3-(4-hydroxy-3-methoxyphenyl)propyl-1-O-[β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside]

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-(4-hydroxy-3-methoxyphenyl)propyl-1-O-[β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside]
• 英文别名: descaudatine A
• 化学式: C₂₀H₃₀O₁₂
• 分子量: 462.451
• InChiKey: SNJFYKBEIJOIFV-QVNJDCLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.43
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  187.76
• 氢给体数：
  7.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  3-(4-hydroxy-3-methoxyphenyl)propyl-1-O-[β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside] 在 水 作用下， 生成 D-apiose 、 葡萄糖 、 L-(-)-葡萄糖
  参考文献：
  名称：

  Phenolic glycosides and flavonoids with antioxidant and anticancer activities from Desmodium caudatum

  摘要：

  Descaudatine A (1), an undescribed phenolic glycoside, along with a known analogue (2) and ten flavonoids (3-12), were isolated from the whole plant of Desmodium caudatum. Compounds 1 and 4 exhibited potent antioxidant activities with the IC50 of 58.59 mu M and 31.31 mu M, respectively, which were approached to that of the positive control Vitamin C (IC50 = 46.32 mu M). Meanwhile, 12 showed moderate antioxidant activity with the IC50 of 173.9 mu M. Besides, compounds 3 and 6 inhibited the proliferation of HeLa cells with IC50 values of 56.14 mu M and 69.04 mu M, respectively. Further studies indicated that 3 and 6 could dose-dependently induce PARP cleavage and might trigger caspase-3, 8, 9 activation to induce apoptosis. RXR alpha is an ideal anticancer target of nuclear receptor. The reporter gene assay of RXR alpha indicated that 3 and 6 could inhibited the 9-cis-RA induced RXR alpha transcription in a concentration-dependent manner.

  DOI：

  10.1080/14786419.2020.1739044