purpurogallin carboxylic acid | 5146-12-3

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: purpurogallin carboxylic acid
• 英文别名: purpurogallin-4-carboxylic acid；Purpurogallin-4-carbonsaeure；2,3,4,6-Tetrahydroxy-5-oxobenzo[7]annulene-8-carboxylic acid；2,3,4,6-tetrahydroxy-5-oxobenzo[7]annulene-8-carboxylic acid
• CAS: 5146-12-3
• 化学式: C₁₂H₈O₇
• 分子量: 264.191
• InChiKey: PJSKCCANFAFYHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  135
• 氢给体数：
  5
• 氢受体数：
  7

制备方法与用途

生物活性

紫草酸是从麦蓝菜（Macleaya microcarpa (Maxim.) Fedde）中分离出来的，也是没食子酸在发酵茶中的氧化产物。紫草酸具有抗癌活性。

体外研究

紫草酸对乳腺癌（MCF7细胞系）和肺癌（A549细胞系）癌细胞表现出抑制作用。

反应信息

• 作为反应物：
  描述：

  purpurogallin carboxylic acid 在 喹啉 、 铜 作用下， 生成 红倍酚
  参考文献：
  名称：

  293.purpurogallin。第七部分 紫嘌呤没食子酸酯羧酸的组成

  摘要：

  DOI：

  10.1039/jr9510001325
• 作为产物：
  描述：

  表茶黄棓灵3-O-没食子酸酯 在 单宁酶 、 碳酸氢钠 、 potassium hexacyanoferrate(III) 作用下， 以 水 为溶剂， 反应 0.84h， 生成 purpurogallin carboxylic acid
  参考文献：
  名称：

  Tannins and related compounds. XXXVI. Isolation and structures of theaflagallins, new red pigments from black tea.

  摘要：

  对黑茶多酚的化学分析导致了三种新红色颜料的分离，分别是木韵鞣酸3-O-鞣酸盐（1）、表木韵鞣酸（2）和木韵鞣酸（3），以及已知的茶黄素4-7。茶黄素1-3的结构是基于光谱和化学数据确定的，属于通过没食子酸和所谓的没食子儿茶素的氧化缩合形成的非凡的苯并特罗醇。

  DOI：

  10.1248/cpb.34.61

文献信息

• Benzotropolone derivatives and modulation of inflammatory response
  申请人：Ho Chi-Tang

  公开号：US20050049284A1

  公开（公告）日：2005-03-03

  The present invention provides novel benzotropolone derivatives represented by the general formula: including neotheaflavate B and EGCGCa. The benzotropolone derivatives of the present invention are effective antioxidant and anti-inflammatory agents. The present invention also provides novel method of synthesizing benzotropolone compounds in high yields and method of treating inflammatory conditions using benzotropolone containing compounds.

  本发明提供了一种由通式表示的新型苯并三酮衍生物： 包括新茶黄素B和EGCGCa。本发明的苯并三酮衍生物是有效的抗氧化剂和抗炎药物。本发明还提供了一种高产率合成苯并三酮化合物的新方法，以及使用含有苯并三酮的化合物治疗炎症症状的方法。
• ANTI-OBESITY AGENT COMPRISING COMPOUND CONTAINING BENZOTROPOLONE RING
  申请人：Fukui Yuko

  公开号：US20120065410A1

  公开（公告）日：2012-03-15

  The object of the present invention is to provide an anti-obesity agent which contains a tea-derived component and which is safe and does not compromise the flavor of foods and beverages. According to the present invention, a safe and palatable anti-obesity agent can be provided by incorporating a benzotropolone ring-containing compound which has tea-derived, high inhibitory activities against lipase and alfa-glucosidase. The anti-obesity agent of the present invention does not compromise the flavor of foods and beverage, has palatability, and can be used in various use applications including foods and beverages intended for health enhancement such as reduction in triglycerides.

  本发明的目的是提供一种抗肥胖剂，其中包含一种来源于茶叶的成分，既安全又不会影响食品和饮料的味道。根据本发明，通过将含苯并环戊酮环的化合物纳入其中，可以提供一种安全而美味的抗肥胖剂，该化合物具有来源于茶叶的高抑制脂肪酶和α-葡萄糖苷酶的活性。本发明的抗肥胖剂不会影响食品和饮料的味道，具有口感，可以用于各种用途，包括旨在提高健康的食品和饮料，如降低三酰甘油。
• Virtual screening of National Cancer Institute database for claudin‐4 inhibitors: Synthesis, biological evaluation, and molecular dynamics studies
  作者：Majji Rambabu、Sivaraman Jayanthi

  DOI：10.1002/jcb.28147

  日期：2019.5

  overexpressed in cancer and other malignancies. The three-dimensional structure of human CLDN4 was constructed based on homology modeling approach. A total of 265 242 molecules from the National Cancer Institute (NCI) database has been utilized as a dataset for this study. In the present work, structure-based virtual screening is performed with the NCI database using Glide. By molecular docking, 10 candidate

  Claudin-4 (CLDN4) 是紧密连接蛋白的重要成员，通常在癌症和其他恶性肿瘤中过度表达。基于同源建模方法构建了人类CLDN4的三维结构。来自国家癌症研究所 (NCI) 数据库的总共 265 242 个分子已被用作本研究的数据集。在目前的工作中，基于结构的虚拟筛选是使用 Glide 与 NCI 数据库一起执行的。通过分子对接，鉴定出10个与CLDN4活性位点结合的具有高评分功能的候选分子。随后，膜蛋白的分子动力学模拟被用于在动态系统中优化前三个先导化合物（NCI110039、NCI344682 和 NCI661251）与 CLDN4。合成了来自 NCI 数据库 NCI11039（紫没食子酸）的先导分子，并用 A549、MCF7 细胞系评估了细胞毒性。我们的对接和动力学模拟预测 ARG31、ASN142、ASP146 和 ARG158 是参与 CLDN4 活性的极其重要的残基。最后，NCI
• Methods for treating congenital disorders of glycosylation
  申请人：Maggie's Pearl, LLC

  公开号：US11160794B2

  公开（公告）日：2021-11-02

  The present disclosure relates generally to compounds and pharmaceutical compositions for increasing glycosylation and treating congenital disorders of glycosylation.

  本公开一般涉及用于增加糖基化和治疗先天性糖基化紊乱的化合物和药物组合物。
• Enzymatic synthesis of tea theaflavin derivatives and their anti-inflammatory and cytotoxic activities
  作者：Shengmin Sang、Joshua D Lambert、Shiying Tian、Jungil Hong、Zhe Hou、Jae-He Ryu、Ruth E Stark、Robert T Rosen、Mou-Tuan Huang、Chung S Yang、Chi-Tang Ho

  DOI：10.1016/j.bmc.2003.10.024

  日期：2004.1

  Derivatives based on a benzotropolone skeleton (9-26) have been prepared by the enzymatic coupling (horseradish peroxidase/H2O2) of selected pairs of compounds (1-8), one with a vic-trihydroxyphenyl moiety, and the other with an ortho-dihydroxyphenyl structure. Some of these compounds have been found to inhibit TPA-induced mice ear edema, nitric oxide (NO) synthesis, and arachidonic acid release by LPS-stimulated RAW 264.7 cells. Their cytotoxic activites against KYSE 150 and 510 human esophageal squamous cell carcinoma and HT 29 human colon cancer cells were also evaluated. (C) 2003 Elsevier Ltd. All rights reserved.