尿石素M5 | 91485-02-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 中文名称: 尿石素M5
• 英文名称: 3,4,8,9,10-pentahydroxydibenzo[b,d]pyran-6-one
• 英文别名: urolithin M5；3,4,8,9,10-pentahydroxy-dibenzopyran-6-one；3,4,8,9,10-pentahydroxy-6H-benzo[c]chromen-6-one；3,4,8,9,10-pentahydroxybenzo[c]chromen-6-one
• CAS: 91485-02-8
• 化学式: C₁₃H₈O₇
• 分子量: 276.202
• InChiKey: ZELMDXUEWHBWPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  尿石素M5 在 氢氧化钾 作用下， 反应 0.05h， 生成 2,2',3,3',4,4'-联苯六醇
  参考文献：
  名称：

  3,4,8,9,10-Pentahydroxy-dibenzo[b,d]pyran-6-one 来自 Tamarix nilotica

  摘要：

  摘要 从柽柳花中分离得到一种新的天然产物 3,4,8,9,10-pentahydroxy-dibenzo-[b,d]pyran-6-one，其中还含有已知化合物鞣花酸、2,3 ,7,8-四羟基 [1]benzopyrano[5,4,3-cde][1]benzopyran-5,10-dione。新化合物的结构是通过化学和光谱方法确定的。记录并分配鞣花酸的 13C MNR 谱。

  DOI：

  10.1016/0031-9422(84)83057-5
• 作为产物：
  描述：

  鞣花酸 在 氢氧化钾 作用下， 以 水 为溶剂， 反应 0.17h， 生成 尿石素M5
  参考文献：
  名称：

  3,4,8,9,10-Pentahydroxy-dibenzo[b,d]pyran-6-one 来自 Tamarix nilotica

  摘要：

  摘要 从柽柳花中分离得到一种新的天然产物 3,4,8,9,10-pentahydroxy-dibenzo-[b,d]pyran-6-one，其中还含有已知化合物鞣花酸、2,3 ,7,8-四羟基 [1]benzopyrano[5,4,3-cde][1]benzopyran-5,10-dione。新化合物的结构是通过化学和光谱方法确定的。记录并分配鞣花酸的 13C MNR 谱。

  DOI：

  10.1016/0031-9422(84)83057-5

文献信息

• Urolithin as a Converging Scaffold Linking Ellagic acid and Coumarin Analogues: Design of Potent Protein Kinase CK2 Inhibitors
  作者：Giorgio Cozza、Alessandra Gianoncelli、Paolo Bonvini、Elisa Zorzi、Riccardo Pasquale、Angelo Rosolen、Lorenzo A. Pinna、Flavio Meggio、Giuseppe Zagotto、Stefano Moro

  DOI：10.1002/cmdc.201100338

  日期：2011.12.9

  Ki=60 nM). Comparing the crystallographic binding modes of both ellagic acid and DBC, an X‐ray structure‐driven merging approach was taken to design novel CK2 inhibitors with improved target affinity. A urolithin moiety is proposed as a possible bridging scaffold between the two known CK2 inhibitors, ellagic acid and DBC. Optimization of urolithin A as the bridging moiety led to the identification of 4‐bromo‐3

  酪蛋白激酶2（CK2）是一种普遍存在的，必不可少的，高度多效的蛋白激酶。其异常高的本构活性被怀疑是其在瘤形成和其他相关疾病中的致病潜能的基础。以前，使用不同的计算机筛选方法，我们小组确定了两种有效的选择性CK2抑制剂：鞣花酸，天然存在的鞣酸衍生物（K i = 20 n M）和3,8-dibromo‐7‐hydroxy‐4 -甲基铬n-2-one（DBC，K i = 60 n M）。比较鞣花酸和DBC的晶体学结合模式，采用X射线结构驱动的合并方法设计了具有改善的靶标亲和力的新型CK2抑制剂。尿石素部分被提议作为两种已知的CK2抑制剂鞣花酸和DBC之间的可能搭桥支架。优化尿石素A作为桥联部分导致鉴定出4-溴-3,8-二羟基苯并[c] chromen-6-one作为新型，有效和选择性的CK2抑制剂，其K i值为7 n M对抗蛋白激酶，与两个亲本片段相比，对靶标的亲和力显着提高。
• Ellagic Acid and Its Metabolites as Potent and Selective Allosteric Inhibitors of Liver Pyruvate Kinase
  作者：Umberto Maria Battisti、Chunixa Gao、Fady Akladios、Woonghee Kim、Hong Yang、Cemil Bayram、Ismail Bolat、Metin Kiliclioglu、Nursena Yuksel、Ozlem Ozdemir Tozlu、Cheng Zhang、Jihad Sebhaoui、Shazia Iqbal、Saeed Shoaie、Ahmet Hacimuftuoglu、Serkan Yildirim、Hasan Turkez、Mathias Uhlen、Jan Boren、Adil Mardinoglu、Morten Grøtli

  DOI：10.3390/nu15030577

  日期：——

  Liver pyruvate kinase (PKL) has recently emerged as a new target for non-alcoholic fatty liver disease (NAFLD), and inhibitors of this enzyme could represent a new therapeutic option. However, this breakthrough is complicated by selectivity issues since pyruvate kinase exists in four different isoforms. In this work, we report that ellagic acid (EA) and its derivatives, present in numerous fruits and vegetables, can inhibit PKL potently and selectively. Several polyphenolic analogues of EA were synthesized and tested to identify the chemical features responsible for the desired activity. Molecular modelling studies suggested that this inhibition is related to the stabilization of the PKL inactive state. This unique inhibition mechanism could potentially herald the development of new therapeutics for NAFLD.

  肝丙酮酸激酶（PKL）最近已成为治疗非酒精性脂肪肝（NAFLD）的新靶点，这种酶的抑制剂可能是一种新的治疗选择。然而，由于丙酮酸激酶存在四种不同的同工酶，这一突破因选择性问题而变得复杂。在这项工作中，我们报告了存在于多种水果和蔬菜中的鞣花酸（EA）及其衍生物可以有效地、选择性地抑制 PKL。我们合成并测试了几种鞣花酸的多酚类似物，以确定产生所需活性的化学特征。分子模型研究表明，这种抑制作用与 PKL 非活性状态的稳定有关。这种独特的抑制机制可能预示着非酒精性脂肪肝新疗法的开发。
• Xanthine oxidase inhibitor and method for producing the same
  申请人：ITO EN, LTD.

  公开号：US20020051825A1

  公开（公告）日：2002-05-02

  In order to provide a xanthine oxidase inhibitor having as an effective component an extract from highly safe plants, ten kinds of plant materials were compared for the xanthine oxidase inhibition activity, and in consequence Lagerstroemia speciosa (banaba) was found to have the strongest activity. In addition, it was found that the xanthine oxidase inhibition activity was present in an “crude extract” obtained by extracting banaba with hot water or the like, “resin adsorbed components” obtained by adsorbing the crude extract on a styrene-divinyl benzene synthetic resin or the like, and “organic solvent soluble components” obtained by the partition of the resin adsorbed component between water and an organic solvent. Among them, the “organic solvent soluble components” described above were purified with high performance liquid chromatography to obtain “ellagic acid,” an “ellagic acid derivative,” an “ellagic acid analog compound” and a “lignan,” which were found to have a more superior xanthine oxidase inhibitor activity. The present invention provides a xanthine oxidase inhibitor having each of these extracted materials as an effective component.

  为了提供一种以安全性高的植物提取物为有效成分的黄嘌呤氧化酶抑制剂，对十种植物材料的黄嘌呤氧化酶抑制活性进行了比较，结果表明 发现 (banaba) 的活性最强。此外，研究还发现，黄嘌呤氧化酶抑制活性存在于用热水等萃取 banaba 而得的 "粗萃取物"、将粗萃取物吸附在苯乙烯-二乙烯基苯合成树脂等上而得的 "树脂吸附成分"，以及将树脂吸附成分在水和有机溶剂之间分配而得的 "有机溶剂可溶成分 "中。其中，上述 "有机溶剂可溶组分 "经高效液相色谱纯化后得到 "鞣花酸"、"鞣花酸衍生物"、"鞣花酸类似化合物 "和 "木质素"，发现它们具有更优异的黄嘌呤氧化酶抑制活性。本发明提供了一种黄嘌呤氧化酶抑制剂，其有效成分包括上述每种提取物。
• Nierenstein, Chemische Berichte, 1908, vol. 41, p. 3018
  作者：Nierenstein

  DOI：——

  日期：——
• Nierenstein; Rixon, Justus Liebigs Annalen der Chemie, 1912, vol. 394, p. 251
  作者：Nierenstein、Rixon

  DOI：——

  日期：——