(E)-resveratrol 3,5-O-β-diglucoside

• 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)-resveratrol 3,5-O-β-diglucoside
• 英文别名: (E)-1-(3,5-bis-β-D-glucopyranosyloxyphenyl)-2-(4-hydroxyphenyl)ethene；resveratrol 3,5-di-O-β-D-glucoside；resveratrol 3,5-β-D-diglucoside；3,5-bis-(β-D-glucopyranosyloxy)-4'-hydroxystilbene；trans-resveratrol-3,5-di-O-β-D-glucopyranoside；resveratrol 3,5-di-O-β-D-glucopyranoside；resveratrol-3,5-O-β-D-diglucopyranoside；(E)-resveratrol 3,5-O-β-D-diglucoside；3,5-resveratrol diglucoside；resveratrol-3,5-O-diglucoside (trans-resveratrol-3,5-di-O-β-D-glucopyranoside)；resveratrol-3,5-di-β-D-glucopyranoside；resv-3,5-digluc；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[3-[(E)-2-(4-hydroxyphenyl)ethenyl]-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenoxy]oxane-3,4,5-triol
• 化学式: C₂₆H₃₂O₁₃
• 分子量: 552.532
• InChiKey: LKWXYXPBNAKWNA-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：

  虎杖甙 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 sodium perborate 、 三氟甲磺酸三甲基硅酯 、 Burkholderia cepacia lipase (Amano PS-IM) 、 异丙醇 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 生成 (E)-resveratrol 3,5-O-β-diglucoside
  参考文献：
  名称：

  Synthesis of acacetin and resveratrol 3,5-di-O-β-glucopyranoside using lipase-catalyzed regioselective deacetylation of polyphenol glycoside peracetates as the key step

  摘要：

  Acacetin and re sveratrol 3,5-di-O-beta-glucopyranoside were synthesized from naturally abundant naringin and piceid in 65% and 62% overall yield, respectively. The key steps were the regioselective deacetylation of the peracetates of the glycosylated forms with Candida antarctica lipase B (Novozym 435) and Burkholderia cepacia lipase (Amano PS-IM). Deacetylation occurred exclusively at the least hindered position of the aromatic moieties and all acetyl groups in the sugar side chain remained intact. This excellent selectivity enabled regiospecific transformation of the liberated phenolic hydroxy groups, resulting in efficient synthesis of the target molecules. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2016.03.001

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）。
• COMPOUNDS HAVING ANTI-INFLAMMATORY ACTIVITY
  申请人：Espin De Gea Juan Carlos

  公开号：US20120309699A1

  公开（公告）日：2012-12-06

  Compounds of general formula (I) for the treatment of inflammatory processes involved in numerous diseases such as intestinal inflammatory diseases. The invention moreover refers to compounds included within such general formula and to the procedure of the obtainment thereof.

  通用公式（I）的化合物用于治疗涉及多种疾病的炎症过程，如肠道炎症性疾病。此外，该发明还涉及包含在这种通用公式内的化合物以及其获得方法。
• 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。
• Creating a Water-Soluble Resveratrol-Based Antioxidant by Site-Selective Enzymatic Glucosylation
  作者：Alexander Lepak、Alexander Gutmann、Sandra T. Kulmer、Bernd Nidetzky

  DOI：10.1002/cbic.201500284

  日期：2015.9.7

  Site‐selective 5‐O‐β‐D‐glucosylation of the naturally abundant piceid by an UDP‐glucose‐dependent apple glucosyltransferase was used to prepare the highly water‐soluble resveratrol 3,5‐β‐D‐diglucoside in high yield. The diglucoside was shown to exhibit antioxidant activity similar to that of the unglucosylated resveratrol, which is barely soluble in water.

  位点选择性5- ö -β- d -glucosylation天然丰富苷由UDP-葡萄糖依赖性苹果葡糖的混合物用于制备高度水溶性白藜芦醇3,5-β- d以高收率-diglucoside。该二糖苷显示出与几乎不溶于水的未糖基化白藜芦醇相似的抗氧化活性。
• Preventive Oral Treatment with Resveratrol Pro-prodrugs Drastically Reduce Colon Inflammation in Rodents
  作者：Mar Larrosa、Joao Tomé-Carneiro、María J. Yáñez-Gascón、David Alcántara、María V. Selma、David Beltrán、María T. García-Conesa、Cristina Urbán、Ricardo Lucas、Francisco Tomás-Barberán、Juan C. Morales、Juan Carlos Espín

  DOI：10.1021/jm1007006

  日期：2010.10.28

  There is no pharmaceutical or definitive surgical cure for inflammatory bowel diseases (IBDs). The naturally occurring polyphenol resveratrol exerts anti-inflammatory properties. However, its rapid metabolism diminishes its effectiveness in the colon. The design of prodrugs to targeting active molecules to the colon provides an opportunity for therapy of IBDs. Herein we explore the efficacy of different resveratrol prodrugs and pro-prodrugs to ameliorate colon inflammation in the murine dextran sulfate sodium (DSS) model. Mice fed with a very low dose (equivalent to 10 mg for a 70 kg-person) of either resveratrol-3-O-(6'-O-butanoyl)-beta-D-glucopyranoside (6) or resveratrol-3-O-(6'-O-octanoyl)-beta-D-glucopyranoside (7) did not develop colitis symptoms and improved 6-fold the disease activity index (DAI) compared to resveratrol. Our results indicate that these pro-prodrugs exerted a dual effect: (1) they prevented the rapid metabolism of resveratrol and delivered higher quantities of resveratrol to the colon and (2) they reduced mucosal barrier imbalance and prevented diarrhea, which consequently facilitated the action of the delivered resveratrol in the colon mucosa.