azukisapogenol methyl ester | 20476-10-2

• 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: azukisapogenol methyl ester
• 英文别名: 3β.24-Dihydroxy-Δ¹²-oleanen-29-saeuremethylester；methyl (2R,4aS,6aR,6aS,6bR,8aR,9S,10S,12aR,14bR)-10-hydroxy-9-(hydroxymethyl)-2,4a,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2-carboxylate
• CAS: 20476-10-2
• 化学式: C₃₁H₅₀O₄
• 分子量: 486.736
• InChiKey: OLFMGIZTWHFEJC-HQNLPALYSA-N

物化性质

• 沸点：
  559.671±50.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.114±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  azukisapogenol methyl ester 在 lead(IV) acetate 作用下， 以 吡啶 、 苯 为溶剂， 生成 3β.24-Diacetoxy-29-nor-oleanadien-(12.20(30))
  参考文献：
  名称：

  Canonica,L. et al., Gazzetta Chimica Italiana, 1968, vol. 98, p. 712 - 728

  摘要：

  DOI：
• 作为产物：
  描述：

  Azukisaponin VI 在 盐酸 、 甲醇 、 sodium hydroxide 、 sodium tetrahydroborate 、 Dowex 50w*8(H⁺) 、 silver carbonate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 16.0h， 生成 azukisapogenol methyl ester
  参考文献：
  名称：

  Saponin and sapogenol. XXXIII. Chemical constituents of the seeds of Vigna angularis (Willd.) Ohwi et Ohashi. (3). Azukisaponins V and VI.

  摘要：

  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。

  DOI：

  10.1248/cpb.31.683

文献信息

• Saponin and sapogenol. XXXI. Chemical constituents of the seeds of Vigna angularis (Willd.) Ohwi et Ohashi. (1). Triterpenoidal sapogenols and 3-furanmethanol .BETA.-D-glucopyranoside.
  作者：ISAO KITAGAWA、HUIKANG WANG、MASAYUKI SAITO、MASAYUKI YOSHIKAWA

  DOI：10.1248/cpb.31.664

  日期：——

  3-Furanmethanol β-D-glucopyranoside (1) and (+)-catechin 7-O-β-D-glucopyranoside (3) were isolated from azuki beans, the seeds of Vigna angularis (WILLD.) OHWI et OHASHI (Leguminosae) and their structures were substantiated. The saponin mixture designated as total azukisaponin was also isolated from azuki beans. By means of enzymatic hydrolysis, acidic hydrolysis, and photochemical degradation, four genuine sapogenols, which included three known sapogenols, sophoradiol (7), soyasapogenol B (8), gypsogenic acid (9), and a new sapogenol named azukisapogenol (10), were isolated from total azukisaponin and the structure of 10 was elucidated. As one of the artifact sapogenols which were liberated by acidic hydrolysis of total azukisaponin, a new sapogenol named anhydrosophoradiol (5) was isolated and its structure was elucidated.

  从赤豆（Vigna angularis (Willd.) Ohwi et Ohashi 豆科）种子中分离得到3-呋喃甲醇β-D-吡喃葡糖苷（1）和（+）-儿茶素7-O-β-D-吡喃葡糖苷（3），并确定了它们的结构。从赤豆中还分离得到了总赤豆皂苷混合物。通过酶解、酸解和光化学降解，从总赤豆皂苷中分离出了4种真正的皂苷元，其中包括3种已知的皂苷元：染料木苷元（7）、大豆苷元B（8）、皂土酸（9）和一个新的皂苷元，命名为赤豆皂苷元（10），并阐明了其结构。作为总赤豆皂苷酸解释放的假皂苷元之一，分离得到了一个新的皂苷元，命名为无水染料木苷元（5），并阐明了其结构。
• 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。
• 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。
• Canonica,L. et al., Gazzetta Chimica Italiana, 1968, vol. 98, p. 712 - 728
  作者：Canonica,L. et al.

  DOI：——

  日期：——