(3β,17α,25R)-spirost-5-ene-3,17-diol-3-O-α-L-arabinofuranosyl-(1->4)-β-D-glucopyranoside

• 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,17α,25R)-spirost-5-ene-3,17-diol-3-O-α-L-arabinofuranosyl-(1->4)-β-D-glucopyranoside
• 英文别名: (25R)-spirost-5-ene-3β,17α-diol-3-O-α-L-arabinofuranosyl-(1→4)-β-D-glucopyranoside；pennogenin 3-O-α-L-arabinofuranosyl-(1->4)-β-D-glucopyranoside；pennogenin-3-O-α-L-arabibofuranosyl-(1→4)-β-D-glucopyranoside；(2R,3R,4R,5S,6R)-5-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-6-(hydroxymethyl)-2-[(1R,2S,4S,5'R,6R,7S,8S,9S,12S,13R,16S)-8-hydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxyoxane-3,4-diol
• 化学式: C₃₈H₆₀O₁₃
• 分子量: 724.887
• InChiKey: ALUZSYRNQHZWCW-PUZPRVRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  51
• 可旋转键数：
  6
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  197
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (3β,17α,25R)-spirost-5-ene-3,17-diol-3-O-α-L-arabinofuranosyl-(1->4)-β-D-glucopyranoside 在 盐酸 、 水 作用下， 反应 4.0h， 生成 D-葡萄糖 、 L-arabinose
  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
• 作为产物：
  描述：

  paris saponin H 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112.7 mg的产率得到(3β,17α,25R)-spirost-5-ene-3,17-diol-3-O-α-L-arabinofuranosyl-(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

文献信息

• The substrate specificity of a glucoamylase with steroidal saponin-rhamnosidase activity from Curvularia lunata
  作者：Bing Feng、Li-ping Kang、Bai-ping Ma、Bo Quan、Wen-bin Zhou、Yong-ze Wang、Yu Zhao、Yi-xun Liu、Sheng-qi Wang

  DOI：10.1016/j.tet.2007.04.076

  日期：2007.7

  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.
• 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.