hexagalloyl β-D-glucose | 99877-82-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: hexagalloyl β-D-glucose
• 英文别名: 3-O-digalloyl-1,2,4,6-tetra-O-beta-D-galloylglucose；[(2R,3R,4S,5R,6S)-4-[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxybenzoyl]oxy-3,5,6-tris[(3,4,5-trihydroxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
• CAS: 99877-82-4
• 化学式: C₄₈H₃₆O₃₀
• 分子量: 1092.8
• InChiKey: ZYDLAYCPLOHXHH-YHNAUUMRSA-N

物化性质

• 沸点：
  1492.6±65.0 °C(Predicted)
• 密度：
  2.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  78
• 可旋转键数：
  19
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  511
• 氢给体数：
  17
• 氢受体数：
  30

反应信息

• 作为反应物：
  描述：

  hexagalloyl β-D-glucose 、 1-没食子酸酰葡萄糖 在 beta-glucogallin O-galloyltransferase citrate buffer 作用下， 以 水 为溶剂， 反应 2.0h， 生成 3-O-trigalloyl-1,2,4,6-tetra-O-beta-D-galloylglucose
  参考文献：
  名称：

  Gallotannin biosynthesis: purification of β -glucogallin: 1,2,3,4,6-pentagalloyl- β -d-glucose galloyltransferase from sumac leaves fn1 fn1In honour of Professor G. H. Neil Towers’ 75th birthday.

  摘要：

  An enzyme from leaves of staghorn sumac (Rhus typhina) that catalysed the galloylation of 1,2,3,4, 6-penta-O-galloyl-beta-D-glucose to the gallotannin, 3-O-digalloyl-1,2,4,6-tetra-O-galloyl-beta-D-glucose, was purified more than 500-fold to apparent homogeneity. beta-Glucogallin (1-O-galloyl-beta-D-glucopyranose) served as activated acyl donor in this conversion. For the native enzyme, a M(r) value of 170,000 was determined by gel filtration, while a single polypeptide band of M(r) 42,000 was detected by SDS-PAGE. The acyltransferase had pH and temperature optima of 4-4.5 and 25 degrees, respectively, and was most stable between pH 3 and 4.5. Besides the major substrate, pentagalloylglucose, also 1,2,3,6-tetragalloylglucose and hexa- to nona-substituted gallotannins were accepted as minor substrates by this new enzyme for which the systematic name "beta-glucogallin: 1,2,3,4,6-pentagalloyl-beta-D-glucose (3-O-galloyl)-galloyltransferase" (EC 2.3.1.-) is proposed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)00014-4
• 作为产物：
  描述：

  3-O-[3’-(3”,4”,5”-tribenzyloxybenzoyl)-4’,5’-(diphenylmethylenedioxy)benzoyl]-1,2,4,6-tetrakis-O-(3’,4’,5’-tribenzyloxybenzoyl)-β-D-glucopyranose 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 3-O-digalloyl-1,2,4,6-tetra-O-galloyl-β-D-glucose 、 hexagalloyl β-D-glucose
  参考文献：
  名称：

  Gallotannins和单宁酸：首次化学合成和对阿尔茨海默氏症淀粉样β肽聚集的体外抑制活性。

  摘要：

  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。

  DOI：

  10.1002/anie.201411606

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。
• Gallotannin biosynthesis: purification of β -glucogallin: 1,2,3,4,6-pentagalloyl- β -d-glucose galloyltransferase from sumac leaves fn1 fn1In honour of Professor G. H. Neil Towers’ 75th birthday.
  作者：Ruth Niemetz、Georg G Gross

  DOI：10.1016/s0031-9422(98)00014-4

  日期：1998.9

  An enzyme from leaves of staghorn sumac (Rhus typhina) that catalysed the galloylation of 1,2,3,4, 6-penta-O-galloyl-beta-D-glucose to the gallotannin, 3-O-digalloyl-1,2,4,6-tetra-O-galloyl-beta-D-glucose, was purified more than 500-fold to apparent homogeneity. beta-Glucogallin (1-O-galloyl-beta-D-glucopyranose) served as activated acyl donor in this conversion. For the native enzyme, a M(r) value of 170,000 was determined by gel filtration, while a single polypeptide band of M(r) 42,000 was detected by SDS-PAGE. The acyltransferase had pH and temperature optima of 4-4.5 and 25 degrees, respectively, and was most stable between pH 3 and 4.5. Besides the major substrate, pentagalloylglucose, also 1,2,3,6-tetragalloylglucose and hexa- to nona-substituted gallotannins were accepted as minor substrates by this new enzyme for which the systematic name "beta-glucogallin: 1,2,3,4,6-pentagalloyl-beta-D-glucose (3-O-galloyl)-galloyltransferase" (EC 2.3.1.-) is proposed. (C) 1998 Elsevier Science Ltd. All rights reserved.