1β,20-(S)-dihydroxydammar-24(25)-ene-3β-O-stearate | 880162-08-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1β,20-(S)-dihydroxydammar-24(25)-ene-3β-O-stearate
• 英文别名: bruguierin A；bruguierins A；[(1R,3S,5S,8R,9S,10R,13R,14R,17S)-1-hydroxy-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] octadecanoate
• CAS: 880162-08-3
• 化学式: C₄₈H₈₆O₄
• 分子量: 727.208
• InChiKey: BCRQTNOYBAWCDF-XRYSTRTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.6
• 重原子数：
  52
• 可旋转键数：
  22
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 1β,20-(S)-dihydroxydammar-24(25)-ene-3β-O-stearate 在 氢氧化钾 作用下， 反应 3.0h， 以3.0 mg的产率得到硬酯酸甲酯C18
  参考文献：
  名称：

  Bioactive Dammarane Triterpenes from the Mangrove Plant Bruguiera gymnorrhiza

  摘要：

  Three new dammarane triterpenes, bruguierins A-C (1-3), were isolated from a petroleum ether extract of the flowers of Bruguiera gymnorrhiza. Their structures were determined on the basis of physical and spectroscopic data interpretation. With stably transfected HepG2 cells, the three isolates activated antioxidant response element (ARE luciferase activation) with EC50 values of 7.8, 9.4, and 15.7 mu M, respectively. Bruguierin A (1) also inhibited phorbol ester-induced NF kappa B (nuclear factor-kappa B) luciferase activation with an IC50 value of 1.4 mu M and selectively inhibited cyclooxygenase-2 (COX2) activity with an IC50 value of 0.37 mu M. Compounds 2 and 3 were not active in these bioassays.

  DOI：

  10.1021/np058112x

文献信息

• Bioactive Dammarane Triterpenes from the Mangrove Plant <i>Bruguiera </i><i>g</i><i>ymnorrhiza</i>
  作者：Sudarat Homhual、Nuntavan Bunyapraphatsara、Tamara Kondratyuk、Angkana Herunsalee、Wongsatit Chaukul、John M. Pezzuto、Harry H. S. Fong、Hong-Jie Zhang

  DOI：10.1021/np058112x

  日期：2006.3.1

  Three new dammarane triterpenes, bruguierins A-C (1-3), were isolated from a petroleum ether extract of the flowers of Bruguiera gymnorrhiza. Their structures were determined on the basis of physical and spectroscopic data interpretation. With stably transfected HepG2 cells, the three isolates activated antioxidant response element (ARE luciferase activation) with EC50 values of 7.8, 9.4, and 15.7 mu M, respectively. Bruguierin A (1) also inhibited phorbol ester-induced NF kappa B (nuclear factor-kappa B) luciferase activation with an IC50 value of 1.4 mu M and selectively inhibited cyclooxygenase-2 (COX2) activity with an IC50 value of 0.37 mu M. Compounds 2 and 3 were not active in these bioassays.

表征谱图