trans-emodin dianthrone

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: trans-emodin dianthrone
• 英文别名: trans-emodin bianthrone；(10R)-1,3,8-trihydroxy-6-methyl-10-[(9R)-2,4,5-trihydroxy-7-methyl-10-oxo-9H-anthracen-9-yl]-10H-anthracen-9-one
• 化学式: C₃₀H₂₂O₈
• 分子量: 510.5
• InChiKey: UUXPVUHOWQPCSC-DNQXCXABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  38
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  156
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(3-(but-3-yn-1-yl)-3H-diazirin-3-yl)ethan-1-ol 、 trans-emodin dianthrone 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以16.3 %的产率得到
  参考文献：
  名称：

  来自何首乌的二蒽酮衍生物：抗糖尿病活性、构效关系 (SAR) 和作用方式

  摘要：

  PTP1B 作为与胰岛素受体信号转导相关的酪氨酸磷酸化的关键负调节剂，在糖尿病和肥胖治疗中发挥着重要作用。本研究探讨了何首乌中二蒽酮衍生物的抗糖尿病活性及其构效关系、机制和分子对接。在这些类似物中，反式大黄素二蒽酮（化合物1）通过上调 HepG2 细胞中的胰岛素信号通路增强胰岛素敏感性，并在 db/db 小鼠中显示出相当大的抗糖尿病活性。通过使用光亲和标记和基于质谱的蛋白质组学，我们发现反式大黄素二蒽酮（化合物1) 可能与螺旋 α6/α7 处的 PTP1B 变构口袋结合，这为新型抗糖尿病药物的鉴定提供了新的见解。

  DOI：

  10.1016/j.bioorg.2023.106491
• 作为产物：
  描述：

  emodin emodin-8-O-β-D-glucopyranoside dianthrone 在 β-glucosidase from almonds 作用下， 反应 20.0h， 生成 trans-emodin dianthrone
  参考文献：
  名称：

  香叶内酯C1-C4; 从何首乌的根中提取少量的二蒽酮糖苷。

  摘要：

  从何首乌的干燥根中分离出了四个新的二蒽醌苷C1-C4（1-4），以及两种已知的大黄素双蒽醌（5-6）。针对L-02细胞系评估了它们的肝毒性。化合物1-4对L-02细胞系的肝毒性较弱，IC 50值分别为313.05、205.20、294.20和207.35μM。

  DOI：

  10.1080/10286020.2016.1171758

文献信息

• Cytotoxicity of Rhamnosylanthraquinones and Rhamnosylanthrones from <i>Rhamnus nepalensis</i>
  作者：Le Phuong Mai、Françoise Guéritte、Vincent Dumontet、Mai Van Tri、Bridget Hill、Odile Thoison、Daniel Guénard、Thierry Sévenet

  DOI：10.1021/np010030v

  日期：2001.9.1

  fractionation led to the isolation of a series of known anthraquinones and anthrones, one new rhamnosylanthraquinone, 3'-O-acetylfrangulin A (8), several new rhamnosylanthrones, the prinoidin-emodin bianthrones (9A-D), the prinoidin bianthrones (10A,B), and the rhamnepalins (11A-C). A structure-cytotoxic activity relationship study was performed on these isolates and some semisynthetic derivatives.

  越南华平省收集的尼泊尔鼠李的果实提取物对KB细胞具有细胞毒性。生物测定指导的分馏导致分离出一系列已知的蒽醌和蒽酮，一个新的鼠李糖基蒽醌，3'-O-乙酰基花甲素A（8），几个新的鼠李糖基蒽醌，类卟啉-大黄素联蒽醌（9A-D），类rininin bianthrones（10A，B）和rhannepalins（11A-C）。对这些分离物和一些半合成衍生物进行了结构-细胞毒性活性关系研究。
• On the synthesis of hypericin by oxidative trimethylemodin anthrone and emodin anthrone dimerization: Isohypericin
  作者：Heinz Falk、Gerhard Schoppel

  DOI：10.1007/bf00811548

  日期：1992.10

  The base catalyzed oxidative dimerization of emodin anthrone exclusively yields hypericin. However, on oxidative dimerization of trimethylemodinanthrone a mixture of hexamethylhypericin and hexamethylisohypericin was obtained. Chromatographic separation of the hexabenzoyl derivatives was achieved, and by saponification about equal amounts of hypericin and isohypericrin were produced. Isohypericin could be characterized for the first time by its spectroscopic data and its protonation and deprotonation pK(a) and pK(a)* values.
• Effects of skeleton structure on necrosis targeting and clearance properties of radioiodinated dianthrones
  作者：Dongjian Zhang、Cuihua Jiang、Shengwei Yang、Meng Gao、Dejian Huang、Xiaoning Wang、Haibo Shao、Yuanbo Feng、Ziping Sun、Yicheng Ni、Jian Zhang、Zhiqi Yin

  DOI：10.3109/1061186x.2015.1113541

  日期：2016.7.2

  Necrosis avid agents (NAAs) can be used for diagnose of necrosis-related diseases, evaluation of therapeutic responses and targeted therapeutics of tumor. In order to probe into the effects of molecular skeleton structure on necrosis targeting and clearance properties of radioiodinated dianthrones, four dianthrone compounds with the same substituents but different skeletal structures, namely Hypericin (Hyp), protohypericin (ProHyp), emodin dianthrone mesomer (ED-1) and emodin dianthrone raceme (ED-2) were synthesized and radioiodinated. Then radioiodinated dianthrones were evaluated in vitro for their necrosis avidity in A549 lung cancer cells untreated and treated with H2O2. Their biodistribution and pharmacokinetic properties were determined in rat models of induced necrosis. In vitro cell assay revealed that destruction of rigid skeleton structure dramatically reduced their necrosis targeting ability. Animal studies demonstrated that destruction of rigid skeleton structure dramatically reduced the necrotic tissue uptake and speed up the clearance from the most normal tissues for the studied compounds. Among these (131)I-dianthrones, (131)I-Hyp exhibited the highest uptake and persistent retention in necrotic tissues. Hepatic infarction could be clearly visualized by SPECT/CT using (131)I-Hyp as an imaging probe. The results suggest that the skeleton structure of Hyp is the lead structure for further structure optimization of this class of NAAs.
• New metabolites from Psorospermum tenuifolium☆
  作者：Giuliano Delle Monache、Franco Delle Monache、Rosella Di Benedetto、James U. Oguakwa

  DOI：10.1016/s0031-9422(00)83889-3

  日期：——
• Dianthrone Derivatives from Polygonum multiflorum Thunb: Anti-Diabetic Activity, Structure-Activity Relationships (SARs), and Mode of Action
  作者：Jian-Bo Yang、Cheng-Shuo Yang、Jiang Li、Guo-Zhu Su、Jin-Ying Tian、Ying Wang、Yue Liu、Feng Wei、Yong Li、Fei Ye、Shuang-Cheng Ma

  DOI：10.1016/j.bioorg.2023.106491

  日期：2023.3

  phosphorylation associated with insulin receptor signaling in the therapy for diabetes and obesity. In this study, the anti-diabetic activity of dianthrone derivatives from Polygonum multiflorum Thunb., as well as the structure–activity relationships, mechanism, and molecular docking were explored. Among these analogs, trans-emodin dianthrone (compound 1) enhances insulin sensitivity by upregulating the

  PTP1B 作为与胰岛素受体信号转导相关的酪氨酸磷酸化的关键负调节剂，在糖尿病和肥胖治疗中发挥着重要作用。本研究探讨了何首乌中二蒽酮衍生物的抗糖尿病活性及其构效关系、机制和分子对接。在这些类似物中，反式大黄素二蒽酮（化合物1）通过上调 HepG2 细胞中的胰岛素信号通路增强胰岛素敏感性，并在 db/db 小鼠中显示出相当大的抗糖尿病活性。通过使用光亲和标记和基于质谱的蛋白质组学，我们发现反式大黄素二蒽酮（化合物1) 可能与螺旋 α6/α7 处的 PTP1B 变构口袋结合，这为新型抗糖尿病药物的鉴定提供了新的见解。