3-O-β-D-glucuronopyranosyl-soyasapogenol B monomethyl ester | 111545-31-4

• 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: 3-O-β-D-glucuronopyranosyl-soyasapogenol B monomethyl ester
• 英文别名: soyasapogenol B methyl 3-O-β-D-glucopyranosiduronate；β-D-Glucuronopyranosylsoyasapogenol B methyl ester；methyl (2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-9-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylate
• CAS: 111545-31-4
• 化学式: C₃₇H₆₀O₉
• 分子量: 648.878
• InChiKey: SBYYLRAYJGDHBT-YUILQSKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  46
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-O-β-D-glucuronopyranosyl-soyasapogenol B monomethyl ester 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以11 mg的产率得到3-Glc-soyasapogenol B
  参考文献：
  名称：

  Effects of Triterpenoids from Pueraria lobata on Immunohemolysis: β-D-Glucuronic Acid Plays an Active Role in Anticomplementary Activity in Vitro

  摘要：

  在体外研究了来自葛根的凯卡皂苷 III (4) 和大豆皂苷 I (8) 及其水解类似物的抗补体特性。二糖苷皂苷 [kaikasaponin I (3)、大豆皂苷 III (7)] 显示出最有效的抗补体活性，其次是单糖苷皂苷 [soyasapogenol B monoglucuronide (6)、sophoradiol monoglucuronide (2)] 和三糖苷皂苷 [soyasaponin I (8)、kaikasaponin] III (4)]，而槐二醇 (1) 和大豆皂醇 B (5) 在补体系统经典途径中在血清存在下显示出溶血增强。但它们对补体系统旁路途径的抗补体活性均非常弱或无抗补体活性。皂苷的抗补体活性受到葡萄糖醛酸性质的影响，其中游离酸形式（-COOH）比钠盐形式（-COO - Na+）或甲酯形式（-COOCH3）表现出更强的活性，并且还原形式（-CH2OH）显着降低活性。

  DOI：

  10.1055/s-2000-8614
• 作为产物：
  描述：

  黄芪甲苷 在 甲醇 、 草酸 、 potassium carbonate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 84.0h， 生成 3-O-β-D-glucuronopyranosyl-soyasapogenol B monomethyl ester
  参考文献：
  名称：

  Saponin and sapogenol. XXXVII. Chemical constituents of astragali radix, the root of Astragalus membranaceus Bunge. (4). Astragalosides VII and VIII.

  摘要：

  通过酶降解以及针对葡萄糖苷连接的选择性裂解方法结合碳-13核磁共振（13C-NMR）分析，阐明了从黄芪根（韩国黄芪，豆科植物）中分离出的两种黄芪苷的结构，这两种黄芪苷是十一种黄芪苷中的两种：黄芪苷VII为3-O-β-D-木糖吡喃糖基-6-O-β-D-葡萄糖吡喃糖基-25-O-β-D-葡萄糖吡喃糖基-环黄芪醇（4），黄芪苷VIII为3-O-[α-L-鼠李吡喃糖（1→2）-β-D-木糖吡喃糖（1→2）-β-D-葡萄糖醛酸吡喃糖]大豆皂苷B（8）。黄芪苷VII（4）是一个前所未有的三萜-三糖苷的例子。

  DOI：

  10.1248/cpb.31.716

文献信息

• Triterpene glycosides of alfalfa VIII. Medinoside E from the leaves
  作者：A. É. Timbekova、A. S. Shashkov、N. K. Abubakirov

  DOI：10.1007/bf00630212

  日期：1993.9
• Saponin and sapogenol. XXXVII. Chemical constituents of astragali radix, the root of Astragalus membranaceus Bunge. (4). Astragalosides VII and VIII.
  作者：ISAO KITAGAWA、HUIKANG WANG、MASAYUKI YOSHIKAWA

  DOI：10.1248/cpb.31.716

  日期：——

  By means of enzymatic degradation and by application of a selective cleavage method for the glucuronide linkage, as well as by the carbon-13 nuclear magnetic resonance (13C-NMR) analysis, the structures of two astragalosides, which were isolated as two of eleven astragalosidesfrom Astragali Radix (the root of Korean Astragalus membranaceus, Leguminosae), were elucidated : astragaloside VII is 3-O-β-D-xylopyranosyl-6-O-β-D-glucopyranosyl-25-O-β-D-glucopyranosyl-cycloastragenol (4) and astragaloside VIII is 3-O-[α-L-rhamnopyranosyl (1→2)-β-D-xylopyranosyl (1→2)-β-D-glucuronopyranosyl] soyasap-ogenl B (8). Astragaloside VII (4) is an unprecedented example of a triterpene-tridesmoside.

  通过酶降解以及针对葡萄糖苷连接的选择性裂解方法结合碳-13核磁共振（13C-NMR）分析，阐明了从黄芪根（韩国黄芪，豆科植物）中分离出的两种黄芪苷的结构，这两种黄芪苷是十一种黄芪苷中的两种：黄芪苷VII为3-O-β-D-木糖吡喃糖基-6-O-β-D-葡萄糖吡喃糖基-25-O-β-D-葡萄糖吡喃糖基-环黄芪醇（4），黄芪苷VIII为3-O-[α-L-鼠李吡喃糖（1→2）-β-D-木糖吡喃糖（1→2）-β-D-葡萄糖醛酸吡喃糖]大豆皂苷B（8）。黄芪苷VII（4）是一个前所未有的三萜-三糖苷的例子。
• Effects of Triterpenoids from Pueraria lobata on Immunohemolysis: β-D-Glucuronic Acid Plays an Active Role in Anticomplementary Activity in Vitro
  作者：Sei-Ryang Oh、Junei Kinjo、Yuichi Shii、Tuyoshi Ikeda、Toshihiro Nohara、Kyung Seop Ahn、Jung Hee Kim、Hyeong-Kyu Lee

  DOI：10.1055/s-2000-8614

  日期：2000.8

  The anticomplementary properties of kaikasaponin III (4) and soyasaponin I (8) from Pueraria lobata and their hydrolytic analogs were investigated in vitro. Diglycosidic saponins [kaikasaponin I (3), soyasaponin III (7)] showed most potent anticomplementary activities, followed by monoglycosidic saponins [soyasapogenol B monoglucuronide (6), sophoradiol monoglucuronide (2)] and triglycosidic saponins [soyasaponin I (8), kaikasaponin III (4)], whereas sophoradiol (1) and soyasapogenol B (5) showed enhancement of hemolysis under the presence of serum on the classical pathway of complement system. But all of them showed very weak or no anticomplementary activities on the alternative pathway of complement system. The anticomplementary activity of the saponins was influenced by the nature of glucuronic acid, where the free acid forms (-COOH) showed much more potent activity than the sodium salt forms (-COO - Na+) or methyl ester forms (-COOCH3), and the reduced forms (-CH2OH) decreased the activity significantly.

  在体外研究了来自葛根的凯卡皂苷 III (4) 和大豆皂苷 I (8) 及其水解类似物的抗补体特性。二糖苷皂苷 [kaikasaponin I (3)、大豆皂苷 III (7)] 显示出最有效的抗补体活性，其次是单糖苷皂苷 [soyasapogenol B monoglucuronide (6)、sophoradiol monoglucuronide (2)] 和三糖苷皂苷 [soyasaponin I (8)、kaikasaponin] III (4)]，而槐二醇 (1) 和大豆皂醇 B (5) 在补体系统经典途径中在血清存在下显示出溶血增强。但它们对补体系统旁路途径的抗补体活性均非常弱或无抗补体活性。皂苷的抗补体活性受到葡萄糖醛酸性质的影响，其中游离酸形式（-COOH）比钠盐形式（-COO - Na+）或甲酯形式（-COOCH3）表现出更强的活性，并且还原形式（-CH2OH）显着降低活性。