银莲花甙 | 59252-95-8

• 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
• 中文名称: 银莲花甙
• 英文名称: <α-L-arabinofuranosyl-(1-> 4)-β-D-glucuronopyranosyl-(1-> 3)>-3β-hydroxyolean-12-en-28-oic acid
• 英文别名: oleanolic acid 3-O-α-L-arabinofuranosyl(1->4)-β-D-glucopyranosiduronic acid；oleanolic acid 3-O-α-L-arabinofuranosyl-(1->4)-O-β-D-glucuronopyranoside；29-O-deglucosyl-chikusetsusaponin IV；28-deglucosyl-chikusetsusaponin IV；desglucosylchikusetsusaponin IV；narcissiflorine；(2S,3S,4R,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxyoxane-2-carboxylic acid
• CAS: 59252-95-8
• 化学式: C₄₁H₆₄O₁₃
• 分子量: 764.951
• InChiKey: DDHCJXBGKMDIFP-LLUWHUROSA-N

物化性质

• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  54
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  213
• 氢给体数：
  7
• 氢受体数：
  13

制备方法与用途

生物活性方面，Tarasaponin VI 是一种从阿罗力叶中提取的天然产物，具有较强的抑制酒精吸收的作用。

反应信息

• 作为反应物：
  描述：

  银莲花甙 在 lithium aluminium tetrahydride 、 硫酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 154.0h， 生成 (2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-((3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-hydroxymethyl-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picen-3-yloxy)-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  Narcissiflorine, narcissiflorinine and narcissifloridine, three triterpene saponins from Anemone narcissiflora

  摘要：

  DOI：

  10.1016/s0031-9422(00)98553-4
• 作为产物：
  描述：

  α-L-rhamnopyranosyl-(1->4)-β-D-glucopyranosyl-(1->6)-β-D-glucopyranosyl oleanate-(3)-α-L-arabinofuranosyl-(1->4)-methyl-(β-D-glucopyranosid)uronate 在 氢氧化钾 作用下， 反应 6.0h， 生成 L-鼠李糖 、 葡萄糖 、 银莲花甙
  参考文献：
  名称：

  Triterpenoid glycosides from the roots of Tetrapanax papyriferum K. Koch. III. Structures of four new saponins.

  摘要：

  从 Tetrapanax papyriferum K. KOCH.KOCH.其特征为 β-D-吡喃葡萄糖齐墩果酸酯-(3)-[α-L-阿拉伯呋喃糖基-(1→4)]-[β-D-吡喃半乳糖基-(1→2)]-甲基-(β-D-吡喃葡萄糖苷) 尿酸酯 (1)、α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl oleanate-(3)-α-L-arabinofuranosyl-(1→4)-methyl-(β-D-glucopyranosid) uronate (2)、β-D-glucopyranosyl oleanate-(3)-β-D-galactopyranosyl-(1→2)-methyl-(β-D-glucopyranosid) uronate (3)，甲基 oleanate-(3)-[α-L-arabinofuranosyl-(1→4)]-[β-D-galactopyranosyl-(1→2)]-methyl-(β-D-glucopyranosid) uronate (4)、根据化学和光谱证据，还发现了β-谷甾醇 β-D-吡喃葡萄糖苷（5）和齐墩果酸-(3)-β-D-吡喃半乳糖基-(1→2)-β-D-吡喃岩藻糖苷（6）。

  DOI：

  10.1248/cpb.33.4701

文献信息

• Molluscicidal saponins from Cussonia spicata
  作者：Jan Gunzinger、Jerome D. Msonthi、Hostettmann Kurt

  DOI：10.1016/s0031-9422(00)84496-9

  日期：1986.1
• Triterpenoid glycosides from the roots of Tetrapanax papyriferum K. Koch. III. Structures of four new saponins.
  作者：SEIICHI TAKABE、TADAHIRO TAKEDA、YINGJIE CHEN、YUKIO OGIHARA

  DOI：10.1248/cpb.33.4701

  日期：——

  Six compounds were isolated from the roots of Tetrapanax papyriferum K. KOCH. and characterized as β-D-glucopyranosyl oleanate-(3)-[α-L-arabinofuranosyl-(1→4)]-[β-D-galactopyranosyl-(1→2)]-methyl-(β-D-glucopyranosid) uronate (1), α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl oleanate-(3)-α-L-arabinofuranosyl-(1→4)-methyl-(β-D-glucopyranosid) uronate (2), β-D-glucopyranosyl oleanate-(3)-β-D-galactopyranosyl-(1→2)-methyl-(β-D-glucopyranosid) uronate (3), methyl oleanate-(3)-[α-L-arabinofuranosyl-(1→4)]-[β-D-galactopyranosyl-(1→2)]-methyl-(β-D-glucopyranosid) uronate (4), β-sitosterol β-D-glucopyranoside (5) and oleanolic acid-(3)-β-D-galactopyranosyl-(1→2)-β-D-fucopyranoside (6) on the bases of chemical and spectroscopic evidence.

  从 Tetrapanax papyriferum K. KOCH.KOCH.其特征为 β-D-吡喃葡萄糖齐墩果酸酯-(3)-[α-L-阿拉伯呋喃糖基-(1→4)]-[β-D-吡喃半乳糖基-(1→2)]-甲基-(β-D-吡喃葡萄糖苷) 尿酸酯 (1)、α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl oleanate-(3)-α-L-arabinofuranosyl-(1→4)-methyl-(β-D-glucopyranosid) uronate (2)、β-D-glucopyranosyl oleanate-(3)-β-D-galactopyranosyl-(1→2)-methyl-(β-D-glucopyranosid) uronate (3)，甲基 oleanate-(3)-[α-L-arabinofuranosyl-(1→4)]-[β-D-galactopyranosyl-(1→2)]-methyl-(β-D-glucopyranosid) uronate (4)、根据化学和光谱证据，还发现了β-谷甾醇 β-D-吡喃葡萄糖苷（5）和齐墩果酸-(3)-β-D-吡喃半乳糖基-(1→2)-β-D-吡喃岩藻糖苷（6）。
• Narcissiflorine, narcissiflorinine and narcissifloridine, three triterpene saponins from Anemone narcissiflora
  作者：M. Masood、P.K. Minocha、K.P. Tiwari、K.C. Srivastava

  DOI：10.1016/s0031-9422(00)98553-4

  日期：1981.1