原花青素三聚体 | 97233-06-2

• 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: 原花青素三聚体
• 英文名称: epicatechin-(2β->O->7, 4β->8)-epicatechin-(4β->8)-catechin
• 英文别名: epicatechin-(4β→8;2β→O→7)-epicatechin-(4β→8)-catechin；cinnamtannin D-1；cinnamtannin D1；(1R,5R,6R,7S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol
• CAS: 97233-06-2
• 化学式: C₄₅H₃₆O₁₈
• 分子量: 864.77
• InChiKey: BYSRPHRKESMCPO-HMQYECKYSA-N

物化性质

• 密度：
  1.789±0.06 g/cm3(Predicted)
• 物理描述：
  Solid
• 熔点：
  300°C

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  63
• 可旋转键数：
  4
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  320
• 氢给体数：
  14
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  原花青素三聚体 在 对甲苯磺酸 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 61.0h， 生成 (2R,3R,4R,8S,14R,15R)-4-((2R,3S)-6-bromo-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychroman-8-yl)-2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-2H,14H-8,14-methanobenzo[7,8][1,3]dioxocino[4,5-h]chromene-3,5,11,13,15-pentaol
  参考文献：
  名称：

  Tannins and related compounds. XXXV. Proanthocyanidins with a doubly linked unit from the root bark of Cinnamomum sieboldii Meisner.

  摘要：

  从月桂科植物 Cinnamomum sieboldii MEISNER 的根皮中分离出了一种原花青素三聚体（1）、两种四聚体（2 和 3）和一种五聚体（4）。通过酸催化硫解降解以及质子和碳 13 核磁共振分析，确定了这些化合物的结构。此外，还证明了该植物中存在(-)-儿茶素（13）、(+)-儿茶素（14）和已知的原花青素 B-1 (5)、B-2 (6)和 B-5 (7)、三聚体（8 和 9）、四聚体（10 和 11）以及五聚体（12）。

  DOI：

  10.1248/cpb.33.4338
• 作为产物：
  描述：

  (2R,3R,4R,8S,14R,15R)-4-((2R,3S)-6-bromo-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychroman-8-yl)-2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-2H,14H-8,14-methanobenzo[7,8][1,3]dioxocino[4,5-h]chromene-3,5,11,13,15-pentaol 在 甲酸 、 锌 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 原花青素三聚体
  参考文献：
  名称：

  Tannins and related compounds. XXXV. Proanthocyanidins with a doubly linked unit from the root bark of Cinnamomum sieboldii Meisner.

  摘要：

  从月桂科植物 Cinnamomum sieboldii MEISNER 的根皮中分离出了一种原花青素三聚体（1）、两种四聚体（2 和 3）和一种五聚体（4）。通过酸催化硫解降解以及质子和碳 13 核磁共振分析，确定了这些化合物的结构。此外，还证明了该植物中存在(-)-儿茶素（13）、(+)-儿茶素（14）和已知的原花青素 B-1 (5)、B-2 (6)和 B-5 (7)、三聚体（8 和 9）、四聚体（10 和 11）以及五聚体（12）。

  DOI：

  10.1248/cpb.33.4338

文献信息

• Inhibited expression of PD-L1 and enhanced expression of PD-1
  申请人：IN Ingredients, Inc.

  公开号：US10478418B2

  公开（公告）日：2019-11-19

  Processes for decreasing expression of a CD274 gene and/or a PD-L1 protein and increasing expression of a PDCD1 gene and/or a PD-1 protein in a subject in need of such expression changes are provided. The processes include administering to the subject a composition including at least 0.5% of cinnamtannin D-1 and/or cinnamtannin B-1. The processes further include decreasing expression of a CD274 gene and/or a PD-L1 protein and increasing expression of a PDCD1 gene and/or a PD-1 protein in the subject by the step of administering at the desired concentration or for the desired time wherein the composition may increase or decrease the relative expression levels of the genes or proteins while simultaneously ameliorating, preventing, or modulating a cardiac event in the subject.

  本发明提供了在需要改变表达的受试者中降低 CD274 基因和/或 PD-L1 蛋白表达和增加 PDCD1 基因和/或 PD-1 蛋白表达的方法。这些过程包括向受试者施用包括至少0.5%肉桂单宁D-1和/或肉桂单宁B-1的组合物。该工艺进一步包括通过以所需浓度或在所需时间内给药的步骤，降低受试者体内 CD274 基因和/或 PD-L1 蛋白的表达，增加 PDCD1 基因和/或 PD-1 蛋白的表达，其中该组合物可增加或降低基因或蛋白的相对表达水平，同时改善、预防或调节受试者的心脏事件。
• Methods and compositions for the inhibition of the expression of PD-L1 in tumor cells
  申请人：IN Ingredients, Inc.

  公开号：US10894030B2

  公开（公告）日：2021-01-19

  Processes for decreasing expression of a CD274 gene and/or a PD-L1 protein in a subject in need of such expression changes are provided. The processes include administering to the subject a composition including at least 0.5% of an active ingredient by weight. The active ingredient includes cinnamtannin D1 and/or cinnamtannin B1. The processes further include decreasing expression of a CD274 gene and/or a PD-L1 protein in the subject by the step of administering.

  本研究提供了降低需要改变表达的受试者体内 CD274 基因和/或 PD-L1 蛋白表达的方法。该工艺包括向受试者施用一种组合物，该组合物包括按重量计至少0.5%的活性成分。活性成分包括肉桂单宁 D1 和/或肉桂单宁 B1。所述过程进一步包括通过给药步骤降低受试者体内 CD274 基因和/或 PD-L1 蛋白的表达。
• Structures and Antioxidant and Intestinal Disaccharidase Inhibitory Activities of A-Type Proanthocyanidins from Peanut Skin
  作者：Huiwen Zhang、Yerigui、Yumei Yang、Chaomei Ma

  DOI：10.1021/jf402518k

  日期：2013.9.18

  Nine compounds including a new A-type proanthocyanidin trimer, epicatechin-(2 beta -> O -> 7,4 beta -> 8)-[catechin-(6 -> 4 beta)]-epicatechin (8), and a known trimer, epicatechin-(4 beta -> 8)-epicatechin-(2 beta -> O -> 7,4 beta -> 8)-catechin (9), being reported for peanut skin for the first time, were isolated and purified. Their structures were determined by spectroscopic methods and by degradation reactions with L-cysteine in acidic conditions. The DPPH radical scavenging activity and the inhibitory activity on maltase and sucrase of the isolated compounds were investigated. All compounds showed strong DPPH scavenging activities (EC50 < 20 mu g/mL). Compound 8 showed the strongest inhibitory activity on maltase with an IC50 value of 0.088 mg/mL, while compound 9 exhibited the strongest inhibition on sucrase with an IC50 value of 0.091 mg/mL.
• Methods and Compositions for the Inhibition of the Expression of PD-L1 in Tumor Cells
  申请人：IN Ingredients, Inc.

  公开号：US20190076393A1

  公开（公告）日：2019-03-14

  Processes for decreasing expression of a CD274 gene and/or a PD-L1 protein in a subject in need of such expression changes are provided. The processes include administering to the subject a composition including at least 0.5% of an active ingredient by weight. The active ingredient includes cinnamtannin D1 and/or cinnamtannin B1. The processes further include decreasing expression of a CD274 gene and/or a PD-L1 protein in the subject by the step of administering.
• Inhibited Expression of PD-L1 and Enhanced Expression of PD-1
  申请人：IN Ingredients, Inc.

  公开号：US20190076397A1

  公开（公告）日：2019-03-14

  Processes for decreasing expression of a CD274 gene and/or a PD-L1 protein and increasing expression of a PDCD1 gene and/or a PD-1 protein in a subject in need of such expression changes are provided. The processes include administering to the subject a composition including at least 0.5% of cinnamtannin D-1 and/or cinnamtannin B-1. The processes further include decreasing expression of a CD274 gene and/or a PD-L1 protein and increasing expression of a PDCD1 gene and/or a PD-1 protein in the subject by the step of administering at the desired concentration or for the desired time wherein the composition may increase or decrease the relative expression levels of the genes or proteins while simultaneously ameliorating, preventing, or modulating a cardiac event in the subject.