3-hydroxy-5,7-dimethoxy-2-(4-methoxy-phenyl)-chromenylium; chloride | 37715-28-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3-hydroxy-5,7-dimethoxy-2-(4-methoxy-phenyl)-chromenylium; chloride
• CAS: 37715-28-9
• 化学式: C₁₈H₁₇O₅*Cl
• 分子量: 348.783
• InChiKey: OPPFWDOYJGWPIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.12
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  59.22
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-hydroxy-5,7-dimethoxy-2-(4-methoxy-phenyl)-chromenylium; chloride 在 乙醇 、 铂 作用下， 生成 (+/-)-cis-Atzelechin-trimethylether
  参考文献：
  名称：

  King et al., Journal of the Chemical Society, 1955, p. 2948,2954

  摘要：

  DOI：
• 作为产物：
  描述：

  硫酸二甲酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 生成 3-hydroxy-5,7-dimethoxy-2-(4-methoxy-phenyl)-chromenylium; chloride
  参考文献：
  名称：

  Karrer et al., Helvetica Chimica Acta, 1927, vol. 10, p. 748

  摘要：

  DOI：

文献信息

• The Aryl Hydrocarbon Receptor (AhR) Mediates the Counter-Regulatory Effects of Pelargonidins in Models of Inflammation and Metabolic Dysfunctions
  作者：Michele Biagioli、Adriana Carino、Chiara Fiorucci、Giannamaria Annunziato、Silvia Marchianò、Martina Bordoni、Rosalinda Roselli、Cristina Di Giorgio、Federica Castiglione、Patrizia Ricci、Agostino Bruno、Andrea Faccini、Eleonora Distrutti、Monia Baldoni、Gabriele Costantino、Stefano Fiorucci

  DOI：10.3390/nu11081820

  日期：——

  Pelargonidins are anthocyanidins thought to be beneficial for the human health, although controversies exist over the doses needed and the unclear mechanism of action, along with poor systemic bioavailability. One putative target of pelargonidins is the aryl hydrocarbon receptor (AhR). A synthetic pelargonidin (Mt-P) was synthesized by the methylation of the pelargonidin (the natural compound indicated as P). Mt-P transactivated the AhR with an EC50 of 1.97 µM and was ~2-fold more potent than the natural compound. In vitro Mt-P attenuated pro-inflammatory activities of Raw264.7 macrophage cells in an AhR-dependent manner. In vivo, administration of the Mt-P in Balb/c mice resulted in a dose-dependent attenuation of signs and symptoms of colitis induced by TNBS. A dose of 5 mg/kg Mt-P, but not the natural compound P, reversed intestinal inflammation and increased expression of Tnf-α, Ifn-ƴ, and Il-6, while promoted the expansion of regulatory T cells and M2 macrophages. In C57BL/6J mice fed a high fat diet (HFD), Mt-P attenuated body weight gain, intestinal and liver inflammation, and ameliorated insulin sensitivity, while worsened liver steatosis by up-regulating the liver expression of Cd36 and Apo100b. These effects were abrogated by AhR gene ablation. Mt-P is a synthetic pelargonidin endowed with robust AhR agonist activity that exerts beneficial effects in murine models of inflammation and metabolic dysfunction.

  芹菜素是一种花青素，被认为对人体健康有益，尽管存在有关所需剂量和作用机制不明确以及系统生物利用度低的争议。芹菜素的一个潜在靶点是芳香族碳氢化合物受体（AhR）。通过对芹菜素（自然化合物P）进行甲基化合成了合成芹菜素（Mt-P）。Mt-P以EC50为1.97微米的效力激活AhR，比自然化合物强大约两倍。在体外实验中，Mt-P以AhR依赖的方式减轻了Raw264.7巨噬细胞的促炎活性。在体内实验中，给予Balb/c小鼠Mt-P，可导致TNBS诱导的结肠炎症状和体征的剂量依赖性减轻。5mg/kg的Mt-P剂量可以逆转肠道炎症，并增加Tnf-α，Ifn-ƴ和Il-6的表达，同时促进调节性T细胞和M2巨噬细胞的扩张。在C57BL/6J小鼠喂高脂饮食（HFD）时，Mt-P减轻了体重增加、肠道和肝脏炎症，并改善了胰岛素敏感性，但通过上调Cd36和Apo100b的肝脏表达加重了脂肪肝。这些效应被AhR基因敲除所消除。Mt-P是一种具有强大AhR激动剂活性的合成芹菜素，在炎症和代谢功能障碍的小鼠模型中具有有益效果。