selaginellin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: selaginellin
• 英文别名: 4-[[3-(hydroxymethyl)-6-(4-hydroxyphenyl)-2-[2-(4-hydroxyphenyl)ethynyl]phenyl]-(4-hydroxyphenyl)methylidene]cyclohexa-2,5-dien-1-one
• 化学式: C₃₄H₂₄O₅
• 分子量: 512.562
• InChiKey: SJSFYXIEVFIZJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  selaginellin 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以9 mg的产率得到
  参考文献：
  名称：

  Selaginpulvilins A–D，一种新的磷酸二酯酶-4抑制剂，具有前所未有的骨架，来自Selaginella pulvinata

  摘要：

  Selaginpulvilins A-d（1 - 4），具有前所未有的9,9-二苯基-1-（苯基乙炔基）-9-四个新的酚类ħ芴骨架，具有四个已知selaginellins（一起5 - 8）从分离卷柏垫状。通过光谱分析和化学相关性阐明了它们的结构。通过单晶X射线衍射确认1的结构。化合物1 – 8对磷酸二酯酶4（PDE4）表现出显着的抑制活性（IC 50值在0.11–5.13μM范围内），这是治疗哮喘和慢性阻塞性肺疾病的药物靶标。

  DOI：

  10.1021/ol403282f

文献信息

• A New Unusual Natural Pigment from <i>Selaginella </i><i>sinensis</i> and Its Noticeable Physicochemical Properties
  作者：Li-Ping Zhang、Yong-Min Liang、Xiu-Cheng Wei、Dong-Liang Cheng

  DOI：10.1021/jo0701177

  日期：2007.5.1

  [GRAPHICS]A new unusual pigment with a novel carbon framework named selaginellin (1) was isolated from the acetone extract of Selaginella sinensis, and its methoxy derivative (1a) was synthesized. Both selaginellin 1 and 1a are racemic compounds. The structure of selaginellin 1 was established as (R,S)-4-[(4'-hydroxy-4-(hydroxymethyl)-3-((4-hydroxyphenyl)ethynyl)biphenyl-2-yl)(4-hydroxyphenyl)methylene]-2,5-cyclohexadien-1-one and 1a> as (R,S)-4-[(4'-methoxy-4-(methoxymethyl)-3-((4-methoxyphenyl)ethynyl)biphenyl-2-yl)(4-methoxyphenyl)methylene]-2,5-cyclohexadien-1-one by the analysis of one- and two-dimensional NMR data, HR-ESIMS, EI-MS, IR, UV, CD, and single-crystal X-ray experiments, and the mechanism of their color change according to different pH values and fluorescent properties was studied.
• Insulin-Mimetic Selaginellins from <i>Selaginella tamariscina</i> with Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitory Activity
  作者：Phi-Hung Nguyen、Bing-Tian Zhao、Md Yousof Ali、Jae-Sue Choi、Dong-Young Rhyu、Byung-Sun Min、Mi-Hee Woo

  DOI：10.1021/np5005856

  日期：2015.1.23

  As part of an ongoing search for new antidiabetic agents from medicinal plants, three new (2, 4, and 5) and two known selaginellin derivatives (1 and 3) were isolated from a methanol extract of Selaginella tamariscina. The structures of the new compounds were determined by spectroscopic data analysis. All isolates showed strong glucose uptake stimulatory effects in 3T3-L1 adipocyte cells at a concentration of 5 mu M. Furthermore, these compounds were found to possess inhibitory effects on PTP1B enzyme activity with IC50 values ranging from 4.6 +/- 0.1 to 21.6 +/- 1.5 mu M. Compound 2 showed the greatest potency, with an IC50 value of 4.6 +/- 0.1 mu M, when compared with the positive control (ursolic acid, IC50 = 3.5 +/- 0.1 mu M). Therefore, these selaginellin derivatives may have value as new lead compounds for the development of agents against type 2 diabetes.