1-(3,4-dihydroxyphenyl)-ethan-2-ol elenolic acid ester | 50915-70-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-(3,4-dihydroxyphenyl)-ethan-2-ol elenolic acid ester
• 英文别名: 3,4-dihydroxyphenylethanol-elenolic acid；oleuropein aglycone；3,4-DHPEA-EA；methyl (2S,3S,4S)-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl]-3-formyl-2-methyl-3,4-dihydro-2H-pyran-5-carboxylate
• CAS: 50915-70-3
• 化学式: C₁₉H₂₂O₈
• 分子量: 378.379
• InChiKey: DEBZOPZQKONWTK-FPMFFAJLSA-N

物化性质

• 沸点：
  559.4±50.0 °C(Predicted)
• 密度：
  1.329±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  oleuropein 在 β-Glycosidase 作用下， 生成 1-(3,4-dihydroxyphenyl)-ethan-2-ol elenolic acid ester
  参考文献：
  名称：

  Powerful Protective Role of 3,4-Dihydroxyphenylethanol−Elenolic Acid Dialdehyde against Erythrocyte Oxidative-Induced Hemolysis

  摘要：

  The present work studied and compared the capacity of four important olive oil polyphenolic compounds, oleuropein, hydroxytyrosol, and the oleuropein aglycones 3,4-dihydroxyphenylethanol-elenolic acid (3,4-DHPEA-EA) and 3,4-dihydroxyphenylethanol-elenolic acid dialdehyde (3,4-DHPEA-EDA), to protect red blood cells (RBCs) from oxidative hemolysis induced by the physiological initiator H2O2. The amount of hemolysis was evaluated spectrophotometrically. The compounds were also tested in the presence and absence of the naturally occurring antioxidant ascorbic acid. All compounds were revealed to significantly protect RBCs from oxidative hemolysis induced by H2O2 at 40 and 80 mu M, with the order of activity being 3,4-DHPEA-EDA > 3,4-DHPEA-EA > hydroxytyrosol = oleuropein. At 20, 10, and 5 mu M, only 3,4-DHPEA-EDA showed a significant protection against the oxidative injury. In the presence of ascorbic acid at physiological concentration, the addition of individual compounds at 40 mu M increased the stability of erythrocytes. The addition of phenolic compounds at 20 and 10 mu M did not produce further protection when compared with the protection given by ascorbic acid alone, except for 3,4-DHPEA-EDA. This compound was shown to produce further protection even at 5 mu M. In summary, 3,4-DHPEA-EDA plays an important protective role against reactive oxygen species-induced oxidative injury in RBCs, and this effect is more potent than the one evidenced by hydroxytyrosol or oleuropein.

  DOI：

  10.1021/jf9031052

文献信息

• Antioxidant Activity of the Main Bioactive Derivatives from Oleuropein Hydrolysis by Hyperthermophilic β-Glycosidase
  作者：Raffaella Briante、Francesco La Cara、Maria Pia Tonziello、Ferdinando Febbraio、Roberto Nucci

  DOI：10.1021/jf001342r

  日期：2001.7.1

  The main reaction products obtainable by the hydrolysis of commercially available oleuropein by hyperthermophilic beta -glycosidase were purified and structurally characterized by UV and H-1 and C-13 NMR analyses. Their antioxidant activity, in particular their capacity to inhibit the fatty acid peroxidation rate, was studied. The molecular structures assigned revealed the presence of two elenolic acid forms presenting different antioxidant abilities closely correlated to their molecular structures, as well as an unstable elenolate which is a rearrangement product of the oleuropein aglycon. This molecule, under the reaction conditions (pH 7.0, 60 degreesC) required for beta -glycosidase activity, rapidly gives rise to 3,4-dihydroxy-phenylethanol (hydroxytyrosol).
• Powerful Protective Role of 3,4-Dihydroxyphenylethanol−Elenolic Acid Dialdehyde against Erythrocyte Oxidative-Induced Hemolysis
  作者：Fátima Paiva-Martins、João Fernandes、Vera Santos、Lisete Silva、Fernanda Borges、Susana Rocha、Luis Belo、Alice Santos-Silva

  DOI：10.1021/jf9031052

  日期：2010.1.13

  The present work studied and compared the capacity of four important olive oil polyphenolic compounds, oleuropein, hydroxytyrosol, and the oleuropein aglycones 3,4-dihydroxyphenylethanol-elenolic acid (3,4-DHPEA-EA) and 3,4-dihydroxyphenylethanol-elenolic acid dialdehyde (3,4-DHPEA-EDA), to protect red blood cells (RBCs) from oxidative hemolysis induced by the physiological initiator H2O2. The amount of hemolysis was evaluated spectrophotometrically. The compounds were also tested in the presence and absence of the naturally occurring antioxidant ascorbic acid. All compounds were revealed to significantly protect RBCs from oxidative hemolysis induced by H2O2 at 40 and 80 mu M, with the order of activity being 3,4-DHPEA-EDA > 3,4-DHPEA-EA > hydroxytyrosol = oleuropein. At 20, 10, and 5 mu M, only 3,4-DHPEA-EDA showed a significant protection against the oxidative injury. In the presence of ascorbic acid at physiological concentration, the addition of individual compounds at 40 mu M increased the stability of erythrocytes. The addition of phenolic compounds at 20 and 10 mu M did not produce further protection when compared with the protection given by ascorbic acid alone, except for 3,4-DHPEA-EDA. This compound was shown to produce further protection even at 5 mu M. In summary, 3,4-DHPEA-EDA plays an important protective role against reactive oxygen species-induced oxidative injury in RBCs, and this effect is more potent than the one evidenced by hydroxytyrosol or oleuropein.