原花青素B13-O-没食子酸酯 | 79907-45-2

• 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B13-O-没食子酸酯
• 英文名称: 3-O-galloyl-epicatechin-(4β->8)-catechin
• 英文别名: (−)-epicatechin gallate-(4,8)-(+)-catechin；procyanidin B₁ 3-O-gallate；procyanidin B-1 3'-O-gallate；procyanidin B-1 3-O-gallate；3-O-galloylprocyanidin B-1；3-O-galloylprocyanidin B1；procyanidin B1 3-O-gallate；[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
• CAS: 79907-45-2
• 化学式: C₃₇H₃₀O₁₆
• 分子量: 730.636
• InChiKey: BXWABJPTCUDBMM-NNJCKQBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  53
• 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：
  288
• 氢给体数：
  12
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  原花青素B13-O-没食子酸酯 在 单宁酶 作用下， 生成 原花青素(OPC)
  参考文献：
  名称：

  Stilbene glycoside gallates and proanthocyanidins from Polygonum multiflorum

  摘要：

  Two new stilbene glycoside gallates and proanthocyanidins were isolated from P. multiflorum. The stilbenes were 2"- and 3"-O-monogalloyl esters of 2,3,5,4''-tetrahydroxystilbene 2-O-.beta.-D-glucopyranoside.

  DOI：

  10.1016/s0031-9422(00)95282-8
• 作为产物：
  描述：

  在 palladium dihydroxide 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.0h， 以75%的产率得到原花青素B13-O-没食子酸酯
  参考文献：
  名称：

  Systematic synthesis of galloyl-substituted procyanidin B1 and B2, and their ability of DPPH radical scavenging activity and inhibitory activity of DNA polymerases

  摘要：

  Six galloyl-substituted procyanidin B1 and B2, 3-O-gallate, 3"-O-gallate, and 3,3"-di-O-gallate, were systematically synthesized with the condensation method using TMSOTf as a catalyst. Their ability of DPPH radical scavenging activity and DNA polymerase inhibitory activity were also investigated. The results indicated that the galloyl group of these compounds is very important for both activities. 3,3"-Di-O-gallate dimers acted as strong inhibitor against DNA polymerase alpha and beta, whereas the desgalloyl and monogalloyl compounds did not exhibit any appreciable inhibitory activity against the DNA polymerase beta. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.023

文献信息

• Tannins and related compounds. XLVIII Rhubarb. 7 Isolation and characterization of new dimeric and trimeric procyanidins.
  作者：YOSHIKI KASHIWADA、GEN-ICHIRO NONAKA、ITSUO NISHIOKA

  DOI：10.1248/cpb.34.4083

  日期：——

  Together with the known flavan-3-ols and procyanidins, a new procyanidin dimer (11) and several new trimers (14, 15, 16, 20, 22, 24 and 26) have been isolated from high-quality rhubarb ( ?? ?? ?? ). On the basis of chemical and spectroscopic data, the structures of these compounds were characterized as procyanidin B-5 3, 3'-di-O-gallate (11), procyanidin C-1 3', 3''-di-O-gallate (14), procyanidin C-1 3, 3', 3''-tri-O-gallate (15), 3-O-galloylepicatechin-(4β→6)-3-O-galloylepicatechin-(4β→8)-3-O-galloylepicatechin (20), 3-O-galloylepicatechin-(4β→6)-3-O-galloylepicatechin-(4β→6)-3-O-galloylepicatechin (22), 3-O-galloylepicatechin-(4β→6)-3-O-galloylepicatechin-(4β→8)-catechin (26), 3-O-galloylepicatechin-(4β→8)-3-O-galloylepicatechin-(4β→8)-catechin (16) and 3-O-galloylepicatechin-(4β→8)-3-O-galloylepicatechin-(4β→6)-catechin (24).

  与已知的黄烷-3-醇和原花青素一起，从优质大黄 (?? ? ？？）。根据化学和光谱数据，这些化合物的结构被表征为原花青素 B-5 3, 3'-二-O-没食子酸酯 (11)、原花青素 C-1 3', 3''-二-O-没食子酸酯 (14)、原花青素 C-1 3, 3', 3''-三-O-没食子酸酯 (15)、3-O-没食子酰儿茶素-(4β→6)-3-O-没食子酰儿茶素-(4β→8) -3-O-没食子酰儿茶素 (20)、3-O-没食子酰儿茶素-(4β→6)-3-O-没食子酰儿茶素-(4β→6)-3-O-没食子酰儿茶素 (22)、3-O-没食子酰儿茶素-( 4β→6)-3-O-没食子酰儿茶素-(4β→8)-儿茶素 (26), 3-O-没食子酰儿茶素-(4β→8)-3-O-没食子酰儿茶素-(4β→8)-儿茶素 (16)和 3-O-没食子酰儿茶素-(4β→8)-3-O-没食子酰儿茶素-(4β→6)-儿茶素 (24)。
• Nonaka, Gen-Ichiro; Nishioka, Itsuo; Nagasawa, Tetsuro, Chemical and pharmaceutical bulletin, 1981, vol. 29, # 10, p. 2862 - 2870
  作者：Nonaka, Gen-Ichiro、Nishioka, Itsuo、Nagasawa, Tetsuro、Oura, Hikokichi

  DOI：——

  日期：——
• Systematic synthesis of galloyl-substituted procyanidin B1 and B2, and their ability of DPPH radical scavenging activity and inhibitory activity of DNA polymerases
  作者：Akiko Saito、Yoshiyuki Mizushina、Hiroshi Ikawa、Hiromi Yoshida、Yuki Doi、Akira Tanaka、Noriyuki Nakajima

  DOI：10.1016/j.bmc.2005.02.023

  日期：2005.4

  Six galloyl-substituted procyanidin B1 and B2, 3-O-gallate, 3"-O-gallate, and 3,3"-di-O-gallate, were systematically synthesized with the condensation method using TMSOTf as a catalyst. Their ability of DPPH radical scavenging activity and DNA polymerase inhibitory activity were also investigated. The results indicated that the galloyl group of these compounds is very important for both activities. 3,3"-Di-O-gallate dimers acted as strong inhibitor against DNA polymerase alpha and beta, whereas the desgalloyl and monogalloyl compounds did not exhibit any appreciable inhibitory activity against the DNA polymerase beta. (c) 2005 Elsevier Ltd. All rights reserved.
• Stilbene glycoside gallates and proanthocyanidins from Polygonum multiflorum
  作者：Gen-Ichiro Nonaka、Naoko Miwa、Itsuo Nishioka

  DOI：10.1016/s0031-9422(00)95282-8

  日期：1982.1

  Two new stilbene glycoside gallates and proanthocyanidins were isolated from P. multiflorum. The stilbenes were 2"- and 3"-O-monogalloyl esters of 2,3,5,4''-tetrahydroxystilbene 2-O-.beta.-D-glucopyranoside.