4-hydroxy-3,5-bis(3'-methyl-2-butenyl)benzoic acid-O-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxy-3,5-bis(3'-methyl-2-butenyl)benzoic acid-O-β-D-glucopyranoside
• 英文别名: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 4-hydroxy-3,5-bis(3-methylbut-2-enyl)benzoate
• 化学式: C₂₃H₃₂O₈
• 分子量: 436.502
• InChiKey: LIWBQFPPTPWDET-SQKWCZRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3,5-bis(3'-methyl-2-butenyl)benzoic acid-O-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 葡萄糖
  参考文献：
  名称：

  Phenolic glycosides from Ficus tikoua and their cytotoxic activities

  摘要：

  Four new phenolic glycosides, named 2-ethylene-3,5,6-trimethyl-4-phenol-1-O-beta-D-xylopyranosyl-(1 -> 6)-beta-D-glucopyranoside (1), 3-methoxy-4-O-beta-D-apiofuranosyl-(1 -> 2)-beta-D-glucopyranosylpropiophenone (2), 3-hydroxy-1-(4-O-beta-D-glucopyranosyl-3-methoxyphenyl) propan-1-one (3) and 4-hydroxy-3,5-bis(3'-methyl-2-butenyl) benzoic acid-O-beta-D-glucopyranoside (4), were isolated from the ethanol extract of Ficus tikoua, together with six known compounds: 3,4,5-trimethoxyphenol-1-O-beta-D-apiofuranosyl-(1 -> 6)-beta-D-glucopyranoside (5), 3,4,5-trimethoxyphenol-1-O-beta-D-glucopyranoside (6), 3-methoxy-4-O-beta-D-apiofuranosyl-(1 -> 6)-beta-D-glucopyranosylpropiophenone (7), baihuaqianhuoside (8), 3,5-dimethoxy-4-hydroxybenzoic acid-O-beta-D-glucopyranoside (9) and 2-methoxy-4-allylphenyl-1-O-beta-D-apiofuranosyl-(1 -> 6)-beta-D-glucopyranoside (10). The structures of the four new compounds were elucidated by chemical methods and MS and IR, as well as 1D and 2D NMR analyses. The cytotoxicities of the 10 compounds against HeLa, K562, HL60 and HepG2 cell lines were assessed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.09.008

文献信息

• Phenolic glycosides from Ficus tikoua and their cytotoxic activities
  作者：Zhi-Yong Jiang、Shi-Yuan Li、Wen-Juan Li、Jun-Ming Guo、Kai Tian、Qiu-Fen Hu、Xiang-Zhong Huang

  DOI：10.1016/j.carres.2013.09.008

  日期：2013.12

  Four new phenolic glycosides, named 2-ethylene-3,5,6-trimethyl-4-phenol-1-O-beta-D-xylopyranosyl-(1 -> 6)-beta-D-glucopyranoside (1), 3-methoxy-4-O-beta-D-apiofuranosyl-(1 -> 2)-beta-D-glucopyranosylpropiophenone (2), 3-hydroxy-1-(4-O-beta-D-glucopyranosyl-3-methoxyphenyl) propan-1-one (3) and 4-hydroxy-3,5-bis(3'-methyl-2-butenyl) benzoic acid-O-beta-D-glucopyranoside (4), were isolated from the ethanol extract of Ficus tikoua, together with six known compounds: 3,4,5-trimethoxyphenol-1-O-beta-D-apiofuranosyl-(1 -> 6)-beta-D-glucopyranoside (5), 3,4,5-trimethoxyphenol-1-O-beta-D-glucopyranoside (6), 3-methoxy-4-O-beta-D-apiofuranosyl-(1 -> 6)-beta-D-glucopyranosylpropiophenone (7), baihuaqianhuoside (8), 3,5-dimethoxy-4-hydroxybenzoic acid-O-beta-D-glucopyranoside (9) and 2-methoxy-4-allylphenyl-1-O-beta-D-apiofuranosyl-(1 -> 6)-beta-D-glucopyranoside (10). The structures of the four new compounds were elucidated by chemical methods and MS and IR, as well as 1D and 2D NMR analyses. The cytotoxicities of the 10 compounds against HeLa, K562, HL60 and HepG2 cell lines were assessed. (C) 2013 Elsevier Ltd. All rights reserved.