quillaic acid 3-O-β-D-galactopyranosyl-(1->2)-[β-D-galactopyranosyl-(1->3)]-β-D-glucuronopyranoside | 1028100-28-8

• 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: quillaic acid 3-O-β-D-galactopyranosyl-(1->2)-[β-D-galactopyranosyl-(1->3)]-β-D-glucuronopyranoside
• 英文别名: 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyranosylquillaic acid；(2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8R,8aR,12aS,14aR,14bR)-8a-carboxy-4-formyl-8-hydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-hydroxy-4,5-bis[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxane-2-carboxylic acid
• CAS: 1028100-28-8
• 化学式: C₄₈H₇₄O₂₁
• 分子量: 987.103
• InChiKey: YTFDABRYMDDCFK-YEGSMWMSSA-N

物化性质

• 沸点：
  1102.3±65.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  69
• 可旋转键数：
  11
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  349
• 氢给体数：
  12
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  quillaic acid 3-O-β-D-galactopyranosyl-(1->2)-[β-D-galactopyranosyl-(1->3)]-β-D-glucuronopyranoside 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 生成 D-木糖 、 口服葡萄糖 、 3-O-β-D-glucuronopyranosylquillaic acid
  参考文献：
  名称：

  来自 Silene armeria 的齐墩果型三萜皂苷

  摘要：

  从 Silene armeria 的整个植物中分离出 12 种三萜皂苷，包括迄今为止未知的 7 种化合物（即 armerosides AG）。它们的结构是基于广泛的光谱分析和化学方法建立的。从生物合成的角度来看，皂苷元的 C-23 氧化似乎是糖基化途径中的关键因素。

  DOI：

  10.1016/j.phytochem.2016.07.011

文献信息

• New triterpenoid saponins with strong α-glucosidase inhibitory activity from the roots of Gypsophila oldhamiana
  作者：Jian-Guang Luo、Li Ma、Ling-Yi Kong

  DOI：10.1016/j.bmc.2007.12.053

  日期：2008.3.15

  Seven new triterpenoid saponins (1-7), have been isolated and elucidated from the roots of Gypsophila oldhamiana together with five known triterpenoid saponins (8-12). These saponins which could be classified into three series: 3-O-monoglucosides (1, 8, 9), 28-O-monoglucosides (24, 12) and 3, 28-O-bidesmosides (5-7, 10, 11), have been evaluated for their a-glucosidase inhibition activity. As a result, the preliminary structure-activity relationships were discussed based on the position of sugar linkage attached to the aglycone, and 28-O-monoglucosides 2-4 and 12 showed significant inhibitory activities on a-glucosidase. (C) 2008 Elsevier Ltd. All rights reserved.
• Oleanane-type triterpenoid saponins from Silene armeria
  作者：Nobuyuki Takahashi、Wei Li、Kazuo Koike

  DOI：10.1016/j.phytochem.2016.07.011

  日期：2016.9

  Twelve triterpenoid saponins, including seven compounds (i.e., armerosides A-G) hitherto unknown, were isolated from whole plants of Silene armeria. Their structures were established based on extensive spectroscopic analyses and chemical methods. From a biosynthetic perspective, C-23 oxidation of the sapogenin appears to be a key factor in the glycosylation pathway.

  从 Silene armeria 的整个植物中分离出 12 种三萜皂苷，包括迄今为止未知的 7 种化合物（即 armerosides AG）。它们的结构是基于广泛的光谱分析和化学方法建立的。从生物合成的角度来看，皂苷元的 C-23 氧化似乎是糖基化途径中的关键因素。