3-O-[α-L-rhamnopyranosyl(1->2)-β-D-glucopyranosyl(1->2)-β-D-glucuronopyranosyl]olean-12-en-3β,22β,24-triol | 82793-05-3

• 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-[α-L-rhamnopyranosyl(1->2)-β-D-glucopyranosyl(1->2)-β-D-glucuronopyranosyl]olean-12-en-3β,22β,24-triol
• 英文别名: 3-O-[α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranosyl-(1->2)-β-D-glucuronopyranosyl]-soyasapogenol B；soyasapogenol B 3-O-[α-L-rhamnopyranosyl-(1-2)-β-D-glucopyranosyl-(1-2)-β-D-glucuronopyranoside]；azukisaponin V；adzukisaponin V；(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]-5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxyoxane-2-carboxylic acid
• CAS: 82793-05-3
• 化学式: C₄₈H₇₈O₁₈
• 分子量: 943.137
• InChiKey: PTDAHAWQAGSZDD-NADIDOHQSA-N

物化性质

• 熔点：
  244-246 °C
• 沸点：
  1024.2±65.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  66
• 可旋转键数：
  9
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  295
• 氢给体数：
  11
• 氢受体数：
  18

反应信息

• 作为反应物：
  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 24.0h， 生成 大豆甾醇 B
  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. XXXIII. Chemical constituents of the seeds of Vigna angularis (Willd.) Ohwi et Ohashi. (3). Azukisaponins V and VI.
  作者：ISAO KITAGAWA、HUIKANG WANG、MASAYUKI SAITO、MASAYUKI YOSHIKAWA

  DOI：10.1248/cpb.31.683

  日期：——

  The chemical structures of azukisaponins V (1) and VI (5), two of the six oligoglycosidic ingredients of total azukisaponin isolated from azuki beans, the seeds of Vigna angularis (WILLD.) OHWI et OHASHI (Leguminosae), were investigated. By means of photochemical degradation and chemical analyses, the structures of azukisaponins V and VI were elucidated to be 3-O-[α-L-rhamnopyranosyl (1→2)-β-D-glucopyranosyl (1→2)-β-D-glucuronopyranosyl]-soyasapogenol B (1) and 3-O-[β-D-glucopyranosyl (1→2)-β-D-glucuronopyranosyl]-29-O-[β-D-glucopyranosyl (1→6)-β-D-glucuronopyranosyl] azukisapogenol (5), respectively. Azukisaponin VI (5) is the first reported example of a 3, 29-bisdesmoside of an oleanene oligoglycoside.

  研究了从红豆（Vigna angularis (WILLD.) OHWI et OHASHI）中提取的总红豆皂苷的六种寡糖苷成分中的两种：红豆皂苷V（1）和VI（5）的化学结构。通过光化学降解和化学分析，阐明了红豆皂苷V和VI的结构分别为3-O-[α-L-鼠李糖吡喃基（1→2）-β-D-葡萄糖吡喃基（1→2）-β-D-葡萄糖醛酸吡喃基]-大豆皂苷醇B（1）和3-O-[β-D-葡萄糖吡喃基（1→2）-β-D-葡萄糖醛酸吡喃基]-29-O-[β-D-葡萄糖吡喃基（1→6）-β-D-葡萄糖醛酸吡喃基]红豆皂苷醇（5）。红豆皂苷VI（5）是首次报道的三、二十九双配糖体的鞘脂寡糖苷。
• Oleanene glycosides from seeds of Trifolium alexandrinum
  作者：Khaled M. Mohamed、Kazuhiro Ohtani、Ryoji Kasai、Kazuo Yamasaki

  DOI：10.1016/0031-9422(95)00430-f

  日期：1995.11

  From the seeds of Trifolium alexandrinum, two new oleanene-type triterpene glycosides were isolated as their methyl esters, together with five known saponins. The structures of the isolated compounds were determined by NMR and mass spectral analyses.
• Pelizzoni, Francesca; Verotta, Luisella; Nicastro, Giuseppe, Gazzetta Chimica Italiana, 1996, vol. 126, # 10, p. 657 - 662
  作者：Pelizzoni, Francesca、Verotta, Luisella、Nicastro, Giuseppe、Tato, Marco、El-Sebakhy, Nadia A.、et al.

  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].