3-O-[β-D-glucopyranosyl(1->2)-β-D-glucuronopyranosyl]olean-12-en-3β,22β,24-triol | 82793-03-1

• 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-glucopyranosyl(1->2)-β-D-glucuronopyranosyl]olean-12-en-3β,22β,24-triol
• 英文别名: 3-O-[β-D-glucopyranosyl-(1′′-2′)-β-D-glucuronopyranosyl] soyasapogenol B；azukisaponin II；(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-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
• CAS: 82793-03-1
• 化学式: C₄₂H₆₈O₁₄
• 分子量: 796.994
• InChiKey: OKIHRVKXRCAJFQ-RVAPODRHSA-N

物化性质

• 沸点：
  910.8±65.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  56
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  236
• 氢给体数：
  9
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  3-O-[β-D-glucopyranosyl(1->2)-β-D-glucuronopyranosyl]olean-12-en-3β,22β,24-triol 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以7.9 mg的产率得到大豆甾醇 B
  参考文献：
  名称：

  Fukunaga, Takehiko; Nishiya, Koichi; Takeya, Koichi, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 4, p. 1610 - 1614

  摘要：

  DOI：
• 作为产物：
  描述：

  3-O-[α-L-rhamnopyranosyl(1->2)-β-D-glucopyranosyl(1->2)-β-D-glucuronopyranosyl]olean-12-en-3β,22β,24-triol 在 硫酸 作用下， 以 水 为溶剂， 反应 4.0h， 以7 mg的产率得到3-O-[β-D-glucopyranosyl(1->2)-β-D-glucuronopyranosyl]olean-12-en-3β,22β,24-triol
  参考文献：
  名称：

  Triterpene and steroidal glycosides of the genus Melilotus and their genins. VI. Melilotoside A2 and adzukisaponin V from the roots of M. tauricus

  摘要：

  从 Melilotus tauricus (L.) Pall.（豆科植物）的根中分离出了两种齐墩果烷系列的三萜苷，即 Melilotoside A2 和以前已知的 adzukisaponin V。(豆科）根中分离出来。这些苷的结构是通过化学转化得到证实的。Melilotoside A2 的结构为 soyasapogenol B 3-O-β-D-glucouronopyranoside; adzukisaponin V, soyasapogenol B 3-O-[α-L-rhamnopyranosyl-(1-2)-β-Dglucopyranosyl-(1-2)-β-D-glucuronopyranoside].

  DOI：

  10.1007/s10600-013-0455-x

文献信息

• Saponin and sapogenol. XXXII. Chemical constituents of the seeds of Vigna angularis (Willd.) Ohwi et Ohashi. (2). Azukisaponins I,II,III, and IV.
  作者：ISAO KITAGAWA、HUIKANG WANG、MASAYUKI SAITO、MASAYUKI YOSHIKAWA

  DOI：10.1248/cpb.31.674

  日期：——

  Six oleanene-oligoglycosides named azukisaponins I (1), II (2), III (3), IV (4), V, and VI were isolated from azuki beans, the seeds of Vigna angularis (WILLD.) OHWI et OHASHI (Leguminosae). Among them, the structures of azukisaponins I, II, III, and IV were elucidated as 3-O-[β-D-glucopyranosyl (1→2)-β-D-glucuronopyranosyl] sophoradiol (1), 3-O-[β-D-glucopyranosyl (1→2)-β-D-glucuronopyranosyl] soyasapogenol B (2), 3-O[β-D-glucopyranosyl (1→2)-β-D-glucuronopyranosyl] azukisapogenol (3), and 3-O-(β-D-glucopyranosyl)-28-O-[β-D-glucopyranosyl (1→6)-β-D-glucuronopyranosyl] gypsogenic acid (4), respectively on the basis of chemical and physicochemical evidence.

  从赤小豆（Vigna angularis (WILLD.) OHWI et OHASHI (豆科) 的种子）中分离出六种名为赤小豆皂苷 I (1)、II (2)、III (3)、IV (4)、V和 VI 的烯烃醇寡糖苷。其中，赤小豆皂苷 I、II、III 和 IV 的结构分别阐明为 3-O-[β-D-吡喃葡萄糖（1→2）-β-D-葡萄糖醛酸吡喃] 番荔枝醇 (1)、3-O-[β-D-吡喃葡萄糖（1→2）-β-D-葡萄糖醛酸吡喃] 大豆皂苷醇 B (2)、3-O[β-D-吡喃葡萄糖（1→2）-β-D-葡萄糖醛酸吡喃] 赤小豆皂苷醇 (3)、以及 3-O-(β-D-吡喃葡萄糖)-28-O-[β-D-吡喃葡萄糖（1→6）-β-D-葡萄糖醛酸吡喃] 石膏酸 (4)，这些均是基于化学和物理化学证据的结果。
• Fukunaga, Takehiko; Nishiya, Koichi; Takeya, Koichi, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 4, p. 1610 - 1614
  作者：Fukunaga, Takehiko、Nishiya, Koichi、Takeya, Koichi、Itokawa, Hideji

  DOI：——

  日期：——
• Triterpene and steroidal glycosides of the genus Melilotus and their genins. VI. Melilotoside A2 and adzukisaponin V from the roots of M. tauricus
  作者：G. V. Khodakov

  DOI：10.1007/s10600-013-0455-x

  日期：2013.1

  Two triterpene glycosides of the oleanane series, melilotoside A2 and previously known adzukisaponin V, were isolated from the roots of Melilotus tauricus (L.) Pall. (Fabaceae). The structures of the glycosides were proved based on chemical transformations. Melilotoside A2 had the structure soyasapogenol B 3-O-β-D-glucouronopyranoside; adzukisaponin V, soyasapogenol B 3-O-[α-L-rhamnopyranosyl-(1-2)-β-Dglucopyranosyl-(1-2)-β-D-glucuronopyranoside].

  从 Melilotus tauricus (L.) Pall.（豆科植物）的根中分离出了两种齐墩果烷系列的三萜苷，即 Melilotoside A2 和以前已知的 adzukisaponin V。(豆科）根中分离出来。这些苷的结构是通过化学转化得到证实的。Melilotoside A2 的结构为 soyasapogenol B 3-O-β-D-glucouronopyranoside; adzukisaponin V, soyasapogenol B 3-O-[α-L-rhamnopyranosyl-(1-2)-β-Dglucopyranosyl-(1-2)-β-D-glucuronopyranoside].