erythro-(7R,8S)-guaiacylglycerol β-O-4'-coniferyl alcohol 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: erythro-(7R,8S)-guaiacylglycerol β-O-4'-coniferyl alcohol ether
• 英文别名: erythro-guaiacylglycerol-β-O-4′-coniferyl ether；7R,8S-guaiacylglycerol-8-O-4'-(coniferyl alcohol) ether；(1R,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-VQTJNVASSA-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

• 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.