borealoside C | 143016-86-8

• 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: borealoside C
• 英文别名: (3S,5S,6S,8S,9R,10S,13R,14S,15S,17R)-17-[(2R,5S)-5-[(2S,3R,4S,5R)-3,5-dihydroxy-4-methoxyoxan-2-yl]oxy-6-methylheptan-2-yl]-10,13-dimethyl-1,2,3,4,5,6,7,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,6,8,15-tetrol
• CAS: 143016-86-8
• 化学式: C₃₃H₅₈O₉
• 分子量: 598.818
• InChiKey: PBCGIJBWPSEVKN-SMHIHPMASA-N

物化性质

• 沸点：
  735.4±60.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  42
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  149
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  phrygioside B 在 吡啶 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以4.3 mg的产率得到borealoside C
  参考文献：
  名称：

  Phrygiasterol, a Cytotoxic Cyclopropane-Containing Polyhydroxysteroid, and Related Compounds from the Pacific Starfish Hippasteria phrygiana

  摘要：

  The new cyclopropane-containing steroid phrygiasterol (1) and steroid glycoside phrygioside B (2), along with previously known borealoside C (2a) and (20R,24S)-5 alpha-cholesta-3 beta,6 alpha,8,15 alpha,24-pentaol (3), have been isolated from the Pacific starfish Hippasteria phrygiana. On the basis of spectroscopic analyses, using 1D and 2D NMR techniques and some chemical transformations, the structures of 1 and 2 have been established as (20R,24R*,25R*)-24,26-cyclo-5 alpha-cholesta-3 beta,6 alpha,8,15 alpha,16 beta,27-hexaol (1) and the sodium salt of (20R,24S)-24-O-(3-O-methyl-4-O-sulfate-beta-D-xylopyranosyl)-5 alpha-cholesta-3 beta,6 alpha,8,15 alpha,24-pentaol (2), respectively. Compound I inhibited the growth of Ehrlich carcinoma cells with an IC50 of 50 mu g/mL, whereas 2 induced apoptosis of the same cells (EC50 = 70 mu g/mL) and inhibited Ca-2 divided by influx into mouse spleenocytes (EC50 = 20 mu g/mL).

  DOI：

  10.1021/np049610t