4-β-(S-cysteinyl)epicatechin

• 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: 4-β-(S-cysteinyl)epicatechin
• 英文别名: 4β-(S-L-cysteinyl)-(-)-epicatechin；(2R)-2-azaniumyl-3-[[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]sulfanyl]propanoate
• 化学式: C₁₈H₁₉NO₈S
• 分子量: 409.417
• InChiKey: ZHFDCDCPUIRJFV-VCUZQBHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  199
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  epicatechin-(2β→O→7,4β→8)-[catechin-(6→4β)]-epicatechin 、 L-半胱氨酸盐酸盐无水物 以 甲醇 为溶剂， 反应 24.0h， 生成 原花青素A1 、 4-β-(S-cysteinyl)epicatechin
  参考文献：
  名称：

  Structures and Antioxidant and Intestinal Disaccharidase Inhibitory Activities of A-Type Proanthocyanidins from Peanut Skin

  摘要：

  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.

  DOI：

  10.1021/jf402518k

文献信息

• SULFUR-CONTAINING PROANTHOCYANIDIN OLIGOMER COMPOSITION AND PRODUCTION METHOD THEREOF
  申请人：NONAKA Gen-ichiro

  公开号：US20110021792A1

  公开（公告）日：2011-01-27

  Provided are: method of producing a sulfur-containing proanthocyanidin oligomer by reducing the molecular weight of proanthocyanidin in plants so that they can be readily absorbed through the intestine of an organism; and a health food composition and a pharmaceutical composition which contain the resultant sulfur-containing proanthocyanidin oligomer as an active ingredient and which are useful for treating and preventing various lifestyle-related diseases and brain diseases caused by generation of active oxygen species as well as for preventing aging.
• US7833553B2
  申请人：——

  公开号：US7833553B2

  公开（公告）日：2010-11-16
• US7939116B2
  申请人：——

  公开号：US7939116B2

  公开（公告）日：2011-05-10
• US8088419B2
  申请人：——

  公开号：US8088419B2

  公开（公告）日：2012-01-03
• 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.