furcreastatin

• 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: furcreastatin
• 英文别名: (1R,2S,4S,5'R,6R,7S,8R,9S,12S,13S,16S,18S)-16-[(2R,3R,4R,5R,6R)-5-[(2S,3R,4S,5R,6R)-3-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-10-one
• 化学式: C₆₃H₁₀₂O₃₃
• 分子量: 1387.48
• InChiKey: CIFSKMQPNGXEMV-ILRIWLSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.3
• 重原子数：
  96
• 可旋转键数：
  17
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  510
• 氢给体数：
  18
• 氢受体数：
  33

反应信息

• 作为反应物：
  描述：

  furcreastatin 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以11.8 mg的产率得到海柯吉宁
  参考文献：
  名称：

  A new bioactive steroidal saponin, furcreastatin, from the plant Furcraeafoetida

  摘要：

  Microbial and plant secondary metabolites were screened for compounds that are selectively cytotoxic to mutant p53-expressing mouse fibroblasts. As a result, furcreastatin, a novel steroidal saponin, was isolated from an EtOH extract of the leaves of Furcraea foetida. Furcreastatin consisted of hecogenin as the aglycone and a hexasaccharide containing D-galactose, L-rhamnose and four D-glucose residues. The structure was determined to be (3 beta,5 alpha,25R)- 3-hydroxyspirostan-12-one 3-O-[alpha-L-Rhap-(1-->4)-beta-D-Glcp-(1-->3)-¿beta-D-Glcp-(1-->3) -beta-D- Glcp-(1-->2)¿-beta-D-Glcp-(1-->4)-beta-D-Galp] by extensive NMR spectroscopic studies. Furcreastatin decreased the viability of mutant p53-over-expressing cells with an ED50 of 4.0 micrograms/mL, and decreased that of the parental cell-line with an ED50 of 9.6 micrograms/mL.

  DOI：

  10.1016/s0008-6215(99)00255-4