2,3,5,4'‐tetrahydroxystilbene‐2‐O‐β‐D‐glucoside | 55327-45-2

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 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: 2,3,5,4'‐tetrahydroxystilbene‐2‐O‐β‐D‐glucoside
• 英文别名: 2,3,5,4’-tetrahydroxystilbene-2-O-β-D-glucoside；2,3,5,4′-tetrahydroxystilbene-2-O-β-D-glucoside；2,3,5,4′-tetrahydroxyl diphenylethylene-2-O-glucoside；2,3,5,4'-tetrahydroxy-stilbene-2-O-β-D-glucoside；2,3,5,4'-tetrahydroxystilbene-2-O-β-D-glucoside；2,3,5,4-tetrahydroxystilbene-2-O-β-D-glucoside；(2S,3R,4S,5S,6R)-2-[2,4-Dihydroxy-6-[2-(4-hydroxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 55327-45-2
• 化学式: C₂₀H₂₂O₉
• 分子量: 406.389
• InChiKey: JAYVHSBYKLLDJC-NUABRCLCSA-N

物化性质

• 沸点：
  715.0±60.0 °C(Predicted)
• 密度：
  1.593

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  160
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3,5,4'‐tetrahydroxystilbene‐2‐O‐β‐D‐glucoside 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 14.0h， 以32%的产率得到2,3,5,4‘-tetrahydroxystilbene
  参考文献：
  名称：

  2,3,5,4'-四羟基芪降低乳腺肿瘤的耐药性以显示协同化疗效果。

  摘要：

  由于癌细胞对抗癌药物产生多药耐药性，化疗药物在乳腺癌中的疗效有限。在这项研究中，我们通过修饰 2,3,5,4'-四羟基芪-2-O-β-D-葡萄糖苷 (THSG) 开发了一种新型衍生物 2,3,5,4'-四羟基芪 (TG1)。斑马鱼体内胚胎试验表明，TG1 具有低毒性。DOX或DTX与TG1在MCF-7/Adr中的等毒组合降低了DOX或DTX的IC50，并且组合指数（CI）在1:3摩尔比的DTX:TG1和1:5摩尔比显示出强烈的协同效应DOX：TG1的比率。此外，荧光图像证实了在 MCF-7/Adr 中与 TG1 结合时 DOX 的细胞摄取。Western印迹分析表明用TG1处理MCF-7/Adr后p-糖蛋白(P-gp)的下调。综上所述，DTX或DOX与TG1的联合治疗通过抑制p-糖蛋白外排泵增加药物疗效。这些结果表明，TG1 可能对乳腺癌患者有潜在的用途，尤其是那些具有多药耐药性的患者。

  DOI：

  10.1371/journal.pone.0260533

文献信息

• One-pot β-cyclodextrin-assisted extraction of active ingredients from Xue–Zhi–Ning basing its encapsulated ability
  作者：Hui-Jie Zhang、Ya-Nan Liu、Meng Wang、Yue-Fei Wang、Yan-Ru Deng、Ming-Lei Cui、Xiao-Liang Ren、Ai-Di Qi

  DOI：10.1016/j.carbpol.2015.06.072

  日期：2015.11

  Xue-Zhi-Ning (XZN) is a traditional Chinese medicine formula, containing active ingredients with poor solubility in water, which has been demonstrated to be helpful for patients with hyperlipidemia. One-pot beta-cyclodextrin ( beta-CD)-assisted extraction of active ingredients from XZN has been carried out to develop an efficient and eco-friendly extraction process. Five active compounds rubrofusarin gentiobioside, 2,3,5,4'-tetrahydroxy-stilbene-2-O-beta-D-glucoside, emodin, nuciferine and quercetin were identified by UPLC/DAD/MS and used as indexes to evaluate the process optimized by an orthogonal test. The results showed that addition of beta-CD significantly enhanced the extraction ratios of all five components. The enhancement of extraction ratios was positively correlated with the apparent formation constants between beta-CD and the compounds. The study also showed that the stabilities and dissolution rates of the active ingredients were improved in the presence of beta-CD. This one-pot beta-cyclodextrin-assisted extraction has the potential to be applied in pharmaceutical preparations directly. (C) 2015 Elsevier Ltd. All rights reserved.
• 2,3,5,4′-Tetrahydroxy stilbene-2-Ο-β-D-glucoside, a mechanism-based inactivator of CYP2C19 and CYP3A4, potentiates hepatic protein adduction and hepatotoxicity induced by emodin in vivo
  作者：Xu Wang、Lingwen Dong、Guode Zhao、Weiwei Li、Ying Peng、Jiang Zheng

  DOI：10.1016/j.cbi.2022.110234

  日期：2022.12