Quercetin 3'-Glucuronide | 328006-77-5

• 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: 3'-O-β-D-glucopyranuronosylquercetin；quercetin 3‐O‐glucuronide；quercetin 3'-O-β-D-glucuronide；quercetin 3-O-β-D-glucuronide；quercetin-3-O-β-glucuronide；quercetin-3′-glucuronide；Quercetin-3'-glucuronide；(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-hydroxy-5-(3,5,7-trihydroxy-4-oxochromen-2-yl)phenoxy]oxane-2-carboxylic acid
• CAS: 328006-77-5
• 化学式: C₂₁H₁₈O₁₃
• 分子量: 478.366
• InChiKey: LBJLXDMWOKJIPQ-JENRNSKYSA-N

物化性质

• 沸点：
  886.5±65.0 °C(Predicted)
• 密度：
  1.911±0.06 g/cm3(Predicted)

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：

  槲皮素 在 sodium hypochlorite 、 2,2,6,6-四甲基哌啶氧化物 、 20 % Pd(OH)2/C 、 三(3,6-二氧杂庚基)胺 、 四丁基溴化铵 、 氢气 、 sodium methylate 、 potassium carbonate 、 potassium bromide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 65.5h， 生成 Quercetin 3'-Glucuronide
  参考文献：
  名称：

  Regiospecific synthesis of quercetin O-β-d-glucosylated and O-β-d-glucuronidated isomers

  摘要：

  Quercetin, the polyphenolic compound, which has the highest daily intake, is well known for its protective effects against aging diseases and has received a lot of attention for this reason. Both quercetin 3-O-beta-D-glucuronide and quercetin 3'-O-beta-D-glucuronide are human metabolites, which, together with their regioisomers, are required for biological as well as physical chemistry studies. We present here a novel synthetic route based on the sequential and selective protections of the hydroxyl functions of quercetin allowing selective glycosylation, followed by TEMPO-mediated oxidation to the glucuronide. This methodology enabled us to synthesize the five O-beta-D-glucosides and four O-beta-D-glucuronides of quercetin, including the major human metabolite, quercetin 3-O-beta-D-glucuronide. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2011.03.110

文献信息

• Regioselectivity of Phase II Metabolism of Luteolin and Quercetin by UDP-Glucuronosyl Transferases
  作者：Marelle G. Boersma、Hester van der Woude、Jan Bogaards、Sjef Boeren、Jacques Vervoort、Nicole H. P. Cnubben、Marlou L. P. S. van Iersel、Peter J. van Bladeren、Ivonne M. C. M. Rietjens

  DOI：10.1021/tx0101705

  日期：2002.5.1

  The regioselectivity of phase II conjugation of flavonoids is expected to be of importance for their biological activity. In the present study, the regioselectivity of phase II biotransformation of the model flavonoids luteolin and quercetin by UDP-glucuronosyltransferases was investigated. Identification of the metabolites formed in microsomal incubations with luteolin or quercetin was done using HPLC, LC-MS, and H-1 NMR. The results obtained demonstrate the major sites for glucuronidation to be the 7-, 3-, 3'-, or 4'-hydroxyl moiety. Using these unequivocal identifications, the regioselectivity of the glucuronidation of luteolin and quercetin by microsomal samples from different origin, i.e., rat and human intestine and liver, as well as by various individual human UDP-glueuronosyltransferase isoenzymes was characterized. The results obtained reveal that regioselectivity is dependent on the model flavonoid of interest, glucuronidation of luteolin and quercetin not following the same pattern, depending on the isoenzyme of UDP-glucuronosyltransferases (UGT) involved. Human UGT1A1, UGT1A8, and UGT1A9 were shown to be especially active in conjugation of both flavonoids, whereas UGT1A4 and UGT1A10 and the isoenzymes from the UGTB family, UGT2B7 and UGT2B15, were less efficient. Due to the different regioselectivity and activity displayed by the various UDP-glucuronosyltransferases, regioselectivity and rate of flavonoid conjugation varies with species and organ. Qualitative comparison of the regioselectivities of glucuronidation obtained with human intestine and liver microsomes to those obtained with human UGT isoenzymes indicates that, in human liver, especially UGT1A9 and, in intestine, UGT1A1 and UGT1A8 are involved in glucuronidation of quercetin and luteolin. Taking into account the fact that the anti-oxidant action as well as the pro-oxidant toxicity of these catechol-type flavonoids is especially related to their 3',4'-dihydroxyl moiety, it is of interest to note that the human intestine UGT's appear to be especially effective in conjugating this 3',4' catechol unit. This would imply that upon glucuronidation along the transport across the intestinal border, the flavonoids loose a significant part of these biological activities.
• Regiospecific synthesis of quercetin O-β-d-glucosylated and O-β-d-glucuronidated isomers
  作者：Mohammed Kajjout、Christian Rolando

  DOI：10.1016/j.tet.2011.03.110

  日期：2011.6

  Quercetin, the polyphenolic compound, which has the highest daily intake, is well known for its protective effects against aging diseases and has received a lot of attention for this reason. Both quercetin 3-O-beta-D-glucuronide and quercetin 3'-O-beta-D-glucuronide are human metabolites, which, together with their regioisomers, are required for biological as well as physical chemistry studies. We present here a novel synthetic route based on the sequential and selective protections of the hydroxyl functions of quercetin allowing selective glycosylation, followed by TEMPO-mediated oxidation to the glucuronide. This methodology enabled us to synthesize the five O-beta-D-glucosides and four O-beta-D-glucuronides of quercetin, including the major human metabolite, quercetin 3-O-beta-D-glucuronide. (C) 2011 Published by Elsevier Ltd.