diosgenin-3β-yl α-L-rhamnopyranosyl-(1->4)-[α-L-rhamnopyranosyl-(1->2)]-α-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: diosgenin-3β-yl α-L-rhamnopyranosyl-(1->4)-[α-L-rhamnopyranosyl-(1->2)]-α-D-glucopyranoside
• 英文别名: (2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6S)-4-hydroxy-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]oxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• 化学式: C₄₅H₇₂O₁₆
• 分子量: 869.057
• InChiKey: VNONINPVFQTJOC-RWQHVEEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  61
• 可旋转键数：
  7
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  236
• 氢给体数：
  8
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  1,2,3,4,6-alpha-D-葡萄糖五乙酸酯 在 三氟化硼乙醚 氢氧化钾 、 四(三苯基膦)钯 、 三氟化硼乙醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 6.0h， 生成 diosgenin-3β-yl α-L-rhamnopyranosyl-(1->4)-[α-L-rhamnopyranosyl-(1->2)]-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of neosaponins having an α- l -rhamnopyranosyl-(1→4)-[α- l -rhamnopyranosyl-(1→2)]- d -glucopyranosyl glyco-linkage

  摘要：

  To verify the role of the alpha -L-rhamnopyranosyl-(1 --> 4)-[alpha -L-rhamnopyranosyl-( 1 -->2)]-beta -D-glucopyranosyl (chacotriosyl) moiety of steroidal glycosides from Solaum plants in their antitumor and antivirus activities, chacotriosides of diosgenin, cholesterol, and glycrrhetic acid were synthesized by developing our trans-oligoglycosidation. The chacotriosyl trichloroacetimidate was linked to the aglycones to afford neoglycosides as a mixture of alpha and beta anomers, that was easily separated with ODS chromatography. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00173-3

文献信息

• Synthesis of neosaponins and neoglycolipids containing a chacotriosyl moiety
  作者：Hiroyuki Miyashita、Tsuyoshi Ikeda、Toshihiro Nohara

  DOI：10.1016/j.carres.2007.06.008

  日期：2007.11

  -(1-->4)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-glucopyr anose (chacotriose) is the oligosaccharide moiety of dioscin. Chacotriosyl trichloroacetimidate was synthesized from d-glucose and l-rhamnose, and glycosylated to mevalonate (diosgenin, cholesterol, and glycyrrhetic acid) to yield dioscin and neosaponins. In order to simplify the structure of the aglycone part, the mevalonate moiety was replaced

  α-L-鼠李吡喃糖基-（1→4）-[α-L-鼠李吡喃糖基-（1→2）]-β-D-吡喃葡萄糖（chacotriose）是薯os的寡糖部分。Chacotriosyl trichloroacetimidate由d-葡萄糖和l-鼠李糖合成，并被糖基化为甲羟戊酸酯（洋地黄毒苷，胆固醇和甘草次酸），生成薯di皂苷和新皂苷。为了简化糖苷配基部分的结构，将甲羟戊酸酯部分替换为模仿糖基神经酰胺的双链新糖脂。细胞毒性试验表明，天然存在的β-形式的糖苷键很重要，薯di和最长链的新糖脂显示中等活性。
• Efficient synthesis of α- and β-chacotriosyl glycosides using appropriate donors, and their cytotoxic activity
  作者：Hiroyuki Miyashita、Yuuki Kai、Toshihiro Nohara、Tsuyoshi Ikeda

  DOI：10.1016/j.carres.2008.02.012

  日期：2008.6

  Natural steroidal glycosides containing alpha-L-rhamnopyranosyl-(1 -> 4)-[alpha-L-rhamnopyranosyl-(1 -> 2)]-beta-D-glucopyranose (chacotriose) at the oligosaccharide moiety exhibit anti-cancer and anti-herpes activities. To investigate the structure-Activity relationships of the aglycone parts of chacotriosides, we developed a synthesis method for chacotriosyl glycosides having various aglycones. In the process, it was revealed that alpha-chacotriosyl glycosides could be obtained mainly by using a trichloroacetimidate donor, while beta-chacotriosyl glycosides were afforded by using phosphite and phosphate donors. In cytotoxicity tests using the A549 and HepG2 cell lines, naturally occurring beta-chacotriosyl diosgenin and cholestanol exhibited higher activities than the corresponding alpha-chacotriosyl glycosides. (C) 2008 Elsevier Ltd. All rights reserved.
• Substrate specificity, purification and identification of a novel pectinase with the specificity of hydrolyzing the α-1,4-glycosyl residue in steroidal saponin
  作者：Bing Feng、Hong-zhi Huang、Wen-bin Zhou、Li-ping Kang、Peng Zou、Yi-xun Liu、He-shui Yu、Bin-qing Han、Ya-yong Li、Ling-ling Zhang、Tao Zhang、Bai-ping Ma

  DOI：10.1016/j.procbio.2010.05.009

  日期：2010.8

  It is known that the sugar chain linked to steroidal frame plays an important role in physiological and pharmacological activities. In the previous research, we found and confirmed that the terminal C3-O-alpha-1,2-rhamnosyl moiety linked to the C-3 of steroidal saponin is the key group of platelet aggregation and cytotoxicity. In order to make a complete approach for the structure-activity relationship, we have tried to find the specific enzymes modifying the structure of C3-sugar chain. In the present paper, we describe a novel enzyme from, Klerzyme-150 (K-150), which is specifically capable of hydrolyzing the alpha-1,4-glycosyl residues at C-3 postion of steroidal saponins. 15 steroidal saponins with different monosaccharides at C3-sugar chains were chosen as substrates to investigate the substrate specificity of K-150. The results showed, based on TLC. HPLC and spectra data analyses, that all products were determined as secondary saponins with the alpha-1, 4-glycosyl residues removed, which indicated that the enzyme exhibited strict regioselectivity and stereoselectivity. The novel enzyme was purified from K-150 to apparent homogeneity and its structure was identified as rhamnogalacturonan lyase A (Rgl A). The molecular mass of the purified enzyme was 52.08 kDa. (C) 2010 Elsevier Ltd. All rights reserved.