2α,3β,12β,20(S)-tetrahydroxydammar-25-en-24-one-3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-20-O-β-D-xylopyranosyl-(1→6)-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: 2α,3β,12β,20(S)-tetrahydroxydammar-25-en-24-one-3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-20-O-β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside
• 英文别名: 3-O-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-]-20-O-[β-D-xylopyranosyl-(1→6)-β-D-glucopyranosyl]-2α,3β,12β-trihydroxydammar-25-en-24-one；gypenoside J3
• 化学式: C₅₃H₈₈O₂₄
• 分子量: 1109.27
• InChiKey: PYHJGMKZRCFKNG-YGLQIJNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.41
• 重原子数：
  77.0
• 可旋转键数：
  16.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  394.36
• 氢给体数：
  15.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  2α,3β,12β,20(S)-tetrahydroxydammar-25-en-24-one-3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-20-O-β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside 在 盐酸 作用下， 以 水 为溶剂， 反应 6.0h， 生成 D-木糖 、 葡萄糖
  参考文献：
  名称：

  Novel dammarane-type saponins from Gynostemma pentaphyllum and their neuroprotective effect

  摘要：

  Three novel dammarane-type saponins, 2 alpha,3 beta,12 beta,20(S),24(S)-pentahydroxydammar-25-ene-3-O-beta-D-glucopyranosyl-(1 -> 2)-beta-D-glucopyranosyl-20-O-beta-D-glucopyranoside (1, namely gypenoside J1), 2 alpha,3 beta,12 beta,20(S),25-pentahydroxydammar-23-ene-3-O-beta-D-glucopyranosyl-(1 -> 2)-beta-D-glucopyranosyl-20-O-beta-D-glucopyranoside (2, namely gypenoside J2) and 2 alpha,3 beta,12 beta,20(S)-tetrahydroxydammar-25-en-24-one-3-O-beta-D-glucopyranosyl-(1 -> 2)-beta-D-glucopyranosyl-20-O-beta-D-xylopyranosyl-(1 -> 6)-beta-D-glucopyranoside (3, namely gypenoside J3) along with one known gypenoside (gypenoside LVII) were isolated from the aerial parts of G. pentaphyllum using various chromatographic methods. Their structures were elucidated on the basis of IR, 1D- (H-1 and C-13), 2D-NMR spectroscopy (HSQC, HMBC and COSY), and mass spectrometry (ESI-MS/MS). Their activity was tested using CCK-8 assay. These four compounds showed little anti-cancer activity with IC50 values more than 100 mu M against four types of human cancer lines. The effects of them against H2O2-induced oxidative stress in human neuroblastoma SH-SY5Y cells were evaluated and they all showed potential neuroprotective effects with 3.64-18.16% higher cell viability than the H2O2-induced model group.

  DOI：

  10.1080/14786419.2018.1495638

文献信息

• Novel dammarane-type saponins from <i>Gynostemma pentaphyllum</i> and their neuroprotective effect
  作者：Shao-Fang Xing、Man Lin、Yu-Rong Wang、Tuo Chang、Wei-Ye Cui、Xiang-Lan Piao

  DOI：10.1080/14786419.2018.1495638

  日期：2020.3.3

  Three novel dammarane-type saponins, 2 alpha,3 beta,12 beta,20(S),24(S)-pentahydroxydammar-25-ene-3-O-beta-D-glucopyranosyl-(1 -> 2)-beta-D-glucopyranosyl-20-O-beta-D-glucopyranoside (1, namely gypenoside J1), 2 alpha,3 beta,12 beta,20(S),25-pentahydroxydammar-23-ene-3-O-beta-D-glucopyranosyl-(1 -> 2)-beta-D-glucopyranosyl-20-O-beta-D-glucopyranoside (2, namely gypenoside J2) and 2 alpha,3 beta,12 beta,20(S)-tetrahydroxydammar-25-en-24-one-3-O-beta-D-glucopyranosyl-(1 -> 2)-beta-D-glucopyranosyl-20-O-beta-D-xylopyranosyl-(1 -> 6)-beta-D-glucopyranoside (3, namely gypenoside J3) along with one known gypenoside (gypenoside LVII) were isolated from the aerial parts of G. pentaphyllum using various chromatographic methods. Their structures were elucidated on the basis of IR, 1D- (H-1 and C-13), 2D-NMR spectroscopy (HSQC, HMBC and COSY), and mass spectrometry (ESI-MS/MS). Their activity was tested using CCK-8 assay. These four compounds showed little anti-cancer activity with IC50 values more than 100 mu M against four types of human cancer lines. The effects of them against H2O2-induced oxidative stress in human neuroblastoma SH-SY5Y cells were evaluated and they all showed potential neuroprotective effects with 3.64-18.16% higher cell viability than the H2O2-induced model group.