diosgenin 3-O-α-L-rhamnopyranosyl(1->4)-β-D-glucopyranoside | 19057-68-2

• 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: diosgenin 3-O-α-L-rhamnopyranosyl(1->4)-β-D-glucopyranoside
• 英文别名: prosapogenin B；(25R)-spirost-5-en-3β-yl O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranoside；diosgenin-3-O-α-L-rhamnopyranosyl-(1→4)-β-D-glycopyranoside；Progenin II；(2S,3R,4R,5R,6S)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-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]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• CAS: 19057-68-2
• 化学式: C₃₉H₆₂O₁₂
• 分子量: 722.914
• InChiKey: ZUMDKMTZYHACBK-HCTICQNOSA-N

物化性质

• 熔点：
  267 °C (decomp)(Solv: chloroform (67-66-3); methanol (67-56-1))
• 沸点：
  838.8±65.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  51
• 可旋转键数：
  5
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  177
• 氢给体数：
  6
• 氢受体数：
  12

安全信息

• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  diosgenin 3-O-α-L-rhamnopyranosyl(1->4)-β-D-glucopyranoside 在 硫酸 作用下， 以 乙醇 为溶剂， 生成 地索苷 、 薯蓣皂素
  参考文献：
  名称：

  来自薯蓣块茎的螺甾烷薯蓣皂苷元前体

  摘要：

  摘要 薯蓣新鲜块茎中的主要皂苷为薯蓣皂苷，发酵物质为3-O-[α-l-吡喃鼠李糖基(1→4)-β-d-吡喃葡萄糖基]薯蓣皂苷。皂苷的 13 C NMR 化学位移用于确定其结构。没有从新鲜块茎中分离出游离的皂苷元。

  DOI：

  10.1016/s0031-9422(00)95278-6
• 作为产物：
  描述：

  薯蓣皂甙 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.5h， 以1.8 mg的产率得到diosgenin 3-O-α-L-rhamnopyranosyl(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  Cytotoxic Activities and Structure-Cytotoxic Relationships of Steroidal Saponins.

  摘要：

  我们系统地研究了主要从百合科植物中分离出来的甾体皂甙对 HL-60 人类早幼粒细胞白血病细胞的细胞毒活性，发现了几种结构-活性关系。检测系统中评估的一些甾体皂苷显示出相当强的细胞毒活性，其效力几乎与作为阳性对照的依托泊苷相当。研究发现，这些活性对构成糖分子的单糖及其序列以及苷元的结构非常敏感。

  DOI：

  10.1248/bpb.24.1286

文献信息

• The microbiological transformation of steroidal saponins by Curvularia lunata
  作者：Bing Feng、Bai-ping Ma、Li-ping Kang、Cheng-qi Xiong、Sheng-qi Wang

  DOI：10.1016/j.tet.2005.08.115

  日期：2005.12

  The microbiological transformation of polyphyllin I (compound I), polyphyllin III (compound II), polyphyllin V (compound III) and polyphyllin VI (compound IV) by Curvularia lunata into their corresponding subsaponins, for example, diosgenin-3-O-α-l-arabinofuranosyl (1→4)-β-d-glucopyranoside (compound V), diosgenin-3-O-α-l-rhamnopyranosyl (1→4)-β-d-glucopyranoside (compound VI), diosgenin-3-O-β-d-glucopyranoside

  皂苷的微生物转化I（化合物我），皂苷III（化合物II），皂苷V（化合物III）和皂苷VI（化合物IV通过）弯孢菌为它们相应的subsaponins，例如，薯蓣皂苷配基-3- ö -α- 1-阿拉伯呋喃糖基（1→4）-β-d-吡喃葡萄糖苷（化合物V），薯os皂苷元3- O -α-l-鼠李糖吡喃糖基（1→4）-β-d-吡喃葡萄糖苷（化合物VI），薯os皂苷元-3- O - β -d-吡喃葡萄糖苷（化合物VII）和Pennogenin-3- O - β -d-吡喃葡萄糖苷（化合物VIII）），在本文中进行了研究。弯孢弯曲菌能够水解通过1→2 C–键与甾体皂苷在C-3位糖残基连接的末端鼠李糖基，具有很高的活性和区域选择性。
• Microbial transformation of pseudoprotodioscin by <i>Gibberella fujikuroi</i>
  作者：Hong-Xiu Hu、Ran-Ran Gao、Zhao-Hui Gao、Yue Qiao、Xin-Ran Dong、Gang Ding、Di-An Sun

  DOI：10.1080/10286020.2018.1468438

  日期：2018.7.3

  obtained from the fermentation broth of pseudoprotodioscin (PPD) incubated with a fungus Gibberella fujikuroi CGMCC 3.4663. Structures of the metabolites were elucidated by 1-D (1H, 13C), 2-D (HMBC, HSQC, NOESY) NMR, and HR-MS analyses. The biotransformation pathway of pseudoprotodioscin by Gibberella fujikuroi CGMCC 3.4663 was proposed. Compounds 1–11 were tested in vitro for their cytotoxic activities

  三个新的（6,9，和12从与真菌孵育pseudoprotodioscin（PPD）的发酵液得到）和9个已知的甾体皂苷赤霉恶苗CGMCC 3.4663。通过1-D（1 H，13 C），2-D（HMBC，HSQC，NOESY）NMR和HR-MS分析阐明了代谢物的结构。提出了藤原赤霉菌CGMCC 3.4663对拟原生物素的生物转化途径。体外测试了化合物1-11对两种人类癌细胞系（HepG2和Hela）的细胞毒活性。化合物1，6，9，和10表现出针对HepG2细胞的细胞毒活性。化合物10显示出对Hela细胞的细胞毒性。
• 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.
• Lipase-catalyzed regioselective acylation of diosgenyl saponins
  作者：Biao Yu、Guowen Xing、Yongzheng Hui、Xiuwen Han

  DOI：10.1016/s0040-4039(01)01051-6

  日期：2001.8

  Diosgenyl saponins were regio selectively acylated by Novozyme 435 with vinyl esters as acylating agents in THF to afford the corresponding mono- or diacyl diosgenyl saponins. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Tsukamoto et al., Pharmaceutical Bulletin, 1956, vol. 4, p. 35,41
  作者：Tsukamoto et al.

  DOI：——

  日期：——