2,3-(S)-hexahydroxydiphenoyl-D-glucose

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 2,3-(S)-hexahydroxydiphenoyl-D-glucose
• 英文别名: 2,3-O-(S)-hexahydroxydiphenoyl-D-glucose；(10R,13R,14R,15S)-3,4,5,11,14,20,21,22-octahydroxy-13-(hydroxymethyl)-9,12,16-trioxatetracyclo[16.4.0.02,7.010,15]docosa-1(22),2,4,6,18,20-hexaene-8,17-dione
• 化学式: C₂₀H₁₈O₁₄
• 分子量: 482.355
• InChiKey: GEAGRKQCZVLNAU-NNIZZFLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  34
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  244
• 氢给体数：
  9
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  硫酸二甲酯 、 2,3-(S)-hexahydroxydiphenoyl-D-glucose 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.5h， 以21 mg的产率得到methyl 2,3-(hexamethoxydiphenoyl)glucoside
  参考文献：
  名称：

  Nonaka, Gen-ichiro; Tanaka, Takashi; Nishioka, Itsuo, Journal of the Chemical Society. Perkin transactions I, 1982, p. 1067 - 1074

  摘要：

  DOI：
• 作为产物：
  描述：

  praecoxin B 在 单宁酶 作用下， 生成 2,3-(S)-hexahydroxydiphenoyl-D-glucose
  参考文献：
  名称：

  Praecoxin B,C,D and E, novel ellagitannins from Stachyurus praecox.

  摘要：

  从早春小水杉（Stachyurus praecox）中分离出了普雷香素C（6）、D（7）和E（8），这些是具有酯链的椰子单宁，以及普雷香素B（9），它是堇菜苷I（1）的异构体。

  DOI：

  10.1248/cpb.31.333

文献信息

• Dimeric ellagitannins from Alnus japonica
  作者：Min-Won Lee、Takashi Tanaka、Gen-Ichiro Nonaka、Itsuo Nishioka

  DOI：10.1016/0031-9422(92)83642-c

  日期：1992.8

  Abstract Two new hydrolysable tannins, alnusjaponins A and B, were isolated from the leaves of Alnus japonica , along with 12 known hydrolysable tannins and related compounds, namely 5- O -galloyl-(−)-shikimic acid, 2,3-( S )-hexahydroxydiphenoyl- d -glucose, 4,6-di- O -galloyl- d -glucose, 1,4-di- O -galloyl-β- d -glucose, 4,6-( S )-valoneoyl- d -glucose, strictinin, gemin D, pedunculagin, praecoxin

  摘要 从桤木的叶子中分离出两种新的可水解单宁，即桤木 A 和 B，以及 12 种已知的可水解单宁和相关化合物，即 5-O-没食子酰-(-)-莽草酸、2,3-(S )-六羟基二苯甲酰-d-葡萄糖、4,6-二-O-没食子酰-d-葡萄糖、1,4-二-O-没食子酰-β-d-葡萄糖、4,6-(S)-戊二酰-d-葡萄糖、严格素、gemin D、pedunculagin、preecoxin A、flosin A、stachyurin 和木麻黄素。基于光谱和化学证据阐明了桤木 A 和 B 的结构，即由花梗素和严格素部分组成的二聚体鞣花单宁，其中连接方式不同。
• Tannins and Related Compounds. CXXIV. Five New Ellagitannins, Platycaryanins A, B, C, and D, and Platycariin, and a New Complex Tannin, Strobilanin, from the Fruits and Bark of Platycarya strobilacea SIEB et ZUCC., and Biomimetic Synthesis of C-Glycosidic Ellagitannins from Glucopyranose-Based Ellagitannins.
  作者：Takashi TANAKA、Shinji KIRIHARA、Gen-ichiro NONAKA、Itsuo NISHIOKA

  DOI：10.1248/cpb.41.1708

  日期：——

  Five new ellagitannins, platycaryanins A (27), B (26), C (30), and D (25), and platycariin (31), and a new complex tannin, strobilanin (32), have been isolated from the fruits and bark of Platycarya strobilacea SIEB. et ZUCC. (Juglandaceae), together with twenty-six known compounds. On the basis of spectroscopic and chemical evidence, platycaryanins A, B and C, and platycariin have been characterized as the ellagitannins having a tergalloyl ester group, while platycaryanin D was found to be an unusual ellagitannin possessing (R)-hexahydroxydiphenoyl esters at the glucopyranose 2, 3- and 4, 6-positions. During these chemical studies, re-examination of the similar ellagitannins, alnusnins A and B, which were previously reported from Alnus sieboldiana, led us to revise their structures to 29 and 28, respectively, in which the tergalloyl group forms a lactone ring. Furthermore, biomimetic conversion of ellagitannins having a glucopyranose core into C-glycosidic ellagitannins was successfully achieved for the first time, and the reaction was applied to the structure elucidation of platycariin (31).

  从Platycarya strobilacea SIEB. et ZUCC.（胡桃科）的果实和树皮中分离出了五种新的鞣花酸类化合物，分别是platycaryanins A（27）、B（26）、C（30）和D（25），以及platycariin（31），同时还分离出了二十六种已知化合物。根据光谱学和化学证据，platycaryanins A、B和C以及platycariin被鉴定为具有军团酸酯基团的鞣花酸类化合物，而platycaryanin D则被发现是一种不寻常的鞣花酸，具有在葡萄糖吡喃糖2、3位和4、6位的(R)-六羟基二苯酸酯。在这些化学研究过程中，对以前从Alnus sieboldiana分离出的相似鞣花酸alnusnins A和B进行了重新审查，导致我们修正了它们的结构，分别为29和28，其中军团酸基团形成了内酯环。此外，首次成功实现了将具有葡萄糖吡喃核的鞣花酸转化为C-糖苷鞣花酸的生物仿生转化，该反应被应用于platycariin（31）的结构阐明。
• Dimeric ellagitannins in plants of melastomataceae.
  作者：Takashi Yoshida、Yoshitaka Ikeda、Hideyuki Ohbayashi、Koukichi Ishihara、Wakayo Ohwashi、Tetsuro Shingu、Takuo Okuda

  DOI：10.1248/cpb.34.2676

  日期：——

  Six novel ellagitannins, four of which are dimers mutually correlated in their structures, have been isolated from Tibouchina semidecandra, and Medinilla magnifica. Their structures were elucidated based on spectral and chemical evidence.

  从Tibouchina semidecandra和Medinilla magnifica中分离出了六种新型橡胶单宁，其中四种是结构上相互关联的二聚体。它们的结构是根据光谱和化学证据进行阐明的。
• Tannins of rosaceous medicinal plants. I. Structures of potentillin, agrimonic acids A and B, and agrimoniin, a dimeric ellagitannin.
  作者：TAKUO OKUDA、TAKASHI YOSHIDA、MASAAKI KUWAHARA、M.USMAN MEMON、TETSURO SHINGU

  DOI：10.1248/cpb.32.2165

  日期：——

  Four new ellagitannins, potentillin (1), agrimoniin (2), and agrimonic acids A (3) and B (4), have been isolated from the roots of Agrimonia japonica (MIQ.) KOIDZ., and their structures, with an α-glucosidic linkage, were elucidated on the basis of spectral and chemical evidence. Potentillin (1) and agrimoniin (2) have also been isolated from Potentilla kleiniana WIGHT et ARNOTT.

  从日本茯苓（Agrimonia japonica (MIQ.) KOIDZ.）的根部分离出了四种新的鞣酸酯，分别是强鞣酸（potentillin, 1）、苦荨麻素（agrimoniin, 2）以及苦荨麻酸A（agrimonic acid A, 3）和B（agrimonic acid B, 4），它们的结构具有α-葡萄糖苷键，基于光谱和化学证据进行了阐明。强鞣酸（potentillin, 1）和苦荨麻素（agrimoniin, 2）也从小草莓（Potentilla kleiniana WIGHT et ARNOTT）中分离出来。
• The metabolism of gallic acid and hexahydroxydiphenic acid in plants. Part 2. Esters of (S)-hexahydroxydiphenic acid with D-glucopyranose (4 C 1)
  作者：Raj K. Gupta、Sabah M. K. Al-Shafi、Keith Layden、Edwin Haslam

  DOI：10.1039/p19820002525

  日期：——

  One form of further metabolism of β-penta-O-galloyl-D-glucose in higher plants is that in which intramolecular oxidative coupling takes place between adjacent galloyl ester groups (2,3, and 4,6). This route of biosynthesis is confined to certain plants and details of the structure elucidation of some of the principal metabolites are recorded.

  在高等植物中，β-五元-O - galloyl - D-葡萄糖进一步代谢的一种形式是其中在相邻的没食子酰基酯基团（2,3和4,6）之间发生分子内氧化偶联的形式。这种生物合成途径仅限于某些植物，并且记录了一些主要代谢产物的结构阐明细节。