licorice saponin B2 | 118536-86-0

• 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: licorice saponin B2
• 英文别名: licorice-saponin B2；licoricesaponin B2；glycyrrhizic acid；(2S,3S,4S,5R,6R)-6-[(2R,3R,4S,5S,6S)-2-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bR)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-6-carboxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 118536-86-0
• 化学式: C₄₂H₆₄O₁₅
• 分子量: 808.961
• InChiKey: BCNKILSUUHWRTG-JVHDORQOSA-N

物化性质

• 熔点：
  209-210 °C
• 沸点：
  936.8±65.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  57
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  250
• 氢给体数：
  8
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  licorice saponin B2 在 盐酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 4.0h， 生成 methyl 3β-hydroxy-18β-olean-12-en-30-oate
  参考文献：
  名称：

  Saponin and Sapogenol. XLVII. On the Constituents of the Roots of Glycyrrhiza uralensis Fischer from Northeastern China. 1. Licorice-Saponins A3, B2, and C2.

  摘要：

  从中国东北地区采集的风干的乌拉尔甘草根中，分离出 10 种新的齐墩果烷型三萜寡糖苷以及甘草甜素 (1) 和几种已知的黄酮类化合物。在新分离的三萜低聚糖苷中，根据化学和理化证据，已确定甘草皂苷 A3 (2)、甘草皂苷 B2 (3) 和甘草皂苷 C2 (4) 的化学结构为表示为 30-O-β-D-吡喃葡萄糖基甘草酸、11-脱氧甘草酸，以及分别为3-O-[β-D-吡喃葡萄糖醛酸基(1→2)-β-D-吡喃葡萄糖醛酸基]oleana-11、13(18)-dien-30-oic酸。在这些研究过程中，已经实现了从甘草酸 (1) 到甘草皂苷 A3 (2)、B2 (3) 和 C2 (4) 的轻松转化。

  DOI：

  10.1248/cpb.41.43
• 作为产物：
  描述：

  (3beta,20beta)-3-羟基-11-氧代-齐墩果-12-烯-29-酸甲酯 在 platinum(IV) oxide calcium sulfate 、 氢氧化钾 、 氨 、 氢气 、 silver trifluoromethanesulfonate 、 氰化汞 、 silver carbonate 、 1,1,3,3-四甲基脲 、 mercury dibromide 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 153.0h， 生成 licorice saponin B2
  参考文献：
  名称：

  Studies on synthesis and structure-activity relationships against cytoprotective activity of triterpenoidal diglycosides with an acid saccharide, d-glucopyranosuronic acid

  摘要：

  Several triterpenoid alpha- and beta-diglycosides of oleanoic acid (1), 11-deoxoglycyrrhetic acid (4) and 11-deoxoglycyrrhetol (5) were synthesized. The synthetic diglycosides induced one or both D-glucopymanosuronic acids as sugar components. Cytoprotective activities of the diglycosides against carbon tetrachloride-induced hepatotoxicity were investigated using mice. The activities of the synthetic diglycosides were estimated by assay of aspartate transaminase and alanine transaminase, which were released from the injured hepatocytes and compared with that of glycyrrhizin (9). The beta-diglycosides of 1 and 4 showed potent activities in contrast to those of 5; none of the alpha-glycosides showed remarkable activity. Reduction of the carbonyl group (C=O) at C-11 on the C-ring of the aglycons slightly enhanced the activity over that of 9, and replacement of the carboxyl group (COOH) on the aglycons by a hydroxylmethyl group (CH2OH) drastically decreased the activity.

  DOI：

  10.1016/0223-5234(94)90073-6

文献信息

• Studies on synthesis and structure-activity relationships against cytoprotective activity of triterpenoidal diglycosides with an acid saccharide, d-glucopyranosuronic acid
  作者：S Saito、S Sumita、T Furumoto、J Ebashi、Y Sasaki、Y Nagamura、I Ishiguro

  DOI：10.1016/0223-5234(94)90073-6

  日期：1994.1

  Several triterpenoid alpha- and beta-diglycosides of oleanoic acid (1), 11-deoxoglycyrrhetic acid (4) and 11-deoxoglycyrrhetol (5) were synthesized. The synthetic diglycosides induced one or both D-glucopymanosuronic acids as sugar components. Cytoprotective activities of the diglycosides against carbon tetrachloride-induced hepatotoxicity were investigated using mice. The activities of the synthetic diglycosides were estimated by assay of aspartate transaminase and alanine transaminase, which were released from the injured hepatocytes and compared with that of glycyrrhizin (9). The beta-diglycosides of 1 and 4 showed potent activities in contrast to those of 5; none of the alpha-glycosides showed remarkable activity. Reduction of the carbonyl group (C=O) at C-11 on the C-ring of the aglycons slightly enhanced the activity over that of 9, and replacement of the carboxyl group (COOH) on the aglycons by a hydroxylmethyl group (CH2OH) drastically decreased the activity.
• Saponin and Sapogenol. XLVII. On the Constituents of the Roots of Glycyrrhiza uralensis Fischer from Northeastern China. 1. Licorice-Saponins A3, B2, and C2.
  作者：Isao KITAGAWA、Kazuyuki HORI、Toshio TANIYAMA、Jun-Liang ZHOU、Masayuki YOSHIKAWA

  DOI：10.1248/cpb.41.43

  日期：——

  From the air-dried root of Glycyrrhiza uralensis, collected in the northeastern part of China, ten new oleanane-type triterpene oligoglycosides were isolated together with glycyrrhizin (1) and several known flavonoids. Among the newly isolated triterpene oligoglycosides, the chemical structures of licorice-saponin A3 (2), licorice-saponin B2 (3), and licorice-saponin C2 (4) have been determined, on the basis of chemical and physicochemical evidence, to be expressed as 30-O-β-D-glucopyranosylglycyrrhizm, 11-deoxo-glycyrrhizin, and 3-O-[β-D-glucuronopyranosyl(1→2)-β-D-glucuronopyranosyl]oleana-11, 13(18)-dien-30-oic acid, respectively. During the course of these studies, facile conversions from glycyrrhizn (1) to licorice-saponins A3 (2), B2 (3), and C2 (4) have been accomplished.

  从中国东北地区采集的风干的乌拉尔甘草根中，分离出 10 种新的齐墩果烷型三萜寡糖苷以及甘草甜素 (1) 和几种已知的黄酮类化合物。在新分离的三萜低聚糖苷中，根据化学和理化证据，已确定甘草皂苷 A3 (2)、甘草皂苷 B2 (3) 和甘草皂苷 C2 (4) 的化学结构为表示为 30-O-β-D-吡喃葡萄糖基甘草酸、11-脱氧甘草酸，以及分别为3-O-[β-D-吡喃葡萄糖醛酸基(1→2)-β-D-吡喃葡萄糖醛酸基]oleana-11、13(18)-dien-30-oic酸。在这些研究过程中，已经实现了从甘草酸 (1) 到甘草皂苷 A3 (2)、B2 (3) 和 C2 (4) 的轻松转化。