原纤细薯蓣皂甙 | 54848-30-5

• 物质功能分类: 生物化工 - 提取物
• 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: 原纤细薯蓣皂甙
• 中文别名: 原纤细薯蓣皂苷
• 英文名称: protogracillin
• 英文别名: rutin；(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-2-[[(1S,2S,4S,6R,7S,8R,9S,12S,13R,16S)-6-hydroxy-7,9,13-trimethyl-6-[(3R)-3-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutyl]-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-en-16-yl]oxy]-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• CAS: 54848-30-5
• 化学式: C₅₁H₈₄O₂₃
• 分子量: 1065.21
• InChiKey: GMCGZPQYTRHQRU-DKWQWWTLSA-N

物化性质

• 密度：
  1.49±0.1 g/cm3(Predicted)
• 溶解度：
  DMF：30mg/mL；二甲基亚砜：30mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  74
• 可旋转键数：
  15
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  366
• 氢给体数：
  14
• 氢受体数：
  23

制备方法与用途

C-27甾体配糖体是一类重要的天然产物，广泛存在于多种植物中，尤其是药用植物中。原纤细薯蓣皂苷是这类化合物的一种活性成分。

这种天然产物具有多方面的生理活性。富含C-27甾体配糖体的植物通常对于风湿关节炎、动脉粥样硬化、高血脂、冠心病、心绞痛、癌症和糖尿病等有一定的治疗和预防作用。

Protogracillin是从Dioscorea zingiberensis Wright (DZW) 中分离得到的一种甾体皂苷。从DZW根状茎中提取的甾体皂苷具有抗血栓作用，有助于降低心血管疾病的风险。

反应信息

• 作为反应物：
  描述：

  原纤细薯蓣皂甙 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17.3 mg的产率得到纤细薯蓣皂苷
  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：

  methyl protogracillin 以 水 、 丙酮 为溶剂， 反应 24.0h， 以394 mg的产率得到原纤细薯蓣皂甙
  参考文献：
  名称：

  A furostanol glycoside from rhizomes of Dioscorea collettii var. hypoglauca

  摘要：

  DOI：

  10.1016/s0031-9422(96)00750-9

文献信息

• Antineoplastic Agents II: Four Furostanol Glycosides from Rhizomes of<i>Dioscorea collettii</i>var.<i>hypoglauca</i>
  作者：Ke Hu、Aijun Dong、Xinsheng Yao、Hisayoshi Kobayashi、Shigeo Iwasaki

  DOI：10.1055/s-2006-957636

  日期：1997.4

  During activity-guided fractionations to screen for antineoplastic agents, further studies by means of preparative HPLC led to the isolation of four known furostanol saponins: protoneodioscin, protodioscin, protoneogracillin, protogracillin, along with their corresponding artifacts: methyl protoneodioscin, methyl protodioscin, methyl protoneogracillin, and methyl protogracillin, from the rhizomes of Dioscorea collettii var. hypoglauca. Among them, protoneodioscin, protodioscin, and protoneogracillin are first reported from the title plant. The structures of the compounds were established on the basis of chemical evidence and spectral analysis (1H-NMR, 13C-IMMR, 1H-1H COSY, HMQC, HMBC, and FAB-MS). These eight compounds all caused morphological abnormality of Pyricularia oryzae mycelia. They also showed cytotoxic activities against the cancer cell line of K562 in vitro as antineoplastic agents.

  在筛选抗肿瘤药物的活性引导分馏过程中，通过制备型高效液相色谱法的进一步研究，从薯蓣根茎中分离出了四种已知的呋喃甾醇皂甙：原薯蓣皂甙、原薯蓣皂甙、原薯蓣皂甙和原薯蓣皂甙，以及它们的相应伪品：甲基原薯蓣皂甙、甲基原薯蓣皂甙、甲基原薯蓣皂甙和甲基原薯蓣皂甙。其中，protoneodioscin、protodioscin 和 protoneogracillin 是首次从该植物中发现。根据化学证据和光谱分析（1H-NMR、13C-IMMR、1H-1H COSY、HMQC、HMBC 和 FAB-MS）确定了这些化合物的结构。这八种化合物都会导致桔梗疫霉菌丝体形态异常。作为抗肿瘤药物，它们还在体外对 K562 癌细胞株显示出细胞毒性活性。
• 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.
• A furostanol glycoside from rhizomes of Dioscorea collettii var. hypoglauca
  作者：Ke Hu、Ai-Jun Dong、Xin-Sheng Yao、Hisayoshi Kobayashi、Shigeo Iwasaki

  DOI：10.1016/s0031-9422(96)00750-9

  日期：1997.4