epicatechin-(4β->8,2β->O->7)-epiafzelechin-(4α->8)-epicatechin | 130918-29-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: epicatechin-(4β->8,2β->O->7)-epiafzelechin-(4α->8)-epicatechin
• 英文别名: epicatechin-(2β->7,4β->8)-epiafzelechin-(4α->8)-epicatechin；(1R,5R,6R,7S,13S,21R)-13-(3,4-dihydroxyphenyl)-7-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-5-(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol
• CAS: 130918-29-5
• 化学式: C₄₅H₃₆O₁₇
• 分子量: 848.771
• InChiKey: VHLRMFIKYQEKRY-LQNPQWRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  62
• 可旋转键数：
  4
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  300
• 氢给体数：
  13
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  epicatechin-(4β->8,2β->O->7)-epiafzelechin-(4α->8)-epicatechin 在 Raney-nickel (W-4) 、 溶剂黄146 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 11.5h， 生成 epicatechin-(4β->8,2β->O->7)-epiafzelechin
  参考文献：
  名称：

  Tannins and related compounds. XCI. Isolation and characterization of proanthocyanidins with an intramolecularly doubly-linked unit from the fern, Dicranopteris pedata Houtt.

  摘要：

  通过对蕨类植物 Dicranopteris pedata HOUTT.的多酚类成分进行化学研究，分离出了 8 种新的原花青素，它们与已知的黄烷-3-醇和原花青素都具有双链（A 型）单元。根据化学和光谱证据，它们的特征是表儿茶素-(4β→8, 2β→O→7)-epeniafzelechin-(4α→8)-epiafzelechin(8), 表儿茶素-(4β→8、2β→O→7)-epiafzelechin-(4α→8)-epiafzelechin(9), epiafzelechin-(4β→8, 2β→O→7)-epizfzelechin-(4α→8)-epicatechin(10), epiafzelechin-(4β→8, 2β→O→7)-epicatechin-(4α→8)-epicatechin (11)、表儿茶素-(4β→8, 2β→O→7)-epiafzelechin-(4α→8)-epicatechin (12)、表儿茶素-(4β→8, 2β→O→7)-epicatechin-(4α→8)-epiafzelechin (13)、表儿茶素-(4β→8、2β→O→7)-epicatechin-(4α→8)-epigallocatechin (14) 和 epiafzelechin-(4β→8)epicatechin-(4β→8, 2β→O→β→7)-epicatechin-(4α→8)-epicatechin (15)。

  DOI：

  10.1248/cpb.38.856

文献信息

• Proanthocyanidins and a phloroglucinol derivative from Rumex acetosa L.
  作者：J. Bicker、F. Petereit、A. Hensel

  DOI：10.1016/j.fitote.2009.08.015

  日期：2009.12

  From the ethyl acetate soluble fraction of an acetone-water extract of the aerial parts of Rumex acetosa L. (Polygonaceae), a variety of monomeric flavan-3-ols (catechin, epicatechin, epicatechin-3-O-gallate), A- and B-type procyanidins and propelargonidins (15 dimers, 7 trimers, 2 tetramers) were isolated with 5 so far unknown natural products. Dimers: procyanidin B1, B2, B3, B4, B5, B7, A2, epia

  从鼠尾草（Polygonaceae）的地上部分的丙酮-水提取物中的乙酸乙酯可溶级分中，可以得到各种单体黄烷-3-醇（儿茶素，表儿茶素，表儿茶素-3-O-没食子酸酯），A- B型原花青素和炔丙基炔醇（15个二聚体，7个三聚体，2个四聚体）与5种迄今未知的天然产物分离。二聚体：原花青素B1，B2，B3，B4，B5，B7，A2，表阿哌齐林-（4beta-> 8）-表儿茶素，表阿哌齐林-（4beta-> 8）-表儿茶素-3-O-没食子酸酯（新的天然产物），Epiafzelechin-（4β-> 6）-表儿茶素-3-O-没食子酸酯（新天然产物），epiafzelechin-3-O-没食子酸酯-（4beta-> 8）-epicatechin-3-O-没食子酸酯，B2 -3'-O-没食子酸酯，B2-3,3'-二-O-没食子酸酯，B5-3'-O-没食子酸酯和B5-3,3'-二-O-没食子酸酯。三聚体：原花青素C1，表阿奇西林-（4beta->
• KASHIWADA, YOSHIKI;MORITA, MASAFUMI;NONAKA, GEN-ICHIRO;NISHIOKA, ITSUO, CHEM. AND PHARM. BULL., 38,(1990) N, C. 856-860
  作者：KASHIWADA, YOSHIKI、MORITA, MASAFUMI、NONAKA, GEN-ICHIRO、NISHIOKA, ITSUO

  DOI：——

  日期：——
• Tannins and related compounds. XCI. Isolation and characterization of proanthocyanidins with an intramolecularly doubly-linked unit from the fern, Dicranopteris pedata Houtt.
  作者：Yoshiki KASHIWADA、Masafumi MORITA、Gen-ichiro NONAKA、Itsuo NISHIOKA

  DOI：10.1248/cpb.38.856

  日期：——

  A chemical examination of the polyphenolic constituents of the fern, Dicranopteris pedata HOUTT., has led to the isolation of eight new proanthocyanidins possessing a doubly-linked (A-type) unit, together with known flavan-3-ols and proanthocyanidins. On the basis of chemical and spectroscopic evidence, they are characterized as epiafzelechin-(4β→8, 2β→O→7)-eniafzelechin-(4α→8)-epiafzelechin(8), epicatechin-(4β→8, 2β→O→7)-epiafzelechin-(4α→8)-epiafzelechin(9), epiafzelechin-(4β→8, 2β→O→7)-epizfzelechin-(4α→8)-epicatechin(10), epiafzelechin-(4β→8, 2β→O→7)-epicatechin-(4α→8)-epicatechin (11), epicatechin-(4β→8, 2β→O→7)-epiafzelechin-(4α→8)-epicatechin (12), epicatechin-(4β→8, 2β→O→7)-epicatechin-(4α→8)-epiafzelechin (13), epicatechin-(4β→8, 2β→O→7)-epicatechin-(4α→8)-epigallocatechin (14) and epiafzelechin-(4β→8)epicatechin-(4β→8, 2β→O→β→7)-epicatechin-(4α→8)-epicatechin (15).

  通过对蕨类植物 Dicranopteris pedata HOUTT.的多酚类成分进行化学研究，分离出了 8 种新的原花青素，它们与已知的黄烷-3-醇和原花青素都具有双链（A 型）单元。根据化学和光谱证据，它们的特征是表儿茶素-(4β→8, 2β→O→7)-epeniafzelechin-(4α→8)-epiafzelechin(8), 表儿茶素-(4β→8、2β→O→7)-epiafzelechin-(4α→8)-epiafzelechin(9), epiafzelechin-(4β→8, 2β→O→7)-epizfzelechin-(4α→8)-epicatechin(10), epiafzelechin-(4β→8, 2β→O→7)-epicatechin-(4α→8)-epicatechin (11)、表儿茶素-(4β→8, 2β→O→7)-epiafzelechin-(4α→8)-epicatechin (12)、表儿茶素-(4β→8, 2β→O→7)-epicatechin-(4α→8)-epiafzelechin (13)、表儿茶素-(4β→8、2β→O→7)-epicatechin-(4α→8)-epigallocatechin (14) 和 epiafzelechin-(4β→8)epicatechin-(4β→8, 2β→O→β→7)-epicatechin-(4α→8)-epicatechin (15)。