(2R,2''R,3R,3''R,4R)-[4,8]-2,3-cis-3,4-trans-(-)-epigallocatechin-(-)-epigallocatechin-3''-O-gallate | 86588-88-7

• 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: (2R,2''R,3R,3''R,4R)-[4,8]-2,3-cis-3,4-trans-(-)-epigallocatechin-(-)-epigallocatechin-3''-O-gallate
• 英文别名: 2R,3R,4R-epigallocatechin-(4β->8)-2R,3R-epigallocatechin-3-O-gallate；epigallocatechin-(4β->8)-epigallocatechin-3-O-gallate；epigallocatechin(4β→8)epigallocatechin 3-O-gallate；epigallocatechin-(4β->8)-epigallocatechingallate；epigallocatechin-(4β-8)-epigallocatechin-3-O-gallate；3'-O-galloyl prodelphinidin B-2；epigallocatechin-(4beta->8)-epigallocatechin-3-O-gallate；[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-8-[(2R,3R,4R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
• CAS: 86588-88-7
• 化学式: C₃₇H₃₀O₁₈
• 分子量: 762.634
• InChiKey: JSBXKZFDEDBAQA-WUFIRYPCSA-N

物化性质

• 沸点：
  1120.9±65.0 °C(Predicted)
• 密度：
  2.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  55
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  328
• 氢给体数：
  14
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  (2R,2''R,3R,3''R,4R)-[4,8]-2,3-cis-3,4-trans-(-)-epigallocatechin-(-)-epigallocatechin-3''-O-gallate 在 盐酸 作用下， 反应 0.33h， 生成 氯化花翠素
  参考文献：
  名称：

  Dimeric prodelphinidins from Limonium gmelinii roots. III.

  摘要：

  通过聚酰胺吸附色谱法从Limonium gmelinii根的水醇提取物的乙酸乙酯部分中分离出两种二聚原花青素，分别鉴定为2R,3R,4R-(-)-表没食子儿茶素-(4β→ 8)-2R,3R-(-)-表没食子儿茶素-3-O-没食子酸酯和2R,3R,4R-(-)-表没食子儿茶素-(4β→ 8)-(-)-2R,3R,3,5,7,3′,4′,6′-六羟基黄烷。前者首次从海薰衣草中分离得到，而后者是一种新化合物。

  DOI：

  10.1007/s10600-006-0068-8
• 作为产物：
  描述：

  (2R,2''R,3R,3''R,4R)-[4,8]-2,3-cis-3,4-trans-trideca-O-benzyl-(-)-epigallocatechin-(-)-epigallo-catechin-3''-gallate 在 Pd(OH)2/C, 20% 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 12.0h， 以21%的产率得到(2R,2''R,3R,3''R,4R)-[4,8]-2,3-cis-3,4-trans-(-)-epigallocatechin-(-)-epigallocatechin-3''-O-gallate
  参考文献：
  名称：

  Structure–Activity Relationship of Oligomeric Flavan-3-ols: Importance of the Upper-Unit B-ring Hydroxyl Groups in the Dimeric Structure for Strong Activities

  摘要：

  原花青素是由低聚黄烷-3-醇单位组成的，存在于各种食品（如水果、蔬菜和饮料）中，是一种具有很强生物活性的化合物。我们研究了原花青素结构中哪种元素主要负责这种功能。在这项研究中，我们阐明了 4-8 缩合二聚体黄烷-3-醇上部单元对酿酒酵母（S. cerevisiae）和宫颈上皮样癌细胞株 HeLa S3 增殖抑制活性的重要性。(-)-表没食子儿茶素-[4,8]-(-)-表没食子儿茶素-3-O-没食子酸酯，以及(+)-儿茶素-[4,8]-(-)-表没食子儿茶素，并进行了结构-活性关系（SAR）研究。 除了对葡萄孢菌的抗菌活性和对 HeLa S3 细胞的增殖抑制活性外，2,2-二苯基-l-苦基肼自由基清除活性与酚羟基数目的相关性较低。根据我们的 SAR 研究结果，我们得出结论：二聚体上部单元的 B 环羟基对于强有效的活性至关重要。

  DOI：

  10.3390/molecules201018870

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。
• Dimeric prodelphinidins from Limonium gmelinii roots. III.
  作者：G. E. Zhusupova、S. A. Abil’kaeva

  DOI：10.1007/s10600-006-0068-8

  日期：2006.3

  Two dimeric proanthocyanidines identified as 2R,3R,4R-(-)-epigallocatechin-(4β→ 8)-2R,3R-(-)-epigallocatechin-3-O-gallate and 2R,3R,4R-(-)-epigallocatechin-(4β→8)-(-)-2R,3R,3,5,7,3′,4′,6′-hexahydroxyflavan were isolated by adsorption chromatography over polyamide of the ethylacetate fraction of the aqueous alcohol extract of Limonium gmelinii roots. The former proanthocyanidine was isolated for the first time from sea lavender whereas the latter is new.

  通过聚酰胺吸附色谱法从Limonium gmelinii根的水醇提取物的乙酸乙酯部分中分离出两种二聚原花青素，分别鉴定为2R,3R,4R-(-)-表没食子儿茶素-(4β→ 8)-2R,3R-(-)-表没食子儿茶素-3-O-没食子酸酯和2R,3R,4R-(-)-表没食子儿茶素-(4β→ 8)-(-)-2R,3R,3,5,7,3′,4′,6′-六羟基黄烷。前者首次从海薰衣草中分离得到，而后者是一种新化合物。
• Structure–Activity Relationship of Oligomeric Flavan-3-ols: Importance of the Upper-Unit B-ring Hydroxyl Groups in the Dimeric Structure for Strong Activities
  作者：Yoshitomo Hamada、Syota Takano、Yoshihiro Ayano、Masahiro Tokunaga、Takahiro Koashi、Syuhei Okamoto、Syoma Doi、Masahiko Ishida、Takashi Kawasaki、Masahiro Hamada、Noriyuki Nakajima、Akiko Saito

  DOI：10.3390/molecules201018870

  日期：——

  Proanthocyanidins, which are composed of oligomeric flavan-3-ol units, are contained in various foodstuffs (e.g., fruits, vegetables, and drinks) and are strongly biologically active compounds. We investigated which element of the proanthocyanidin structure is primarily responsible for this functionality. In this study, we elucidate the importance of the upper-unit of 4–8 condensed dimeric flavan-3-ols for antimicrobial activity against Saccharomyces cerevisiae (S. cerevisiae) and cervical epithelioid carcinoma cell line HeLa S3 proliferation inhibitory activity. To clarify the important constituent unit of proanthocyanidin, we synthesized four dimeric compounds, (−)-epigallocatechin-[4,8]-(+)-catechin, (−)-epigallocatechin-[4,8]-(−)-epigallocatechin, (−)-epigallocatechin-[4,8]-(−)-epigallocatechin-3-O-gallate, and (+)-catechin-[4,8]-(−)-epigallocatechin and performed structure–activity relationship (SAR) studies. In addition to antimicrobial activity against S. cerevisiae and proliferation inhibitory activity on HeLa S3 cells, the correlation of 2,2-diphenyl-l-picrylhydrazyl radical scavenging activity with the number of phenolic hydroxyl groups was low. On the basis of the results of our SAR studies, we concluded that B-ring hydroxyl groups of the upper-unit of the dimer are crucially important for strong and effective activity.

  原花青素是由低聚黄烷-3-醇单位组成的，存在于各种食品（如水果、蔬菜和饮料）中，是一种具有很强生物活性的化合物。我们研究了原花青素结构中哪种元素主要负责这种功能。在这项研究中，我们阐明了 4-8 缩合二聚体黄烷-3-醇上部单元对酿酒酵母（S. cerevisiae）和宫颈上皮样癌细胞株 HeLa S3 增殖抑制活性的重要性。(-)-表没食子儿茶素-[4,8]-(-)-表没食子儿茶素-3-O-没食子酸酯，以及(+)-儿茶素-[4,8]-(-)-表没食子儿茶素，并进行了结构-活性关系（SAR）研究。 除了对葡萄孢菌的抗菌活性和对 HeLa S3 细胞的增殖抑制活性外，2,2-二苯基-l-苦基肼自由基清除活性与酚羟基数目的相关性较低。根据我们的 SAR 研究结果，我们得出结论：二聚体上部单元的 B 环羟基对于强有效的活性至关重要。