(epi)afzelechin‐(4‐8)‐(epi)catechin | 114715-49-0

• 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: (epi)afzelechin‐(4‐8)‐(epi)catechin
• 英文别名: epiafzelechin-(4β->8)-epicatechin；epiafzelechin-(4β→8)-epicatechin；(-)-Epiafzelechin-(4beta-8)-(-)-epicatechin；(2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
• CAS: 114715-49-0
• 化学式: C₃₀H₂₆O₁₁
• 分子量: 562.53
• InChiKey: KUODBSWFMJMVJV-NFJBMHMQSA-N

物化性质

• 沸点：
  922.2±65.0 °C(Predicted)
• 密度：
  1.651±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  41
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  201
• 氢给体数：
  9
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (epi)afzelechin‐(4‐8)‐(epi)catechin 在 Raney-nickel (W-4) 、 溶剂黄146 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 8.5h， 生成 (-)-表阿夫儿茶精
  参考文献：
  名称：

  Morimoto, Satoshi; Nonaka, Gen-Ichiro; Chen, Rong-Fu, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 1, p. 39 - 47

  摘要：

  DOI：

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->
• Bioassay-Guided Fractionation of a Leaf Extract from Combretum mucronatum with Anthelmintic Activity: Oligomeric Procyanidins as the Active Principle
  作者：Verena Spiegler、Jandirk Sendker、Frank Petereit、Eva Liebau、Andreas Hensel

  DOI：10.3390/molecules200814810

  日期：——

  Combretum mucronatum Schumach. & Thonn. is a medicinal plant widely used in West African traditional medicine for wound healing and the treatment of helminth infections. The present study aimed at a phytochemical characterization of a hydroalcoholic leaf extract of this plant and the identification of the anthelmintic compounds by bioassay-guided fractionation. An EtOH-H2O (1:1) extract from defatted leaves was partitioned between EtOAc and H2O. Further fractionation was performed by fast centrifugal partition chromatography, RP18-MPLC and HPLC. Epicatechin (1), oligomeric proanthocyanidins (OPC) 2 to 10 (mainly procyanidins) and flavonoids 11 to 13 were identified as main components of the extract. The hydroalcoholic extract, fractions and purified compounds were tested in vitro for their anthelmintic activity using the model nematode Caenorhabditis elegans. The bioassay-guided fractionation led to the identification of OPCs as the active compounds with a dose-dependent anthelmintic activity ranging from 1 to 1000 μM. Using OPC-clusters with a defined degree of polymerization (DP) revealed that a DP ≥ 3 is necessary for an anthelmintic activity, whereas a DP > 4 does not lead to a further increased inhibitory effect against the helminths. In summary, the findings rationalize the traditional use of C. mucronatum and provide further insight into the anthelmintic activity of condensed tannins.

  Combretum mucronatum Schumach. & Thonn.是一种药用植物，在西非传统医学中被广泛用于伤口愈合和治疗蠕虫感染。本研究旨在对该植物的水醇叶提取物进行植物化学鉴定，并通过生物测定指导分馏法鉴定抗蠕虫化合物。脱脂叶片的 EtOH-H2O (1:1) 提取物在 EtOAc 和 H2O 之间分配。通过快速离心分离层析、RP18-MPLC 和 HPLC 进行了进一步分馏。表儿茶素（1）、低聚原花青素（OPC）2 至 10（主要是原花青素）和黄酮类化合物 11 至 13 被鉴定为提取物的主要成分。利用模式线虫秀丽隐杆线虫对水醇提取物、馏分和纯化化合物的驱虫活性进行了体外测试。生物测定指导下的分馏结果表明，OPCs 是活性化合物，具有 1 至 1000 μM 的剂量依赖性驱虫活性。使用具有确定聚合度（DP）的 OPC 簇发现，DP ≥ 3 是抗蠕虫活性的必要条件，而 DP > 4 不会进一步增加对蠕虫的抑制作用。总之，这些发现合理解释了 C. mucronatum 的传统用途，并进一步揭示了缩合单宁的驱虫活性。
• Morimoto, Satoshi; Nonaka, Gen-Ichiro; Chen, Rong-Fu, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 1, p. 39 - 47
  作者：Morimoto, Satoshi、Nonaka, Gen-Ichiro、Chen, Rong-Fu、Nishioka, Itsuo

  DOI：——

  日期：——