chlorogenin 3-O-[α-L-rhamnopyranosyl-(1->4)-β-D-glucopyranosyl-(1->3)-{β-D-glucopyranosyl-(1->3)-β-D-glucopyranosyl-(1->2)}-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside]

• 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: chlorogenin 3-O-[α-L-rhamnopyranosyl-(1->4)-β-D-glucopyranosyl-(1->3)-{β-D-glucopyranosyl-(1->3)-β-D-glucopyranosyl-(1->2)}-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside]
• 英文别名: chlorogenin-3-O-{α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→3)-O-[β-D-glucopyranosyl-(1→3)-O-β-D-glucopyranosyl-(1→2)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside}；(2S,3R,4R,5R,6S)-2-[(2R,3S,4R,5R,6S)-6-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S,18S,19S)-19-hydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxyoxan-3-yl]oxy-3-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• 化学式: C₆₃H₁₀₄O₃₃
• 分子量: 1389.5
• InChiKey: MXCYMXTYPMLSIS-ABIOYLFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5
• 重原子数：
  96
• 可旋转键数：
  17
• 环数：
  12.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  514
• 氢给体数：
  19
• 氢受体数：
  33

反应信息

• 作为反应物：
  描述：

  chlorogenin 3-O-[α-L-rhamnopyranosyl-(1->4)-β-D-glucopyranosyl-(1->3)-{β-D-glucopyranosyl-(1->3)-β-D-glucopyranosyl-(1->2)}-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside] 在 硫酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.5h， 以1.0 mg的产率得到绿莲皂苷元
  参考文献：
  名称：

  New chlorogenin hexasaccharide isolated from Agave fourcroydes with cytotoxic and cell cycle inhibitory activities

  摘要：

  A new chlorogenin hexasaccharide (1) was isolated from leaves of Agave fourcroydes (Agavaceae). The structure of the new saponin was elucidated as chlorogenin 3-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->3)-{beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->2)}-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside] (1) by spectroscopic analysis and the result of acidic hydrolysis. The new saponin (1) as well as known hexasaccharides (3 and 5) isolated here showed cytotoxicity against HeLa cells, and I exhibited a cell cycle inhibitory effect at the G2/M stage at the concentration of 7.5 and 10 mug/mL. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.004