(25R)-3β-O-[2,4-di-O-(α-L-rhamnopyranosyl)-β-D-glucopyranosyl]-12,13-seco-5α-spirostan-12-oic acid | 1391747-47-9

• 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: (25R)-3β-O-[2,4-di-O-(α-L-rhamnopyranosyl)-β-D-glucopyranosyl]-12,13-seco-5α-spirostan-12-oic acid
• 英文别名: 2-[(1S,2R,4aS,6S,8aS)-2-[(2R,3S,3aS,4S,5S,5'R,6aS)-4-hydroxy-3,4,5'-trimethylspiro[3a,5,6,6a-tetrahydro-3H-cyclopenta[b]furan-2,2'-oxane]-5-yl]-6-[(2R,3R,4S,5S,6R)-4-hydroxy-6-(hydroxymethyl)-3,5-bis[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy]oxan-2-yl]oxy-8a-methyl-2,3,4,4a,5,6,7,8-octahydro-1H-naphthalen-1-yl]acetic acid
• CAS: 1391747-47-9
• 化学式: C₄₅H₇₄O₁₉
• 分子量: 919.071
• InChiKey: VFKLYFUEZQORTR-WMIZRKRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  64
• 可旋转键数：
  10
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  293
• 氢给体数：
  10
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以120 mg的产率得到(25R)-3β-O-[2,4-di-O-(α-L-rhamnopyranosyl)-β-D-glucopyranosyl]-12,13-seco-5α-spirostan-12-oic acid
  参考文献：
  名称：

  Effect of C-ring modifications on the cytotoxicity of spirostan saponins and related glycosides

  摘要：

  Twelve C-ring modified spirostanyl glycosides were synthesized and evaluated for their cytotoxicity against the human myeloid leukemia cell line (HL-60). With the aim of assessing the influence of the hydrophobic character, the conformational flexibility and the stereochemistry of the C-ring functionalities on the cytotoxic activity, a variety of spirostanic aglycones incorporating methylene, methoxyl, alpha,beta-unsaturated ketone and lactone groups were subjected to a linear glycosylation strategy leading to glycosides derived from the 3,6-dipivaloylated beta-D-glucoside and the beta-chacotrioside moieties. The 3,6-dipivaloylated spirostanyl beta-D-glucosides showed moderate to good cytotoxic activity against HL-60, but no significant cytotoxicity against benign blood cells. However, the cytotoxicity of spirostanyl beta-chacotriosides was highly dependent on the nature of the C-ring functional groups of the steroidal aglycones. Actually, the chacotrioside-based saponins either with no functionality or bearing a hydrophobic methylene group at C-12 were the most cytotoxic ones against both HL-60 and benign blood cells. On the other hand, the incorporation of very polar functionalities and the opening of the ring C with the consequent loss of rigidity led to a significant drop in the cytotoxicity against HL-60. These results confirm that spirostanyl beta-chacotriosides including very lipophilic aglycones are the most cytotoxic ones among their congeners. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.018