槲皮素-7-葡萄糖苷 | 491-50-9

• 物质功能分类: 生物化工 - 提取物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 槲皮素-7-葡萄糖苷
• 中文别名: 槲皮素-7-O-葡萄糖苷；槲皮素-7-O-葡萄糖苷槲皮素-7-O-β-D-葡萄糖苷；槲皮素-7-O-Β-D-葡萄糖苷；槲皮素-7-O-beta-D-吡喃葡萄糖苷；槲皮素-7-O-BETA-D-吡喃葡萄糖苷；槲皮素-7-O-葡萄糖苷；槲皮素-7-O-β-D-葡萄糖苷； 槲皮素-7-O-beta-D-吡喃葡萄糖苷
• 英文名称: quercetin 7-O-β-D-glucopyranoside
• 英文别名: Quercetin 7-O-glucoside；3,5-dihydroxy-2-(3,4-dihydroxyphenyl)-7-(β-D-glucopyranosyloxy)-4H-1-benzopyran-4-one；quercetine-7-O-β-D-glucopyranoside；quercetin 3-O-β-D-glucopyranoside；quercetin-7-O-β-D-glucopyranoside；luteolin-7-O-β-D-glucopyranoside；Quercimeritrin；2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• CAS: 491-50-9
• 化学式: C₂₁H₂₀O₁₂
• 分子量: 464.383
• InChiKey: BBFYUPYFXSSMNV-HMGRVEAOSA-N

物化性质

• 溶解度：
  DMF：10mg/mL； DMSO：10mg/mL； PBS（pH 7.2）：0.3 mg/mL
• 熔点：
  248 °C
• 沸点：
  859.2±65.0 °C(Predicted)
• 密度：
  1.809±0.06 g/cm3(Predicted)
• LogP：
  -0.367 (est)

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

安全信息

• WGK Germany：
  3

制备方法与用途

生物活性

Quercimeritrin 是从齿状苦艾叶中分离出的，具有明显的淀粉酶活性。这种物质是一种黄色结晶性粉末，能够溶解于甲醇、乙醇和DMSO等有机溶剂中，来源于银杏叶（Ginkgo biloba L.）。

用途

Quercimeritrin 广泛用于含量测定、鉴定以及药理实验等领域。它具有一定的抗氧化和抗衰老作用。

反应信息

• 作为反应物：
  描述：

  槲皮素-7-葡萄糖苷 以68%的产率得到槲皮素
  参考文献：
  名称：

  Flavonoids from Cephalaria gigantea flowers

  摘要：

  从千层塔（Ledeb.）Bobr.（地肤子科）花中分离出了木犀草素、槲皮素、槲皮苷、槲皮苷和新的黄酮醇生物苷千层塔苷A。通过光谱特性和化学转化，确定了千层塔苷 A 的结构为槲皮素-7-O-[α-L-阿拉伯吡喃糖基（1→6）]-β-D-吡喃葡萄糖苷。

  DOI：

  10.1007/s10600-006-0250-z
• 作为产物：
  描述：

  2-(2,2-diphenyl-benzo[1,3]dioxol-5-yl)-3,5-bisbenzyloxy-7-β-D-glucopyranosyloxy-4H-chromen-4-one 在 20 % Pd(OH)2/C 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 12.0h， 以78%的产率得到槲皮素-7-葡萄糖苷
  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

• Flavonoids from Salix caprea
  作者：M. Moohammadnor、X. Tursun、M. Qiong Ling、A. Sultan、K. A. Eshbakova

  DOI：10.1007/s10600-010-9747-6

  日期：2010.11

  and their derivatives [8], flavonoids chultenin [3], kaempferol, luteolin, apigenin, naringenin, quercetin, isorhamnetin [9], luteolin 7-O--D-glucopyranoside, baccoside, salicaprin [10-12], diosmetin, caperoside, salicaperoside [13, 14], astragalin, quercemeritrin, and quercetin 3,7-di-O-glucoside [15] were isolated from S. caprea. Ground air-dried flowers of S. caprea (1000 g) that were collected

  Salix caprea L. (Salicaceae) 在民间医学中广泛用于治疗风湿性关节炎、疟疾、各种出血、痛风、神经痛和肠道疾病，作为解热、镇痛、抗炎、抗菌、止血、镇静和抗蠕虫剂[1]。 , 2]。碳水化合物 [3]、鞣剂 [4]、类固醇 [5]、酚糖苷 [6]、生物碱、维生素 [7]、酚羧酸及其衍生物 [8]、黄酮类化合物 chultenin [3]、山奈酚、木犀草素、芹菜素、柚皮素, 槲皮素, 异鼠李素 [9], 木犀草素 7-O--D-吡喃葡萄糖苷, baccoside, salicaprin [10-12], diosmetin, caperoside, salicaperoside [13, 14], astragalin, quercemeritrin, and 3,7-ercetin- O-葡萄糖苷 [15] 是从 S. caprea 中分离出来的。新疆和田地区采收的 S
• β-Glucosidase Activity in the Rat Small Intestine toward Quercetin Monoglucosides
  作者：Kana IOKU、Yutana PONGPIRIYADACHA、Yotaro KONISHI、Yoko TAKEI、Nobuji NAKATANI、Junji TERAO

  DOI：10.1271/bbb.62.1428

  日期：1998.1

  In order to evaluate the positional specificity for a glucoside group in the hydrolysis of flavonoid glucosides in the rat small intestine, β-glucosidase activity was measured with the quercetin monoglucosides, quercetin-3-O-β-D-glucopyranoside (Q3G), quercetin-4′-O-β-D-glucopyranoside (Q4′G) and quercetin-7-O-β-D-glucopyranoside (Q7G), as well as with quercetin-3-O-rutinoside (rutin) and p-nitrophenyl-β-D-glucopyranoside (NPG) by using the HPLC technique. Enzymes were prepared from rat small intestinal mucosa of the duodenum, jejunum and ileum, among which the enzyme activity of the jejunum was highest for all the glycosides tested. Q4′G was the richest substrate for a β-glucosidase solution among these glycosides, while rutin and NPG were both poor substrates. This suggests that dietary flavonoid glucosides are primarily hydrolyzed and liberated aglycones in the jejunum.

  为了评估大鼠小肠水解黄酮苷过程中葡萄糖苷基的位置特异性，用槲皮素单葡萄糖苷、槲皮素-3-O-β-D-吡喃葡萄糖苷（Q3G）、槲皮素-4′-O-β-D-吡喃葡萄糖苷（Q4′G）和槲皮素-7-O-β-D-吡喃葡萄糖苷（Q7G）测定了β-葡萄糖苷酶的活性、槲皮素-4′-O-β-D-吡喃葡萄糖苷（Q4′G）和槲皮素-7-O-β-D-吡喃葡萄糖苷（Q7G），以及槲皮素-3-O-芸香糖苷（芦丁）和对硝基苯基-β-D-吡喃葡萄糖苷（NPG）。从大鼠十二指肠、空肠和回肠的小肠粘膜中制备酶，其中空肠粘膜对所有苷类化合物的酶活性最高。在这些苷类中，Q4′G 是β-葡萄糖苷酶溶液最丰富的底物，而芦丁和 NPG 都是较差的底物。这表明膳食中的黄酮苷主要在空肠中水解并释放出苷元。
• Nitrate prodrugs able to release nitric oxide in a controlled and selective way and their use for prevention and treatment of inflammatory, ischemic and proliferative diseases
  申请人：Scaramuzzino, Giovanni

  公开号：EP1336602A1

  公开（公告）日：2003-08-20

  New pharmaceutical compounds of general formula (I): F-(X)q where q is an integer from 1 to 5, preferably 1; -F is chosen among drugs described in the text, -X is chosen among 4 groups -M, -T, -V and -Y as described in the text. The compounds of general formula (I) are nitrate prodrugs which can release nitric oxide in vivo in a controlled and selective way and without hypotensive side effects and for this reason they are useful for the preparation of medicines for prevention and treatment of inflammatory, ischemic, degenerative and proliferative diseases of musculoskeletal, tegumental, respiratory, gastrointestinal, genito-urinary and central nervous systems.

  通式（I）的新药物化合物：F-（X）q，其中q是1到5的整数，最好是1；-F是在文本中描述的药物中选择的，-X是在文本中描述的4个组-M，-T，-V和-Y中选择的。通式（I）的化合物是硝酸盐前药，可以在体内以受控和选择性的方式释放一氧化氮，而不会产生降压副作用，因此它们非常适用于制备用于预防和治疗肌肉骨骼，皮肤，呼吸，消化，泌尿和中枢神经系统的炎症，缺血，退行性和增生性疾病的药物。
• Flavonoids from Cephalaria grossheimii
  作者：I. S. Movsumov、E. A. Garaev、M. I. Isaev

  DOI：10.1007/s10600-009-9328-8

  日期：2009.5

  liquor was evaporated to dryness. Recrystallization of the solid from acetone afforded quercimeritrin, C21H20O12, mp 250-252°C, [ ] α D 20 −58 ± 2° (c 0.3, Py:MeOH). UV spectrum (λmax, MeOH, nm): 370, 256; +CH3COONa: 350, 256. Acid hydrolysis produced quercetin (65%) and D-glucose. The acetone solution was evaporated to dryness. Recrystallization of the solid from aqueous EtOH afforded cinaroside, C21H20O11

  我们继续研究来自 Dipsacaceae Lindl 家族代表的化学成分。(teasel) [1, 2]，其中一种 Cephalariagrosheimii Bobr. 是阿塞拜疆的特有种 [3]。根据 Cherepanov [4]，该物种与 C. kotschyi Boiss et Hoh 同义。然而，这与关于这些植物植物化学的文献相矛盾。因此，C. kotschyi 的根含有生物碱龙胆碱、龙胆碱和龙胆碱 [5] 而在 C.grossheimii 中未观察到生物碱。C. kotschyi 的花含有黄酮类化合物山奈酚、金丝桃苷、槲皮苷、cinaroside、cephaside 和 cephacoside [2]。尚未研究 C.grossheimii 的类黄酮成分。因此，我们研究了 C.grossheimii 花的类黄酮成分。这种植物的花除了芹菜素、金丝桃苷、槲皮苷、cinaroside 和palustroside
• Bioactive Depside and Anthocyanin Compounds, Compositions, and Methods of Use
  申请人：D'Armiento Jeanine

  公开号：US20110110885A1

  公开（公告）日：2011-05-12

  Methods for modulating the level of a chemokine in a cell by administering to a cell an effective amount of a depside or an anthocyanin are provided. More particularly, a method for modulating the level of a chemokine in a cell by administering to a cell an effective amount of a depside having the structure of formula (IV): Formula (IV) wherein R is selected from H or CH 3 or an anthocyanin selected from cyanidin 3-glucoside, delphinidin 3-glucoside, or combinations thereof, or an enantiomer, optical isomer, diastereomer, N-oxide, crystalline form, hydrate, or pharmaceutically acceptable salt thereof is provided. Also provided are compounds according to Formulas I-IV, pharmaceutical compositions, unit dosage forms, and food or feed supplements containing such compounds. Methods for treating a condition in a mammal and for treating or ameliorating a condition, such as for example, chronic obstructive pulmonary disease (COPD) by administering an effective amount of a composition containing such compounds are also provided. Further provided is an extract obtained from the fruit of Myrciaria cauliflora containing at least one compound of the present invention in substantially pure form.

  本文提供了通过向细胞注射有效量的脲苷或花青素来调节化学趋化因子水平的方法。更具体地，本文提供了一种通过向细胞注射具有公式（IV）结构的脲苷的有效量来调节化学趋化因子水平的方法：公式（IV）其中R选自H或CH3，或选择青藤花苷、海棠花苷3-葡萄糖苷或其组合的花青素，或其对映体、光学异构体、对映异构体、N-氧化物、结晶形式、水合物或药学上可接受的盐。还提供了根据公式I-IV的化合物、制药组合物、单位剂量形式以及含有这些化合物的食品或饲料补充剂。本文还提供了通过注射含有这些化合物的组合物的有效量来治疗哺乳动物的疾病和治疗或缓解疾病的方法，例如慢性阻塞性肺疾病（COPD）。此外，本文还提供了从Myrciaria cauliflora果实中提取得到的至少一种本发明化合物的纯度高的提取物。