7-O-glucuronosyl quercetin

• 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: 7-O-glucuronosyl quercetin
• 英文别名: quercetin 7-O-glucuronide；quercetin-7-O-glucuronide；(2S,3S,4S,5R)-6-[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• 化学式: C₂₁H₁₈O₁₃
• 分子量: 478.366
• InChiKey: JXWGCVLNCGCZRU-WQUGZTNDSA-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

反应信息

• 作为产物：
  描述：

  uridine 5'-diphosphoglucuronic acid trisodium salt 、 槲皮素 在 human UDP-glucuronosyltransferase UGT₁A₉ 作用下， 以 甲醇 、 水 为溶剂， 生成 7-O-glucuronosyl quercetin
  参考文献：
  名称：

  Regioselectivity of human UDP-glucuronosyltransferase isozymes in flavonoid biotransformation by metal complexation and tandem mass spectrometry

  摘要：

  Based on reactions with five flavonoids, the regioselectivities of twelve human UDP-glucuronosyltransferase (UGT) isozymes were elucidated. The various flavonoid glucuronides were differentiated based on LC-MS/MS fragmentation patterns of [Co(II)(flavonoid-H)(4,7-diphenyl-1,10-phenanthroline)(2)](+) complexes generated upon post-column complexation. Glucuronide distributions were evaluated to allow a systematic assessment of the regioselectivity of each isozyme. The various UGT enzymes, including eight UGT1A and four UGT2B, displayed a remarkable range of selectivities, both in terms of the positions of glucuronidation and relative reactivity with flavanones versus flavonols. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bcp.2011.08.015

文献信息

• Accurate Prediction of Glucuronidation of Structurally Diverse Phenolics by Human UGT1A9 Using Combined Experimental and In Silico Approaches
  作者：Baojian Wu、Xiaoqiang Wang、Shuxing Zhang、Ming Hu

  DOI：10.1007/s11095-012-0666-z

  日期：2012.6

  Catalytic selectivity of human UGT1A9, an important membrane-bound enzyme catalyzing glucuronidation of xenobiotics, was determined experimentally using 145 phenolics and analyzed by 3D-QSAR methods. Catalytic efficiency of UGT1A9 was determined by kinetic profiling. Quantitative structure activity relationships were analyzed using CoMFA and CoMSIA techniques. Molecular alignment of substrate structures was made by superimposing the glucuronidation site and its adjacent aromatic ring to achieve maximal steric overlap. For a substrate with multiple active glucuronidation sites, each site was considered a separate substrate. 3D-QSAR analyses produced statistically reliable models with good predictive power (CoMFA: q2 = 0.548, r2 = 0.949, r pred 2  = 0.775; CoMSIA: q2 = 0.579, r2 = 0.876, r pred 2  = 0.700). Contour coefficient maps were applied to elucidate structural features among substrates that are responsible for selectivity differences. Contour coefficient maps were overlaid in the catalytic pocket of a homology model of UGT1A9, enabling identification of the UGT1A9 catalytic pocket with a high degree of confidence. CoMFA/CoMSIA models can predict substrate selectivity and in vitro clearance of UGT1A9. Our findings also provide a possible molecular basis for understanding UGT1A9 functions and substrate selectivity.

  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。
• UDP-GLUCURONYL TRANSFERASE AND POLYNUCLEOTIDE ENCODING THE SAME
  申请人：Suntory Holdings Limited

  公开号：EP2199388A1

  公开（公告）日：2010-06-23

  The present invention provides a novel UDP-glucuronosyltransferase and a polynucleotide encoding the same (for example, a polynucleotide comprising a polynucleotide consisting of one nucleotide sequence selected from the group consisting of the nucleotide sequence at positions 1 to 1359 in the nucleotide sequence represented by SEQ ID NO: 4, the nucleotide sequence at positions 1 to 1365 in the nucleotide sequence represented by SEQ ID NO: 10, the nucleotide sequence at positions 1 to 1371 in the nucleotide sequence represented by SEQ ID NO: 12, and the nucleotide sequence at positions 1 to 1371 in the nucleotide sequence represented by SEQ ID NO: 22; or a polynucleotide comprising a polynucleotide encoding a protein having one amino acid sequence selected from the group consisting of SEQ IDNOS: 5, 11, 13 and 23), etc. This provides a novel UDP-glucuronosyltransferase with a broad substrate specificity.

  本发明提供了一种新型的UDP-葡萄糖醛酸基转移酶和编码该酶的多核苷酸（例如，由一个核苷酸序列组成的多核苷酸，该核苷酸序列选自由SEQ ID NO: 4所代表的核苷酸序列中1至1359位的核苷酸序列、SEQ ID NO: 10所代表的核苷酸序列中1至1365位的核苷酸序列、SEQ ID NO: 12所代表的核苷酸序列中1至1371位的核苷酸序列和SEQ ID NO: 13所代表的核苷酸序列中1至1371位的核苷酸序列组成的组：10 所代表的核苷酸序列中第 1 位至第 1371 位的核苷酸序列、SEQ ID NO: 12 所代表的核苷酸序列中第 1 位至第 1371 位的核苷酸序列和 SEQ ID NO: 22 所代表的核苷酸序列中第 1 位至第 1371 位的核苷酸序列；或包含编码具有选自 SEQ IDNOS: 5、11、13 和 23 所组成的组的一个氨基酸序列的蛋白质的多核苷酸的多核苷酸等。这就提供了一种具有广泛底物特异性的新型 UDP-葡萄糖醛酸基转移酶。
• Increasing the bioavailability of hydroxycinnamic acids
  申请人：Nestec S.A.

  公开号：EP2596704A1

  公开（公告）日：2013-05-29

  The present invention generally relates to the field of nutrition, health and wellness. For example, the present invention relates to hydroxycinnamic acids and their health benefits. The present invention discloses compositions that allow increasing the bioavailability and/or bioefficacy of hydroxycinnamic acids. According to the invention, this can be achieved by co-administering at least one flavonoid and/or its glycoside conjugate with hydroxycinnamic acids.

  本发明一般涉及营养、健康和保健领域。例如，本发明涉及羟基肉桂酸及其对健康的益处。本发明公开了可提高羟基肉桂酸的生物利用率和/或生物功效的组合物。根据本发明，这可以通过将至少一种类黄酮和/或其糖苷与羟基肉桂酸共同施用来实现。
• Glycosylation modification of bioactive compounds and drugs by plant glycosyltransferases (UGTs)
  申请人：UNIVERSITY OF NORTH TEXAS

  公开号：US11261477B2

  公开（公告）日：2022-03-01

  In alternative embodiments, provided are methods for the glycosylation modification of bioactive compounds and drugs using isolated, recombinant or genetically modified uridine diphosphate glycosyl-transferases (UGTs). In alternative embodiments, provided are methods for modifying UGTs to generate recombinant UGTs with altered donor and/or acceptor specificities. In alternative embodiments, provided are methods for screening for recombinantly engineered UGTs with new or altered properties, for example, for new or altered donor and/or acceptor specificities, where in alternative embodiments the screening comprise use of bacterial, yeast or baculovirus expression system.

  在另一个实施方案中，提供了使用分离的、重组的或遗传修饰的二磷酸尿苷糖基转移酶（UGTs）对生物活性化合物和药物进行糖基化修饰的方法。在另一些实施方案中，提供了对 UGTs 进行修饰以产生具有改变的供体和/或受体特异性的重组 UGTs 的方法。在另一个实施方案中，提供了筛选具有新的或改变的特性的重组工程UGT的方法，例如，筛选新的或改变的供体和/或受体特异性的方法，其中在另一个实施方案中，筛选包括使用细菌、酵母或杆状病毒表达系统。
• INCREASING THE BIOAVAILABILITY OF HYDROXYCINNAMIC ACIDS
  申请人：Nestec S.A.

  公开号：EP2785203B1

  公开（公告）日：2018-03-07