β-[4-[(1E)-2-(3,5-dimethoxyphenyl)-ethenyl]phenoxy]-α-(4-hydroxyphenyl)-3,5-dimethoxybenzeneethanol | 952418-33-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: β-[4-[(1E)-2-(3,5-dimethoxyphenyl)-ethenyl]phenoxy]-α-(4-hydroxyphenyl)-3,5-dimethoxybenzeneethanol
• 英文别名: (E)-4-{2-(3,5-dimethoxyphenyl)-2-[4-(3,5-dimethoxystyryl)phenoxy]-1-hydroxyethyl}phenol；4-[2-(3,5-dimethoxyphenyl)-2-[4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenoxy]-1-hydroxyethyl]phenol
• CAS: 952418-33-6
• 化学式: C₃₂H₃₂O₇
• 分子量: 528.602
• InChiKey: QBLHFYFNTARLAL-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  紫檀芪 在 horseradish peroxidase type II 、 双氧水 作用下， 生成 4-{3-(3,5-Dimethoxy-phenyl)-5-[(E)-2-(3,5-dimethoxy-phenyl)-vinyl]-2,3-dihydro-benzofuran-2-yl}-phenol 、 β-[4-[(1E)-2-(3,5-dimethoxyphenyl)-ethenyl]phenoxy]-α-(4-hydroxyphenyl)-3,5-dimethoxybenzeneethanol 、 4-[3-(3,5-dimethoxyphenyl)-5-[(Z)-2-(3,5-dimethoxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-2-yl]phenol
  参考文献：
  名称：

  Kinetic mechanism and product characterization of the enzymatic peroxidation of pterostilbene as model of the detoxification process of stilbene-type phytoalexins

  摘要：

  The enzymatic peroxidation of pterostilbene, a strong antifungal belonging to the stilbene family, by peroxidase (POX), is reported for the first time as a model of phytoalexin detoxification carried out by the enzymatic pool of pathogens. Kinetic characterization of the pterostilbene oxidation reaction pointed to an optimum pH of 7.0, at which value the thermal stability of POX was studied. Moreover, the data showed that pterostilbene inhibits POX activity at high concentrations of substrate. Several kinetic parameters, including V-max K-m and K-I, were calculated and values of 0.16 Delta Abs min(-1), 14.61 mu M, and 31.41 mu M were reported. To understand the possible physiological role of this reaction in the phytoalexin detoxification process, the products of pterostilbene oxidation were identified using HPLC-MS and a radical-radical coupling reaction mechanism was proposed. Three main products with a high molecular weight and pronounced hydrophobicity were identified: pterostilbene cis dehydromer, pterostilbene trans dehydromer and pterostilbene open dimer. The dimeric structures of these molecules indicate that the pterostilbene oxidation reaction took place at the 4'-OH position of the hydroxystilbenic moieties and the three above mentioned dimeric products were found, due to the ability of electron-delocalized radicals to couple at various sites. Finally, the capacity of cyclodextrins (CDs) as starch model molecules in plants to complex both the substrate and the products of the oxidation reaction was evaluated. The inhibition process of POX activity was modified at high pterostilbene concentrations due to sequestering of the substrate reaction and to the different affinity of the reaction products for CDs. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2010.10.009

文献信息

• [EN] ANTI-BACTERIAL AND ANTI-VIRAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIBACTÉRIENS ET ANTIVIRAUX
  申请人：UNIV GENEVE

  公开号：WO2021219664A1

  公开（公告）日：2021-11-04

  The invention relates to anti-bacterial and/or anti-viral compounds and agents as well as their uses in the treatment or prevention of bacterial and/or viral infections. The invention also provides a method for prevention, alleviation, and/or treatment of bacterial and/or viral infections comprising applying the anti-bacterial and/or anti-viral compounds or agents of the invention to a subject in need thereof.

  该发明涉及抗菌和/或抗病毒化合物和药剂，以及它们在治疗或预防细菌和/或病毒感染方面的用途。该发明还提供了一种预防、缓解和/或治疗细菌和/或病毒感染的方法，包括将该发明的抗菌和/或抗病毒化合物或药剂应用于需要的对象。
• Generation of Antifungal Stilbenes Using the Enzymatic Secretome of <i>Botrytis cinerea</i>
  作者：Katia Gindro、Sylvain Schnee、Davide Righi、Laurence Marcourt、Samad Nejad Ebrahimi、Josep Massana Codina、Francine Voinesco、Emilie Michellod、Jean-Luc Wolfender、Emerson Ferreira Queiroz

  DOI：10.1021/acs.jnatprod.6b00760

  日期：2017.4.28

  The protein secretome of Botrytis cinerea was used to perform the biotransformation of resveratrol, pterostilbene, and a mixture of both. Metabolite profiling by UHPLC-HRMS revealed the presence of compounds with unusual molecular formula, suggesting the existence of new products. To isolate these products, the reactions were scaled up, and 21 analogues were isolated and fully characterized by NMR and HRESIMS analyses. The reaction with pterostilbene afforded five new compounds, while the reaction with-a mixture Of pterostilbene and resveratrol afforded seven unusual stilbene dimers: The antifungal propertieS of these compounds were evaluated using in vitro bioassays against Plasmopara viticola. The cytological effects of the isolated antifungal compounds on the ultrastructure of P. viticola were also evaluated.