重楼皂苷B | 50773-42-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: 重楼皂苷B
• 中文别名: 七叶莲提取物
• 英文名称: paris saponin II
• 英文别名: diosgenin 3-O-α-L-rhamnopyranosyl(1->4)-α-L-rhamnopyranosyl(1->4)-[α-L-rhamnopyranosyl(1->2)]-β-D-glucopyranoside；polyphyllin II；formosanin C；diosgenyl α-L-rhamnopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->4)-[α-L-rhamnopyranosyl-(1->2)]-β-D-glucopyranoside；(25R*)-spirost-5-en-3β-yl α-L-rhamnopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside；polyphyllin B；(2S,3R,4R,5R,6S)-2-[(2S,3R,4S,5R,6S)-4,5-dihydroxy-6-[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-2-methyloxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• CAS: 50773-42-7
• 化学式: C₅₁H₈₂O₂₀
• 分子量: 1015.2
• InChiKey: OZIHYFWYFUSXIS-HDDFSWBLSA-N

物化性质

• 熔点：
  222～231℃
• 密度：
  1.43±0.1 g/cm3(Predicted)
• 溶解度：
  溶于吡啶；

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  71
• 可旋转键数：
  9
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  295
• 氢给体数：
  10
• 氢受体数：
  20

安全信息

• WGK Germany：
  3

制备方法与用途

生物活性

Polyphyllin B（Formosanin C，FC）是从七叶莲中分离得到的一种薯蓣皂苷，不仅具有显著的抗肿瘤活性，还能调节免疫功能。这种化合物能够诱导细胞凋亡。

化学性质

Polyphyllin B 可溶于甲醇、乙醇和 DMSO 等有机溶剂，来源于七叶莲提取物。

用途

它具有多种生物活性，包括止血、祛痰和抑菌作用、镇静及镇痛效果，还具备抗早孕、杀灭精子的能力，并能对抗细胞毒性。此外，Polyphyllin B 还可以用于含量测定、鉴定以及药理实验等。

药理药效

这种化合物具有广泛的药理活性，包括抗炎、抗肿瘤、抗病毒作用，能够降低胆固醇水平和血压。

反应信息

• 作为反应物：
  描述：

  重楼皂苷B 在 Curvularia lunata 3.4381 1,4-α-D-glucan glucohydrolase 作用下， 以 phosphate buffer 为溶剂， 反应 6.0h， 以31.0 mg的产率得到diosgenin 3-O-α-L-rhamnopyranosyl(1->4)-α-L-rhamnopyranosyl(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  The substrate specificity of a glucoamylase with steroidal saponin-rhamnosidase activity from Curvularia lunata

  摘要：

  In previous work, we studied and reported that an enzyme from Curvularia lunata 3.4381 had the novel specificity to hydrolyze the terminal rhamnosyl at C-3 position of steroidal saponin and obtained four transformed products; the enzyme was purified and ascertained as glucoamylase (EC 3.2.1.3 GA). In this work, the enzyme exhibiting steroidal saponin-rhamnosidase activity was systematically studied on 21 steroidal saponins and 6 ginsenosides. The results showed that the alpha-1,2-linked end-rhamnosyl residues at C-3 position of steroidal saponins could be hydrolyzed to corresponding secondary steroidal saponins, among which 18 compounds were isolated and identified, including 3 new secondary compounds. For the furostanosides having glucosyl residues at the C-26 position, hydrolysis occurred first at end- rhamnosyl at C-3 position to produce secondary furostanosides. The reaction of hydrolyzing glucosyl at C-26 position depended considerably on longer reaction times yielding the corresponding secondary spirostanosides ( without rhamnosyl and glucosyl residues). The enzyme had the strict specificity for the terminal alpha-1,2-linked rhamnosyl residues of linear chain, or the terminal alpha-1,2-linked rhamnosyl residues with branched chain of 1,4-linked glycosyl residues of sugar chain at C-3 position of steroidal saponins, it was not specific for different aglycones, different glycons, and the number of glycon of sugar chain of steroidal saponin. The end- rhamnosyl of ginsenosides and p-nitrophenyl-a-L-rhamnopyranoside (pNPR) could not be hydrolyzed by the enzyme from C. lunata. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.076
• 作为产物：
  描述：

  在 sodium hydroxide 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 重楼皂苷B
  参考文献：
  名称：

  Synthesis of a group of diosgenyl saponins with combined use of glycosyl trichloroacetimidate and thioglycoside donors

  摘要：

  通过结合使用糖基三氯乙亚胺酯和硫代糖苷，一系列天然薯蓣皂苷元的皂苷（1-6）被高效地合成，无论是逐步合成还是“一锅法”合成。三氯乙亚胺酯作为糖基化反应中糖基三氯乙亚胺酯的临时羟基保护组，表现出高效性。硫代糖苷参与的糖基化反应中，分子的烷硫基转移被证实是一种常见的副反应。

  DOI：

  10.1039/a909218h

文献信息

• Synthesis of spirostanol saponins via gold(I)‐catalyzed glycosylation in the presence of Ga(OTf) ₃ , In(OTf) ₃ , or HOTf
  作者：Teddy Stephen Ehianeta、Dacheng Shen、Peng Xu、Biao Yu

  DOI：10.1002/cjoc.201900126

  日期：2019.8

  gold(I)‐catalyzed glycosylation has been reported in the synthesis of a panel of the representative natural spirostanol saponins, namely polyphyllin D (1), polyphyllin V (2), dioscin (3), formosanin C (4), and a derivative of polyphyllin D bearing a terminal azide group (5). This approach highlights the engagement of low loadings of Ph3AuPOTf (≤ 0.5 mol%) in the presence of Ga(OTf)3, In(OTf)3, or HOTf

  An effective approach relying on a Lewis acid‐ or Brønsted acid‐assisted gold(I)‐catalyzed glycosylation has been reported in the synthesis of a panel of the representative natural spirostanol saponins, namely polyphyllin D (1), polyphyllin V (2), dioscin (3), formosanin C (4), and a derivative of polyphyllin D bearing a terminal azide group (5). This approach highlights the engagement of low loadings
• Synthesis of novel diosgenyl saponin analogs and evaluation effects of rhamnose moeity on their cytotoxic activity
  作者：Xin Meng、Yiwu Pan、Tao Liu、Chen Luo、Shuli Man、Yongmin Zhang、Yan Zhang

  DOI：10.1016/j.carres.2021.108359

  日期：2021.8

  type of natural products derived from plants, are the main active component of traditional chinese medicine. Inspiringly, a large number of natural diosgensyl saponins have been shown to exert excellent toxicity to hepatocellular cancer (HCC) cells. In order to better understand the relationship between the structures and their biological effects, a group of diosgenyl saponins (1–4 as natural products

  薯蓣皂苷是一类从植物中提取的天然产物，是中药的主要活性成分。令人鼓舞的是，大量天然薯蓣皂苷已被证明对肝细胞癌细胞（HCC）具有极好的毒性。为了更好地理解其结构与其生物效应之间的关系，高效合成了一组薯蓣皂苷（ 1-4为天然产物， 5和6为其类似物）。在人肝细胞癌 (HepG2) 细胞上评估了这些化合物的细胞毒活性。构效关系研究表明，五糖或六糖皂苷类似物的活性比相应的二糖类似物或薯蓣皂苷的活性相对较低。这些皂苷上4支链鼠李糖部分的延伸对其细胞毒活性没有表现出明显的影响，这表明一定数量的鼠李糖部分和连接方式可以影响类固醇皂苷对HepG2细胞的细胞毒性。
• Synthesis of a group of diosgenyl saponins by a one-pot sequential glycosylation
  作者：Biao Yu、Hai Yu、Yongzheng Hui、Xiuwen Han

  DOI：10.1016/s0040-4039(99)01839-0

  日期：1999.12

  A group of natural diosgenyl saponins was synthesized in a highly efficient manner employing the 'one-pot sequential glycosylation' protocol with the combined use of glycosyl trichloroacetimidates and thioglycosides. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Hirai, Yasuaki; Sanada, Shuichi; Ida, Yoshiteru, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 10, p. 4003 - 4011
  作者：Hirai, Yasuaki、Sanada, Shuichi、Ida, Yoshiteru、Shoji, Junzo

  DOI：——

  日期：——
• Steroidal saponins from Paris polyphylla var. yunnanensis
  作者：Xia Wu、Lei Wang、Hui Wang、Yi Dai、Wen-Cai Ye、Yao-Lan Li

  DOI：10.1016/j.phytochem.2012.05.034

  日期：2012.9

  Eleven steroidal saponins, along with seven known steroidal saponins, were isolated from rhizomes of Paris polyphylla var. yunnanensis. Their chemical structures were elucidated on the basis of spectroscopic analyses and acid hydrolysis. Two of these compounds contained a spirostanol saponin aglycone, hitherto unknown in Nature. The isolated compounds were tested for their cytotoxic effects on human nasopharyngeal carcinoma epithelial (CNE) cells, and seven compounds displayed more potent inhibitory effects than cisplatin (the positive control). One compound with diosgenin and tetrasaccharide moieties possessed the strongest inhibitory effect on CNE cells through the induction of apoptosis and cell cycle arrest. (C) 2012 Elsevier Ltd. All rights reserved.