isoquercitrin | 19254-30-9

• 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: isoquercitrin
• 英文别名: 2-[3-(β-D-glucopyranosyloxy)-4-hydroxyphenyl]-3,5,7-trihydroxy-4H-1-benzopyran-4-one；quercetin-3′-O-β-D-glucoside；quercetin 3'-O-β-D-glucopyranoside；quercetin-3'-O-β-D-glucopyranoside；quercetin-4'-O-β-D-glucopyranoside；quercetin 3'-O-β-D-glucoside；Quercetin-3'-glucoside；3,5,7-trihydroxy-2-[4-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
• CAS: 19254-30-9
• 化学式: C₂₁H₂₀O₁₂
• 分子量: 464.383
• InChiKey: YLWQTYZKYGNKPI-HMGRVEAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  207
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  isoquercitrin 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 槲皮素
  参考文献：
  名称：

  Urgineaglyceride A: a new monoacylglycerol from the Egyptian Drimia maritima bulbs

  摘要：

  One new compound, (2S)-1-O-(Z)-tetracos-6-enoate glycerol (1) named urgineaglyceride A, along with six known compounds, 3,5,7,3',5'-pentahydroxydihydroflavonol (2), stigmasterol (3), (25S)-5β-furostane-3β-22α-26-triol (4), scillaridin A (5), (2S)-(+)-2-hydroxynaringenin-4'-O-β-D-glucopyranoside (6) and quercetin-3'-O-β-D-glucopyranoside (7), were isolated from the EtOAc fraction of Drimia maritima (L.) Stearn bulbs. Their structures were secured based on their IR, UV, 1D and 2D NMR data, in addition to HR-MS data and comparison with the literature data. The isolated compounds were evaluated for their in vitro growth inhibitory activity against A549 non-small cell lung cancer (NSCLC), U373 glioblastoma (GBM) and PC-3 prostate cancer cell lines. Compounds 2 and 3 displayed variable activities against the tested cancer cell lines. Compound 2 was a selective inhibitor of the NSCLC cell line with an IC₅₀ of 2.3 μM, whereas 3 was selective against GBM with IC₅₀ of 0.5 μM and against PC-3 with 2.0 μM.

  DOI：

  10.1080/14786419.2014.927468
• 作为产物：
  描述：

  槲皮素 在 20 % Pd(OH)2/C 、 三(3,6-二氧杂庚基)胺 、 氢气 、 sodium methylate 、 potassium carbonate 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 64.5h， 生成 isoquercitrin
  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

• Who Is the King? The<i>α</i>-Hydroxy-<i>β</i>-oxo-<i>α</i>,<i>β</i>-enone Moiety or the Catechol B Ring: Relationship between the Structure of Quercetin Derivatives and Their Pro-Oxidative Abilities
  作者：Pei-Yan Liu、Kun Li、Ji Zhang、Da-Wei Zhang、Hong-Hui Lin、Xiao-Qi Yu

  DOI：10.1002/cbdv.200900032

  日期：2010.1

  Quercetin and other flavonoids have been reported to exhibit both antioxidant and pro-oxidant properties. Most studies about the pro-oxidative ability were conducted in the presence of metal ions, and the essential functional moiety of quercetin responsible for the pro-oxidative effect is still unclear. In this study, we evaluated the pro-oxidative abilities in the absence of metal ions of two quercetin

  据报道，槲皮素和其他类黄酮具有抗氧化剂和促氧化剂特性。关于促氧化能力的大多数研究是在金属离子的存在下进行的，而负责促氧化作用的槲皮素的基本功能部分仍不清楚。在这项研究中，我们评估了两种槲皮素衍生物，即槲皮素3'-O-β-D-葡萄糖苷（1）和槲皮素-3-O-β-D-的金属离子不存在时的促氧化能力葡萄糖苷（2），通过评估DNA裂解和HO（*）自由基的产生。通过荧光和粘度滴定法研究了这些化合物与DNA之间的结合方式。结果表明：1可以有效诱导质粒DNA的氧化损伤，而2则显示较差的活性。1和2均通过凹槽结合与DNA结合。
• Quercetin (=2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-1- benzopyran-4-one) Glycosides and Sulfates: Chemical Synthesis, Complexation, and Antioxidant Properties
  作者：Bertrand Alluis、Olivier Dangles

  DOI：10.1002/1522-2675(20010516)84:5<1133::aid-hlca1133>3.0.co;2-z

  日期：2001.5.16

  Glycosides, acylated glycosides, and sulfates of quercetin (= 3,3 ' ,4 ' ,5,7-pentahydroxyflavone; 1), which is, together with its derivatives, among the most common polyphenols found in plants and in the human diet, were prepared and quantitatively investigated for their ability to bind metal ions (Al-III, Fe-II, Fe-III), enhance and vary natural colours (anthocyanin copigmentation), and trap potentially damaging radicals (antioxidant activity).
• Biogenesis of Heartwood and Bark Constituents. I. A. New Taxifolin Glucoside¹
  作者：H. L. HERGERT、OTTO GOLDSCHMID

  DOI：10.1021/jo01099a015

  日期：1958.5
• Regioselective formation of quercetin 5-O-glucoside from orally administered quercetin in the silkworm, Bombyx mori
  作者：Chikara Hirayama、Hiroshi Ono、Yasumori Tamura、Kotaro Konno、Masatoshi Nakamura

  DOI：10.1016/j.phytochem.2007.11.009

  日期：2008.3

  The cocoons of some races of the silkworm, Bombyx mori, have been shown to contain 5-O-glucosylated flavonoids, which do not occur naturally in the leaves of their host plant, mulberry (Morus alba). Thus, dietary flavonoids could be biotransformed in this insect. In this study, we found that after feeding silkworms a diet rich in the flavonol quercetin, quercetin 5-O-glucoside was the predominant metabolite in the midgut tissue, while quercetin 5,4'-di-O-glucoside was the major constituent in the hemolymph and silk glands. UDP-glucosyltransferase (UGT) in the midgut could transfer glucose to each of the hydroxyl groups of quercetin, with a preference for formation of 5-O-glucoside, while quercetin 5,4'-di-O-glucoside was predominantly produced if the enzyme extracts of either the fat body or silk glands were incubated with quercetin 5-O-glucoside and UDP-glucose. These results suggest that dietary quercetin was glucosylated at the 5-OP position in the midgut as the first-pass metabolite of quercetin after oral absorption, then glucosylated at the 4'-O position in the fat body or silk glands. The 5-O-glucosylated flavonoids retained biological activity in the insect, since the total free radical scavenging capacity of several tissues increased after oral administration of quercetin. (c) 2007 Elsevier Ltd. All rights reserved.
• [EN] PHARMACEUTICAL COMPOSITION COMPRISING AN EXTRACT FROM OPUNTIA FICUS-INDICA<br/>[FR] COMPOSITION PHARMACEUTIQUE COMPRENANT UN EXTRAIT D'OPUNTIA FICUS-INDICA
  申请人：KOREA INST SCI & TECH

  公开号：WO2008038849A1

  公开（公告）日：2008-04-03

  [EN] The present invention relates to a pharmaceutical composition comprising an extract from Opuntia ficus-indica, more particularly to a pharmaceutical composition comprising a butanol extract from Opuntia ficus-indica or an acid hydrolysate of the extract as an active ingredient, and effective in treating or preventing cranial nerve diseases, cerebrovascular diseases or cardiovascular diseases, for example, stroke, concussion, Alzheimer's disease, Parkinson's disease, cell death, myocardial infarction, and so forth.
  [FR] La présente invention porte sur une composition pharmaceutique comprenant un extrait d'Opuntia ficus-indica, plus particulièrement sur une composition pharmaceutique comprenant un extrait de butanol prélevé sur Opuntia ficus-indica ou un hydrolysat acide de l'extrait agissant comme ingrédient actif et efficace dans le traitement ou la prévention des affections des nerfs crâniens, des maladies cérébrovasculaires ou des maladies cardio-vasculaires telles que l'accident cérébrovasculaire, la commotion, la maladie d'Alzheimer, la maladie de Parkinson, la mort cellulaire, l'infarctus du myocarde, etc.