8,10-dioctyl-bergenin | 1373402-18-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 8,10-dioctyl-bergenin
• 英文别名: (2R,3S,4S,4aR,10bS)-3,4-dihydroxy-2-(hydroxymethyl)-9-methoxy-8,10-bis(octyloxy)-3,4,4a,10b-tetrahydropyrano[3,2-c]isochromen-6(2H)-one；3,4-dihydroxy-2-(hydroxymethyl)-9-methoxy-8,10-bis(octyloxy)-2,3,4,4a-tetrahydropyrano[3,2-c]isochromen-6(10bH)-one；(2R,3S,4S,4aR,10bS)-3,4-dihydroxy-2-(hydroxymethyl)-9-methoxy-8,10-dioctoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one
• CAS: 1373402-18-6
• 化学式: C₃₀H₄₈O₉
• 分子量: 552.706
• InChiKey: LQCWHKQLLNLKFO-YAJGOTFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  39
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 8,10-dioctyl-bergenin
  参考文献：
  名称：

  Synthesis of new bergenin derivatives as potent inhibitors of inflammatory mediators NO and TNF-α

  摘要：

  Bergenin is an isocoumarin natural product which aides in fat loss, healthy weight maintenance, enhancing the lipolytic effects of norepinephrine, inhibiting the formation of interleukin 1 alpha and cyclooxygenases-2. Here we describe the anti-inflammatory activity of new bergenin derivatives 1-15 in the respiratory burst assay. Bergenin was isolated from the crude extract of Mallotus philippenensis after repeated column chromatography and was then subjected to chemical derivatization. The structures of all compounds were elucidated by NMR and mass spectroscopic techniques. Compound 2 was also studied using single crystal X-ray diffraction. Compounds 4, (54.5 +/- 2.2%) 5 (47.5 +/- 0.5%) 5, and 15 (86.8 +/- 1.9%) showed significant (P <= 0.005) NO inhibitory activities whereas 6, 7, 11, 12 and 13 displayed moderate inhibitory activities that ranges between 16% and 31%. Furthermore compounds 4 and 15, were discovered as significant (P <= 0.005) TNF-alpha inhibitors with 98% and 96% inhibition, respectively, while compounds 3, 5, 7, 8, 11, and 12 showed low level of TNF-alpha inhibition (0.4-28%). Compounds 8, 13 and 15 exhibited moderate anti-inflammatory IC50 activities with 212, 222, and 253 mu M, respectively, compared to the standard anti-inflammatory drug indomethacin as well as the parent bergenin compound. No cytotoxic effects could be detected when the compounds were tested on 3T3 cells up to concentrations of 100 mu M. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.096

文献信息

• Synthesis and biological evaluation of bergenin derivatives as new immunosuppressants
  作者：Lihua Deng、Chengcheng Song、Youhong Niu、Qin Li、Meng Wang、Yan-Fen Wu、Xin-Shan Ye

  DOI：10.1039/d1md00210d

  日期：——

  Bergenin, which is isolated from Bergenia species, exhibits various pharmacological properties. In the search for new types of immunosuppressants, a series of bergenin derivatives were designed and synthesized, and their immunosuppressive effects were evaluated by the CCK-8 assay. The experimental data demonstrated that compounds 7 and 13 showed the strongest inhibition effects on mouse splenocyte

  Bergenin 是从Bergenia物种中分离出来的，具有多种药理特性。在寻找新型免疫抑制剂的过程中，设计合成了一系列山毛榉素衍生物，并通过CCK-8法评价了它们的免疫抑制作用。实验数据表明，化合物7和13对小鼠脾细胞增殖的抑制作用最强（IC 50分别为 3.52 和 5.39 μM）。进一步的研究表明，抑制作用可能来自对 IFN-γ 和 IL-4 细胞因子的抑制。具有正己基和正己基的山毛榉素的烷基化衍生物-庚基对两个酚羟基表现出较好的抑制活性。bergenin 衍生物的疏水性、bergenin 中 4-OH 的构型以及C -4 位上的取代基形成氢键的能力对免疫抑制活性很重要。这项工作证明了对bergenin的修饰可能代表了发现一类新的免疫抑制剂的新途径。
• Bergenin of Peltophorum dubium (Fabaceae) Roots and Its Bioactive Semi‑Synthetic Derivatives
  作者：Oscar da Silva Neto、Marla Teodoro、Bruna do Nascimento、Klauber Cardoso、Eliane Silva、Jorge David、Juceni David

  DOI：10.21577/0103-5053.20200141

  日期：——

  This work describes the isolation of pure bergenin from Peltophorum dubium roots with good yields and its further derivatization through Williamson synthesis. The alkyl derivatives of the bergenin were identified by nuclear magnetic resonance and mass spectrometry data analysis. Among them, three derivatives were reported for the first time herein, 8,10-dihexyl-bergenin, 8,10-didecyl-bergenin, and

  这项工作描述了以良好的收率从杜鹃Peltophorum dubium根中分离出纯佛手素，并通过Williamson合成对其进行了进一步衍生。通过核磁共振和质谱数据分析鉴定了佛手素的烷基衍生物。其中，本文首次报道了三种衍生物：8,10-二己基-卑尔根素，8,10-二癸基-卑尔根素和8,10-二十四烷基-卑尔根素，以及三个先前报道的衍生物（8,10-二甲基卑尔根素，8-甲基香菜碱，8,10-二辛基香菜碱）。除8,10-二己基-卑尔根素（50％的致死浓度剂量（LC50）= 70.55μg/ mL）外，大多数的卑尔根素衍生物均显示出对卤虫卤虫的中等细胞毒性。抗菌测定表明，所有衍生物均选择性抑制革兰氏阳性细菌金黄色葡萄球菌，它们中的两个（8,10-二己基香菜素和8,10-二癸基香菜素）具有良好的活性（最低抑菌浓度（MIC）= 5.1-6.2μmolL）。此外，佛手素对乙酰胆碱酯酶表现出有趣的抑制作用（半数最大抑制浓度（IC50）=