2α,3β,12β,20(S)-tetrahydroxy-25-hydroperoxydammar-23-ene-3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-20-O-α-Lrhamnopyranosyl-(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)-tetrahydroxy-25-hydroperoxydammar-23-ene-3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-20-O-α-Lrhamnopyranosyl-(1→6)-β-D-glucopyranoside
• 英文别名: gypenoside GD4
• 化学式: C₅₄H₉₂O₂₅
• 分子量: 1141.31
• InChiKey: OQACYWGPSOYTRY-JKLWUMHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.74
• 重原子数：
  79.0
• 可旋转键数：
  16.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  406.75
• 氢给体数：
  16.0
• 氢受体数：
  25.0

反应信息

• 作为反应物：
  描述：

  2α,3β,12β,20(S)-tetrahydroxy-25-hydroperoxydammar-23-ene-3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-20-O-α-Lrhamnopyranosyl-(1→6)-β-D-glucopyranoside 在 盐酸 、 水 作用下， 反应 3.0h， 生成 L-鼠李糖 、 葡萄糖
  参考文献：
  名称：

  Isolation and Characterization of Dammarane-Type Saponins from Gynostemma pentaphyllum and Their Inhibitory Effects on IL-6-Induced STAT3 Activation

  摘要：

  Five new dammarane-type saponins, gypenosides GD1-GD5 (1-5), along with six known saponins (6-11), were isolated from the aerial parts of Gynostemma pentaphyllum using various chromatographic methods. Their structures were elucidated by a combination of spectroscopic and spectrometric data, including 1D and 2D NMR and HRESIMS. All isolates were tested for their inhibitory effects on IL-6-induced STAT3 promoter activity in Hep3B cells. Compounds 1, 9, and 11 displayed potent inhibitory effects, with IC50 values ranging from 0.27 to 0.59 mu M.

  DOI：

  10.1021/np500803e

文献信息

• Isolation and Characterization of Dammarane-Type Saponins from <i>Gynostemma pentaphyllum</i> and Their Inhibitory Effects on IL-6-Induced STAT3 Activation
  作者：Chul Lee、Jin Woo Lee、Qinghao Jin、Hari Jang、Hyun-Jae Jang、Mun-Chual Rho、Myung Koo Lee、Chong Kil Lee、Mi Kyeong Lee、Bang Yeon Hwang

  DOI：10.1021/np500803e

  日期：2015.5.22

  Five new dammarane-type saponins, gypenosides GD1-GD5 (1-5), along with six known saponins (6-11), were isolated from the aerial parts of Gynostemma pentaphyllum using various chromatographic methods. Their structures were elucidated by a combination of spectroscopic and spectrometric data, including 1D and 2D NMR and HRESIMS. All isolates were tested for their inhibitory effects on IL-6-induced STAT3 promoter activity in Hep3B cells. Compounds 1, 9, and 11 displayed potent inhibitory effects, with IC50 values ranging from 0.27 to 0.59 mu M.