1,2,3,4,6-penta-O-galloyl-β-D-mannopyranose | 889114-86-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 1,2,3,4,6-penta-O-galloyl-β-D-mannopyranose
• 英文别名: US9120744, Cde-002；[(2R,3R,4S,5S,6S)-3,4,5,6-tetrakis[(3,4,5-trihydroxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
• CAS: 889114-86-7
• 化学式: C₄₁H₃₂O₂₆
• 分子量: 940.689
• InChiKey: QJYNZEYHSMRWBK-FSMZTTNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  67
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  444
• 氢给体数：
  15
• 氢受体数：
  26

反应信息

• 作为产物：
  描述：

  Pentakis-O-(3,4,5-triacetoxy-benzoyl)-β-D-mannopyranose 在 sodium hydroxide 、 sodium acetate 、 丙酮 作用下， 生成 1,2,3,4,6-penta-O-galloyl-β-D-mannopyranose
  参考文献：
  名称：

  Chemical Constitution and the Tanning Effect. II. Pentagallates of Glucose and Mannose

  摘要：

  DOI：

  10.1021/ja01248a011

文献信息

• Complete¹H and¹³C NMR assignments of a series of pergalloylated tannins
  作者：Serge Lavoie、Michael Ouellet、Pierre-Yves Fleury、Charles Gauthier、Jean Legault、André Pichette

  DOI：10.1002/mrc.4328

  日期：2016.2

  activities. Because these analogs were only partially characterized by NMR, we would like to report herein the complete H and C assignments of pergalloylated D-glucose (1), D-mannose (2), Dgalactose (3), D-xylose (4), L-ribose (5), L-arabinose (6), L-rhamnose (7), and D-fucose (8) by using a combination of one-dimensional and two-dimensional NMR experiments.

  单宁是广泛分布于植物界的次生代谢物。单宁的一个共同特征是它们的酚单元，它们可以连接在一起形成高度多样化的化学结构。由于这些化合物构成了摄入的食品和饮料的重要组成部分，因此对它们的生物效应进行了彻底的研究。最近，我们对加拿大山茱萸进行了植物化学研究，这是一种在北美野生生长的丰富开花植物，果实可食用。进行了初步的生物活性筛选，结果显示加拿大 C. 的提取物对 1 型单纯疱疹病毒具有活性。在生物测定引导的分级分离之后，鉴定了可水解的单宁。这些化合物之一，即 1,2,3,4,6-penta-O-galloyl-β-D-吡喃葡萄糖 (PGG)，已成为张最近审查的几项药物研究的主题。PGG 的生物学和药用特性多种多样，包括抗癌、抗氧化、抗诱变、抗炎、抗过敏、降胆固醇、抗凝、抗肾结石、抗惊厥、抗病毒和抗菌活性。此外，合成了一系列 PGG 类似物，发现它是刺激脂肪细胞葡萄糖转运的最佳支架。其中一些化合物也
• Plasminogen Activator Inhibitor-1 Inhibitors And Methods Of Use Thereof To Modulate Lipid Metabolism
  申请人：Lawrence Daniel A.

  公开号：US20090011055A1

  公开（公告）日：2009-01-08

  The invention relates to plasminogen activator-1 (PAI-1) inhibitor compounds and uses thereof in the treatment of any disease or condition associated with elevated PAI-1. The invention includes, but is not limited to, the use of such compounds to modulate lipid metabolism and treat conditions associated with elevated PAI-1, cholesterol, or lipid levels.

  该发明涉及纤溶酶原激活物-1（PAI-1）抑制剂化合物及其在治疗与升高的PAI-1相关的任何疾病或状况中的应用。该发明包括但不限于利用这些化合物来调节脂质代谢并治疗与升高的PAI-1、胆固醇或脂质水平相关的疾病。
• Plasminogen Activator Inhibitor-1 Inhibitors and Methods of Use Thereof to Modulate Lipid Metabolism
  申请人：Lawrence Daniel A.

  公开号：US20100137194A1

  公开（公告）日：2010-06-03

  The invention relates to plasminogen activator-1 (PAI-1) inhibitor compounds and uses thereof in the treatment of any disease or condition associated with elevated PAI-1. The invention includes, but is not limited to, the use of such compounds to modulate lipid metabolism and treat conditions associated with elevated PAI-1, cholesterol, or lipid levels.

  本发明涉及纤溶酶原激活剂-1（PAI-1）抑制剂化合物及其在治疗任何与升高的PAI-1相关的疾病或病状中的应用。本发明包括但不限于使用这些化合物来调节脂质代谢并治疗与升高的PAI-1、胆固醇或脂质水平相关的病症。
• PLASMINOGEN ACTIVATOR INHIBITOR-1 INHIBITORS AND METHODS OF USE THEREOF TO MODULATE LIPID METABOLISM
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：US20160009748A1

  公开（公告）日：2016-01-14

  The invention relates to plasminogen activator-1 (PAI-1) inhibitor compounds and uses thereof in the treatment of any disease or condition associated with elevated PAI-1. The invention includes, but is not limited to, the use of such compounds to modulate lipid metabolism and treat conditions associated with elevated PAI-1, cholesterol, or lipid levels.

  本发明涉及纤溶酶原激活物-1（PAI-1）抑制剂化合物及其在治疗与升高的PAI-1相关的任何疾病或病况中的用途。本发明包括但不限于使用这样的化合物来调节脂质代谢并治疗与升高的PAI-1、胆固醇或脂质水平相关的病症。
• Synthesis and Structure−Activity Relationship Study of Antidiabetic Penta-<i>O</i>-galloyl-<scp>d</scp>-glucopyranose and Its Analogues
  作者：Yulin Ren、Klaus Himmeldirk、Xiaozhuo Chen

  DOI：10.1021/jm060087k

  日期：2006.5.1

  The rapid increase of obesity-associated diabetes has created urgent demands for more effective antidiabetic therapies and pharmaceuticals that are able to address the problems of hyperglycemia and weight gain simultaneously. Our previous studies indicated that the alpha- and beta-anomers of penta-O-galloyl-D-glucopyranose (PGG), 2 and 3, act as insulin mimetics that bind to and activate the insulin receptor, stimulate glucose transport in adipocytes, and reduce blood glucose and insulin levels in diabetic and obese animals. In addition, they inhibit differentiation of preadipocytes into adipocytes. These activities suggest that 2 and 3 may reduce blood glucose without increasing adiposity. To investigate the structure-activity relationship of 2 and 3, four series of novel compounds were prepared and their glucose transport stimulatory activities were measured using a radioactive glucose uptake bioassay. The assay results indicate that both the glucose and the galloyl groups are critical to the activity of 2 and 3. It appears that the glucose core provides an optimal scaffold to present the galloyl groups with the correct spatial orientation to induce activity. Moreover, the galloyl groups linked to the 1, 2, 3, and 4 positions of glucose are essential, while the galloyl group connected to the 6 position of 2 is unnecessary for the induction of activity. The discovery that two related novel compounds, 6-deoxytetra-O-galloyl-alpha-D-glucopyranose (43) and tetra-O-galloyl-alpha-D-xylopyranose (59), also possess glucose transport stimulatory activity suggests that 2 may be further modified around position 6 to modulate and enhance its efficacy. To test this hypothesis, we developed a new synthetic method that allows for the stereoselective preparation of derivatives of 2 that are modified on C-6. We found that 6-chloro-6-deoxy- 1,2,3,4-tetra-O-galloyl-alpha-D-glucopyranose (80) exhibits a significantly higher glucose transport stimulatory activity than 2. Its activity is comparable to that of insulin.