3-O-{[β-D-xylopyranosyl-(1->2)]-[β-D-glucopyranosyl-(1->3)]-α-L-arabinopyranosyl}ursolic acid-28-O-[β-D-glucopyranosyl] ester

• 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: 3-O-{[β-D-xylopyranosyl-(1->2)]-[β-D-glucopyranosyl-(1->3)]-α-L-arabinopyranosyl}ursolic acid-28-O-[β-D-glucopyranosyl] ester
• 英文别名: araliasaponin VIII；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-5-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylate
• 化学式: C₅₂H₈₄O₂₁
• 分子量: 1045.23
• InChiKey: HYSRWEMKEPVXRC-XVEHRWKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  73
• 可旋转键数：
  11
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  334
• 氢给体数：
  12
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  3-O-{[β-D-xylopyranosyl-(1->2)]-[β-D-glucopyranosyl-(1->3)]-α-L-arabinopyranosyl}ursolic acid-28-O-[β-D-glucopyranosyl] ester 在 硫酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以23 mg的产率得到熊果酸
  参考文献：
  名称：

  Araliasaponins I-XI，来自Aralia decaisneana根的三萜皂苷

  摘要：

  七种新齐墩果型三萜皂苷和四种新乌萨内型三萜皂苷，命名为五味子皂苷I-XI，与四种已知的三萜皂苷一起从龙脑根中分离得到。根据化学和光谱证据，这些新皂苷的结构阐明如下： 3-O-β-D-吡喃木糖基-(1-->3)-β-D-吡喃葡萄糖基-(1--> 3)-[β-D-吡喃木糖基-(1-->2)]-α-L-阿拉伯吡喃基齐墩果酸28-O-β-D-吡喃葡萄糖基酯，3-O-β-D-吡喃葡萄糖基-(1- ->3)-α-L-阿拉伯吡喃齐墩果酸 28-O-β-D-吡喃葡萄糖基-(1-->6)-β-D-吡喃葡萄糖基酯，3-O-β-D-吡喃葡萄糖基-(1- ->3)-[β-D-吡喃木糖基-(1-->2)]-α-L-阿拉伯吡喃基齐墩果酸28-O-β-D-吡喃葡萄糖基-(1-->6)-β-D-吡喃葡萄糖基酯，3-O-β-D-吡喃葡萄糖基-(1-->

  DOI：

  10.1016/0031-9422(95)00788-1
• 作为产物：
  描述：

  3-O-{[2,3,4-tetra-O-acetyl-β-D-xylopyranosyl-(1->2)]-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)]-4-O-acetyl-α-L-arabinopyranosyl}ursolic acid-28-O-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl] ester 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 以98%的产率得到3-O-{[β-D-xylopyranosyl-(1->2)]-[β-D-glucopyranosyl-(1->3)]-α-L-arabinopyranosyl}ursolic acid-28-O-[β-D-glucopyranosyl] ester
  参考文献：
  名称：

  Synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue

  摘要：

  The focus of this work was on the synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue. Therefore, 3-O-{[beta-D-glucopyranosyl-(1-->2)]-[alpha-L-arabinopyranosyl-(1-->3)]-alpha-L-arabinopyranosyl}ursolic acid-28-O-[beta-D-glucopyranosyl] ester 1 was concisely synthesized by two strategies in 22% and 41% overall yield, respectively, and another congener 3-O-{[beta-D-xylopyranosyl-(1-->2)]-[beta-D-glucopyranosyl-(1-->3)]-alpha-L-arabinopyranosyl}ursolic acid-28-O-[beta-D-glucopyranosyl] ester 2 was also efficiently prepared in 81% overall yield. The H-1 NMR and C-13 NMR signals of saponin 2 are all consistent with those reported for the natural product. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.06.024

文献信息

• Synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue
  作者：Peng Wang、Chunxia Li、Jing Zang、Ni Song、Xiuli Zhang、Yingxia Li

  DOI：10.1016/j.carres.2005.06.024

  日期：2005.9

  The focus of this work was on the synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue. Therefore, 3-O-[beta-D-glucopyranosyl-(1-->2)]-[alpha-L-arabinopyranosyl-(1-->3)]-alpha-L-arabinopyranosyl}ursolic acid-28-O-[beta-D-glucopyranosyl] ester 1 was concisely synthesized by two strategies in 22% and 41% overall yield, respectively, and another congener 3-O-[beta-D-xylopyranosyl-(1-->2)]-[beta-D-glucopyranosyl-(1-->3)]-alpha-L-arabinopyranosyl}ursolic acid-28-O-[beta-D-glucopyranosyl] ester 2 was also efficiently prepared in 81% overall yield. The H-1 NMR and C-13 NMR signals of saponin 2 are all consistent with those reported for the natural product. (C) 2005 Elsevier Ltd. All rights reserved.
• Araliasaponins I–XI, triterpene saponins from the roots of Aralia decaisneana
  作者：Toshio Miyase、Ken-Ichi Shiokawa、Dong Ming Zhang、Akira Ueno

  DOI：10.1016/0031-9422(95)00788-1

  日期：1996.3

  Seven new oleanane-type and four new ursane-type triterpene saponins, named araliasaponins I-XI were isolated from the roots of Aralia decaisneana, together with four known triterpene saponins. On the basis of the chemical and spectroscopic evidence, the structures of these new saponins were elucidated as follows: 3-O-beta-D-xylopyranosyl-(1-->3)-beta-D- glucopyranosyl-(1-->3)-[beta-D-xylopyranosyl-(1-->2)]-alpha-L-

  七种新齐墩果型三萜皂苷和四种新乌萨内型三萜皂苷，命名为五味子皂苷I-XI，与四种已知的三萜皂苷一起从龙脑根中分离得到。根据化学和光谱证据，这些新皂苷的结构阐明如下： 3-O-β-D-吡喃木糖基-(1-->3)-β-D-吡喃葡萄糖基-(1--> 3)-[β-D-吡喃木糖基-(1-->2)]-α-L-阿拉伯吡喃基齐墩果酸28-O-β-D-吡喃葡萄糖基酯，3-O-β-D-吡喃葡萄糖基-(1- ->3)-α-L-阿拉伯吡喃齐墩果酸 28-O-β-D-吡喃葡萄糖基-(1-->6)-β-D-吡喃葡萄糖基酯，3-O-β-D-吡喃葡萄糖基-(1- ->3)-[β-D-吡喃木糖基-(1-->2)]-α-L-阿拉伯吡喃基齐墩果酸28-O-β-D-吡喃葡萄糖基-(1-->6)-β-D-吡喃葡萄糖基酯，3-O-β-D-吡喃葡萄糖基-(1-->