ellagic acid 3-monomethyl ether

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: ellagic acid 3-monomethyl ether
• 英文别名: 3,5,10-Trihydroxy-12-methoxy-2,9-dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),3,5,8(16),10,12-hexaene-7,14-dione；3,5,10-trihydroxy-12-methoxy-2,9-dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),3,5,8(16),10,12-hexaene-7,14-dione
• 化学式: C₁₅H₈O₈
• 分子量: 316.224
• InChiKey: ZHILIOYRCNNMOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-methoxyellagic acid 4,4′-disulfate 在 盐酸 、 水 作用下， 反应 0.25h， 生成 ellagic acid 3-monomethyl ether
  参考文献：
  名称：

  Cytotoxic ellagitannins from Reaumuria vermiculata

  摘要：

  Three ellagitannins and one disulfated flavonol were isolated from the aerial parts of Reaumuria vermiculata L. Besides that, 16 known compounds were characterized as well. The structures of all compounds were elucidated on the basis of spectroscopic data including 1D and 2D NMR and ESI HR-FTMS. The in vivo antioxidant activity using the oxygen radical absorbance capacity (ORAC) method, of the extract, its column fractions and two of the isolated ellagitannins was accomplished. In addition, a possible cytotoxicity of the extract and two of the new ellagitannins on HaCaT human keratinocytes and the activity of both compounds against the prostate cancer cell line (PC-3) were also assessed, whereby a potent cytotoxicity with IC50 less than 1 mu g/ml was determined for both compounds. Besides, the extract exhibited a potential cytotoxic effect against four different solid tumor cell lines, namely liver (Huh-7), colorectal (HCT-116), breast (MCF-7) and prostate (PC-3). The IC(50)s were found to be substantially low (ranged from 1.3 +/- 0.15 to 2.4 +/- 0.22 mu g/ml) with relatively low resistance possibility reaching to 0% in the case of Huh-7 cell. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.fitote.2012.06.007