3'-methoxy-4'-O-β-D-allopyranosylacetophenone

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3'-methoxy-4'-O-β-D-allopyranosylacetophenone
• 英文别名: 1-[3-methoxy-4-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]ethanone
• 化学式: C₁₅H₂₀O₈
• 分子量: 328.319
• InChiKey: QUOZWMJFTQUXON-KJWHEZOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3'-methoxy-4'-O-β-D-allopyranosylacetophenone 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 3.0h， 生成 D-阿洛糖
  参考文献：
  名称：

  Three new phenolic glycosides from the whole plant of Aconitum tanguticum (Maxim.) Stapf

  摘要：

  Three new phenolic glycosides 2-(3-O-beta-D-glucopyranosyl-4-hydroxyphenyl) ethanol 1-O-beta-D-glucopyranoside (1), 2-(4-O-beta-D-fructopyranosylphenyl) ethanol 1-O-beta-D-galactopyranoside (2) and 3-methoxy- 4-O-beta-D-allopyranosyl acetophenone (3), along with nine known compounds (4-12), were isolated from the ethanol extract of the whole plant of Aconitum tanguticum (Maxim.) Stapf. Their structures were elucidated by analysis of spectroscopic data including 1D-, 2D-NMR and HRESIMS, and the reported literature data comparison. All the compounds were evaluated for their potential anti-inflammatory effects by the inhibition of TNF-alpha production on LPS-stimulated RAW264.7 macrophages. Compounds 1, 3, 5 and 7-9 showed certain inhibition activity and their IC50 values were 38.18, 27.64, 3.25, 84.45, 12.76 and 18.44 mu g/mL, respectively. (C) 2015 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.phytol.2015.01.020

文献信息

• Three new phenolic glycosides from the whole plant of Aconitum tanguticum (Maxim.) Stapf
  作者：Yan-Rong Li、Ting Liu、Ren-Yi Yan、Lian-Qiang Hui、Li-mei Lin、Chun-Yu Cao、Shan-shan Guo、Li-Xin Yang、Wei-Hong Feng、Chun Li、Zhi-Ming Wang

  DOI：10.1016/j.phytol.2015.01.020

  日期：2015.3

  Three new phenolic glycosides 2-(3-O-beta-D-glucopyranosyl-4-hydroxyphenyl) ethanol 1-O-beta-D-glucopyranoside (1), 2-(4-O-beta-D-fructopyranosylphenyl) ethanol 1-O-beta-D-galactopyranoside (2) and 3-methoxy- 4-O-beta-D-allopyranosyl acetophenone (3), along with nine known compounds (4-12), were isolated from the ethanol extract of the whole plant of Aconitum tanguticum (Maxim.) Stapf. Their structures were elucidated by analysis of spectroscopic data including 1D-, 2D-NMR and HRESIMS, and the reported literature data comparison. All the compounds were evaluated for their potential anti-inflammatory effects by the inhibition of TNF-alpha production on LPS-stimulated RAW264.7 macrophages. Compounds 1, 3, 5 and 7-9 showed certain inhibition activity and their IC50 values were 38.18, 27.64, 3.25, 84.45, 12.76 and 18.44 mu g/mL, respectively. (C) 2015 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.