原花青素E-1 | 86631-39-2

• 物质功能分类: 分析化学 - 对照品
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 原花青素E-1
• 中文别名: 原花青素A3
• 英文名称: epicatechin-(4β->8)-epicatechin-(4β->8)-epicatechin-(4β->8)-epicatechin-(4β->8)-epicatechin
• 英文别名: epicatechin-(4β→8)-epicatechin-(4β→8)-epicatechin-(4β→8)-epicatechin-(4β→8)-epicatechin；epicatechin-<4β->8>-(epicatechin-<4β->8>-)₃epicatechin；[epicatechin-(4β->8)]4-epicatechin；epicatechin (4β,8)4-pentamer；cinnamtannin A2；cinnamtannin A3；(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
• CAS: 86631-39-2
• 化学式: C₇₅H₆₂O₃₀
• 分子量: 1443.3
• InChiKey: QRFZGLTZLZZHCM-NWYMYRDLSA-N

物化性质

• 密度：
  1.781±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  105
• 可旋转键数：
  9
• 环数：
  15.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  552
• 氢给体数：
  25
• 氢受体数：
  30

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 原花青素E-1 在 吡啶 作用下， 反应 24.0h， 生成 [(2R,3R)-5,7-diacetyloxy-2-(3,4-diacetyloxyphenyl)-8-[(2R,3R,4S)-3,5,7-triacetyloxy-2-(3,4-diacetyloxyphenyl)-8-[(2R,3R,4R)-3,5,7-triacetyloxy-2-(3,4-diacetyloxyphenyl)-8-[(2R,3R,4R)-3,5,7-triacetyloxy-2-(3,4-diacetyloxyphenyl)-8-[(2R,3R,4R)-3,5,7-triacetyloxy-2-(3,4-diacetyloxyphenyl)-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromen-3-yl] acetate
  参考文献：
  名称：

  Bioassay-Guided Fractionation of a Leaf Extract from Combretum mucronatum with Anthelmintic Activity: Oligomeric Procyanidins as the Active Principle

  摘要：

  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。

  DOI：

  10.3390/molecules200814810
• 作为产物：
  描述：

  [4,8:4'',8'':4'''',8'''']-2,3-cis-3,4-trans:2'',3''-cis-3'',4''-trans:2'''',3''''-cis-3'''',4''''-trans-2'''''',3''''''-cis-3'''''',4''''''-trans:2'''''''',3''''''''-cis-eicosa-O-benzyl-(-)-epicatechin-(-)-epicatechin-(-)-epicatechin-(-)-epicatechin-(-)-epicatechin 在 20% Pd(OH)2/C 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 8.0h， 以68%的产率得到原花青素E-1
  参考文献：
  名称：

  表儿茶素系列原花青素寡聚体的多功能合成及其抗氧化剂和DNA聚合酶的抑制活性

  摘要：

  原花青素，称为缩合单宁或低聚类黄酮，存在于许多食用植物中，并显示出各种有趣的生物学活性。我们已经开发了一种简单而通用的合成由（-）-表儿茶素和（+）-儿茶素组成的原花青素低聚物的方法。该方法适用于各种3- O-取代的低聚物的合成。我们在这里报告[4-8]缩合（-）-表儿茶素系列原花青素低聚物的立体选择性和长度控制的合成。我们描述了两种四聚体的合成细节，（-）-表儿茶素-（-）-表儿茶素-（-）-表儿茶素-（-）-表儿茶素和（-）-表儿茶素-（-）-表儿茶素-（- ）-表儿茶素-（+）-儿茶素（槟榔素A1），（-）-表儿茶素五聚体和两个3,3″，3⁗-tri- O-没食子酰基三聚体，（-）-表儿茶素-（-）-表儿茶素-（-）-表儿茶素-3,3″，3′-三-O-没食子酸酯和（-）-表儿茶素-（-）-表儿茶素-（+ ）-儿茶素-3,3″，3′-三-O-没食子酸酯，使用TMSOTf作为催化剂进行缩

  DOI：

  10.1016/j.tet.2009.07.018

文献信息

• Synthesis of dimeric, trimeric, tetrameric pentameric, and higher oligomeric epicatechin-derived procyanidins having 4beta,8-interflavan linkages and their use to inhibit cancer cell growth through cell cycle arrest
  申请人：——

  公开号：US20040116718A1

  公开（公告）日：2004-06-17

  Various processes are disclosed for preparing protected epicatechin oligomers having (4&bgr;,8)-interflavan linkages. In one process, a tetra-O-protected epicatechin monomer or oligomer is coupled with a protected, C-4 activated epicatechin monomer in the presence of an acidic clay such as a mortmorillonite clay. In another process, a 5,7,3′,4′-benzyl protected or a 3-acetyl-, 5,7,3′,4′-benzyl protected epicatechin or catechin monomer or oligomer is reacted with 3-O-acetyl-4-[(2-benzothiazolyl)thio]-5,7,3′,4′-tetra-O-benzylepicatechin in the presence of silver tetrafluoroborate. In another process, two 5,7,3′,4′-benzyl protected epicatechin monomers activated with 2-(benzothiazolyl)thio groups at the C-4 positions are cross-coupled in the presence of silver tetrofluoroborate. A process is also disclosed for reacting an unprotected epicatechin or catechin monomer with 4-(benzylthio) epicatechin or catechin. The use of naturally-derived and synthetically-prepared procyanidin (4&bgr;,8) 4 -pentamers to treat cancer is also disclosed.

  揭示了多种制备具有（4'，8）-交互缬氨酸连接的受保护表儿茶素寡聚物的过程。在一种过程中，通过在存在酸性粘土（如蒙脱石粘土）的情况下，将四重受保护的表儿茶素单体或寡聚体与受保护的C-4活化的表儿茶素单体偶联。在另一种过程中，通过在存在四氟硼酸银的情况下，将5,7,3′,4′-苄基保护或3-乙酰基-，5,7,3′,4′-苄基保护的表儿茶素或儿茶素单体或寡聚体与3-O-乙酰基-4-[（2-苯并噻唑基）硫]-5,7,3′,4′-四重苄基表儿茶素反应。在另一种过程中，两个在C-4位置激活了2-（苯并噻唑基）硫基团的5,7,3′,4′-苄基保护表儿茶素单体交叉偶联，在四氟硼酸银的存在下。还揭示了一种过程，用于将未受保护的表儿茶素或儿茶素单体与4-（苄硫基）表儿茶素或儿茶素反应。还揭示了使用天然衍生和合成制备的（4'，8）4-五聚体前花青素来治疗癌症。
• Tannins and related compounds. XXXVIII. Isolation and characterization of flavan-3-ol glucosides and procyanidin oligomers from cassia bark (Cinnamomum cassia Blume).
  作者：SATOSHI MORIMOTO、GEN-ICHIRO NONAKA、ITSUO NISHIOKA

  DOI：10.1248/cpb.34.633

  日期：——

  A chemical examination of the bark of Cinnamomum cassia( ?? ?? ?? ?? : Lauraceae) has led to the isolation of three flavan-3-ol glucosides (1-3) and three oligomeric procyanidins (4-6) named cinnamtannins A2-A4, together with (-)-epicatechin(7), procyanidins B-2 (8), B-5 (9) and C-1 (11), and a doubly-linked proanthocyanidin (10). On the basis of chemical and spectroscopic evidence, compounds 1-3 were characterized as (-)-epicatechin 3-O-, 8-C- and 6-C-β-D-glucopyranosides, respectively, while compounds 4-6 were shown to be tetrameric, pentameric and hexameric procyanidins, respectively, consisting exclusively of (-)-epicatechin units linked linearly through C(4β)-C(8) bonds.

  通过对肉桂树皮进行化学研究，分离出三种黄烷-3-醇葡糖苷（1-3）和三种低聚原花青素（4-6），分别命名为肉桂单宁 A2-A4，以及(-)-表儿茶素(7)、原花青素 B-2 (8)、B-5 (9)和 C-1 (11)和一种双链原花青素(10)。根据化学和光谱证据，化合物 1-3 的特征分别是(-)-表儿茶素 3-O-、8-C-和 6-C-β-D 吡喃葡萄糖苷，而化合物 4-6 则分别是四聚、五聚和六聚原花青素，完全由通过 C(4β)-C(8) 键线性连接的(-)-表儿茶素单元组成。
• Studies in Polyphenol Chemistry and Bioactivity. 4.¹ Synthesis of Trimeric, Tetrameric, Pentameric, and Higher Oligomeric Epicatechin-Derived Procyanidins Having All-4β,8-Interflavan Connectivity and Their Inhibition of Cancer Cell Growth through Cell Cycle Arrest¹
  作者：Alan P. Kozikowski、Werner Tückmantel、Gesine Böttcher、Leo J. Romanczyk

  DOI：10.1021/jo020393f

  日期：2003.3.1

  members was demonstrated using a dimeric electrophile obtained by self-condensation of compound 12. Both the synthetic and natural pentamer 32 inhibit the growth of several breast cancer cell lines. Using the MDA MB 231 line, it was established that this outcome is based on the induction of cell cycle arrest in the G0/G1 phase. Subsequent cell death is more likely necrotic rather than apoptotic. Control

  我们报道了从5,7,3'，4'-四-O-苄基表儿茶素（（ 1）和5,7,3'，4'-四-O-苄基-4-（2-羟基乙氧基）表儿茶酸（2），方法是用粘土矿物膨润土K-10代替先前使用的路易斯酸四氯化钛。在相同条件下，从苄基保护的全4β，8-三聚体，-四聚体和-戊二聚体是从它们的较低同系物区域选择性地获得的，尽管产率迅速降低。2与2-巯基苯并噻唑和三甲基铝生成的有机硫醇铝反应，然后乙酰化，生成3-O-乙酰基-4-[（2-苯并噻唑基）硫代] -5,7,3'，4'-四-O-苄基表儿茶素（12）。具有4beta的中型受保护寡聚物，通过使用该化合物作为亲电子试剂和四氟硼酸银作为活化剂，可以提高产率获得8-黄酮键，并通过反相HPLC进行分离。通过酯皂化然后氢解将它们脱保护，得到游离的原花青素，其特征为过乙酸盐。通过正相HPLC，合成的原花青素与从可可中分离出的馏分相同。使用通过化合物12的自缩合获得的二聚
• ANTIVIRAL EPICATECHINS, EPICATECHIN OLIGOMERS, OR THIOLATED EPICATECHINS FROM THEOBROMA CACAO FOR TREATMENT OF GENITAL WARTS
  申请人：PRESTON Daniel

  公开号：US20110218241A1

  公开（公告）日：2011-09-08

  Epicatechins, Epicatechin Oligomers, or Thiolated Epicatechins are applied (A) directly to a genital wart in the form of a cream, ointment, paste or solution, (B) directly to the genital wart wherein such cream, ointment, paste or solution contains as an additional active ingredient a skin permeabilizing agent, (C) following electrosurgical resection or removal of the genital wart in such form of a cream, ointment, paste or solution, (D) following chemical resection or extirpation of the genital wart in such form, (E) following surgical resection or removal of the genital wart in such form, wherein said Epicatechins, Epicatechin Oligomers, or Thiolated Epicatechins both provide antiviral activity against multiple strains of human papilloma virus (HPV) and promote healing following resection polymers contained in a vehicle. Disclosed are the compositions, therapeutical kits containing such composition, methods of treatment using such composition, and methods of enhancing the stability of such composition.
• EPICATECHIN COMPOSITIONS AND METHODS
  申请人：PRESTON Daniel

  公开号：US20110280933A1

  公开（公告）日：2011-11-17

  Provided herein are methods and compositions for treating a subject who has pulmonary damage or an injury caused by or who is at risk for an injury caused by an anti-vesicant agent. The compositions comprise cacao extracts that include a mixture of epicatechin and one or more epicatechin oligomers and a pharmaceutically acceptable carrier. Also provided are methods for fermenting cacao to enhance epicatechin and antioxidant content.