甘草皂苷G2 | 118441-84-2

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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: 甘草皂苷G2
• 英文名称: licoricesaponin G2
• 英文别名: (2S,3S,4S,5R,6R)-6-[(2R,3R,4S,5S,6S)-2-[[(3S,4S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4-(hydroxymethyl)-4,6a,6b,8a,11,14b-hexamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy]-6-carboxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 118441-84-2
• 化学式: C₄₂H₆₂O₁₇
• 分子量: 838.944
• InChiKey: WBQVRPYEEYUEBQ-OJVDLISWSA-N

物化性质

• 熔点：
  229-230 °C
• 沸点：
  1005.2±65.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  59
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  287
• 氢给体数：
  9
• 氢受体数：
  17

制备方法与用途

生物活性方面，Licorice Saponin G2 是一种从甘草粗皮（Glycyrrhiza aspera）中分离出的五环三萜类化合物。

反应信息

• 作为反应物：
  描述：

  甘草皂苷G2 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24-hydroxyglycyrrhetinic acid
  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

• UGT73F17, a new glycosyltransferase from <i>Glycyrrhiza uralensis</i>, catalyzes the regiospecific glycosylation of pentacyclic triterpenoids
  作者：Junbin He、Kuan Chen、Zhi-min Hu、Kai Li、Wei Song、Li-yan Yu、Chung-Hang Leung、Dik-Lung Ma、Xue Qiao、Min Ye

  DOI：10.1039/c8cc04215b

  日期：——

  The regiospecific glycosylation of pentacyclic triterpenoids by UGT73F17, a new glycosyltransferase from Glycyrrhiza uralensis, is highlighted. UGT73F17 exhibited strict substrate specificity toward the carboxyl group at C-30/C-29 of pentacyclic triterpenoids, and showed high promiscuity to sugar donors. UGT73F17 represents the first identified triterpenoid 30/29-O-glycosyltransferase, and could be

  突出了UGT73F17（一种来自甘草的新糖基转移酶）对五环三萜类化合物的区域特异性糖基化作用。UGT73F17对五环三萜类化合物的C-30 / C-29处的羧基表现出严格的底物特异性，并与糖供体高度混杂。UGT73F17代表第一个鉴定出的三萜类30 / 29- O-糖基转移酶，可以用作合成糖基酯皂苷的有效生物催化剂。
• Licorice-saponins F3, G2, H2, J2, and K2, five new oleanene-triterpene oligoglycosides from the root of Glycyrrhiza uralensis.
  作者：Isao KITAGAWA、Jun Liang ZHOU、Masahiro SAKAGAMI、Emiko UCHIDA、Masayuki YOSHIKAWA

  DOI：10.1248/cpb.39.244

  日期：——

  Following the structure elucidation of licorice-saponins A3, B2, C2, D3, and E2, the structures of five more new oleanene-triterpene oligoglycosides named licorice-saponins F3 (<1>__∼), G2 (<5>__∼), H2 (<7>__∼), J2 ((10)___∼), and K2 ((12)___∼), concomitantly isolated from the root of Glycyrrhiza uralensis Fischer= (Tohoku-kanzo in Japanese), have been determined on the basis of chemical and physicochemical evidence. During the process, a facile chemical conversion method from olean-12-ene or olean-12-en-11-one oligoglycosides to an olean-11, 13-diene oligoglycoside, has been found.

  继阐明甘草皂苷 A3、B2、C2、D3 和 E2 的结构之后，又从甘草根中分离出五种新的齐墩果烯-三萜类低聚糖苷，分别命名为甘草皂苷 F3 (＜1＞__∼)、G2 (＜5＞__∼)、H2 (＜7＞__∼)、J2 ((10)__∼)和 K2 ((12)__∼)、根据化学和物理化学证据，确定了从 Glycyrrhiza uralensis Fischer=（日文为 Tohoku-kanzo）的根中同时分离出的 J2（(10)___∼）和 K2（(12)___∼）。在此过程中，发现了一种从齐墩果-12-烯或齐墩果-12-烯-11-酮寡糖苷到齐墩果-11、13-二烯寡糖苷的简便化学转化方法。
• 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)。
• GuRhaGT, a highly specific saponin 2′′-<i>O</i>-rhamnosyltransferase from <i>Glycyrrhiza uralensis</i>
  作者：Zi-Long Wang、Jia-Jing Zhou、Bo-Yun Han、Aobulikasimu Hasan、Ya-Qun Zhang、Jia-He Zhang、Hai-Dong Wang、Bin Li、Xue Qiao、Min Ye

  DOI：10.1039/d1cc07021e

  日期：——

  GuRhaGT is the first saponin 2′′-O-rhamnosyltransferase with broad substrate promiscuity, high sugar donor- and regio-specificity. It could be an efficient biocatalyst for the synthesis of bioactive saponins.

  GuRhaGT是第一个具有广泛底物多样性、高糖供体和位置特异性的皂苷2''-O-鲁曼糖基转移酶。它可以作为合成生物活性皂苷的高效生物催化剂。
• KITAGAWA, ISAO;ZHOU, JUN LIANG;SAKAGAMI, MASAHIRO;UCHIDA, EMIKO;YOSHIKAWA+, CHEM. AND PHARM. BULL., 39,(1991) N, C. 244-246
  作者：KITAGAWA, ISAO、ZHOU, JUN LIANG、SAKAGAMI, MASAHIRO、UCHIDA, EMIKO、YOSHIKAWA+

  DOI：——

  日期：——