diosgenyl α-L-rhamnopyranosyl-(1->3)-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: diosgenyl α-L-rhamnopyranosyl-(1->3)-β-D-glucopyranoside
• 英文别名: diosgenin 3-O-α-L-rhamnosyl-(1-3)-β-D-glucoside；polyphillin C；polyphyllin C；(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5R,6R)-3,5-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-4-yl]oxy-6-methyloxane-3,4,5-triol
• 化学式: C₃₉H₆₂O₁₂
• 分子量: 722.914
• InChiKey: OJCPWEBMROBPTK-GTCMQMDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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

反应信息

• 作为产物：
  描述：

  taccaoside 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.5h， 以2.0 mg的产率得到diosgenyl α-L-rhamnopyranosyl-(1->3)-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

• Chemical Synthesis of Several 2'-<i>O</i>-, 3'-<i>O</i>-Glycosylated Diosgenyl β-D-Glucopyranosides
  作者：Chuan Li、Biao Yu、Yongzheng Hui

  DOI：10.1080/07328309908544058

  日期：1999.1

  Six 2'-O-, 3'-O-glycosylated diosgenyl beta-D-glucopyranosides (4-9), which have a typical structural pattern of diosgenyl saponins, were synthesized; their synthetic routes are discussed.
• Cytotoxic Activities and Structure-Cytotoxic Relationships of Steroidal Saponins.
  作者：Yoshihiro MIMAKI、Akihito YOKOSUKA、Minpei KURODA、Yutaka SASHIDA

  DOI：10.1248/bpb.24.1286

  日期：——

  We have systematically examined the cytotoxic activities of the steroidal saponins mainly isolated from the Liliaceae plants against HL-60 human promyelocytic leukemia cells and found several structure-activity relationships. Some steroidal saponins evaluated in the assay system showed considerable cytotoxic activities, which were almost as potent as that of etoposide used as a positive control. The activities were found to be sensitive to the monosaccharides constituting the sugar moieties and their sequences, as well as to the structures of the aglycons.

  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。