3β-[(α-L-arabinopyranosyl)oxy]-19α-hydroxyolean-12-en-28-oic acid 28-β-D-glucopyranosyl ester | 356785-71-2

• 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-[(α-L-arabinopyranosyl)oxy]-19α-hydroxyolean-12-en-28-oic acid 28-β-D-glucopyranosyl ester
• 英文别名: 3β-[(α-L-arabinopyranosyl)oxy]-19α-hydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranoside；3β-[(α-L-arabinopyranosyl)oxy]-19α-hydroxyolean-12-en-28-oic acid 28-β-D-glucopyranoside；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1S,4aR,6aR,6aS,6bR,8aR,10S,12aR,14bS)-1-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
• CAS: 356785-71-2
• 化学式: C₄₁H₆₆O₁₃
• 分子量: 766.967
• InChiKey: SLQHZBXUSQZYTB-VJZGPKJVSA-N

物化性质

• 沸点：
  841.9±65.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  54
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  216
• 氢给体数：
  8
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  3β-[(α-L-arabinopyranosyl)oxy]-19α-hydroxyolean-12-en-28-oic acid 28-β-D-glucopyranosyl ester 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以3.2 mg的产率得到siaresinolic acid
  参考文献：
  名称：

  Triterpene glycosides from the roots of Sanguisorba officinalis

  摘要：

  Five triterpene glycosides were isolated from the MeOH extract of Sanguisorba officinalis (Rosaceae) roots, as confirmed by detailed analysis of their H-1, C-13, and two-dimensional NMR data, and by the results of hydrolytic cleavage. Three known triterpenes and six known triterpene glycosides were also isolated and identified. The isolated compounds were evaluated for their cytotoxic activities against HSC-2 cells and HGF. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(01)00083-8

文献信息

• Terpene Glycosides from the Roots of Sanguisorba officinalis L. and Their Hemostatic Activities
  作者：Wei Sun、Zi-Long Zhang、Xin Liu、Shuang Zhang、Lu He、Zhe Wang、Guang-Shu Wang

  DOI：10.3390/molecules17077629

  日期：——

  Guided by a hemostasis bioassay, seven terpene glycosides were isolated from the roots of Sanguisorba officinalis L. by silica gel column chromatography and preparative HPLC. On the grounds of chemical and spectroscopic methods, their structures were identified as citronellol-1-O-α-l-arabinofuranosyl-(1→6)-β-d-glucopyranoside (1), geraniol-1-O-α-l-arabinofuranosyl-(1→6)-β-d-glucopyranoside (2), geraniol-1-O-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranoside (3), 3β-[(α-l-arabinopyranosyl)oxy]-19α-hydroxyolean-12-en-28-oic acid 28-β-d-glucopyranoside (4), 3β-[(α-l-arabinopyranosyl)-oxy]-19α-hydroxyurs-12-en-28-oic acid 28-β-d-glucopyranoside (ziyu-glycoside I, 5), 3β,19α-hydroxyolean-12-en-28-oic acid 28-β-d-glucopyranoside (6) and 3β,19α-di-hydroxyurs-12-en-28-oic acid 28-β-d-glucopyranoside (7). Compound 1 is a new mono-terpene glycoside and compounds 2, 3 and 5 were isolated from the Sanguisorba genus for the first time. Compounds 1–7 were assayed for their hemostatic activities with a Goat Anti-Human α2-plasmin inhibitor ELISA kit, and ziyu-glycoside I (5) showed the strongest hemostatic activity among the seven terpene glycosides. This is the first report that ziyu-glycoside Ι has strong hemostatic activity.

  在止血生物测定的指导下，采用硅胶柱层析和制备型高效液相色谱法从山姜（Sanguisorba officinalis L.）根中分离出七种萜烯苷。根据化学和光谱方法，确定其结构为香茅醇-1-O-α-阿拉伯呋喃糖基-(1→6)-β-d-吡喃葡萄糖苷（1）、香叶醇-1-O-α-阿拉伯呋喃糖基-(1→6)-β-d-吡喃葡萄糖苷（2）、香叶醇-1-O-α-阿拉伯呋喃糖基-(1→6)-β-d-吡喃葡萄糖苷（3）、香叶醇-1-O-α-阿拉伯呋喃糖基-(1→6)-β-d-吡喃葡萄糖苷（4）和香叶醇-1-O-α-阿拉伯呋喃糖基-(1→6)-β-d-吡喃葡萄糖苷（5）、3β-[(α-l-arabinopyranosyl)-oxy]-19α-hydroxyolean-12-en-28-oic acid 28-β-d-glucopyranoside (4)、3β-[(α-larabinopyranosyl)-oxy]-19α-羟基乌苏-12-烯-28-酸 28-β-d-glucopyranoside （ziyu-glycoside I、5）、3β,19α-羟基乌苏-12-烯-28-酸 28-β-d-吡喃葡萄糖苷（6）和 3β,19α-二羟基乌苏-12-烯-28-酸 28-β-d-吡喃葡萄糖苷（7）。化合物 1 是一种新的单萜烯苷，化合物 2、3 和 5 是首次从 Sanguisorba 属植物中分离出来的。用山羊抗人α2-磷脂酶抑制剂酶联免疫吸附试剂盒检测了化合物 1-7 的止血活性，结果表明，在七种萜烯苷中，紫玉苷 I（5）的止血活性最强。这是首次报道紫玉糖苷Ι具有很强的止血活性。
• Triterpene glycosides from the roots of Sanguisorba officinalis
  作者：Yoshihiro Mimaki、Masato Fukushima、Akihito Yokosuka、Yutaka Sashida、Shigenori Furuya、Hiroshi Sakagami

  DOI：10.1016/s0031-9422(01)00083-8

  日期：2001.7

  Five triterpene glycosides were isolated from the MeOH extract of Sanguisorba officinalis (Rosaceae) roots, as confirmed by detailed analysis of their H-1, C-13, and two-dimensional NMR data, and by the results of hydrolytic cleavage. Three known triterpenes and six known triterpene glycosides were also isolated and identified. The isolated compounds were evaluated for their cytotoxic activities against HSC-2 cells and HGF. (C) 2001 Elsevier Science Ltd. All rights reserved.