(-)-hopeaphenol permethyl ether | 107822-38-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: (-)-hopeaphenol permethyl ether
• 英文别名: Deca-O-methyl-hopeaphenol
• CAS: 107822-38-8
• 化学式: C₆₆H₆₂O₁₂
• 分子量: 1047.21
• InChiKey: VDTJUIFXLBUCEO-GEXSJERUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.46
• 重原子数：
  78.0
• 可旋转键数：
  15.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  110.76
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  hopeaphenol 在 三甲基硅烷化重氮甲烷 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 以68%的产率得到(-)-hopeaphenol permethyl ether
  参考文献：
  名称：

  Solving the Supply of Resveratrol Tetramers from Papua New Guinean RainforestAnisopteraSpecies That Inhibit Bacterial Type III Secretion Systems

  摘要：

  The supply of (-)-hopeaphenol (1) was achieved via enzymatic biotransformation in order to provide material for preclinical investigation. High-throughput screening of a prefractionated natural product library aimed to identify compounds that inhibit the bacterial virulence type III secretion system (T3SS) identified several fractions derived from two Papua New Guinean Anisoptera species, showing activity against Yersinia pseudotuberculosis outer proteins E and H (YopE and YopH). Bioassay-directed isolation from the leaves of A. thurifera, and similarly A. polyandra, resulted in three known resveratrol tetramers, (-)-hopeaphenol (1), vatalbinoside A (2), and vaticanol B (3). Compounds 1-3 displayed IC50 values of 8.8, 12.5, and 9.9 μM in a luminescent reporter-gene assay (YopE) and IC50 values of 2.9, 4.5, and 3.3 μM in an enzyme-based YopH assay, respectively, which suggested that they could potentially act against the T3SS in Yersinia. The structures of 1-3 were confirmed through a combination of spectrometric, chemical methods, and single-crystal X-ray structure determinations of the natural product 1 and the permethyl ether analogue of 3. The enzymatic hydrolysis of the β-glycoside 2 to the aglycone 1 was achieved through biotransformation using the endogenous leaf enzymes. This significantly enhanced the yield of the target bioactive natural product from 0.08% to 1.3% and facilitates ADMET studies of (-)-hopeaphenol (1).

  DOI：

  10.1021/np500433z

文献信息

• [EN] COMPOUNDS AND USES THEREOF IN THE TREATMENT/PREVENTION OF GRAM-NEGATIVE BACTERIAL INFECTIONS<br/>[FR] COMPOSÉS ET LEURS UTILISATIONS DANS LE TRAITEMENT/LA PRÉVENTION D'INFECTIONS BACTÉRIENNES GRAM NÉGATIVES
  申请人：UNIV GRIFFITH

  公开号：WO2014138823A1

  公开（公告）日：2014-09-18

  The present disclosure relates to compounds of formula I in the treatment and/or prevention of a Gram-negative bacterial infection in a multicellular organism. The disclosure also relates to a pharmaceutical composition comprising said compound, a method of treatment and/or prevention of said infection comprising the administration of said compound, and the use of said compound for the manufacture of a medicament for treating and/or preventing said infection. The disclosure also relates to the modulation of the activity of a type three secretion system in a Gram-negative bacterium.

  本公开涉及公式I的化合物在多细胞生物中治疗和/或预防革兰氏阴性细菌感染。本公开还涉及包含该化合物的制药组合物，包括通过给予该化合物治疗和/或预防该感染的方法，以及使用该化合物制造治疗和/或预防该感染的药物。本公开还涉及调节革兰氏阴性细菌的三型分泌系统的活性。