epicatechin-(4β->8)-epicatechin-(4β->8)-epicatechin-(4β->2)-phloroglucinol

• 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)-epicatechin-(4β->8)-epicatechin-(4β->2)-phloroglucinol
• 英文别名: (2R,3R,4R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-4-[(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4-(2,4,6-trihydroxyphenyl)-3,4-dihydro-2H-chromen-8-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
• 化学式: C₅₁H₄₂O₂₁
• 分子量: 990.882
• InChiKey: QXMBFQSSWOOOLC-NGINHVCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  72
• 可旋转键数：
  6
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  392
• 氢给体数：
  18
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  苄硫醇 、 epicatechin-(4β->8)-epicatechin-(4β->8)-epicatechin-(4β->2)-phloroglucinol 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 间苯三酚 、 (2R,3R,4S)-4-(2,4,6-trihydroxyphenyl)flavan-3,3',4',5,7-pentaol 、 4β-benzylthioepicatechin 、 (2R,3R,4R)-2,3-cis-3,4-trans-3,5,7,3',4'-pentahydroxy-4-<(2R,3S,4S)-2,3-cis-3,4-trans-3,5,7,3',4'-pentahydroxy-4-benzylthioflavan-8-yl>flavan
  参考文献：
  名称：

  花旗松树皮的原花青素聚合物：用间苯三酚降解后的结构

  摘要：

  摘要 花旗松内皮的缩合单宁聚合物与间苯三酚反应生成儿茶素、表儿茶素、原花青素 B-2、儿茶素-(4α→2)-间苯三酚、表儿茶素-(4β→2)-间苯三酚、新型化合物表儿茶素-( 4α→2)-间苯三酚和1,3-二(2,4,6-三羟基苯基)-1-(3,4-二-羟基苯基)-丙-2-醇。还分离出了表儿茶素-(4β→8)-表儿茶素-(4β→2)-间苯三酚、表儿茶素-(4β→6)-表儿茶素-(4β→2)-间苯三酚和其他三种新型间苯三酚加合物，儿茶素-(4α →8)-表儿茶素-(4β→2)-间苯三酚、表儿茶素-(4β→8)-表儿茶素-(4β→8)-表儿茶素-(4β→2)-间苯三酚和表儿茶素-(4β→6)-表儿茶素- (4β→8)-表儿茶素-(4β→2)-间苯三酚。结果表明，扩展单元的配置几乎完全是 2,3-顺式，而终端单元则是混合的，有 2, 3-顺式略占优势。C-4 到 C-8 间黄酮连接以 4:1 的比例超过

  DOI：

  10.1016/0031-9422(89)80303-6

文献信息

• METHOD OF PRODUCING PROANTHOCYANIDIN OLIGOMER
  申请人：Tanaka Takashi

  公开号：US20090047305A1

  公开（公告）日：2009-02-19

  The present invention relates to a composition containing as its main component proanthocyanidin oligomer to which a substance having a phloroglucinol ring structure or resorcinol ring structure has been bonded, and reduced in the molecular weight, which is obtained by heating plant materials containing proanthocyanidin polymer or extract thereof with a substance having a phloroglucinol ring structure or resorcinol ring structure in an acidic aqueous solution, production method thereof, and uses of the composition in health products and pharmaceutical products. According to the invention, proanthocyanidin oligomer having physiological activity, to which a substance having a phloroglucinol ring structure or resorcinol ring structure has been bonded and reduced in the molecular weight to such a level that the oligomer can be absorbed into living body, which has been conventionally difficult to obtain at high yield from plant raw materials, can be produced efficiently and easily.

  本发明涉及一种组合物，其主要成分为与具有邻苯二酚环结构或间苯二酚环结构的物质键合并分子量降低的原花青素寡聚体，该组合物通过在酸性水溶液中将含有原花青素聚合物或其提取物的植物材料与具有邻苯二酚环结构或间苯二酚环结构的物质加热而得到，以及该组合物在健康产品和药品中的用途和其制备方法。根据本发明，具有生理活性的原花青素寡聚体，其分子量已经被降低到能够被生物体吸收的水平，并且与具有邻苯二酚环结构或间苯二酚环结构的物质键合，这在以往从植物原材料中高产得到是困难的，现在可以高效、容易地生产。
• Method of producing proanthocyanidin oligomer
  申请人：Nagasaki University

  公开号：US10183007B2

  公开（公告）日：2019-01-22

  The present invention relates to a composition containing as its main component proanthocyanidin oligomer to which a substance having a phloroglucinol ring structure or resorcinol ring structure has been bonded and reduced in the molecular weight, which is obtained by heating plant materials containing proanthocyanidin polymer or extract thereof with a substance having a phloroglucinol ring structure or resorcinol ring structure in an acidic aqueous solution, production method thereof, and uses of the composition in health products and pharmaceutical products. According to the invention, proanthocyanidin oligomer having physiological activity, to which a substance having a phloroglucinol ring structure or resorcinol ring structure has been bonded and reduced in the molecular weight to such a level that the oligomer can be absorbed into living body, which has been conventionally difficult to obtain at high yield from plant raw materials, can be produced efficiently and easily.

  本发明涉及一种组合物，其主要成分是原花青素低聚物，通过在酸性水溶液中加热含有原花青素聚合物的植物材料或其提取物与具有绿原酸环结构或间苯二酚环结构的物质结合并降低其分子量而得到；本发明还涉及其生产方法以及该组合物在保健品和医药产品中的用途。根据本发明，可以高效简便地生产具有生理活性的原花青素低聚物，该低聚物与具有绿葡萄糖醇环结构或间苯二酚环结构的物质结合，并将分子量降低到可被人体吸收的水平，而传统上很难从植物原料中高产获得这种低聚物。
• ANTI-INFLAMMATORY COMPOSITION
  申请人：Unilever PLC

  公开号：EP2714085B1

  公开（公告）日：2016-06-01
• POLYPHENOL COMPOSITION FOR PREVENTING OR TREATING ATHEROSCLEROSIS
  申请人：Unilever PLC

  公开号：EP2714086B1

  公开（公告）日：2014-12-10
• Procyanidin polymers of Douglas fir bark: Structure from degradation with phloroglucinol
  作者：Lai Yeap Foo、Joseph J. Karchesy

  DOI：10.1016/0031-9422(89)80303-6

  日期：1989.1

  Abstract Reaction of the condensed tannin polymers of Douglas fir inner bark with phloroglucinol yielded catechin, epicatechin, procyanidin B-2, catechin-(4α→2)-phloroglucinol, epicatechin-(4β→2)-phloroglucinol, the novel compound epicatechin-(4α→2)-phloroglucinol and 1,3-di (2,4,6-trihydroxyphenyl)-1-(3,4-di-hydroxyphenyl)-propan-2-ol. Also isolated were epicatechin-(4β→8)-epicatechin-(4β→2)-phloroglucinol

  摘要 花旗松内皮的缩合单宁聚合物与间苯三酚反应生成儿茶素、表儿茶素、原花青素 B-2、儿茶素-(4α→2)-间苯三酚、表儿茶素-(4β→2)-间苯三酚、新型化合物表儿茶素-( 4α→2)-间苯三酚和1,3-二(2,4,6-三羟基苯基)-1-(3,4-二-羟基苯基)-丙-2-醇。还分离出了表儿茶素-(4β→8)-表儿茶素-(4β→2)-间苯三酚、表儿茶素-(4β→6)-表儿茶素-(4β→2)-间苯三酚和其他三种新型间苯三酚加合物，儿茶素-(4α →8)-表儿茶素-(4β→2)-间苯三酚、表儿茶素-(4β→8)-表儿茶素-(4β→8)-表儿茶素-(4β→2)-间苯三酚和表儿茶素-(4β→6)-表儿茶素- (4β→8)-表儿茶素-(4β→2)-间苯三酚。结果表明，扩展单元的配置几乎完全是 2,3-顺式，而终端单元则是混合的，有 2, 3-顺式略占优势。C-4 到 C-8 间黄酮连接以 4:1 的比例超过