4-hydroxy-3-methoxycinnamyl β-D-glucopyranoside | 65995-51-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-hydroxy-3-methoxycinnamyl β-D-glucopyranoside
• 英文别名: isoconiferin；citrusin D；3-(4-Hydroxy-3-methoxyphenyl)-2-propen-1-yl I(2)-D-glucopyranoside；(2R,3R,4S,5S,6R)-2-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 65995-51-9
• 化学式: C₁₆H₂₂O₈
• 分子量: 342.346
• InChiKey: JOIDTHZGWZZGMU-IBEHDNSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  129
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-methoxycinnamyl β-D-glucopyranoside 在 laccase from Trametes versicolor 作用下， 以 aq. acetate buffer 为溶剂， 以34%的产率得到
  参考文献：
  名称：

  Laccase-catalyzed dimerization of glycosylated lignols

  摘要：

  Phenylpropanoid glucosides (PPGs) are naturally occurring and bioactive phenolic derivatives, largely distributed in plants. In this work different PPGs have been chemically or enzymatically synthesized from the lignols coniferyl and p-coumaryl alcohols as substrates for a lactase-catalyzed oxidative coupling. The biooxidation of these PPGs has been investigated here and novel dihydrobenzofuran-based structurally modified analogues have been isolated and characterized. Specifically, the presence of a carbohydrate moiety increased the water solubility of these compounds and reduced the number of dimeric products, as pinoresinol-like structures could not be formed. Looking for a possible sugar-promoted stereochemical enrichment of the obtained diastereomeric mixtures of dimers, different carbohydrate moieties (D-glucose, L-glucose and the disaccharide rutinose) were considered and the respective d.e. values of the dimeric products were measured by H-1 NMR and HPLC. However, it was found that the sugar substituent had a minor effect on the stereochemical outcome of the radical coupling reactions, the best measured result being a d.e. value of 21%. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2016.10.019
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰-β-D-吡喃葡萄糖 在 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 sodium methylate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 1.91h， 生成 4-hydroxy-3-methoxycinnamyl β-D-glucopyranoside
  参考文献：
  名称：

  Laccase-catalyzed dimerization of glycosylated lignols

  摘要：

  Phenylpropanoid glucosides (PPGs) are naturally occurring and bioactive phenolic derivatives, largely distributed in plants. In this work different PPGs have been chemically or enzymatically synthesized from the lignols coniferyl and p-coumaryl alcohols as substrates for a lactase-catalyzed oxidative coupling. The biooxidation of these PPGs has been investigated here and novel dihydrobenzofuran-based structurally modified analogues have been isolated and characterized. Specifically, the presence of a carbohydrate moiety increased the water solubility of these compounds and reduced the number of dimeric products, as pinoresinol-like structures could not be formed. Looking for a possible sugar-promoted stereochemical enrichment of the obtained diastereomeric mixtures of dimers, different carbohydrate moieties (D-glucose, L-glucose and the disaccharide rutinose) were considered and the respective d.e. values of the dimeric products were measured by H-1 NMR and HPLC. However, it was found that the sugar substituent had a minor effect on the stereochemical outcome of the radical coupling reactions, the best measured result being a d.e. value of 21%. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2016.10.019

文献信息

• Synthesis of Some Phenylpropanoid Glycosides (PPGs) and Their Acetylcholinesterase/Xanthine Oxidase Inhibitory Activities
  作者：Xiao-Dong Li、Shuai-Tao Kang、Guo-Yu Li、Xian Li、Jin-Hui Wang

  DOI：10.3390/molecules16053580

  日期：——

  In this research, three categories of phenylpropanoid glycosides (PPGs) were designed and synthesized with PPGs isolated from Rhodiola rosea L. as lead compounds. Their inhibitory abilities toward acetylcholinesterase (AChE) and xanthine oxidase (XOD) were also tested. Some of the synthetic PPGs exhibited excellent enzyme inhibitory abilities.

  在这项研究中，设计和合成了三类苯丙素糖苷（PPGs），以从红景天中分离的PPGs作为先导化合物。同时测试了它们对乙酰胆碱酯酶（AChE）和黄嘌呤氧化酶（XOD）的抑制能力。部分合成PPGs表现出了优异的酶抑制能力。
• Synthesis of Alkyl β -Glucosides by Transglucosylation Using Pyrococcus furiosus β -Glucosidase Immobilized onto Gelatin Gel
  作者：Yoh-ichi Matsushita、Hidetaka Nagatomo、Kazuhiro Sugamoto、Takanao Matsui

  DOI：10.2174/157017809787582762

  日期：2009.3.1

  Synthesis of alkyl β-glucosides such as p-anisyl β-D-glucopyranoside, phenethyl β-D-glucopyranoside, salidroside, cinnamyl β-D-glucopyranoside, citrusin D, 3-methylbutyl β-D-glucopyranoside, 3-methyl-2-butenyl β-Dglucopyranoside, geranyl β-D-glucopyranoside, perilloside A, and cyclohexyl β-D-glucopyranoside was accomplished in moderate yields by transglucosylation using hyperthermostable Pyrococcus furiosus β-glucosidase immobilized onto gelatin gel. Recovered immobilisate was reusable on successive runs in transglucosylation.

  合成烷基 β-吡喃葡萄糖苷，如对甲氧基苯甲酰 β-D-吡喃葡萄糖苷、苯乙基 β-D-吡喃葡萄糖苷、水杨梅苷、肉桂基 β-D-吡喃葡萄糖苷、柑橘苷 D、3-甲基丁基 β-D-吡喃葡萄糖苷、3-甲基-2-丁烯基 β-D-吡喃葡萄糖苷、使用固定在明胶凝胶上的超恒温 Pyrocmostable Furiosus β-葡萄糖苷酶，以中等产量完成了β-D-吡喃葡萄糖苷、香叶基 β-D-吡喃葡萄糖苷、紫苏糖苷 A 和环己基 β-D-吡喃葡萄糖苷的转葡糖基化。回收的固定化物可在连续的反式葡萄糖基化过程中重复使用。