(±)-leachianol G

• 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: (±)-leachianol G
• 英文别名: leachianol G；(1R,2S,3R)-2-(3,5-dihydroxyphenyl)-1-[(R)-hydroxy-(4-hydroxyphenyl)methyl]-3-(4-hydroxyphenyl)-2,3-dihydro-1H-indene-4,6-diol
• 化学式: C₂₈H₂₄O₇
• 分子量: 472.494
• InChiKey: PRITZUOAMIVROM-XEZODYMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  35.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  141.61
• 氢给体数：
  7.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  白藜芦醇 在 双氧水 、 Momordica charantia peroxidase 作用下， 以 丙酮 为溶剂， 反应 8.0h， 以8.0 mg的产率得到(±)-leachianol G
  参考文献：
  名称：

  Oligomers of Resveratrol and Ferulic Acid Prepared by Peroxidase-Catalyzed Oxidation and Their Protective Effects on Cardiac Injury

  摘要：

  Peroxidase extracted from Momordica charantia was used for the oligomerization of trans-resveratrol and ferulic acid on a preparative scale. One new heterocoupling oligomer, trans-3E-3-[(4-hydroxy3-methoxyphenyl)methylene]-4-(3,5-dihydroxyphenyl)-5-(4-hydroxyphenyl)tetrahydro-2-franone (6), and six resveratrol dimers, leachianol G (1), restrytisol B (2), parthenostilbenins A (3) and B (5), 7-O-acetylated leachianol G (4), and resveratrol trans-dehydrodimer (8), and one known ferulic acid dehydrodimer, (3 alpha,3a alpha,6 alpha,6a alpha)tetrahydro-3,6-bis(4-hydroxy-3-methoxyphenyl)-1 H,4H-furo[3,4-c]furan1,4-dione (7) were obtained. Bioactive experiments showed that compounds 6-8 have strong free radical scavenging effects and also have protective effects on doxorubicin-induced cardiac cell injury when tested in vitro.

  DOI：

  10.1021/jf0711486

文献信息

• Potassium Hexacyanoferrate (III)-Catalyzed Dimerization of Hydroxystilbene: Biomimetic Synthesis of Indane Stilbene Dimers
  作者：Jing-Shan Xie、Jin Wen、Xian-Fen Wang、Jian-Qiao Zhang、Ji-Fa Zhang、Yu-Long Kang、You-Wei Hui、Wen-Sheng Zheng、Chun-Suo Yao

  DOI：10.3390/molecules201219872

  日期：——

  isorhapontigenin and resveratrol in aqueous acetone resulted in the isolation of three new indane dimers 4, 6, and 7, together with six known stilbene dimers. Indane dimer 5 was obtained for the first time by direct transformation from isorhapontigenin. The structures and relative configurations of the dimers were elucidated using spectral analysis, and their possible formation mechanisms were discussed

  用六氰合铁酸钾（III）-乙酸钠作为氧化剂，异皂甙元和白藜芦醇在丙酮水溶液中的氧化偶联反应导致分离出三个新的茚满二聚体4、6和7，以及六个已知的二苯乙烯二聚体。首次从异源皂苷元直接转化得到茚满二聚体5。使用光谱分析阐明了二聚体的结构和相对构型，并讨论了其可能的形成机理。结果表明，该反应条件温和，反应产物简单，可作为半合成茚满二聚体的简便方法。
• Concise synthesis of several oligostilbenes from the enzyme-promoted oxidation of brominated resveratrol
  作者：Wenling Li、Tao Dong、Peilan Chen、Xiaolin Liu、Meijie Liu、Xiaoqian Han

  DOI：10.1016/j.tet.2017.04.021

  日期：2017.5

  The simple synthesis of (±)-parthenostilbenins A and B and (±)-quadrangularins A and B, as well as several unnatural resveratrol dimers, was successfully accomplished for the first time. Moreover, (±)-restrytisols B, (±)-leachianols F and G were efficiently prepared with higher yields compared with those in the literatures. The regioselective oxidative coupling reactions of 3,5-dibromo-resveratrol

  首次成功完成了对（±）-单-苯二酚A和B和（±）-四环素A和B以及几种非天然白藜芦醇二聚体的简单合成。此外，与文献中的那些相比，以更高的收率有效地制备了（±）-邻苯二酚B，（±）-花生四醇F和G。在不同的溶剂体系中，不同酶催化的3,5-二溴-白藜芦醇的区域选择性氧化偶联反应被用作关键步骤。还提出了形成独特的二聚体骨架的偶联机制。
• Oligomers of Resveratrol and Ferulic Acid Prepared by Peroxidase-Catalyzed Oxidation and Their Protective Effects on Cardiac Injury
  作者：Bei-Bei Yu、Xiu-Zhen Han、Hong-Xiang Lou

  DOI：10.1021/jf0711486

  日期：2007.9.1

  Peroxidase extracted from Momordica charantia was used for the oligomerization of trans-resveratrol and ferulic acid on a preparative scale. One new heterocoupling oligomer, trans-3E-3-[(4-hydroxy3-methoxyphenyl)methylene]-4-(3,5-dihydroxyphenyl)-5-(4-hydroxyphenyl)tetrahydro-2-franone (6), and six resveratrol dimers, leachianol G (1), restrytisol B (2), parthenostilbenins A (3) and B (5), 7-O-acetylated leachianol G (4), and resveratrol trans-dehydrodimer (8), and one known ferulic acid dehydrodimer, (3 alpha,3a alpha,6 alpha,6a alpha)tetrahydro-3,6-bis(4-hydroxy-3-methoxyphenyl)-1 H,4H-furo[3,4-c]furan1,4-dione (7) were obtained. Bioactive experiments showed that compounds 6-8 have strong free radical scavenging effects and also have protective effects on doxorubicin-induced cardiac cell injury when tested in vitro.