sarsasapogenyl β-D-glucopyranosyl-(1->4)-[α-L-arabinopyranosyl-(1->6)]-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: sarsasapogenyl β-D-glucopyranosyl-(1->4)-[α-L-arabinopyranosyl-(1->6)]-β-D-glucopyranoside
• 英文别名: sarsasapogenin 3-O-β-D-glucopyranosyl-(1->4)-[α-L-arabinopyranosyl-(1->6)]-β-D-glucopyranoside；(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-[(1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S,16S,18R)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxy-2-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₄₄H₇₂O₁₇
• 分子量: 873.045
• InChiKey: ZUIQPSIQYROGAZ-BNNUKMRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  61
• 可旋转键数：
  8
• 环数：
  9.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  256
• 氢给体数：
  9
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  sarsasapogenyl β-D-glucopyranosyl-(1->4)-[α-L-arabinopyranosyl-(1->6)]-β-D-glucopyranoside 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.5h， 以3.0 mg的产率得到丝兰提取物
  参考文献：
  名称：

  Smilax officinalis 的甾体皂苷

  摘要：

  从绣线菊的根茎中分离出三种新的甾体皂苷。这些皂苷的结构是通过广泛的光谱数据、水解和化学相关性建立的，如 sarsasapogenin 3-O-β-D-吡喃葡萄糖基-(1-->4)-[α-L-阿拉伯吡喃糖基-(1-->6) -β-D-吡喃葡萄糖苷、neotigogenin 3-O-β-D-吡喃葡萄糖基-(1-->4)-[α-L-阿拉伯吡喃糖基-(1-->6 )]-β-D-吡喃葡萄糖苷和25S- spirostan-6 beta-ol 3-O-beta-D-吡喃葡萄糖基-(1-->4)-[α-L-阿拉伯吡喃糖基-(1-->6 )]-β-D-吡喃葡萄糖苷。后一种化合物的酸水解得到皂苷元，其在甾体骨架上具有新的羟基取向。提出了一种用于后一种皂苷元生物发生的途径，皂苷元是一种罕见的甾体苷元。

  DOI：

  10.1016/0031-9422(96)00274-9
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-arabinopyranosyl-(1->6)]-2,3-di-O-acetyl-β-D-glucopyranosyl trichloroacetimidate 、 丝兰提取物 在 三氟甲磺酸三甲基硅酯 、 水 、 sodium hydroxide 作用下， 以 二氯甲烷 、 methanool 为溶剂， 反应 3.67h， 以89%的产率得到sarsasapogenyl β-D-glucopyranosyl-(1->4)-[α-L-arabinopyranosyl-(1->6)]-β-D-glucopyranoside
  参考文献：
  名称：

  Concise synthesis and antitumor activities of trisaccharide steroidal saponins

  摘要：

  The naturally derived trisaccharide steroidal saponin 1 and structurally modified derivatives 2 and 3 bearing the same sarsasapogenin aglycon were synthesized concisely via a direct transglycosylation strategy. The antitumor activities of the synthetic trisaccharide saponins 1-3 and their corresponding a-isomers 1a-3a were preliminarily evaluated against human gastric adenocarcinoma cell (MKN-45) and human epithelial cervical cancer cell (HeLa) by CCK-8 assay. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.08.026

文献信息

• Concise synthesis and antitumor activities of trisaccharide steroidal saponins
  作者：Guofeng Gu、Min Fang、Jun Liu、Li Gu

  DOI：10.1016/j.carres.2011.08.026

  日期：2011.11

  The naturally derived trisaccharide steroidal saponin 1 and structurally modified derivatives 2 and 3 bearing the same sarsasapogenin aglycon were synthesized concisely via a direct transglycosylation strategy. The antitumor activities of the synthetic trisaccharide saponins 1-3 and their corresponding a-isomers 1a-3a were preliminarily evaluated against human gastric adenocarcinoma cell (MKN-45) and human epithelial cervical cancer cell (HeLa) by CCK-8 assay. (C) 2011 Elsevier Ltd. All rights reserved.
• Steroidal saponins from Smilax officinalis
  作者：Ribson Roney Bernardo、Antonio Ventura Pinto、JoséPaz Parente

  DOI：10.1016/0031-9422(96)00274-9

  日期：1996.9

  Three new steroidal saponins were isolated from the rhizomes of Smilax officinalis. The structures of these saponins were established by extensive spectral data, hydrolysis and chemical correlation as sarsasapogenin 3-O-beta-D-glucopyranosyl-(1-->4)-[alpha-L-arabinopyranosyl-(1-->6 )-beta- D-glucopyranoside, neotigogenin 3-O-beta-D-glucopyranosyl-(1-->4)-[alpha-L-arabinopyranosyl-(1-->6 )]-beta- D-glucopyranoside

  从绣线菊的根茎中分离出三种新的甾体皂苷。这些皂苷的结构是通过广泛的光谱数据、水解和化学相关性建立的，如 sarsasapogenin 3-O-β-D-吡喃葡萄糖基-(1-->4)-[α-L-阿拉伯吡喃糖基-(1-->6) -β-D-吡喃葡萄糖苷、neotigogenin 3-O-β-D-吡喃葡萄糖基-(1-->4)-[α-L-阿拉伯吡喃糖基-(1-->6 )]-β-D-吡喃葡萄糖苷和25S- spirostan-6 beta-ol 3-O-beta-D-吡喃葡萄糖基-(1-->4)-[α-L-阿拉伯吡喃糖基-(1-->6 )]-β-D-吡喃葡萄糖苷。后一种化合物的酸水解得到皂苷元，其在甾体骨架上具有新的羟基取向。提出了一种用于后一种皂苷元生物发生的途径，皂苷元是一种罕见的甾体苷元。