pedunculagin | 7045-42-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: pedunculagin
• 英文别名: (1R,2S,19R,22R)-7,8,9,12,13,14,20,28,29,30,33,34,35-tridecahydroxy-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.02,19.05,10.011,16.026,31.032,37]nonatriaconta-5,7,9,11,13,15,26,28,30,32,34,36-dodecaene-4,17,25,38-tetrone
• CAS: 7045-42-3
• 化学式: C₃₄H₂₄O₂₂
• 分子量: 784.551
• InChiKey: IYMHVUYNBVWXKH-ZITZVVOASA-N

物化性质

• 沸点：
  1556.9±65.0 °C(Predicted)
• 密度：
  1.959±0.06 g/cm3(Predicted)
• LogP：
  1.293 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  56
• 可旋转键数：
  0
• 环数：
  7.0
• 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：

  pedunculagin 在 borate buffer 作用下， 反应 0.17h， 以17 mg的产率得到2,3-(S)-hexahydroxydiphenoyl-D-glucose
  参考文献：
  名称：

  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.

  摘要：

  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。

  DOI：

  10.1248/cpb.41.1708
• 作为产物：
  描述：

  liquidambin 在 单宁酶 作用下， 以 水 为溶剂， 反应 22.0h， 以3 mg的产率得到pedunculagin
  参考文献：
  名称：

  Liquidambin, an ellagitannin from Liquidambar formosana

  摘要：

  DOI：

  10.1016/s0031-9422(00)81757-4

文献信息

• Ellagitannin Chemistry. First Total Synthesis of the 2,3- and 4,6-Coupled Ellagitannin Pedunculagin
  作者：Ken S. Feldman、Randall S. Smith

  DOI：10.1021/jo952130+

  日期：1996.1.1

  The biomimetic synthesis of pedunculagin (1) was accomplished through the sequential diastereoselective formation of two biphenyl C-C bonds. The synthesis strategy employed is predicated on extensive conformational modeling and involves initial oxidative coupling of the galloyl moieties at the O(2) and O(3) positions of an appropriately protected glucose-derived core, followed by installation and oxidative

  pedunculagin（1）的仿生合成是通过连续两个非对映选择性形成两个联苯CC键来完成的。所采用的合成策略基于广泛的构象模型，涉及在适当保护的葡萄糖衍生核心的O（2）和O（3）位置上的没食子酰基部分的初始氧化偶联，然后在没食子酸酯安装和氧化偶联没食子酸酯O（4）和O（6）位置。
• Tannins and Related Compounds. CXVII. Isolation and Characterization of Three New Ellagitannins, Lagerstannins A,B and C, Having a Gluconic Acid Core, from Lagerstroemia speciosa (L.) PERS.
  作者：Takashi TANAKA、Hui-Hong TONG、Ya-Ming XU、Kanji ISHIMARU、Gen-ichiro NONAKA、Itsuo NISHIOKA

  DOI：10.1248/cpb.40.2975

  日期：——

  Lagerstannins A (6), B (11) and C (8), ellagitannins having a gluconic acid core, have been isolated from the fruits and leaves of Lagerstroemia speciosa (L.) PERS. (=L. flos-reginae RETZ.)(Lythraceae). On the basis of chemical and spectroscopic evidence, their structures were established as 2, 3;4, 6-bis-O-(S)-hexahydroxydiphenoyl-D-gluconic acid (6), 2, 3, 5-O-(S, R)-flavogallonyl-4, 6-O-(S)-hexahydroxydiphenoyl-D-gluconic acid (11), and 5-O-galloyl-4, 6-O-(S)-hexahydroxydiphenoyl-D-gluconic acid (8), respectively. Furthermore, the structure of an ellagitannin, punigluconin, previously isolated from the bark of Punica granatum L., was revised as 2, 5-di-O-galloyl-4, 6-O-(S)-hexahydroxy-diphenoyl-D-gluconic acid (10), based on spectral re-examination.

  从紫薇（Lagerstroemia speciosa (L.) PERS.）的果实和叶子中分离出了Lagerstannins A (6)、B (11)和C (8)，这些埃拉吉单宁以葡萄糖醛酸为核心。根据化学和光谱证据，它们的结构分别确定为2, 3;4, 6-双-O-(S)-六羟基二苯酰-D-葡萄糖醛酸 (6)、2, 3, 5-O-(S, R)-黄酮甘露糖苷-4, 6-O-(S)-六羟基二苯酰-D-葡萄糖醛酸 (11)，以及5-O-没食子酸-4, 6-O-(S)-六羟基二苯酰-D-葡萄糖醛酸 (8)。此外，之前从石榴树皮（Punica granatum L.）中分离出的埃拉吉单宁punigluconin，其结构经过光谱重新审查后修订为2, 5-双-O-没食子酸-4, 6-O-(S)-六羟基二苯酰-D-葡萄糖醛酸 (10)。
• Tannins of Theaceous Plants. V. Camelliatannins F, G and H, Three New Tannins from Camellia japonica L.
  作者：Li HAN、Tsutomu HATANO、Takashi YOSHIDA、Takuo OKUDA

  DOI：10.1248/cpb.42.1399

  日期：——

  Two new complex tannins, camelliatannins F (3) and G (4), were isolated from the leaves of Camellia japonica L. (Theaceae), and their structures, each consisting of an epicatechin unit and a C-glucosidic ellagitannin moiety, were elucidated. A new dimeric hydrolyzable tannin, named camelliatannin H (5), was isolated from the fruits of this plant. Camelliins A (6) and B (7), and camelliatannin A (1) and 3 were also isolated from the fruits.

  从茶花（Camellia japonica L.，山茶科）的叶子中分离出了两种新型复杂单宁，分别为山茶单宁F（3）和G（4），并阐明了它们的结构，每种结构均由一个表儿茶素单元和一个C-葡萄糖苷鞣酸部分组成。此外，还从该植物的果实中分离出一种新的二聚水解单宁，命名为山茶单宁H（5）。同时，从果实中还分离出了山茶素A（6）和B（7），以及山茶单宁A（1）和3。
• Tannis of Casuarina and Stachyurus species. Part 1. Structures of pendunculagin, casuarictin, strictinin, casuarinin, casuariin, and stachyurin
  作者：Takuo Okuda、Takashi Yoshida、Mariko Ashida、Kazufumi Yazaki

  DOI：10.1039/p19830001765

  日期：——

  Three novel C-glucosidic ellagitannins, casuarinin, casauriin, and stachyurin, and two additional new ellagitannins, casuarictin and strictinin, were isolated from the leaves of Casuarina stricta, and their structures elucidated on the basis of chemical and spectral evidence. Pedunculagin and tellimagrandin I were also isolated, and the structure having (S)-4,4′,5,5′,6,6′-hexahydroxydiphenoyl groups

  从木麻黄的叶片中分离出三种新颖的C-葡糖苷鞣花单宁，木麻黄素，酪蛋白和stachyurin，以及另外两种新的鞣花单宁，木麻黄素和丁香精，并根据化学和光谱证据阐明了它们的结构。还分离了pedunculagin和tellimagrandin I，并建立了用于pedunculagin的具有（S）-4,4'，5,5'，6,6'-六羟基二苯甲酰基的结构。这七和鞣花单宁从隔离STRICTA C.已发现也旌早发。
• 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。