Peracetylated catechin-(4α-8)-catechin-(4α-8)-catechin procyanidin trimer | 25664-00-0

• 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: Peracetylated catechin-(4α-8)-catechin-(4α-8)-catechin procyanidin trimer
• 英文别名: C2 acetate；[(2R,3S)-5,7-diacetyloxy-2-(3,4-diacetyloxyphenyl)-8-[(2R,3S,4R)-3,5,7-triacetyloxy-2-(3,4-diacetyloxyphenyl)-8-[(2R,3S,4S)-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-3-yl] acetate
• CAS: 25664-00-0；78392-24-2；82837-95-4；82837-96-5
• 化学式: C₇₅H₆₈O₃₃
• 分子量: 1497.35
• InChiKey: KRPGVSJJSXPITF-JKSKJMCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  108
• 可旋转键数：
  35
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  422
• 氢给体数：
  0
• 氢受体数：
  33

反应信息

• 作为产物：
  描述：

  乙酸酐 、 原花青素C2 在 吡啶 、 4-二甲氨基吡啶 作用下， 以54%的产率得到Peracetylated catechin-(4α-8)-catechin-(4α-8)-catechin procyanidin trimer
  参考文献：
  名称：

  Efficient Stereoselective Synthesis of Proanthocyanidin Trimers with ­TMSOTf-Catalyzed Intermolecular Condensation

  摘要：

  本文描述了使用TMSOTf催化的缩合反应，实现七种苯甲基化原花青素三聚体的立体选择性合成。特别是，表儿茶素-(4β-8)-表儿茶素-(4β-8)-表儿茶素三聚体（原花青素C1）、儿茶素-(4α-8)-儿茶素-(4α-8)-儿茶素三聚体（原花青素C2）、表儿茶素-(4β-8)-表儿茶素-(4β-8)-儿茶素三聚体和表儿茶素-(4β-8)-儿茶素-(4α-8)-表儿茶素三聚体衍生物在大收率下获得。通过比较两种不同缩合方法合成的保护原花青素C2的1H NMR谱图，确认了苯甲基化原花青素C2的结构。最后，脱保护(+)-儿茶素和(-)-表儿茶素三聚体衍生物，获得了四种天然原花青素三聚体，收率良好。

  DOI：

  10.1055/s-2004-822905

文献信息

• Synthesis of Procyanidins C2 and C1 Using Lewis Acid Mediated Equimolar Condensation
  作者：Hidefumi Makabe、Yukiko Oizumi、Miyuki Katoh、Yasunao Hattori、Kazuya Toda、Koichiro Kawaguchi、Hiroshi Fujii

  DOI：10.3987/com-12-12526

  日期：——

  procyanidin trimers. We have already reported a stereoselective synthesis of catechin trimer derivative using equimolar condensation. However, synthesis of epicatechin trimer using equimolar condensation has not been reported yet. In this article, we wish to report total synthesis of procyanidin C2 (1) and the recent progress of the synthesis of procyanidin C1 (2) via equimolar condensation between dimeric

  原花青素 C2 和 C1 的合成是通过等摩尔量的二聚儿茶素或表儿茶素亲核试剂和单体儿茶素或表儿茶素亲核试剂使用路易斯酸进行立体选择性分子间缩合来实现的。在合成原花青素 C2 的情况下，AgBF4 和 AgOTf 以优异的收率提供了缩合产物。对于原花青素C1的合成，Yb(OTf)3对等摩尔缩合有效。简介 原花青素被称为缩合或非水解单宁。这些单宁广泛存在于蔬菜、水果和树皮中。据报道，原花青素具有很强的自由基清除和抗氧化活性。报道了许多生物活性，例如抗肿瘤、抗病毒、抗炎和抑制 DNA 聚合酶。因此，原花青素越来越被认为对人类具有健康益处。来自大自然的单宁提取物提供各种类型的多酚。由于它们的鉴定和纯化极其困难，因此对生物活性（即作用机制）的进一步研究仍未解决。近来，为了获得纯态的原花青素低聚物，人们致力于合成。关于儿茶素和/或表儿茶素三聚体的合成，报道了几项合成研究。典型的合成方法如下。第一个例子是
• Extensive high-resolution reverse 2D NMR analysis for the structural elucidation of procyanidin oligomers
  作者：Laurence Balas、Joseph Vercauteren

  DOI：10.1002/mrc.1260320703

  日期：1994.7

  The structures of the procyanidin dimers catechin‐(4α–8)‐catechin and catechin‐(4α–6)‐catechin were proved by spectroscopic means. To distinguish between the two possible interflavanoid linkages, it is necessary to assign all the quaternary aromatic carbon signals. How these assignments can be made through two‐dimensional NMR spectroscopy is described.

  通过光谱方法证明了原花青素二聚体儿茶素-(4α-8)-儿茶素和儿茶素-(4α-6)-儿茶素的结构。为了区分两种可能的类黄酮间键，有必要分配所有的季芳碳信号。描述了如何通过二维核磁共振光谱进行这些分配。
• Carbon-14 Biolabeling of (+)-Catechin and Proanthocyanidin Oligomers in Willow Tree Cuttings
  作者：Stéphanie Déprez、Isabelle Mila、Augustin Scalbert

  DOI：10.1021/jf981380z

  日期：1999.10.1

  Proanthocyanidin polymers, oligomers, and the structurally related monomer (+)-catechin were labeled by incorporation of radioactive precursors in shoots of willow tree (Salix caprea L.). [1-C-14]-Acetate and [U-C-14]-phenylalanine precursors were fed through the cut stems or petioles of leaves. Optimization of several parameters such as the nature and origin of the plant material, leaf maturity, nature, and quantity of radioactive precursor applied and the duration of metabolism led to incorporation yields of 3.2% and to specific activities of 500 mu Ci/g. Detailed characterization of the products (polymerization degree, procyanidin/prodelphinidin ratio, specific activities) and purification by chromatography are reported. Some sugars bound to radiolabeled proanthocyanidin polymers were removed by enzymic treatment with a mixture of glycosidases. A radioactive purity close to 100% and specific activities suitable for bioavailability studies were obtained.
• Oligomeric flavan-3-ols from medicinal willow bark
  作者：Herbert Kolodziej

  DOI：10.1016/0031-9422(90)80054-k

  日期：——