eschweilenol A

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: eschweilenol A
• 英文别名: 6,7,14-trihydroxy-13-(2,3,4-trihydroxyphenoxy)-2,9-dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione
• 化学式: C₂₀H₁₀O₁₁
• 分子量: 426.293
• InChiKey: LGMNKSBINQXDAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  183
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 eschweilenol A 以 乙醚 、 乙醇 为溶剂， 反应 12.0h， 以2 mg的产率得到2,3,8-Trimethoxy-7-(2,3,4-trimethoxy-phenoxy)-chromeno[5,4,3-cde]chromene-5,10-dione
  参考文献：
  名称：

  Three New Ellagic Acid Derivatives from the Bark of Eschweilera coriacea from the Suriname Rainforest

  摘要：

  Bioassay-guided fractionation of Eschweilera coriacea collected in the lowland wet forest of Suriname yielded the new but only weakly active ellagic acid derivative eschweilenol A (1) and the two new but inactive ellagic acid derivatives eschweilenol B (2) and eschweilenol C (3). The four known compounds, sucrose, ellagic acid, 3-O-galloylepigallocatechin, and epigallocatechin, were also isolated. The structures of the three new compounds were determined by spectrometric methods, primarily from the HMQC, HMBC, NOESY, and ROESY NMR techniques, and chemical methods, including methylation and triethylsilylation. The location of a hydroxyl group in one ellagic acid derivative was determined by a new technique involving an NOE correlation of the protons of a triethylsilyl derivative with a proton on a neighboring aromatic ring.

  DOI：

  10.1021/np980046u
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 eschweilenol A
  参考文献：
  名称：

  Schmidt; Komarek, Justus Liebigs Annalen der Chemie, 1955, vol. 591, p. 156,170

  摘要：

  DOI：

文献信息

• Characterization and Identification of Bioactive Polyphenols in the Trapabispinosa Roxb. Pericarp Extract
  作者：Yuji Iwaoka、Shoichi Suzuki、Nana Kato、Chisa Hayakawa、Satoko Kawabe、Natsuki Ganeko、Tomohiro Uemura、Hideyuki Ito

  DOI：10.3390/molecules26195802

  日期：——

  In this study, we present the isolation and characterization of the structure of six gallotannins (1–6), three ellagitannins (7–9), a neolignan glucoside (10), and three related polyphenolic compounds (gallic acid, 11 and 12) from Trapa bispinosa Roxb. pericarp extract (TBE). Among the isolates, the structure of compound 10 possessing a previously unclear absolute configuration was unambiguously determined

  在这项研究中，我们分离并表征了六种棓单宁 ( 1 – 6 )、三种鞣花单宁 ( 7 – 9 )、一种新木脂素葡萄糖苷 ( 10 ) 和三种相关多酚化合物（没食子酸、 11和12 ）的结构来自Trapa bispinosa Roxb。果皮提取物（TBE）。在分离物中，通过核磁共振和圆二色性分析明确确定了具有先前不清楚的绝对构型的化合物10的结构。评估分离株的α-葡萄糖苷酶活性和糖化抑制作用。脱羧rugosin A ( 8 ) 显示出α-葡萄糖苷酶抑制活性，而可水解单宁则显示出比阳性对照更强的抗糖化活性。此外，通过高效液相色谱结合紫外检测和电喷雾电离质谱分析对 TBE 多酚进行了鉴定和定量，表明没食子酸、鞣花酸和没食子酰葡萄糖占主导地位，表现出明显的抗糖化特性。这些发现表明，TBE 中的多酚作为具有抗糖尿病和抗糖化活性的功能性食品，在食品工业中有潜在的应用。
• Schmidt; Komarek, Justus Liebigs Annalen der Chemie, 1955, vol. 591, p. 156,170
  作者：Schmidt、Komarek

  DOI：——

  日期：——
• Three New Ellagic Acid Derivatives from the Bark of <i>Eschweilera coriacea</i> from the Suriname Rainforest
  作者：Shu-Wei Yang、Bing-Nan Zhou、Jan H. Wisse、Randy Evans、Hendrik van der Werff、James S. Miller、David G. I. Kingston

  DOI：10.1021/np980046u

  日期：1998.7.1

  Bioassay-guided fractionation of Eschweilera coriacea collected in the lowland wet forest of Suriname yielded the new but only weakly active ellagic acid derivative eschweilenol A (1) and the two new but inactive ellagic acid derivatives eschweilenol B (2) and eschweilenol C (3). The four known compounds, sucrose, ellagic acid, 3-O-galloylepigallocatechin, and epigallocatechin, were also isolated. The structures of the three new compounds were determined by spectrometric methods, primarily from the HMQC, HMBC, NOESY, and ROESY NMR techniques, and chemical methods, including methylation and triethylsilylation. The location of a hydroxyl group in one ellagic acid derivative was determined by a new technique involving an NOE correlation of the protons of a triethylsilyl derivative with a proton on a neighboring aromatic ring.