b-D-吡喃葡萄糖苷糖酮酸,(3b,20b,22b)-22,29-环氧-11,29-二羰基齐墩果-12-烯-3-基2-O-b-D-葡萄吡喃糖醛糖基- | 119417-96-8

• 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
• 中文名称: b-D-吡喃葡萄糖苷糖酮酸,(3b,20b,22b)-22,29-环氧-11,29-二羰基齐墩果-12-烯-3-基2-O-b-D-葡萄吡喃糖醛糖基-
• 英文名称: licoricesaponin E₂
• 英文别名: Licoricesaponin E2；(2S,3S,4S,5R,6R)-6-[(2R,3R,4S,5S,6S)-6-carboxy-2-[[(1R,2R,5S,6R,9R,11S,14S,15R,19S,21R)-2,5,6,10,10,14,21-heptamethyl-16,22-dioxo-23-oxahexacyclo[19.2.1.02,19.05,18.06,15.09,14]tetracos-17-en-11-yl]oxy]-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 119417-96-8
• 化学式: C₄₂H₆₀O₁₆
• 分子量: 820.929
• InChiKey: ACCYCJOHUMRMMV-NHJGESHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  58
• 可旋转键数：
  6
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  256
• 氢给体数：
  7
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  b-D-吡喃葡萄糖苷糖酮酸,(3b,20b,22b)-22,29-环氧-11,29-二羰基齐墩果-12-烯-3-基2-O-b-D-葡萄吡喃糖醛糖基- 在 盐酸 、 水 作用下， 以 氯仿 为溶剂， 反应 6.0h， 以13 mg的产率得到齐墩果-12-烯-29-酸,3,22-二羟基-11-羰基-,g-内酯,(3b,20b,22b)-
  参考文献：
  名称：

  Oleanane-type Triterpene Glucuronides from the Roots ofGlycyrrhiza uralensisFischer

  摘要：

  通过对 Glycyrrhiza uralensis Fischer 根部特征成分的研究，分离出了四种新的三萜葡糖苷酸（即 uralsaponins C-F (1-4)）、一种人工产物（即甘草苷的甲酯 (5)）以及六种已知的三萜葡糖苷酸 (6-11)。这些新化合物是通过一维和二维核磁共振光谱分析确定的。评估了所选化合物及其苷元对 HeLa 和 MCF-7 癌细胞株的细胞毒性，并初步阐明了其结构-活性关系。

  DOI：

  10.1055/s-0029-1240907

文献信息

• Saponin and Sapogenol. XLVIII. On the Constituents of the Roots of Glycyrrhiza uralensis FISCHER from Northeastern China. (2). Licorice-saponins D3, E2, F3, G2, H2, J2, and K2.
  作者：Isao KITAGAWA、Kazuyuki HORI、Masahiro SAKAGAMI、Jun-Liang ZHOU、Masayuki YOSHIKAWA

  DOI：10.1248/cpb.41.1337

  日期：——

  Following the characterization of licorice-saponins A3 (2), B2 (3), and C2 (4), the chemical structures of licorice-saponins D3 (5), E2 (6), F3 (7), G2 (8), H2 (9), J2 (10), and K2 (11), seven of the ten oleanane-type triterpene oligoglycosides isolated from the air-dried roots of Glycyrrhiza uralensis FISCHER collected in the northeastern part of China, were investigated. On the basis of chemical and physicochemical evidence, the structures of licorice-saponins D3, E2, F3, G2, H2, J2, and K2 have been determined to be expressed as 3β-[α-L-rhamnopyranosyl(1→2)-β-D-glucuronopyranosyl(1→2)-β-D-glucuronopyranosyloxy]-22β-acetoxyolean-12-en-30-oic acid (5), 3-O-[β-D-glucuronopyranosyl(1→2)-β-D-glucuronopyranosyl]glabrolide (6), 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-glucuronopyranosyl-(1→2)-β-D-glucuronopyranosyl]-11-deoxoglabrolide (7), 24-hydroxyglycyrrhizin (8), 3-O-[β-D-glucuronopyranosyl-(1→2)-β-D-glucuronopyranosyl]liquiritic acid (9), 24-hydroxy-11-deoxoglycyrrhizin (10), and 3β-[β-D-glucuronopyranosyl(1→2)-β-D-glucuronopyranosyloxy]-24-hydroxyoleana-11, 13(18)-dien-30-oic acid (11), respectively.

  loxy]-22β-acetoxyolean-12-en-30-oic acid (11)。
• Oleanane-type Triterpene Glucuronides from the Roots of<i>Glycyrrhiza uralensis</i>Fischer
  作者：Yun-Feng Zheng、Lian-Wen Qi、Xiao-Bing Cui、Guo-Ping Peng、Yong-Bo Peng、Mei-Ting Ren、Xiao-Lan Cheng、Ping Li

  DOI：10.1055/s-0029-1240907

  日期：2010.9

  Investigation of characteristic constituents of the roots of Glycyrrhiza uralensis Fischer led to isolation of four new triterpene glucuronides, namely uralsaponins C–F (1–4), an artificial product, namely the methyl ester of glycyrrhizin (5), as well as six known triterpene glucuronides (6–11). These new compounds were identified by 1D and 2D NMR spectroscopic analysis. The cytotoxicity of the selected compounds and their aglycones were evaluated against HeLa and MCF-7 cancer cell lines, and the preliminary structure-activity relationship was also elucidated.

  通过对 Glycyrrhiza uralensis Fischer 根部特征成分的研究，分离出了四种新的三萜葡糖苷酸（即 uralsaponins C-F (1-4)）、一种人工产物（即甘草苷的甲酯 (5)）以及六种已知的三萜葡糖苷酸 (6-11)。这些新化合物是通过一维和二维核磁共振光谱分析确定的。评估了所选化合物及其苷元对 HeLa 和 MCF-7 癌细胞株的细胞毒性，并初步阐明了其结构-活性关系。