castalin | 19086-75-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: castalin
• 英文别名: Vescalin；(1S,2S,24R,25R,29R)-7,8,9,12,13,14,17,18,19,25,29-undecahydroxy-24-(hydroxymethyl)-3,23,26-trioxahexacyclo[13.10.3.12,6.05,10.011,28.016,21]nonacosa-5(10),6,8,11,13,15(28),16,18,20-nonaene-4,22,27-trione
• CAS: 19086-75-0
• 化学式: C₂₇H₂₀O₁₈
• 分子量: 632.445
• InChiKey: PPUHUWSVCUJGTD-HNBYGWOQSA-N

物化性质

• 沸点：
  1423.6±65.0 °C(Predicted)
• 密度：
  2.047±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  45
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  322
• 氢给体数：
  12
• 氢受体数：
  18

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  castalin 在 盐酸 作用下， 反应 144.0h， 以65%的产率得到vescalin
  参考文献：
  名称：

  葡萄酒中针对人拓扑异构酶II的多酚C-糖苷鞣花单宁的化学反应。

  摘要：

  由于这种饮料在橡木制桶中陈化，因此在葡萄酒中发现了含多酚九羟基萜烯基的C-糖苷橡木鞣花单宁。一旦进入弱酸性葡萄酒（pH约为3-4），其中一些复杂的天然产物（如（-）-维斯卡林（1），而不是其C-1差向异构体（-）-castalagin（2））就可以捕获葡萄衍生的亲核实体，例如乙醇，黄烷醇儿茶素（10a）和表儿茶素（10b），花色苷配体（13b）和硫代谷胱甘肽（16），可提供缩合产物，并在C-1位点保留构型。给出了这种高非对映选择性的计算机辅助原理。这些缩合产物可有助于调节葡萄酒的感官特性，如通过基于新的基于植物素的花青素-鞣花单宁（15b）观察到的23 nm红移色吸光度所证明的那样。在溶剂化条件下水解1提供了另一种新颖的化合物，除了已知的（-）-维斯卡林（18）外，我们称为vesscalene（21）。具有药理学重要性的事实是，这些酒中发现的大多数水溶性鞣花单宁衍生物在抑制top2介导的D

  DOI：

  10.1002/chem.200500428
• 作为产物：
  描述：

  castalagin 在 盐酸 作用下， 反应 24.0h， 生成 castalin
  参考文献：
  名称：

  Identification and Sensory Evaluation of Dehydro- and Deoxy-ellagitannins Formed upon Toasting of Oak Wood (Quercus alba L.)

  摘要：

  Traditionally, spirits such as whiskey are matured in toasted wood barrels to improve the sensory quality of the final beverage. In order to gain first insight into the puzzling road map of thermal ellagitannin transformation chemistry and provide evidence for the changes in sensory active nonvolatiles in oak wood during toasting, the purified oak ellagitannins castalagin and vescalagin, their corresponding dimers roburin A and roburin D, and 33-carboxy-33-deoxyvescalagin were thermally treated in model experiments. Besides mouth-coating and golden-brown colored melanoidin-type polymers, individual major reaction products were produced as transient intermediates which were identified for the first time by means of LC-MS/MS and 1D/2D-NMR spectroscopy. Depending strongly on the stereochemistry, castalagin is oxidized to the previously unreported dehydrocastalagin, whereas its diastereomer vescalagin, differing only in the stereochemistry at carbon C-1, is most surprisingly converted into deoxyvescalagin. Comparative model experiments with 33-carboxy-33-deoxyvescalagin revealed castalagin, vescalagin, dehydrocastalagin, and deoxyvescalagin as typical reaction products, thus indicating decarboxylation as a key step in the thermal degradation of that ellagitannin. Similar to the ellagitannin monomers, LC-MS/MS analyses gave strong evidence that the corresponding dimer roburin A, containing the vescalagin configuration at C-1, was converted into the deoxyroburin A, whereas roburin D, exhibiting the castalagin configuration at C-1, was oxidized to give the dehydroroburin D. Human sensory experiments revealed that the ellagitannin derivatives imparted an astringent mouth-coating sensation with threshold concentrations ranging from 1.1 to 126.0 mu mol/L, depending strongly on their chemical structure.

  DOI：

  10.1021/jf070151m

文献信息

• <i>C</i> -glucosidic Ellagitannins from Lythri herba (<i>European Pharmacopoeia</i> ): Chromatographic Profile and Structure Determination
  作者：Jakub P. Piwowarski、Anna K. Kiss

  DOI：10.1002/pca.2415

  日期：2013.7

  Lythri herba, a pharmacopoeial plant material (European Pharmacopoea), is obtained from flowering parts of purple loosestrife (Lythrum salicaria L.). Although extracts from this plant material have been proven to possess some interesting biological activities and its pharmacopoeial standardisation is based on total tannin content determination, the phytochemical characterisation of this main group

  紫草（Lythri herba ）是一种药材植物材料（欧洲药典），是从紫色珍珠菜（Lythrum salicaria L.）的开花部位获得的。尽管已证明该植物材料的提取物具有某些有趣的生物学活性，并且其药理学标准化是基于总单宁含量的测定，但尚未完全进行这一主要化合物的植物化学表征。
• C-Glycosidic Ellagitannin Metabolites in the Heartwood of Japanese Chestnut Tree (Castanea crenata SIEB. et Zucc.).
  作者：Takashi TANAKA、Nobuko UEDA、Hideo SHINOHARA、Gen-ichiro NONAKA、Toshihiro FUJIOKA、Kunihide MIHASHI、Isao KOUNO

  DOI：10.1248/cpb.44.2236

  日期：——

  HPLC comparison of tannins in the bark, sapwood and heatwood of Castanea crenata showed striking differences of composition. The major tannin of the bark is hamamelitannin, whereas vescalagin and castalagin are dominant in the wood. Inner heatwood contained three new C-glycosidic ellagitannin metabolites, castacrenins A, B and C. Outer heartwood contained dimeric, trimeric (castanenin A), tetrameric (castaneanins B and C) and pentameric (castaneanin D) C-glycosidic ellagitannins composed of vescalagin and castalagin units. Castacrenins and castaneanins are derived from vescalagin and castalagin by intramolecular and intermolecular dehydration, respectively.

  高效液相色谱法比较了蓖麻树树皮、边材和热材中的单宁酸，结果表明它们的成分存在显著差异。树皮中的主要单宁是金缕梅单宁，而木材中的主要单宁是vescalagin 和 castalagin。外心材含有二聚体、三聚体（蓖麻素 A）、四聚体（蓖麻素 B 和 C）和五聚体（蓖麻素 D）C-糖苷鞣单宁，由vescalagin 和 castalagin 单元组成。蓖麻籽鞣素和蓖麻籽鞣素分别由vescalagin 和 castalagin 通过分子内脱水和分子间脱水生成。
• The Chemistry of Wine PolyphenolicC-Glycosidic Ellagitannins Targeting Human Topoisomerase II
  作者：Stéphane Quideau、Michael Jourdes、Dorothée Lefeuvre、Danièle Montaudon、Cédric Saucier、Yves Glories、Patrick Pardon、Philippe Pourquier

  DOI：10.1002/chem.200500428

  日期：2005.11.4

  furnished another novel compound that we refer to as vescalene (21), in addition to the known (-)-vescalin (18). Of pharmacological importance is the fact that most of these found-in-wine water-soluble ellagitannin derivatives are much more potent than etoposide (VP-16) at inhibiting top2-mediated DNA decatenation in vitro (top2=topoisomerase II)). The known (-)-vescalin (18) and the novel vescalene (21) fully

  由于这种饮料在橡木制桶中陈化，因此在葡萄酒中发现了含多酚九羟基萜烯基的C-糖苷橡木鞣花单宁。一旦进入弱酸性葡萄酒（pH约为3-4），其中一些复杂的天然产物（如（-）-维斯卡林（1），而不是其C-1差向异构体（-）-castalagin（2））就可以捕获葡萄衍生的亲核实体，例如乙醇，黄烷醇儿茶素（10a）和表儿茶素（10b），花色苷配体（13b）和硫代谷胱甘肽（16），可提供缩合产物，并在C-1位点保留构型。给出了这种高非对映选择性的计算机辅助原理。这些缩合产物可有助于调节葡萄酒的感官特性，如通过基于新的基于植物素的花青素-鞣花单宁（15b）观察到的23 nm红移色吸光度所证明的那样。在溶剂化条件下水解1提供了另一种新颖的化合物，除了已知的（-）-维斯卡林（18）外，我们称为vesscalene（21）。具有药理学重要性的事实是，这些酒中发现的大多数水溶性鞣花单宁衍生物在抑制top2介导的D
• Identification and Sensory Evaluation of Dehydro- and Deoxy-ellagitannins Formed upon Toasting of Oak Wood (<i>Quercus alba</i> L.)
  作者：Arne Glabasnia、Thomas Hofmann

  DOI：10.1021/jf070151m

  日期：2007.5.1

  Traditionally, spirits such as whiskey are matured in toasted wood barrels to improve the sensory quality of the final beverage. In order to gain first insight into the puzzling road map of thermal ellagitannin transformation chemistry and provide evidence for the changes in sensory active nonvolatiles in oak wood during toasting, the purified oak ellagitannins castalagin and vescalagin, their corresponding dimers roburin A and roburin D, and 33-carboxy-33-deoxyvescalagin were thermally treated in model experiments. Besides mouth-coating and golden-brown colored melanoidin-type polymers, individual major reaction products were produced as transient intermediates which were identified for the first time by means of LC-MS/MS and 1D/2D-NMR spectroscopy. Depending strongly on the stereochemistry, castalagin is oxidized to the previously unreported dehydrocastalagin, whereas its diastereomer vescalagin, differing only in the stereochemistry at carbon C-1, is most surprisingly converted into deoxyvescalagin. Comparative model experiments with 33-carboxy-33-deoxyvescalagin revealed castalagin, vescalagin, dehydrocastalagin, and deoxyvescalagin as typical reaction products, thus indicating decarboxylation as a key step in the thermal degradation of that ellagitannin. Similar to the ellagitannin monomers, LC-MS/MS analyses gave strong evidence that the corresponding dimer roburin A, containing the vescalagin configuration at C-1, was converted into the deoxyroburin A, whereas roburin D, exhibiting the castalagin configuration at C-1, was oxidized to give the dehydroroburin D. Human sensory experiments revealed that the ellagitannin derivatives imparted an astringent mouth-coating sensation with threshold concentrations ranging from 1.1 to 126.0 mu mol/L, depending strongly on their chemical structure.