(3β,16α)-3-(α-L-arabinopyranosyloxy)-16-hydroxy-olean-12-en-28-oic acid

• 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: (3β,16α)-3-(α-L-arabinopyranosyloxy)-16-hydroxy-olean-12-en-28-oic acid
• 英文别名: 3β-[(α-L-arabinopyranosyl)oxy]-16α-hydroxyolean-12-en-28-oic acid；3-O-α-L-arabinopyranoside of echinocystic acid；echinocystic acid 3-O-α-L-arabinopyranoside；3-O-α-L-arabinopyranosyl echinocystic acid；3-O-α-L-arabinopyranosyl-echinocystic acid；3-O-α-L-arabinopyranosylechinocystic acid；(4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• 化学式: C₃₅H₅₆O₈
• 分子量: 604.825
• InChiKey: SZXCDOOFLYYOCZ-HDYQOPGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  43
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3β,16α)-3-(α-L-arabinopyranosyloxy)-16-hydroxy-olean-12-en-28-oic acid 在 硫酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 刺囊酸
  参考文献：
  名称：

  摘要：

  The previously known triterpenoid 3-O-alpha -L-arabinopyranosides of oleanolic and echinocystic acids and hederagenin, 3-O-beta -D-glucopyranosyl-(1 -->2)-O-alpha -L-arabinopyranosides of oleanolic acid and hederagenin, in addition to 28-O-alpha -L-rhamnopyranosyl-(1 -->4)-O-beta -D-glucopyranosyl-(1-6)-O-beta -D-glucopyranosyl ethers of the 3-O-alpha -L-arabinopyranoside of hederagenin, and 3-O-beta -D-glucopyranosyl-(1 -->2)-O-alpha -L-arbinopyranosides of oleanolic acid and hederagenin, respectively, are isolated from leaves of Fatsia japonica (Araliaceae). The structures of the glycosides are confirmed by chemical Methods and (CNMR)-C-13 spectroscopy.

  DOI：

  10.1023/a:1002891507725
• 作为产物：
  描述：

  [(2S,3R,4R,5S,6R)-5-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 (3β,16α)-3-(α-L-arabinopyranosyloxy)-16-hydroxy-olean-12-en-28-oic acid
  参考文献：
  名称：

  八角3,28-O-双糖苷三萜皂苷的结构

  摘要：

  摘要 从粳稻成熟果实中分离得到4种新型3,28-O-双糖苷三萜皂苷。它们被表征为 28- O -α- l -rhamnopyranosyl-(1 → 4)-β- d -glupyranosyl-(1 → 4)-β-d -吡喃葡萄糖苷 3- O -α- l -arabinopyranosyl echinocystic acid , 3-O-α-l-阿拉伯吡喃常春藤苷配基, 3-O-β-d-吡喃葡萄糖基-(1→2)-α-l-阿拉伯吡喃齐墩果酸和3-O-β-d-吡喃葡萄糖基-(1→2) )-α-l-阿拉伯吡喃常春藤苷配基。

  DOI：

  10.1016/s0031-9422(00)98554-6

文献信息

• ——
  作者：V. I. Grishkovets、E. A. Sobolev、A. S. Shashkov、V. Ya. Chirva

  DOI：10.1023/a:1002891507725

  日期：——

  The previously known triterpenoid 3-O-alpha -L-arabinopyranosides of oleanolic and echinocystic acids and hederagenin, 3-O-beta -D-glucopyranosyl-(1 -->2)-O-alpha -L-arabinopyranosides of oleanolic acid and hederagenin, in addition to 28-O-alpha -L-rhamnopyranosyl-(1 -->4)-O-beta -D-glucopyranosyl-(1-6)-O-beta -D-glucopyranosyl ethers of the 3-O-alpha -L-arabinopyranoside of hederagenin, and 3-O-beta -D-glucopyranosyl-(1 -->2)-O-alpha -L-arbinopyranosides of oleanolic acid and hederagenin, respectively, are isolated from leaves of Fatsia japonica (Araliaceae). The structures of the glycosides are confirmed by chemical Methods and (CNMR)-C-13 spectroscopy.
• Structures of 3,28-O-bisglycosidic triterpenoid saponins of Fatsia japonica
  作者：Tadashi Aokia、Kazumi Shido、Yutaka Takahashi、Takayuki Suga

  DOI：10.1016/s0031-9422(00)98554-6

  日期：——

  Abstract Four novel 3,28- O -bisglycosidic triterpenoid saponins were isolated from the mature fruits of F. japonica . They were characterized as the 28- O -α- l -rhamnopyranosyl-(1 → 4)-β- d -glucopyranosyl-(1 → 4)-β- d -glucopyranosides of 3- O -α- l -arabinopyranosyl echinocystic acid, 3- O -α- l -arabinopyranosyl hederagenin, 3- O -β- d -glucopyranosyl-(1 → 2)-α- l -arabinopyranosyl oleanolic acid

  摘要 从粳稻成熟果实中分离得到4种新型3,28-O-双糖苷三萜皂苷。它们被表征为 28- O -α- l -rhamnopyranosyl-(1 → 4)-β- d -glupyranosyl-(1 → 4)-β-d -吡喃葡萄糖苷 3- O -α- l -arabinopyranosyl echinocystic acid , 3-O-α-l-阿拉伯吡喃常春藤苷配基, 3-O-β-d-吡喃葡萄糖基-(1→2)-α-l-阿拉伯吡喃齐墩果酸和3-O-β-d-吡喃葡萄糖基-(1→2) )-α-l-阿拉伯吡喃常春藤苷配基。