(-)-8-(5''S)-N-ethyl-2-pyrrolidinone-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: (-)-8-(5''S)-N-ethyl-2-pyrrolidinone-epicatechin
• 英文别名: (5S)-5-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-1-ethylpyrrolidin-2-one
• 化学式: C₂₁H₂₃NO₇
• 分子量: 401.416
• InChiKey: CLWWYCHTKMHNJB-LCIZUOBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  131
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  茶氨酸 、 表儿茶素 在 甲酸 作用下， 以 甲醇 、 水 为溶剂， 反应 288.0h， 生成 (-)-8-(5''R)-N-ethyl-2-pyrrolidinone-epicatechin 、 (-)-8-(5''S)-N-ethyl-2-pyrrolidinone-epicatechin
  参考文献：
  名称：

  Metabolomics Investigation Reveals That 8-C N-Ethyl-2-pyrrolidinone-Substituted Flavan-3-ols Are Potential Marker Compounds of Stored White Teas

  摘要：

  White teas of different stored ages have varied flavor, bioactivity, and commercial value. In this study, a liquid chromatography-mass spectrometry-based metabolomics investigation revealed that there are distinct differences among the compound patterns of Baihaoyinzhen (BHYZ) and Baimudan (BMD) white teas with various storage durations. The levels of flavan-3-ols, procyanidins, theasinensins, theaflavins, flavonol-O-glycosides, flavone-C-glycosides, and most of the amino acids were reduced after long-term (>4 years) storage. More importantly, 8-C N-ethyl-2-pyrrolidinone-substituted flavan-3-ols (EPSFs), including seven novel compounds discovered in white teas for the first time, were formed from theanine and flavan-3-ols during storage, and their contents were positively correlated with the storage duration. These findings were further confirmed by the linearly increasing formation of EPSFs in reaction solution and BMD white teas stored in an environment-controlled cabinet. In conclusion, EPSFs were detected in white teas for the first time and were discovered as marker compounds and potential indicators for long-term storage of white tea.

  DOI：

  10.1021/acs.jafc.8b02038

文献信息

• Metabolomics Investigation Reveals That 8-C <i>N</i>-Ethyl-2-pyrrolidinone-Substituted Flavan-3-ols Are Potential Marker Compounds of Stored White Teas
  作者：Weidong Dai、Junfeng Tan、Meiling Lu、Yin Zhu、Pengliang Li、Qunhua Peng、Li Guo、Yue Zhang、Dongchao Xie、Zhengyan Hu、Zhi Lin

  DOI：10.1021/acs.jafc.8b02038

  日期：2018.7.11

  White teas of different stored ages have varied flavor, bioactivity, and commercial value. In this study, a liquid chromatography-mass spectrometry-based metabolomics investigation revealed that there are distinct differences among the compound patterns of Baihaoyinzhen (BHYZ) and Baimudan (BMD) white teas with various storage durations. The levels of flavan-3-ols, procyanidins, theasinensins, theaflavins, flavonol-O-glycosides, flavone-C-glycosides, and most of the amino acids were reduced after long-term (>4 years) storage. More importantly, 8-C N-ethyl-2-pyrrolidinone-substituted flavan-3-ols (EPSFs), including seven novel compounds discovered in white teas for the first time, were formed from theanine and flavan-3-ols during storage, and their contents were positively correlated with the storage duration. These findings were further confirmed by the linearly increasing formation of EPSFs in reaction solution and BMD white teas stored in an environment-controlled cabinet. In conclusion, EPSFs were detected in white teas for the first time and were discovered as marker compounds and potential indicators for long-term storage of white tea.