quercetin 3-glucuronide | 778593-28-5

• 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: quercetin 3-glucuronide
• 英文别名: quercetin-3-O-glucuronide；miquelianin；quercetin-3-O-D-glucuronide；quercetin 3-O-glucoronide；(2S,3S,4S,5R)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 778593-28-5
• 化学式: C₂₁H₁₈O₁₃
• 分子量: 478.366
• InChiKey: DUBCCGAQYVUYEU-MBIBTLSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  224
• 氢给体数：
  8
• 氢受体数：
  13

ADMET

代谢

Mikwelianin 是槲皮素的一个已知人类代谢产物。

Mikwelianin is a known human metabolite of Quercetin.

来源:NORMAN Suspect List Exchange

反应信息

• 作为产物：
  描述：

  槲皮素 、 UDP-glucuronic acid 在 human UDP-glucuronosyltransferase 1A₉ 、 magnesium chloride 、 alamethicin 、 糖质酸-1,4-内酯 作用下， 生成 quercetin 3-glucuronide 、 7-O-glucuronosyl quercetin 、 quercetin-3'-O-glucuronide
  参考文献：
  名称：

  Accurate Prediction of Glucuronidation of Structurally Diverse Phenolics by Human UGT1A9 Using Combined Experimental and In Silico Approaches

  摘要：

  通过实验使用145种酚类化合物，并通过3D-QSAR方法分析，确定了人UGT1A9的催化选择性。UGT1A9是一种重要的膜结合酶，催化外源性物质的葡糖醛酸化反应。通过动力学分析确定了UGT1A9的催化效率。使用CoMFA和CoMSIA技术分析了定量结构活性关系。通过将葡糖醛酸化位点及其相邻的芳香环重叠，实现了底物结构的最大立体重叠。对于具有多个活性葡糖醛酸化位点的底物，每个位点被视为单独的底物。3D-QSAR分析产生了统计上可靠的模型，具有良好的预测能力（CoMFA：q2=0.548，r2=0.949，r pred 2=0.775；CoMSIA：q2=0.579，r2=0.876，r pred 2=0.700）。通过轮廓系数图阐明了底物中负责选择性差异的结构特征。将轮廓系数图叠加在UGT1A9的同源模型的催化口袋中，能够高度自信地识别UGT1A9的催化口袋。CoMFA/CoMSIA模型可以预测底物的选择性和UGT1A9的体外清除率。我们的发现还提供了理解UGT1A9功能和底物选择性的可能分子基础。

  DOI：

  10.1007/s11095-012-0666-z

文献信息

• [EN] AN ESTERIFICATION/SAPONIFICATION-BASED METHOD FOR LIPOSOMAL LOADING<br/>[FR] PROCÉDÉ À BASE D'ESTÉRIFICATION/SAPONIFICATION POUR CHARGEMENT LIPOSOMAL
  申请人：ACADEMIA SINICA

  公开号：WO2017120190A1

  公开（公告）日：2017-07-13

  Described herein is a method for loading a hydrophilic compound into liposomes after addition of an alkylester group to form an esterified compound. After loading, the alkylester is hydrolyzed to reform the hydrophilic compound inside the liposomes. Also described is a method for loading drugs under a glucuronide methylester form into liposomes. The glucuronide methylester form of the drug is saponified to a glucuronide form of the drug inside the liposomes for better drug retention. The glucuronide residue conjugated to drugs can be removed inside cells to regenerate the parental drug upon cell uptake, liposomal degradation and enzyme hydrolysis. In case of cancer, this method can be used to safely deliver drugs to tumors.

  本文描述了一种将亲水化合物加载到脂质体中的方法，方法是在加入烷基酯基团后形成酯化化合物。加载后，烷基酯被水解以重新在脂质体内形成亲水化合物。还描述了一种将药物以葡萄糖醛酸甲酯形式加载到脂质体中的方法。将药物的葡萄糖醛酸甲酯形式皂化为脂质体内药物的葡萄糖醛酸形式，以增强药物的保留。与药物结合的葡萄糖醛酸残基可以在细胞内去除，从而在细胞摄取、脂质体降解和酶水解过程中再生母药。在癌症情况下，这种方法可用于安全地将药物输送到肿瘤中。
• [EN] CONJUGATES OF HYALURONIC ACID AND ANTICANCER COMPOUNDS<br/>[FR] CONJUGUÉS D'ACIDE HYALURONIQUE ET DE COMPOSÉS ANTICANCÉREUX.
  申请人：UNIV MANCHESTER

  公开号：WO2018020238A1

  公开（公告）日：2018-02-01

  The present invention relates to a polymer-drug conjugate wherein the polymer is hyaluronic acid and the drug is an anticancer compound. The anticancer compound is covalently linked to the hyaluronic acid by a pH-labile boronic acid-containing linkage. These conjugates can be used for the treatment of cancer.

  本发明涉及一种聚合物-药物共轭物，其中聚合物为透明质酸，药物为抗癌化合物。抗癌化合物通过pH敏感的硼酸酯键与透明质酸共价连接。这些共轭物可用于治疗癌症。
• Quercetin Glycoside Composition and Method of Preparing the Same
  申请人：Ono Yoshiko

  公开号：US20090143317A1

  公开（公告）日：2009-06-04

  The present invention provides an α-glycosyl isoquercitrin-containing novel composition which has a high in vivo absorbability, and hence exhibits a significant in vivo antioxidative activity. The present invention further provides preparation methods for such a composition. The composition contains a mixture of quercetin glycosides represented by the following formula: wherein Glc represents a glucose residue, and n is 0 or a positive integer of 1 or more, includes at least a quercetin glycoside wherein n is 3, and satisfies the following requirement (a): (a) the total proportion of quercetin glycosides in which n is 3, and in which other n values may be 1 or 2, or 1 and 2, is 50 mol % or more, and the total proportion of quercetin glycosides wherein n is 4 or more is 15 mol % or less, in the composition. The composition can be prepared by treating an enzymatically modified isoquercitrin with β-amylase.

  本发明提供了一种含有α-糖基异槲皮苷的新型组合物，其具有高的体内吸收性，因此表现出显著的体内抗氧化活性。本发明还提供了制备这种组合物的方法。该组合物包含由以下式表示的槲皮苷混合物：其中Glc表示葡萄糖残基，n为0或1或更多的正整数，包括至少一种n为3的槲皮苷，并满足以下要求(a)：(a) n为3的槲皮苷和其他n值可能为1或2或1和2的槲皮苷的总比例在组合物中为50摩尔％或更多，n为4或更多的槲皮苷的总比例不超过15摩尔％。该组合物可以通过用β-淀粉酶处理经酶法改性的异槲皮苷来制备。
• [EN] COMPOSITIONS COMPRISING UROLITHINS AND USES THEREOF FOR THE STIMULATION OF INSULIN SECRETION<br/>[FR] COMPOSITIONS COMPRENANT DES UROLITHINES, ET LEURS UTILISATIONS POUR LA STIMULATION DE SÉCRÉTION D'INSULINE
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2015055736A1

  公开（公告）日：2015-04-23

  The present invention relates to a composition comprising urolithin A, urolithin B, urolithin C, urolithin D, or a combination thereof, for the stimulation of insulin secretion, and to the use of a compound chosen among urolithin A, urolithin B, urolithin C, urolithin D, or a combination thereof, intended for the stimulation of insulin secretion. The present invention also relates to a composition comprising an effective amount of urolithin B, urolithin C, urolithin D, or a combination thereof, for the treatment or the prevention of diabetes mellitus, and in particular for the treatment or the prevention of type 2 diabetes, and to the use of a compound chosen among urolithin B, urolithin C, urolithin D, and a combination thereof, intended for the treatment or the prevention of diabetes mellitus, and in particular of type 2 diabetes.

  本发明涉及一种包含乌罗利酸A、乌罗利酸B、乌罗利酸C、乌罗利酸D或其组合的组合物，用于刺激胰岛素分泌，并且涉及使用从乌罗利酸A、乌罗利酸B、乌罗利酸C、乌罗利酸D或其组合中选择的化合物，用于刺激胰岛素分泌。本发明还涉及一种包含有效量的乌罗利酸B、乌罗利酸C、乌罗利酸D或其组合的组合物，用于治疗或预防糖尿病，特别是用于治疗或预防2型糖尿病，并且涉及使用从乌罗利酸B、乌罗利酸C、乌罗利酸D或其组合中选择的化合物，用于治疗或预防糖尿病，特别是2型糖尿病。
• Compositions comprising urolithins and uses thereof for the stimulation of insulin secretion
  申请人：Centre National de la Recherche Scientifique (CNRS)

  公开号：EP2862568A1

  公开（公告）日：2015-04-22

  The present invention relates to a composition comprising an effective amount of urolithin A, urolithin B, urolithin C, urolithin D, or a combination thereof, for the stimulation of insulin secretion, and to the use of a compound chosen among urolithin A, urolithin B, urolithin C, urolithin D, or a combination thereof, for the stimulation of insulin secretion. The present invention also relates to a composition comprising an effective amount of urolithin B, urolithin C, urolithin D, or a combination thereof, for the treatment or the prevention of diabetes mellitus, and to the use of a compound chosen among urolithin B, urolithin C, urolithin D, and a combination thereof, for the treatment or the prevention of diabetes mellitus.

  本发明涉及一种组合物，包括有效量的尿石素A、尿石素B、尿石素C、尿石素D或其组合，用于刺激胰岛素分泌，并且涉及从尿石素A、尿石素B、尿石素C、尿石素D或其组合中选择一种化合物，用于刺激胰岛素分泌的用途。 本发明还涉及一种组合物，包括有效量的尿石素B、尿石素C、尿石素D或其组合，用于治疗或预防糖尿病，并且涉及从尿石素B、尿石素C、尿石素D或其组合中选择一种化合物，用于治疗或预防糖尿病的用途。