₂H₉₄O₂₉
• 分子量: 1303.41
• InChiKey: BJFNIGZQPQQAFL-UTPDYZQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  91
• 可旋转键数：
  20
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  450
• 氢给体数：
  13
• 氢受体数：
  29

反应信息

• 作为反应物：
  描述：

  16,22-O-diacetyl-21-O-angeloyltheasapogenol E 3-O-[β-D-galactopyranosyl(1->2)][β-D-glucopyranosyl(1->2)-α-L-arabinopyranosyl(1->3)]-β-D-glucopyranosiduronic acid 在 氢氧化钾 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以3 mg的产率得到desacyl-assamsaponin F
  参考文献：
  名称：

  Bioactive Saponins and Glycosides. XVII. Inhibitory Effect on Gastric Emptying and Accelerating Effect on Gastrointestinal Transit of Tea Saponins: Structures of Assamsaponins F,G,H,I, and J from the Seeds and Leaves of the Tea Plant.

  摘要：

  Following the investigation of assamsaponins A, B, C, D, and E, four new saponins termed assamsaponins F, G, H, and I were isolated from the seeds of the tea plant (Cammellia sinensis L. var. assamica PIERRE), while assamsaponin J was isolated from its leaves. The structures of assamsaponins F-J were elucidated on the basis of chemical and physicochemical evidence and found to be 16, 22-O-diacetyl-21-O-angeloyltheasapogenol E 3-O-[β-D-galactopyranosyl(1→2)][β-D-glucopyranosyl(1→2)-α-L-arabinopyranosyl(1→3)]-β-D-glucopyranosiduronic acid, 21-O-angeloyl-22-O-acetyltheasapogenol E 3-O-[β-D-galactopyranosyl(1→2)][β-D-glucopyranosyl(1→2)-α-L-arabinopyranosyl(1→3)]-β-D-glucopyranosiduronic acid, 21-O-angeloyl-28-O-acetyltheasapogenol E 3-O-[β-D-galactopyranosyl(1→2)][β-D-glucopyranosyl(1→2)-α-L-arabinopyranosyl(1→3)]-β-D-glucopyranosiduronic acid, 21-O-tigloyl-28-O-acetyltheasapogenol E 3-O-[β-D-galactopyranosyl(1→2)][β-D-glucopyranosyl(1→2)-α-L-arabinopyranosyl(1→3)]-β-D-glucopyranosiduronic acid, and 16, 21-O-biacetyl-22-O-cinnamoyltheasapogenol B 3-O-[β-D-galactopyranosyl(1→2)][β-D-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl(1→3)-β-D-glucopyranosiduronic acid, respectively.The saponin mixture from the seeds of the tea plant was found to exhibit an inhibitory effect no gastric emptying and an accelerating effect on gastrointestinal transit in mice. Theasaponin E1, the principle saponin of the tea plant, showed potent activity, while theasaponin E2 showed none, so that the position of the acyl groups in the sapogenin moiety is important from a pharmacological point of view.

  DOI：

  10.1248/cpb.48.1720

文献信息

• Bioactive Saponins and Glycosides. XVII. Inhibitory Effect on Gastric Emptying and Accelerating Effect on Gastrointestinal Transit of Tea Saponins: Structures of Assamsaponins F,G,H,I, and J from the Seeds and Leaves of the Tea Plant.
  作者：Toshiyuki MURAKAMI、Junko NAKAMURA、Tadashi KAGEURA、Hisashi MATSUDA、Masayuki YOSHIKAWA

  DOI：10.1248/cpb.48.1720

  日期：——

  Following the investigation of assamsaponins A, B, C, D, and E, four new saponins termed assamsaponins F, G, H, and I were isolated from the seeds of the tea plant (Cammellia sinensis L. var. assamica PIERRE), while assamsaponin J was isolated from its leaves. The structures of assamsaponins F-J were elucidated on the basis of chemical and physicochemical evidence and found to be 16, 22-O-diacetyl-21-O-angeloyltheasapogenol E 3-O-[β-D-galactopyranosyl(1→2)][β-D-glucopyranosyl(1→2)-α-L-arabinopyranosyl(1→3)]-β-D-glucopyranosiduronic acid, 21-O-angeloyl-22-O-acetyltheasapogenol E 3-O-[β-D-galactopyranosyl(1→2)][β-D-glucopyranosyl(1→2)-α-L-arabinopyranosyl(1→3)]-β-D-glucopyranosiduronic acid, 21-O-angeloyl-28-O-acetyltheasapogenol E 3-O-[β-D-galactopyranosyl(1→2)][β-D-glucopyranosyl(1→2)-α-L-arabinopyranosyl(1→3)]-β-D-glucopyranosiduronic acid, 21-O-tigloyl-28-O-acetyltheasapogenol E 3-O-[β-D-galactopyranosyl(1→2)][β-D-glucopyranosyl(1→2)-α-L-arabinopyranosyl(1→3)]-β-D-glucopyranosiduronic acid, and 16, 21-O-biacetyl-22-O-cinnamoyltheasapogenol B 3-O-[β-D-galactopyranosyl(1→2)][β-D-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl(1→3)-β-D-glucopyranosiduronic acid, respectively.The saponin mixture from the seeds of the tea plant was found to exhibit an inhibitory effect no gastric emptying and an accelerating effect on gastrointestinal transit in mice. Theasaponin E1, the principle saponin of the tea plant, showed potent activity, while theasaponin E2 showed none, so that the position of the acyl groups in the sapogenin moiety is important from a pharmacological point of view.