1,2,3,4,6-penta-O-galloyl-α-D-glucose | 70470-10-9

• 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-α-D-glucose
• 英文别名: α-pentagalloylglucose；1,2,3,4,6-penta-O-galloyl-α-D-glucopyranose；1,2,3,4,6-Penta-O-galloyl-alpha-D-glucopyranose；(2R,3R,4S,5R,6R)-6-(((3,4,5-Trihydroxybenzoyl)oxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetrakis(3,4,5-trihydroxybenzoate)；[(2R,3R,4S,5R,6R)-3,4,5,6-tetrakis[(3,4,5-trihydroxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
• CAS: 70470-10-9
• 化学式: C₄₁H₃₂O₂₆
• 分子量: 940.689
• InChiKey: QJYNZEYHSMRWBK-HXSHIISNSA-N

物化性质

• 熔点：
  >210 °C (decomp)(Solv: water (7732-18-5))
• 沸点：
  1365.7±65.0 °C(Predicted)
• 密度：
  2.05±0.1 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  1,2,3,4,6-penta-O-galloyl-α-D-glucose 在 sodium carbonate 作用下， 反应 6.0h， 以50%的产率得到鞣花酸
  参考文献：
  名称：

  Synthesis and Antitumor Activity of Ellagic Acid Peracetate

  摘要：

  Ellagic acid (1) was synthesized for the first time from methyl gallate through a-pentagalloylglucose (alpha-PGG), and ellagic acid peracetate (3,4,3',4'-tetra-O-acetylellagic acid, 2) was derived from 1 by acetylation. Oral administration of 2 suppressed melanoma growth significantly in C7BL/6 immunocompetent mice without having any effect on natural killer (NK) cell activity. Comparison of the immunoenhancing activities of 1 and 2 indicated that the latter compound increased white blood cell quantities in peripheral blood and immune cells enriched from the bone marrow and liver of mice. Therefore, both the antitumor efficacy and the immunity enhancement by 2 were greater than those by 1. In addition, on oral administration, neither 1 nor 2 resulted in whole body, liver, or spleen weight changes of normal, tumor-free mice, indicating that these compounds are potentially nontoxic to mice. It was shown that ellagic acid peracetate (2) inhibits B16 melanoma cell growth in vitro and induces B16 cell apoptosis, corresponding to BCL-2 down-regulation. Collectively, the present data imply that 2 can suppress tumor growth by enhancing mouse immunity and inducing tumor cell apoptosis without apparent side effects.

  DOI：

  10.1021/ml300065z
• 作为产物：
  描述：

  1,2,3,4,6-pentakis-O-(3’,4’,5’-tribenzyloxybenzoyl)-α-D-glucopyranose 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以90%的产率得到1,2,3,4,6-penta-O-galloyl-α-D-glucose
  参考文献：
  名称：

  天然产物的高效全合成，以及不自然

  摘要：

  天然产物的合成短（8）， （10）和非天然（13）是基于所述苄没食子酸的高效酯化反应达到5与α，β-吡喃葡萄糖11和4分别。

  DOI：

  10.1016/s0040-4020(97)00702-3

文献信息

• Gallotannins and Tannic Acid: First Chemical Syntheses and In Vitro Inhibitory Activity on Alzheimer’s Amyloid β-Peptide Aggregation
  作者：Tahiri Sylla、Laurent Pouységu、Grégory Da Costa、Denis Deffieux、Jean-Pierre Monti、Stéphane Quideau

  DOI：10.1002/anie.201411606

  日期：2015.7.6

  against Alzheimer’s disease has unveiled several plant polyphenols that are capable of inhibiting the formation of toxic β‐amyloid fibrils. Gallic acid based gallotannins are among these polyphenols, but their antifibrillogenic activity has thus far been examined using “tannic acid”, a commercial mixture of gallotannins and other galloylated glucopyranoses. The first total syntheses of two true gallotannins

  在寻找对抗阿尔茨海默氏病的新先导化合物的过程中，对天然产物的筛选揭示了几种能够抑制有毒β-淀粉样蛋白原纤维形成的植物多酚。在这些多酚中有基于没食子酸的没食子鞣质，但是迄今为止，已经使用“鞣酸”（一种鞣花酸和其他没食子酰化吡喃葡萄糖的商业混合物）检查了它们的抗原纤维形成活性。现在描述两种真实的没食子鞣质，六没食子酰基吡喃葡萄糖和十加铝基化的化合物的首次总合成，该化合物的结构通常用于描绘“鞣酸”。这些去甲没食子鞣质和更简单的没食子酸酯化的葡萄糖衍生物均在体外抑制淀粉样蛋白β肽（Aβ）的聚集，并且单没食子酸酯化的α-葡糖醇和天然β-六没糖基葡萄糖被证明是最强的抑制剂。
• [EN] PGG SEPARATION AND PURIFICATION<br/>[FR] SEPARATION ET PURIFICATION DE PGG
  申请人：UNIV OHIO

  公开号：WO2005070943A1

  公开（公告）日：2005-08-04

  A simple, inexpensive, and efficient method for separation and purification of the α- and β- FORMS OF penta-O-galloyl-D-glucose (PGG) without the need for HPLC. The methods provided herein are useful for separating α-PGG or β-PGG from a mixture that contains α-PGG and β-PGG and other chemicals. The method for separation of α-PGG from a mixture of α-PGG and β-PGG comprises the steps of: adding water to a sample containing 50% or more α-PGG and 50% or less β-PGG; mixing the PGG and water to dissolve the PGG; filtering out any undissolved particles; and allowing the filtered solution to stand undisturbed until crystals form.

  一种简单、廉价且高效的方法，用于分离和纯化α-和β-形式的五-O-没食子醛-D-葡萄糖（PGG），无需高效液相色谱。本文提供的方法可用于从含有α-PGG和β-PGG以及其他化学品的混合物中分离α-PGG或β-PGG。从含有50%或更多α-PGG和50%或更少β-PGG的样品中分离α-PGG的方法包括以下步骤：向样品中加入水以溶解PGG；搅拌PGG和水使PGG溶解；过滤出任何未溶解的颗粒；并让过滤后的溶液静置直到结晶形成。
• 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
• 1,2,3,4,6-Pentakis[-O-(3,4,5-trihydroxybenzoyl)]-α,β-D-glucopyranose (PGG) analogs: design, synthesis, anti-tumor and anti-oxidant activities
  作者：Qurat-ul-ain Shaikh、Meiting Yang、Khadim Hussain Memon、Mehreen Lateef、Du Na、Shengbiao Wan、Deslandes Eric、Lijuan Zhang、Tao Jiang

  DOI：10.1016/j.carres.2016.04.021

  日期：2016.7

  HT29 and H1299 cells with IC50 of 1.76 µM and 3.65 µM, respectively, indicating the mutual contribution of m-methoxy and p-hydroxy groups to the observed cytotoxicities. Moreover, cinnamic acid analogs were less active than the benzoic acid analogs evidenced by higher IC50 values. Furthermore, in cinnamic acid analogs the hydrogenation of double bond to saturated 2-C side chain enhance the cytotoxicities

  1,2,3,4,6-五[[O-（（3,4,5-三羟基苯甲酰基）]-α，β-D-吡喃葡萄糖（PGG）12的抗氧化活性已有报道，其中游离的OH基团在PGG中似乎对活动至关重要。为了探索基于PGG的化合物作为化学治疗剂并分析PGG中特定OH基团对抗癌活性的贡献，我们设计并合成了27种PGG苯甲酸和肉桂酸类似物。测试了这些类似物对两种人肺（A549和H1299）和两种人结肠（HCT116和HT29）癌细胞系的细胞毒性。化合物12（PGG）对HCT116和A549细胞具有最高的细胞毒性，IC50分别为1.61 µM和3.02 µM。相反，化合物16（1,2,3,4,6-戊基[-O-（4-羟基-3-甲氧基苯甲酰基）]-α，β-D-吡喃葡萄糖，PVG）最有效地杀死HT29和H1299细胞，IC50分别为1.76 µM和3.65 µM，表明间甲氧基和对羟基对观察到的细胞毒性具有相互影响。而且，肉桂酸类似物
• Novel hydrolyzable tannins from Nuphar Japonicum DC.
  作者：Makoto Nishizawa、Takashi Yamagishi、Genichiro Nonaka、Itsuo Nishioka、Hideo Bando

  DOI：10.1248/cpb.30.1094

  日期：——

  Two gallotannins (I and II) and an ellagitannin (III) named nupharin A have been isolated from Nuphar japonicum DC. (Nymphaeaceae). On the basis of chemical and spectral evidence, the structures of I, II and III were characterized as 1, 2, 6-tri-O-galloyl-α-D-glucose, 1, 2, 3, 4, 6-penta-O-galloyl-α-D-glucose and 1, 2, 6-tri-O-galloyl-3, 4-(S)-hexahydroxydiphenoyl-α-D-glucose, respectively.

  从日本睡莲（Nuphar japonicum DC.，属于睡莲科）中分离出了两种没食子的鞣酸（I和II）和一种被称为nupharin A的榄仁鞣酸（III）。根据化学和光谱证据，I、II和III的结构分别被鉴定为1, 2, 6-三-O-没食子酸基-α-D-葡萄糖、1, 2, 3, 4, 6-五-O-没食子酸基-α-D-葡萄糖和1, 2, 6-三-O-没食子酸基-3, 4-(S)-六羟基二苯甲酮-α-D-葡萄糖。