纤细薯蓣皂苷 | 19083-00-2

• 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: 纤细薯蓣皂苷
• 英文名称: diosgenyl α-L-rhamnopyranosyl-(1->2)-[β-D-glucopyranosyl-(1->3)]-β-D-glucopyranoside
• 英文别名: gracillin；(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-2-[(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]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: 19083-00-2
• 化学式: C₄₅H₇₂O₁₇
• 分子量: 885.056
• InChiKey: YQEMAEKYNNOCBY-IEMDQPGHSA-N

物化性质

• 熔点：
  290-293℃ (DEC.)
• 密度：
  1.42
• 溶解度：
  溶于DMSO、甲醇和吡啶

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  62
• 可旋转键数：
  8
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  256
• 氢给体数：
  9
• 氢受体数：
  17

安全信息

• WGK Germany：
  3
• 储存条件：
  -20°C

制备方法与用途

作用

该化合物在抗肿瘤、抗菌、杀灭寄生虫、溶血、降血脂、抗骨质疏松、抗突变等方面表现出一定的生理活性。

用途

此化合物具有多种药理作用，包括抗肿瘤、改善心血管功能、调节免疫、抗血小板聚集和降血脂，并且是合成各种甾体激素类药物的重要原料。

生物活性

Gracillin 是一种从植物根部提取的甾体皂苷，具备显著的抗肿瘤特性。

化学性质

纤细薯蓣皂苷为白色粉末状物质，可溶于甲醇、乙醇和DMSO等有机溶剂。这种化合物来源于穿龙薯蓣和小花盾叶薯蓣的根茎，并表现出平喘的作用。

反应信息

• 作为反应物：
  描述：

  苯甲酸 、 纤细薯蓣皂苷 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以0.6 g的产率得到
  参考文献：
  名称：

  纤细薯蓣皂苷衍生物及其抗肿瘤活性应用

  摘要：

  本发明涉及一类纤细薯蓣皂苷衍生物，该化合物为式（Ⅰ）化合物或其药学上可接受的盐或溶剂合物，R1、R2的定义详见说明书。此外，本发明还公开了以该化合物或其盐类为活性成分的药物，主要用于抗肿瘤及相关的疾病，具有抗癌活性高、副作用小且更稳定的优点，为开发新的纤细薯蓣皂苷类抗肿瘤药物提供了一种新的途径。

  公开号：

  CN104098646B
• 作为产物：
  描述：

  diosgenyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)]-4,6-O-benzylidene-β-D-glucopyranoside 在 溶剂黄146 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 以81%的产率得到纤细薯蓣皂苷
  参考文献：
  名称：

  The synthesis of gracillin and dioscin: two typical representatives of spirostanol glycosides

  摘要：

  Two representative spirostanol saponins that have the typical structure for the sugar moiety, diosgenyl alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-glucopyranosyl-(1 --> 3)]-beta-D-glucopyranoside (gracillin) and diosgenyl alpha-L-rhamnopyranosyl-(1 --> 2)-[alpha-L-rhamnopyranosyl-(1 --> 4)]-beta-D-glucopyranoside (dioscin), were easily synthesized by a general approach. A procedure using guanidine for the selective deblocking of acetyl while retaining benzoyl protecting groups is described. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00004-1

文献信息

• Icogenin, a new cytotoxic steroidal saponin isolated from Dracaena draco
  作者：Juan C Hernández、Francisco León、José Quintana、Francisco Estévez、Jaime Bermejo

  DOI：10.1016/j.bmc.2004.06.009

  日期：2004.8

  This paper reports on the cytotoxic effect induced by a new natural steroidal saponin, icogenin, on the myeloid leukemia cell line HL-60. Icogenin was found to be a cytotoxic compound IC(50) 2.6+/-0.9microM at 72h, with growth inhibition caused by the induction of apoptosis, as determined by microscopy of nuclear changes and the fragmentation of poly(ADP-ribose) polymerase-1.

  这篇论文报道了一种新型的天然甾体皂苷（icogenin）对髓样白血病细胞HL-60的杀伤作用。Icogenin被发现是一种细胞毒性化合物IC（50），在72h时为2.6 +/- 0.9microM，其生长抑制作用是由诱导细胞凋亡引起的，如通过核变化的显微镜检查和聚（ADP-核糖）聚合酶的片段化所确定的那样。 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.
• Synthesis of diosgenyl α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→3)]-β-d-glucopyranoside (gracillin) and related saponins
  作者：Chuan Li、Biao Yu、Meizheng Liu、Yongzheng Hui*

  DOI：10.1016/s0008-6215(97)10050-7

  日期：1998.1

  Diosgenyl alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-glucopyranosyl-(1 --> 3)]-beta-D-glucopyranoside (gracillin), a monodesmosidic saponin isolated from paris, dioscorea, and costacea species with promising cardiovascular and antitumor activities, was synthesized by stepwise glycosylation. (C) 1998 Elsevier Science Ltd. All rights reserved.
• A furostanol glucuronide from Solanum lyratum
  作者：Shoji Yahara、Naomi Murakami、Masaki Yamasaki、Toshiyuki Hamada、Jun-ei Kinjo、Toshihiro Nohara

  DOI：10.1016/s0031-9422(00)80717-7

  日期：1985.10
• 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.