Perrottetin F | 89911-98-8

• 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: Perrottetin F
• 英文别名: Perrotettin F；5-[2-(3-hydroxyphenyl)ethyl]-3-[4-[2-(3-hydroxyphenyl)ethyl]phenoxy]benzene-1,2-diol
• CAS: 89911-98-8
• 化学式: C₂₈H₂₆O₅
• 分子量: 442.511
• InChiKey: QFNWXQOYUAXUAF-UHFFFAOYSA-N

物化性质

• 沸点：
  629.8±55.0 °C(Predicted)
• 密度：
  1.298±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Perrottetin F 生成 Perrottetin F tetraacetat
  参考文献：
  名称：

  MEZEY=VANDOR, GABRIELLA; NOGRADI, M.; NOVIKOV, V. P.; WISZT, A.; KAJTAR=P+, LIEBIGS ANN. CHEM., N4, 1989, 401-403

  摘要：

  DOI：
• 作为产物：
  描述：

  3-苄氧基苯甲醛 在 palladium on activated charcoal 氢气 、 sodium methylate 、 三溴化硼 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 1.0h， 生成 Perrottetin F
  参考文献：
  名称：

  Mezey-Vandor, Gabriella; Nogradi, M.; Novikov, V. P., Liebigs Annalen der Chemie, 1989, p. 401 - 404

  摘要：

  DOI：

文献信息

• Synthese von Bryophyten-Inhaltsstoffen 3. Neue Synthesen der Perrottetine E, F und G
  作者：Theophil Eicher、Madeleine Walter

  DOI：10.1055/s-1991-26496

  日期：——

  Synthesis of Bryophyte Components 3. New Syntheses of Perrottetines E, F and G Efficient and expeditious syntheses of the Perrottetines E, F and G (4′,5-bis(m-hydroxyphenethyl)diphenyl ether derivatives) are developed, which give rise to these biologically active linear bis(bibenzyl) derivatives on a preparative scale.

  苔藓成分的合成 3. Perrottetines E, F 和 G 的新合成方法 开发了有效且迅速的 Perrottetines E, F 和 G（4′,5-二(m-羟基苯乙基)二苯醚衍生物）的合成方法，可在准备规模上产生这些具有生物活性的线性双(bibenzyl)衍生物。
• Perrottetins E, F, and G from (liverwort)--isolation, structure determination, and synthesis of perrottetin e
  作者：Masao Toyota、Motoo Tori、Keiko Takikawa、Yoshinori Shiobara、Mitsuaki Kodama、Yoshinori Asakawa

  DOI：10.1016/s0040-4039(00)95135-9

  日期：1985.1

  Perrottetin E, a cytotoxic bis(bibenzyl) ether, was isolated from and its structure determined by spectroscopic methods and total synthesis. Perrottetins F and G were also isolated from the same source and fully characterized.

  从其中分离出具有细胞毒性的双（联苄基）醚Perrottetin E，并通过光谱法和全合成确定其结构。Perrottetins F和G也从同一来源中分离出来并进行了充分表征。
• Biotransformation of Perrottetin F by Aspergillus niger: New Bioactive Secondary Metabolites
  作者：Danka Bukvicki、Miroslav Novakovic、Tatjana Ilic-Tomic、Jasmina Nikodinovic-Runic、Nina Todorovic、Milan Veljic、Yoshinori Asakawa

  DOI：10.25135/rnp.215.20.09.1812

  日期：——

  Biotransformation of bis-bibenzyl perrottetin F (1), isolated from the liverwort Lunularia cruciata by Aspergillus niger, has been investigated. New metabolites (2-4) have been isolated using reversed phase semipreparative HPLC and their structures were established to be 8-hydroxyperrottetin F, C-7-C-8 cleaved product, and perrottetin F 6’-sulfate using 1D and 2D NMR, HR-ESI-MS, IR and UV spectroscopy. The antimicrobial and cytotoxic properties of these compounds were also evaluated. Given the suggested cytotoxic properties of the parent compound, antiproliferative activity against healthy human lung fibroblasts (MRC5) and human lung carcinoma (A549) of three metabolites were evaluated revealing their lower cytotoxic properties in comparison to the starting compound - perrottetin F. The antimicrobial properties of these compounds were also evaluated, with the inhibitory activity against the Pseudomonas aeruginosa PAO1 and Staphylococcus aureus determined between 100 µM and 450 µM. The metabolites showed remarkable ability to inhibit synthesis of bacterial quorum-sensing signal molecules such as short chain acyl homoserine lactones (AHLs). Therefore, biotransformation method represents fast and effective tool for obtaining new bioactive structures.

  对来自千屈菜苔（Lunularia cruciata）的双双苯基过氧化物F（1）进行了由黑曲霉（Aspergillus niger）引起的生物转化的研究。使用反相半制备高效液相色谱法分离出了新代谢物（2-4），并使用1D和2D NMR，HR-ESI-MS，IR和UV光谱法确定它们的结构为8-羟基过氧化物F，C-7-C-8裂解产物和过氧化物F 6'-硫酸酯。还评估了这些化合物的抗微生物和细胞毒性。鉴于母化合物的细胞毒性特性，评估了三种代谢物对健康人肺成纤维细胞（MRC5）和人肺癌（A549）的抗增殖活性，发现它们与起始化合物过氧化物F相比，具有较低的细胞毒性。还评估了这些化合物的抗微生物性能，确定它们对铜绿假单胞菌PAO1和金黄色葡萄球菌的抑制活性在100 µM和450 µM之间。代谢物表现出显着的抑制细菌类群感应信号分子（如短链酰基同半胱氨酸内酯）的合成能力。因此，生物转化方法代表了获取新的生物活性结构的快速有效工具。