(E)-5-{4-[1-(3,5-dimethoxyphenyl)-2-(4-hydroxyphenyl)-2-methoxyethoxy]styryl}benzene-1,3-diol

• 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)-5-{4-[1-(3,5-dimethoxyphenyl)-2-(4-hydroxyphenyl)-2-methoxyethoxy]styryl}benzene-1,3-diol
• 化学式: C₃₁H₃₀O₇
• 分子量: 514.575
• InChiKey: SLQQEZSZMIORLS-TXJNQENTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  38.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  97.61
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  甲醇 、 白藜芦醇 、 紫檀芪 在 Secretome of Botrytis cinerea 作用下， 以 水 为溶剂， 反应 24.0h， 生成 7-O-methylisoresvepterol B 、 7-O-methylresvepterol A 、 7-O-methyl-11,11',13,13’-tetramethoxyleachianol F 、 resvepterol 、 (1S,2R,3S)-2-(3,5-dimethoxyphenyl)-1-[hydroxy-(4-hydroxyphenyl)methyl]-3-(4-hydroxyphenyl)-2,3-dihydro-1H-indene-4,6-diol 、 11',13'-di-O-methyl-trans-δ-viniferin 、 11,13-di-O-methyl-trans-δ-viniferin 、 pterostilbene-trans-dehydromer 、 5-[(E)-2-[(2S,3S)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]ethenyl]benzene-1,3-diol 、 (E)-5-{4-[1-(3,5-dimethoxyphenyl)-2-(4-hydroxyphenyl)-2-methoxyethoxy]styryl}benzene-1,3-diol 、 (E)-5-{1-[4-(3,5-dimethoxystyryl)phenoxy]-2-(4-hydroxyphenyl)-2-methoxyethyl}benzene-1,3-diol 、 pallidol
  参考文献：
  名称：

  Generation of Stilbene Antimicrobials against Multiresistant Strains of Staphylococcus aureus through Biotransformation by the Enzymatic Secretome of Botrytis cinerea

  摘要：

  The biotransformation of a mixture of resveratrol and pterostilbene was performed by the protein secretome of Botrytis cinerea. Several reaction conditions were tested to overcome solubility issues and to improve enzymatic activity. Using MeOH as cosolvent, a series of unusual methoxylated compounds was generated. The reaction was scaled-up, and the resulting mixture purified by semipreparative HPLC-PDA-ELSD-MS. Using this approach, 15 analogues were isolated in one step. Upon full characterization by NMR and HRMS analyses, eight of the compounds were new. The antibacterial activities of the isolated compounds were evaluated in vitro against the opportunistic pathogens Pseudomonas aeruginosa and Staphylococcus aureus. The selectivity index was calculated based on cytotoxic assays performed against human liver carcinoma cells (HepG2) and the human breast epithelial cell line (MCF10A). Some compounds revealed remarkable antibacterial activity against multidrug-resistant strains of S. aureus with moderate human cell line cytotoxicity.

  DOI：

  10.1021/acs.jnatprod.0c00071

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 Stilbene Antimicrobials against Multiresistant Strains of <i>Staphylococcus aureus</i> through Biotransformation by the Enzymatic Secretome of <i>Botrytis cinerea</i>
  作者：Davide Righi、Robin Huber、Alexey Koval、Laurence Marcourt、Sylvain Schnee、Anaïs Le Floch、Verena Ducret、Remo Perozzo、Concetta C. de Ruvo、Nicole Lecoultre、Emilie Michellod、Samad N. Ebrahimi、Elisabeth Rivara-Minten、Vladimir L. Katanaev、Karl Perron、Jean-Luc Wolfender、Katia Gindro、Emerson F. Queiroz

  DOI：10.1021/acs.jnatprod.0c00071

  日期：2020.8.28

  The biotransformation of a mixture of resveratrol and pterostilbene was performed by the protein secretome of Botrytis cinerea. Several reaction conditions were tested to overcome solubility issues and to improve enzymatic activity. Using MeOH as cosolvent, a series of unusual methoxylated compounds was generated. The reaction was scaled-up, and the resulting mixture purified by semipreparative HPLC-PDA-ELSD-MS. Using this approach, 15 analogues were isolated in one step. Upon full characterization by NMR and HRMS analyses, eight of the compounds were new. The antibacterial activities of the isolated compounds were evaluated in vitro against the opportunistic pathogens Pseudomonas aeruginosa and Staphylococcus aureus. The selectivity index was calculated based on cytotoxic assays performed against human liver carcinoma cells (HepG2) and the human breast epithelial cell line (MCF10A). Some compounds revealed remarkable antibacterial activity against multidrug-resistant strains of S. aureus with moderate human cell line cytotoxicity.