2-(4-hydroxyphenyl)ethyl α-D-galactopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-hydroxyphenyl)ethyl α-D-galactopyranoside
• 英文别名: Gal-α-tyr；(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[2-(4-hydroxyphenyl)ethoxy]oxane-3,4,5-triol
• 化学式: C₁₄H₂₀O₇
• 分子量: 300.309
• InChiKey: ILRCGYURZSFMEG-HTOAHKCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  120
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  蜜二糖 、 对羟基苯乙醇 在 α-galactosidase from A. oryzae 作用下， 以 aq. buffer 为溶剂， 反应 1.0h， 生成 2-(4-hydroxyphenyl)ethyl α-D-galactopyranoside
  参考文献：
  名称：

  Comparative study of relationship between structure of phenylethanoid glycopyranosides and their activities using cell-free assays and human cells cultured in vitro

  摘要：

  The study focused on protective potential of phytochemicals applicable in prevention and health protection is of great importance. Various structures of these compounds and a wide range of their biological activities have inspired organic chemists to sythesize their effective analogues in order to further increase their efficacy.The aims of our study were (i) to synthesize phenylethanoid glycopyranosides: salidroside (SALI - tyrosol beta-Dglucopyranoside), tyrosol beta-D-galactopyranoside (TYBGAL), tyrosol alpha-D-galactopyranoside (TYAGAL), tyrosol alpha-D-mannopyranoside (TYAMAN), hydroxytyrosol alpha-D-mannopyranoside (HOTAMA), homosyringyl beta-D-glucopyranoside (HSYGLU), hydroxytyrosol beta-D-xylopyranoside (HOTXYL) and hydroxysalidroside (HOSALI); (ii) to determine their antioxidant capacities (cell-free approaches); (iii) to evaluate their cytotoxicity (MTT test), protectivity against hydrogen peroxide (H2O2; comet assay) and effect on the intracellular glutathione level (iGSH; flow cytometry) in experimental system utilizing human hepatoma HepG2 cells.HOSALI, HOTAMA, HOTXYL and HSYGLU manifested the highest antioxidant capacity in cell-free assays and they were most active in protection of HepG2 cells against H2O2. On the other hand, pre-treatment of HepG2 cells with SALI had protective effects even though SALT displayed almost no activity in cell-free assays.Differences in the efficacy of the analogues revealed that structures of their molecules in terms of aglycone combined with sugar moiety affect their activities.

  DOI：

  10.1016/j.tiv.2019.104646

文献信息

• Biotransformation of Tyrosol into a Novel Valuable α-Galactoside with Increased Solubility and Improved Anti-inflammatory Activities
  作者：Tong Sun、Yan Liu、Ke Wang、Feiyu Duan、Lili Lu

  DOI：10.1021/acs.jafc.3c02529

  日期：2023.6.28

  of galactoside synthesis. Moreover, the galactoside showed 11-fold increased water solubility and reduced cytotoxicity as compared to tyrosol. Also, it exhibited higher antioxidative and anti-inflammatory activities than tyrosol based on lipopolysaccharide-induced activated BV2 cells. These results provided important insights into the application of tyrosol derivatives in functional foods.

  在此，橄榄油和红酒中富含的酪醇[2-(4-羟基苯基)乙醇]通过酶糖基化被转化为新型生物活性半乳糖苷。克隆了嗜热脂肪地芽孢杆菌23的 α-半乳糖苷酶基因，并在大肠杆菌中以催化活性包涵体的形式表达。使用蜜二糖或棉子糖家族寡糖作为糖基供体，催化活性包涵体有效催化酪醇的半乳糖基化，产生产率为 42.2% 或 14.2% 的糖苷。糖苷产物经纯化鉴定为对羟基苯乙基α- d-通过质谱和NMR分析的吡喃半乳糖苷。包涵体可以回收并重新用于至少10个半乳糖苷合成的间歇反应。此外，与酪醇相比，半乳糖苷的水溶性增加了 11 倍，细胞毒性降低。此外，它在脂多糖诱导的活化 BV2 细胞中表现出比酪醇更高的抗氧化和抗炎活性。这些结果为酪醇衍生物在功能食品中的应用提供了重要的见解。
• Enzymatic synthesis of tyrosol glycosides
  作者：Elena Potocká、Mária Mastihubová、Vladimír Mastihuba

  DOI：10.1016/j.molcatb.2014.12.017

  日期：2015.3

  For the purpose of synthesis of tyrosol beta-D-glucopyranoside (salidroside) and its beta-D- and alpha-D-galactopyranoside analogues, transglycosylation of tyrosol with fungal glycosidases (from Aspergillus niger and Aspergillus oryzae) was executed. Cellobiose, lactose and melibiose served as glycosyl donor giving 6.7% yield of salidroside, 10.9% of tyrosol beta-D-galactopyranoside, and 32.2% of alpha-D-galactopyranoside. The glycosylations proceeded on the primary hydroxyl of the tyrosol. (C) 2015 Elsevier B.V. All rights reserved.
• Comparative study of relationship between structure of phenylethanoid glycopyranosides and their activities using cell-free assays and human cells cultured in vitro
  作者：Eva Horvathova、Maria Mastihubova、Elena Karnisova Potocka、Peter Kis、Eliska Galova、Andrea Sevcovicova、Martina Klapakova、Luba Hunakova、Vladimir Mastihuba

  DOI：10.1016/j.tiv.2019.104646

  日期：2019.12

  The study focused on protective potential of phytochemicals applicable in prevention and health protection is of great importance. Various structures of these compounds and a wide range of their biological activities have inspired organic chemists to sythesize their effective analogues in order to further increase their efficacy.The aims of our study were (i) to synthesize phenylethanoid glycopyranosides: salidroside (SALI - tyrosol beta-Dglucopyranoside), tyrosol beta-D-galactopyranoside (TYBGAL), tyrosol alpha-D-galactopyranoside (TYAGAL), tyrosol alpha-D-mannopyranoside (TYAMAN), hydroxytyrosol alpha-D-mannopyranoside (HOTAMA), homosyringyl beta-D-glucopyranoside (HSYGLU), hydroxytyrosol beta-D-xylopyranoside (HOTXYL) and hydroxysalidroside (HOSALI); (ii) to determine their antioxidant capacities (cell-free approaches); (iii) to evaluate their cytotoxicity (MTT test), protectivity against hydrogen peroxide (H2O2; comet assay) and effect on the intracellular glutathione level (iGSH; flow cytometry) in experimental system utilizing human hepatoma HepG2 cells.HOSALI, HOTAMA, HOTXYL and HSYGLU manifested the highest antioxidant capacity in cell-free assays and they were most active in protection of HepG2 cells against H2O2. On the other hand, pre-treatment of HepG2 cells with SALI had protective effects even though SALT displayed almost no activity in cell-free assays.Differences in the efficacy of the analogues revealed that structures of their molecules in terms of aglycone combined with sugar moiety affect their activities.