1,2-di-O-galloyl-(4,6-(S)-hexahydroxydiphenoyl)-β-D-glucopyranose

• 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-di-O-galloyl-(4,6-(S)-hexahydroxydiphenoyl)-β-D-glucopyranose
• 英文别名: 1,2-di-O-galloyl-4,6-HHDP-β-D-glucose；1,2-di-O-galloyl-4,6-O-(S)-hexahydroxydiphenoyl-β-D-glucose；1,2-di-galloyl-4,6-O-(S)-HHDP-β-D-glucose；[(10S,11S,12R,13S,15R)-3,4,5,11,21,22,23-heptahydroxy-8,18-dioxo-13-(3,4,5-trihydroxybenzoyl)oxy-9,14,17-trioxatetracyclo[17.4.0.02,7.010,15]tricosa-1(23),2,4,6,19,21-hexaen-12-yl] 3,4,5-trihydroxybenzoate
• 化学式: C₃₄H₂₆O₂₂
• 分子量: 786.567
• InChiKey: OEAQELZCLQUGBM-BPBQHLHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  56
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  377
• 氢给体数：
  13
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  1,2-di-O-galloyl-(4,6-(S)-hexahydroxydiphenoyl)-β-D-glucopyranose 以 aq. buffer 为溶剂， 生成 鞣花酸
  参考文献：
  名称：

  HPLC / DAD–ESI / QTOF / MS检测的碱性条件下可水解单宁的稳定性和氧化产物

  摘要：

  可水解的丹宁酸存在于人类或食草动物用于食品或药品的植物中。碱性条件会改变单宁的结构，即酚基的氧化会导致有毒醌的形成。以前，已经用比色法或电子顺磁共振法研究了这些不稳定的醌类和其他氧化产物，这些方法只能提供有关产物的有限信息。

  DOI：

  10.1002/pca.2456

文献信息

• Identification of a Major Polyphenol and Polyphenolic Composition in Leaves of Camellia irrawadiensis
  作者：Kensuke Yagi、Keiichi Goto、Fumio Nanjo

  DOI：10.1248/cpb.57.1284

  日期：——

  The polyphenolic composition of Camellia irrawadiensis, which is a closely related species of Camellia sinensis (cultivated tea), was investigated. The most predominant polyphenol, a kind of ellagitannin, was isolated from leaves of C. irrawadiensis. Its structure was established as 1,2-di-O-galloyl-4,6-O-(S)-hexahydroxydiphenoyl-β-D-glucose (2) on the basis of spectral and chemical evidence. Moreover, the polyphenols [catechins, strictinin (1), compound 2, theogallin, and gallic acid] and two methylxanthines (theobromine and caffeine) in leaves of C. irrawadiensis were determined by HPLC-Photodiode array detector analysis, and were compared to those in C. sinensis and Camellia taliensis. Total catechin content in C. irrawadiensis was lower than that in C. sinensis and C. taliensis. Theobromine content in C. irrawadiensis was higher than that in C. sinensis and C. taliensis. The content of 2 in C. irrawadiensis was 8.4% of dry leaf weight and comprised approximately 60% of the total polyphenols detected, while the compound was not detected in C. sinensis and was reported to be 2.4% in C. taliensis.

  对与栽培茶密切相关的Camellia irrawadiensis的多酚组成进行了研究。最主要的多酚是一种鞣花酸，从C. irrawadiensis的叶子中分离出来。根据光谱和化学证据，其结构被确定为1,2-di-O-galloyl-4,6-O-(S)-六羟基二苯酰-β-D-葡萄糖（2）。此外，使用高效液相色谱-光二极管阵列检测器分析，确定了C. irrawadiensis叶子中的多酚（儿茶素、严格素（1）、化合物2、茶鞣酸和没食子酸）以及两种甲基黄嘌呤（可可碱和咖啡因），并与C. sinensis和Camellia taliensis进行了比较。C. irrawadiensis中的儿茶素总含量低于C. sinensis和C. taliensis中的含量。C. irrawadiensis中的可可碱含量高于C. sinensis和C. taliensis。化合物2在C. irrawadiensis中的含量为干叶重的8.4%，约占检测到的总多酚的60%，而在C. sinensis中未检测到，在C. taliensis中则报告为2.4%。