diosgenin 3-O-β-D-galactopyranoside | 14270-72-5

• 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-β-D-galactopyranoside
• 英文别名: capsicoside A3；(25r)-spirost-5-en-3beta-ol 3-O-beta-d-galactopyranoside；(2R,3R,4S,5R,6R)-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]oxyoxane-3,4,5-triol
• CAS: 14270-72-5
• 化学式: C₃₃H₅₂O₈
• 分子量: 576.771
• InChiKey: WXMARHKAXWRNDM-OOLDBQHSSA-N

物化性质

• 熔点：
  240-242 °C(Solv: ethanol (64-17-5))
• 沸点：
  705.1±60.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  41
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  118
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  diosgenin 3-O-β-D-galactopyranoside 在 硫酸 作用下， 反应 12.0h， 生成 薯蓣皂素
  参考文献：
  名称：

  Steroid glycosides of the roots ofCapsicum annuum. II. The structure of the capsicosides

  摘要：

  DOI：

  10.1007/bf00598758
• 作为产物：
  描述：

  (25R)-spirost-5-en-3β-ol-O-α-L-rhmanopyranosyl-(1-2)-β-D-glucopyranoside 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184.0 mg的产率得到diosgenin 3-O-β-D-galactopyranoside
  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

• [EN] TIMOSAPONIN COMPOUNDS<br/>[FR] COMPOSÉS TIMOSAPONINE
  申请人：CHE CHIMING

  公开号：WO2013149580A1

  公开（公告）日：2013-10-10

  Provided herein are timosaponin compounds of Frmula I, II, IIΙ, I', II' and IIΙ', pharmaceutical compositions comprising the coumpounds, and processes of preparation thereof. Also provided are uses of said timosaponin compounds for preparing medicament for the treatment of diseases associated with beta-amyloid in hosts or subjects in need thereof.

  提供的是I、II、IIΙ、I'、II'和IIΙ'公式的地高辛化合物，包括所述化合物的药物组合物及其制备方法。还提供了所述地高辛化合物用于制备用于治疗与宿主或需要的人体中的β-淀粉样蛋白相关的疾病的药物。
• Glucosylation and galactosylation of diosgenin and solasodine by soluble glycosyltransferase(s) from Solanum melongena leaves
  作者：Cezary Pa̧czkowski、Zdzisa̵w A. Wojciechowski

  DOI：10.1016/s0031-9422(00)86869-7

  日期：1994.4.19

  sugar transfer from both UDPGlc and UDPGal. Good substrates for both the glucosyltransferase and galactosyltransferase reactions consist of, apart from diosgenin and solasodine, some other spirostane-type sapogenins structurally related to diosgenin, i.e. tigogenin, yamogenin and hecogenin, as well as tomatidine which is a spirosolane-type steroidal alkaloid closely related to solasodine. In contrast

  摘要 当来自茄属植物叶的粗制、脂质耗尽的细胞溶质部分（105 000 g 上清液）与 UDP-[ 14 C] 葡萄糖和薯蓣皂苷元（一种螺甾烷型甾体皂苷元）或茄莨菪碱（螺环烷型甾体生物碱）一起孵育时，主要反应产物为薯蓣皂苷元或茄碱单糖苷。然而，也会合成少量（通常小于 5%）相应的单半乳糖苷。使用UDP-[ 14 C]半乳糖作为糖源，形成几乎等量的单葡糖苷和单半乳糖苷衍生物。这些结果可以通过所研究的酶制剂中存在高活性 UDP-葡萄糖 4-差向异构酶来解释。发现通过向反应混合物中加入 0.1 mM UDP-木糖几乎可以完全阻断这种差向异构酶。这种抑制剂的使用允许比较一些潜在的类固醇受体的葡萄糖基化和半乳糖基化的特异性。结果表明，这两种反应的特异性模式非常相似，这表明单一酶催化来自 UDPGlc 和 UDPGal 的糖转移。葡糖基转移酶和半乳糖基转移酶反应的良好底物包括，除了薯蓣皂甙元和茄莨菪碱，
• Studies on the constituents of Aspidistra elatior Blume. I. On the steroids of the underground part.
  作者：YASUAKI HIRAI、TENJI KONISHI、SHUICHI SANADA、YOSHITERU IDA、JUNZO SHOJI

  DOI：10.1248/cpb.30.3476

  日期：——

  Five steroidal compounds were isolated from the dried underground part of Aspidistra elatior BLUME (Liliaceae), and four of them were elucidated to be aspidistrin (diosgenin 3-O-β-lycotetraoside), proto-aspidistrin, methyl proto-aspidistrin, and 1β, 2β, 3β, 4β, 5β-pentahydroxyspirost-25 (27)-ene (Δ25 (27)-pentologenin or Δ25 (27)-neopentologenin), on the basis of physical and chemical investigations. The remaining steroidal compound is suggested to be a new spirostanol compound.

  从干燥的 Aspidistra elatior BLUME（百合科）地下部分中分离出了五种类固醇化合物，其中四种被鉴定为：阿斯比斯特林（地高辛3-O-β-光四糖苷）、原阿斯比斯特林、甲基原阿斯比斯特林和1β, 2β, 3β, 4β, 5β-五羟基螺甾烯（Δ25 (27)-五羟基甾烯或Δ25 (27)-新五羟基甾烯），这些鉴定基于物理和化学研究。剩余的类固醇化合物被建议为一种新的螺甾醇化合物。
• Highly Efficient Glycosylation of Sapogenins
  作者：Shaojiang Deng、Biao Yu、Jianming Xie、Yongzheng Hui

  DOI：10.1021/jo990603x

  日期：1999.9.1
• 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.