3β,12β,25-trihydroxydammar-20E(22)-ene-3-O-β-D-glucopyranoside

• 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: 3β,12β,25-trihydroxydammar-20E(22)-ene-3-O-β-D-glucopyranoside
• 英文别名: (3β,12β,20E)-12,25-dihydroxydammar-20(22)-en-3-yl β-D-glucopyranoside；ginsenoside Rh₁₀；(2R,3R,4S,5S,6R)-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-17-[(E)-6-hydroxy-6-methylhept-2-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]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₃₆H₆₂O₈
• 分子量: 622.883
• InChiKey: YCDZBVXSGVWFFX-AZEZESTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  44
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  140
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  人参皂甙 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 4.0h， 以1.21 g的产率得到3β,12β,25-trihydroxydammar-20E(22)-ene-3-O-β-D-glucopyranoside
  参考文献：
  名称：

  Semi-synthesis of Twelve Known 20<i>Z</i>/<i>E</i> Pseudo-Ginsenosides and Their Comparative Study of Antioxidative Activity in Free Radical Induced Hemolysis of Rabbit Erythrocytes

  摘要：

  在温和条件下，通过简单的乙酰化、消除-加成和皂化三步合成了十二种假人参皂苷。筛选了这12种拟人参皂苷对2,2'-偶氮双（2-脒基丙烷盐酸盐）（AAPH）引起的兔红细胞溶血的抑制作用。结果发现，IC50值遵循以下顺序：(20Z)假原人参三醇(假PPT)<(20Z)假原人参二醇(假PPD)<(20Z)假Rh2<(20E)假PPT<( 20E)伪PPD<(20E)伪Rh2<(20Z)伪Rg2<(20E)伪Rg2

  DOI：

  10.1248/cpb.c17-00779

文献信息

• Synthesis and anti-cancer cell activity of pseudo-ginsenoside Rh2
  作者：Guangtao Qian、Zhicai Wang、Jinyu Zhao、Dandan Li、Wei Gao、Baohui Wang、Dayuan Sui、Xiangru Qu、Yanping Chen

  DOI：10.1016/j.steroids.2014.08.021

  日期：2014.12

  beta-D-Glucopyranoside, (3 beta,12 beta,20E)-12,25-dihydroxydammar-20(22)-en-3-yl (pseudo-ginsenoside Rh2) and its 20Z-isomer were synthesized from ginsenoside Rh2 under a mild condition, via a simple three-step called acetylation, elimination-addition and saponification. In addition, their activities were evaluated by eight different human tumor cells, compared with ginsenoside Rh2 group. Results indicated that the reaction in the side chain might greatly enhance the anti-proliferative activity of ginsenosides. (C) 2014 Elsevier Inc. All rights reserved.