(3β,25S)-spirost-5-ene-3,27-diol-3-O-α-L-rhamnopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->4)-[α-L-rhamnopyranosyl-(1->2)]-β-D-glucopyranoside | 1392827-02-9

• 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
• 英文名称: (3β,25S)-spirost-5-ene-3,27-diol-3-O-α-L-rhamnopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->4)-[α-L-rhamnopyranosyl-(1->2)]-β-D-glucopyranoside
• 英文别名: (25R)-spirost-5-ene-3β,27-diol-3-O-α-L-rhamnopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside；(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'S,6R,7S,8R,9S,12S,13R,16S)-5'-(hydroxymethyl)-7,9,13-trimethylspiro[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: 1392827-02-9
• 化学式: C₅₁H₈₂O₂₁
• 分子量: 1031.2
• InChiKey: XZNUFERMMWDNRA-YORMGNCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  72
• 可旋转键数：
  10
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  315
• 氢给体数：
  11
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  (3β,25S)-spirost-5-ene-3,27-diol-3-O-α-L-rhamnopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->4)-[α-L-rhamnopyranosyl-(1->2)]-β-D-glucopyranoside 在 盐酸 、 水 作用下， 反应 4.0h， 生成 D-葡萄糖 、 L-rhamnopyranose
  参考文献：
  名称：

  Steroidal saponins from Paris polyphylla var. yunnanensis

  摘要：

  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.

  DOI：

  10.1016/j.phytochem.2012.05.034

文献信息

• 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.