1-desgalloyleugeniin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 1-desgalloyleugeniin
• 英文别名: tellimagrandin I；[(10R,11S,12R,13R,15R)-3,4,5,13,21,22,23-heptahydroxy-8,18-dioxo-12-(3,4,5-trihydroxybenzoyl)oxy-9,14,17-trioxatetracyclo[17.4.0.02,7.010,15]tricosa-1(23),2,4,6,19,21-hexaen-11-yl] 3,4,5-trihydroxybenzoate
• 化学式: C₃₄H₂₆O₂₂
• 分子量: 786.567
• InChiKey: YKDNTEQLKGYZHT-JSAIFSMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  56
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  377
• 氢给体数：
  13
• 氢受体数：
  22

反应信息

• 作为产物：
  描述：

  rugosin D 生成 1-desgalloyleugeniin
  参考文献：
  名称：

  HATANO, TSUTOMU;OGAWA, NOBORU;SHINGU, TETSURO;OKUDA, TAKUO, CHEM. AND PHARM. BULL., 38,(1990) N2, C. 3341-3346

  摘要：

  DOI：

文献信息

• Synthesis and biological profiling of tellimagrandin I and analogues reveals that the medium ring can significantly modulate biological activity
  作者：Shaojun Zheng、Luca Laraia、Cornelius J. O' Connor、David Sorrell、Yaw Sing Tan、Zhaochao Xu、Ashok R. Venkitaraman、Wenjun Wu、David R. Spring

  DOI：10.1039/c2ob25065a

  日期：——

  A novel synthesis of the ellagitannin natural product tellimagrandin I and a series of medium ring analogues is described. These compounds were all subsequently screened for redox activity, ability to precipitate protein and cellular phenotype in HeLa cells. From this we have shown that all properties can be modulated independently by varying ring size and by moving the ester out of conjugation with the biaryl ring system. Increasing ring size increased redox activity and cytotoxicity, leading to the identification of a compound (10) which was significantly more cytotoxic. In addition compounds identified with a redox active scaffold and low cytotoxicity may be employed as a new class of redox probes.

  本文描述了一种新的合成方法，用于制备原天然物质ellagitannin的tellimagrandin I及其一系列中等环系类似物。随后对这些化合物进行了氧化还原活性、蛋白质沉淀能力和在HeLa细胞中的细胞表型的筛选。结果表明，通过改变环的大小和将酯基移出联芳环系统的共轭结构，可以独立调控所有这些性质。环的增大增加了氧化还原活性和细胞毒性，从而鉴定出一种化合物（10），其细胞毒性显著更高。此外，具有氧化还原活性骨架和低细胞毒性的化合物可能被用作一类新的氧化还原探针。
• Dimeric and trimeric ellagitannins from Corylus heterophylla
  作者：Zhe-Xiong Jin、Hideyuki Ito、Takashi Yoshida

  DOI：10.1016/s0031-9422(97)01091-1

  日期：1998.5

  Besides previously reported tannins and related polyphenols, additional two new hydrolysable tannins, heterophylliins F and G, were isolated from the leaf extract of Corylus heterophylla, and characterized by spectral and chemical evidence as dimeric and trimeric ellagitannins, respectively, in which monomeric units are linked to each other through a valoneoyl group. (C) 1998 Elsevier Science Ltd. All rights reserved.
• HATANO, TSUTOMU;OGAWA, NOBORU;SHINGU, TETSURO;OKUDA, TAKUO, CHEM. AND PHARM. BULL., 38,(1990) N2, C. 3341-3346
  作者：HATANO, TSUTOMU、OGAWA, NOBORU、SHINGU, TETSURO、OKUDA, TAKUO

  DOI：——

  日期：——