(E)-1-[3-β-D-(glucopyranosyloxy)-5-hydroxyphenyl]-2-(4-β-D-glucopyranosyloxyphenyl)ethene

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-1-[3-β-D-(glucopyranosyloxy)-5-hydroxyphenyl]-2-(4-β-D-glucopyranosyloxyphenyl)ethene
• 英文别名: resveratrol 3,4′-O-di-β-D-glucopyranoside；trans-resveratrol-3,4'-di-O-β-D-glucopyranoside；resveratrol 3,4'-(O,O'-di-β-D-glucopyranoside)；resveratrol 3,4'-O,O'-di-β-D-glucopyranoside；resveratrol 3,4'-di-O-β-D-glucopyranoside；resveratrol-3,4'-di-β-D-glucopyranoside；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-[(E)-2-[3-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]ethenyl]phenoxy]oxane-3,4,5-triol
• 化学式: C₂₆H₃₂O₁₃
• 分子量: 552.532
• InChiKey: YGQPMDDXSJHKJT-VUNDNAJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  219
• 氢给体数：
  9
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  (E)-1-[3-{[tert-butyl(dimethyl)silyl]oxy}-5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyloxy)phenyl]-2-[4-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyloxy)phenyl]ethene 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 以99%的产率得到(E)-1-[3-β-D-(glucopyranosyloxy)-5-hydroxyphenyl]-2-(4-β-D-glucopyranosyloxyphenyl)ethene
  参考文献：
  名称：

  Synthesis of Mono- and Di-O-β-d-glucopyranoside Conjugates of (E)-Resveratrol

  摘要：

  从市售天然产物（E）-白藜芦醇（1）出发，通过一步反应制备了四种选择性叔丁基二甲基硅基（TBS）保护的（E）-白藜芦醇衍生物 6-9。以 6-9 作为糖基受体，三氟乙酰亚胺 11 作为糖基供体，高效地通过两步反应合成了三种具有生物活性的天然葡萄糖苷（E）-白藜芦醇偶联物 2-4 和一个新化合物（5）。

  DOI：

  10.1055/s-2006-926394

文献信息

• Synthesis of Mono- and Di-<i>O</i>-β-<scp>d</scp>-glucopyranoside Conjugates of (<i>E</i>)-Resveratrol
  作者：Zhaojun Zhang、Biao Yu、Richard Schmidt

  DOI：10.1055/s-2006-926394

  日期：2006.4

  Starting from the commercially available natural product (E)-resveratrol (1), the four selectively tert-butyldimethylsilyl (TBS) protected (E)-resveratrols 6-9 were prepared by one reaction. Using 6-9 as glucosyl acceptors and trifluoroacetimidate 11 as glucosyl donor, three bioactive natural glucopyranoside conjugates of (E)-resveratrol 2-4 and one novel compound (5) were efficiently prepared in two steps.

  从市售天然产物（E）-白藜芦醇（1）出发，通过一步反应制备了四种选择性叔丁基二甲基硅基（TBS）保护的（E）-白藜芦醇衍生物 6-9。以 6-9 作为糖基受体，三氟乙酰亚胺 11 作为糖基供体，高效地通过两步反应合成了三种具有生物活性的天然葡萄糖苷（E）-白藜芦醇偶联物 2-4 和一个新化合物（5）。
• Assessing the Regioselectivity of OleD-Catalyzed Glycosylation with a Diverse Set of Acceptors
  作者：Maoquan Zhou、Adel Hamza、Chang-Guo Zhan、Jon S. Thorson

  DOI：10.1021/np300890h

  日期：2013.2.22

  To explore the acceptor regioselectivity of OleD-catalyzed glucosylation, the products of OleD-catalyzed reactions with six structurally diverse acceptors flavones— (daidzein), isoflavones (flavopiridol), stilbenes (resveratrol), indole alkaloids (10-hydroxycamptothecin), and steroids (2-methoxyestradiol)—were determined. This study highlights the first synthesis of flavopiridol and 2-methoxyestradiol

  为了探索 OleD 催化葡萄糖基化的受体区域选择性，OleD 催化反应的产物与六种结构不同的受体黄酮（黄豆苷原）、异黄酮（flavopiridol）、芪（白藜芦醇）、吲哚生物碱（10-羟基喜树碱（10-羟基喜树碱）、 2-甲氧基雌二醇）-测定。该研究重点介绍了黄酮醇和 2-甲氧基雌二醇糖苷的首次合成，并证实了 OleD 对芳香族和脂肪族亲核试剂进行葡萄糖基化的能力。在所有情况下，分子动力学模拟与确定的产品分布一致，并表明开发虚拟筛选模型以识别其他 OleD 底物的潜力。
• Regioselective Glucosylation of Aromatic Compounds: Screening of a Recombinant Glycosyltransferase Library to Identify Biocatalysts
  作者：Markus Weis、Eng-Kiat Lim、Neil Bruce、Dianna Bowles

  DOI：10.1002/anie.200504505

  日期：2006.5.19
• Substrate specificities of family 1 UGTs gained by domain swapping
  作者：Esben Halkjær Hansen、Sarah A. Osmani、Charlotte Kristensen、Birger Lindberg Møller、Jørgen Hansen

  DOI：10.1016/j.phytochem.2009.01.013

  日期：2009.3

  Family 1 glycosyltransferases are a group of enzymes known to embrace a large range of different substrates. This study devises a method to enhance the range of substrates even further by combining domains from different glycosyltransferases to gain improved substrate specificity and catalytic efficiency. Chimeric glycosyltransferases were made by combining domains from seven different family 1 glycosyltransferases, UGT71C1, UGT71C2, UGT71E1, UGT85C1, UGT85B1, UGT88B1 and UGT94B1. Twenty different chimeric glycosyltransferases were formed of which twelve were shown to be catalytically active. The chimeric enzymes of Arabidopsis thaliana UGT71C1 and UGT71C2 showed major changes in acceptor substrate specificity and were able to glycosylate etoposide significantly better than the parental UGT71C1 and UGT71C2 enzymes, with K-cat and efficiency coefficients 3.0 and 2.6 times higher, respectively. Chimeric glycosyltransferases of UGT71C1 combined with Stevia rebaudiana UGT71E1, also afforded enzymes with high catalytic efficiency, even though the two enzymes only display 38% amino acid sequence identity. These chimeras show a significantly altered regiospecificity towards especially trans-resveratrol, enabling the production of trans-resveratrol-beta-4'-O-glucoside (resveratroloside). The study demonstrates that it is possible to obtain improved catalytic properties by combining domains from both closely as well as more distantly related glycosyltransferases. The substrate specificity gained by the chimeras is difficult to predict because factors determining the acceptor specificity reside in the N-terminal as well as the C-terminal domains. (C) 2009 Elsevier Ltd. All rights reserved.
• [EN] COMPOSITION COMPRISING A MORUS ALBA EXTRACT, AND ITS COSMETIC USES<br/>[FR] COMPOSITION COMPRENANT UN EXTRAIT DE MORUS ALBA ET SES UTILISATIONS COSMÉTIQUES
  申请人：OREAL

  公开号：WO2020201432A1

  公开（公告）日：2020-10-08

  The present invention relates to a composition comprising, in a physiologically acceptable medium, at least mulberroside A and mulberroside E. It also relates to cosmetic uses of said composition, especially for depigmenting, lightening and/or bleaching keratin materials, in particular the skin.