(E)-2-(3-methyl-2-buten-1-yl)-3,4',5-trihydroxystilbene | 868611-44-3

• 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)-2-(3-methyl-2-buten-1-yl)-3,4',5-trihydroxystilbene
• 英文别名: (E)-5-(4-hydroxystyryl)-4-(3-methylbut-2-en-1-yl)benzene-1,3-diol；2-C-prenyl resveratrol；trans-2-C-prenylresveratrol；(e)-3,5,4'-Trihydroxy-2-prenylstilbene；5-[(E)-2-(4-hydroxyphenyl)ethenyl]-4-(3-methylbut-2-enyl)benzene-1,3-diol
• CAS: 868611-44-3
• 化学式: C₁₉H₂₀O₃
• 分子量: 296.366
• InChiKey: YALYFPINNOJDOZ-QPJJXVBHSA-N

物化性质

• 沸点：
  487.3±14.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-甲基丁-2-烯基膦酰磷酸氢酯 、 白藜芦醇 在 Tris-HCl buffer 作用下， 生成 (E)-2-(3-methyl-2-buten-1-yl)-3,4',5-trihydroxystilbene
  参考文献：
  名称：

  Chemoenzymatic syntheses of prenylated aromatic small molecules using Streptomyces prenyltransferases with relaxed substrate specificities

  摘要：

  NphB is a soluble prenyltransferase from Streptomyces sp. strain CL190 that attaches a geranyl group to a 1,3,6,8-tetrahydroxynaphthalene-derived polyketide during the biosynthesis of anti-oxidant naphterpin. Here we report multiple chemoenzymatic syntheses of various prenylated compounds from aromatic substrates including flavonoids using two prenyltransferases NphB and SCO7190, a NphB homolog from Streptomyces coelicolor A3( 2), as biocatalysts. NphB catalyzes carbon-carbon-based and carbon-oxygen-based geranylation of a diverse collection of hydroxyl-containing aromatic acceptors. Thus, this simple method using the prenyltransferases can be used to explore novel prenylated aromatic compounds with biological activities. Kinetic studies with NphB reveal that the prenylation reaction follows a sequential ordered mechanism. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.052
• 作为试剂：
  描述：

  次黄嘌呤 在 xanthine oxidase 乙二胺四乙酸 、 (E)-2-(3-methyl-2-buten-1-yl)-3,4',5-trihydroxystilbene 、 sodium 3,3'-<1-<(phenylamino)carbonyl>-3,4-tetrazolium>-bis(4-methoxy-6-nitro)benzenesulfonic acid 作用下， 以 水 为溶剂， 生成 尿酸
  参考文献：
  名称：

  [EN] BIOLOGICALLY-ACTIVE STILBENE DERIVATIVES AND COMPOSITIONS THEREOF
  [FR] DÉRIVÉS DE STILBÈNE BIOLOGIQUEMENT ACTIFS ET LEURS COMPOSITIONS

  摘要：

  本发明涉及一种具有广泛生物活性的苯乙烯衍生物，特别是具有抗癌、抗氧化和抗炎活性，包含这些化合物的药物和营养补充剂组合物以及它们作为治疗剂或营养补充剂的用途。

  公开号：

  WO2009012910A1

文献信息

• Catalytic prenylation of natural polyphenols
  作者：Yi Du、Iman Korchi、Aleksandr E. Rubtsov、Andrei V. Malkov

  DOI：10.1039/d3nj04371a

  日期：——

  Prenylated polyphenols occur naturally and exhibit biological activity superior to the ubiquitous parent polyphenols. However, their low abundance limits the wider application of these derivatives. In this work, we present an expedient, single-step catalytic protocol for introducing terpene fragments into the aromatic rings of the widely available natural stilbenoids and flavonoids to upgrade their

  异戊二烯化多酚天然存在，并表现出优于普遍存在的母体多酚的生物活性。然而，它们的低丰度限制了这些衍生物的更广泛应用。在这项工作中，我们提出了一种便捷的单步催化方案，用于将萜烯片段引入广泛使用的天然二苯乙烯类化合物和黄酮类化合物的芳环中，以提高其治疗潜力。
• Hepatoprotective Activity and Mechanisms of Prenylated Stilbenoids
  作者：Bailin Li、Shengtao Bo、Zhili Sheng、Hong Zhu、Yueming Jiang、Bao Yang

  DOI：10.1021/acs.jafc.3c09515

  日期：2024.1.24
• Chemoenzymatic syntheses of prenylated aromatic small molecules using Streptomyces prenyltransferases with relaxed substrate specificities
  作者：Takuto Kumano、Stéphane B. Richard、Joseph P. Noel、Makoto Nishiyama、Tomohisa Kuzuyama

  DOI：10.1016/j.bmc.2008.07.052

  日期：2008.9

  NphB is a soluble prenyltransferase from Streptomyces sp. strain CL190 that attaches a geranyl group to a 1,3,6,8-tetrahydroxynaphthalene-derived polyketide during the biosynthesis of anti-oxidant naphterpin. Here we report multiple chemoenzymatic syntheses of various prenylated compounds from aromatic substrates including flavonoids using two prenyltransferases NphB and SCO7190, a NphB homolog from Streptomyces coelicolor A3( 2), as biocatalysts. NphB catalyzes carbon-carbon-based and carbon-oxygen-based geranylation of a diverse collection of hydroxyl-containing aromatic acceptors. Thus, this simple method using the prenyltransferases can be used to explore novel prenylated aromatic compounds with biological activities. Kinetic studies with NphB reveal that the prenylation reaction follows a sequential ordered mechanism. (C) 2008 Elsevier Ltd. All rights reserved.
• [EN] BIOLOGICALLY-ACTIVE STILBENE DERIVATIVES AND COMPOSITIONS THEREOF<br/>[FR] DÉRIVÉS DE STILBÈNE BIOLOGIQUEMENT ACTIFS ET LEURS COMPOSITIONS
  申请人：UNIV DEGLI STUDI MILANO

  公开号：WO2009012910A1

  公开（公告）日：2009-01-29

  The invention relates to stilbene derivatives displaying a large spectrum of biological activities, particularly anti-cancer, antioxidant and antiinflammatory activities, pharmaceutical and nutraceutical compositions containing such compounds and their uses as therapeutic agents or nutritional supplements.

  本发明涉及一种具有广泛生物活性的苯乙烯衍生物，特别是具有抗癌、抗氧化和抗炎活性，包含这些化合物的药物和营养补充剂组合物以及它们作为治疗剂或营养补充剂的用途。