threo-guaiacylglycerol-β-coniferyl ether

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: threo-guaiacylglycerol-β-coniferyl ether
• 英文别名: treo-3,3'-dimethoxy-4,8'-oxyneoligna-9,4',7',9'-tetraol-7(8)-ene；(1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxyprop-1-enyl)-2-methoxyphenoxy]propane-1,3-diol
• 化学式: C₂₀H₂₄O₇
• 分子量: 376.406
• InChiKey: FYEZJIXULOZDRT-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  109
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  松柏醇 在 双氧水 、 horseradish peroxidase 作用下， 以 aq. phosphate buffer 为溶剂， 反应 5.5h， 以7.2 μmol的产率得到threo-guaiacylglycerol-β-coniferyl ether
  参考文献：
  名称：

  In Vitro Activity-Guided Identification of Antioxidants in Aged Garlic Extract

  摘要：

  Activity-guided fractionation was applied on an aged garlic extract (AGE), reported to show strong antioxidant activity, in order to locate the key in vitro antioxidant ingredients by means of the hydrogen peroxide scavenging (HPS) assay as well as the ORAC assay. Besides the previously reported four tetrahydro-beta-carbolines, (1R,3S)- and (1S,3S)-1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid and (1R,3S)- and (1S,3S)-1-methyl-1,2,3,4-tetrahydro-beta-carboline-1,3-dicarboxylic acid, LC-MS/MS, LC-TOF-MS, and 1D/2D-NMR experiments led to the identification of coniferyl alcohol and its dilignols (-)-(2R,3S)-dihydrodehydrodiconiferyl alcohol, (+)-(2S,3R)-dehydrodiconiferyl alcohol, erythro-guaiacylglycerol-beta-O-4'-coniferyl ether, and threo-guaiacylglycerol-beta-O-4'-coniferyl ether as the major antioxidants in AGE. The purified individual compounds showed high antioxidant activity, with EC50 values of 9.7-11.8 mu M (HPS assay) and 2.60-3.65 mu mol TE/mu mol (ORAC assay), respectively.

  DOI：

  10.1021/jf305549g

文献信息

• Biomimetic Oxidation of Monolignol Acetate and <i>p</i>-Coumarate by Silver Oxide in 1,4-Dioxane
  作者：Ayana Yamashita、Takao Kishimoto、Masahiro Hamada、Noriyuki Nakajima、Daisuke Urabe

  DOI：10.1021/acs.jafc.9b07682

  日期：2020.2.19

  Lignin acylated with acetate and/or p-coumarate is common in many herbaceous plants. Herein, the biomimetic oxidation of γ-acylated monolignols with Ag2O was studied to understand the effect of γ-acyl groups on monolignol polymerization. The oxidation of sinapyl acetate gave γ-acylated and α-acylated β-O-4 dimers in 71 and 9.5% yields, respectively. The oxidation of sinapyl p-coumarate produced γ-acylated

  用乙酸盐和/或对香豆酸盐酰化的木质素在许多草本植物中很常见。在本文中，研究了用Ag2O仿生氧化γ-酰化的单木质醇，以了解γ-酰基对单木质醇聚合的影响。乙酸芥子酸酯的氧化分别以71和9.5％的产率得到γ-酰化的和α-酰化的β-O-4二聚体。芥子酸对香豆酸酯的氧化分别以53％和16％的产率产生了γ-酰化的β-O-4和γ-酰化的四氢化萘β-β二聚体。仅对-香豆酸酯中的芥子醇部分反应，并且对-香豆酸酯部分保持不变，这表明对香豆酸未结合到酰化的木质素中的木质素主链中。本研究中使用的所有γ-酰化单木酚均生成γ-酰化的β-O-4二聚体，这表明γ-酰化的单木酚充当木质素单体。
• In Vitro Activity-Guided Identification of Antioxidants in Aged Garlic Extract
  作者：Toshiaki Matsutomo、Timo D. Stark、Thomas Hofmann

  DOI：10.1021/jf305549g

  日期：2013.3.27

  Activity-guided fractionation was applied on an aged garlic extract (AGE), reported to show strong antioxidant activity, in order to locate the key in vitro antioxidant ingredients by means of the hydrogen peroxide scavenging (HPS) assay as well as the ORAC assay. Besides the previously reported four tetrahydro-beta-carbolines, (1R,3S)- and (1S,3S)-1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid and (1R,3S)- and (1S,3S)-1-methyl-1,2,3,4-tetrahydro-beta-carboline-1,3-dicarboxylic acid, LC-MS/MS, LC-TOF-MS, and 1D/2D-NMR experiments led to the identification of coniferyl alcohol and its dilignols (-)-(2R,3S)-dihydrodehydrodiconiferyl alcohol, (+)-(2S,3R)-dehydrodiconiferyl alcohol, erythro-guaiacylglycerol-beta-O-4'-coniferyl ether, and threo-guaiacylglycerol-beta-O-4'-coniferyl ether as the major antioxidants in AGE. The purified individual compounds showed high antioxidant activity, with EC50 values of 9.7-11.8 mu M (HPS assay) and 2.60-3.65 mu mol TE/mu mol (ORAC assay), respectively.