Quercetin-7-O-beta-D-glucopyranosideCAS# 491-50-9 |
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| Cas No. | 491-50-9 | SDF | Download SDF |
| PubChem ID | 5282160 | Appearance | Yellow powder |
| Formula | C21H20O12 | M.Wt | 464.38 |
| Type of Compound | Flavonoids | Storage | Desiccate at -20°C |
| Synonyms | Quercimeritroside;Quercimeritrin | ||
| Solubility | Soluble in methan | ||
| Chemical Name | 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 | ||
| SMILES | C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O)O)O | ||
| Standard InChIKey | BBFYUPYFXSSMNV-HMGRVEAOSA-N | ||
| Standard InChI | InChI=1S/C21H20O12/c22-6-13-15(26)17(28)19(30)21(33-13)31-8-4-11(25)14-12(5-8)32-20(18(29)16(14)27)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,19,21-26,28-30H,6H2/t13-,15-,17+,19-,21-/m1/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Quercetin-7-O-beta-D-glucopyranoside has antibacterial activity, it shows promising activity against Staphylococcus aureus. Quercetin 7-O-beta-D-glucopyranoside exhibits strong antioxidative, and anti-inflammatory activities, inhibiting expression of inducible nitric oxide synthase and release of nitric oxide by lipopolysaccharide-stimulated RAW 264.7 macrophages in a dose-dependent manner. It inhibits overexpression of cyclooxygenase-2 and granulocyte macrophage-colony-stimulating factor. |
| Targets | NO | COX | Antifection |
| In vitro | Phenolic compounds in leaves of Alchornea triplinervia: anatomical localization, mutagenicity, and antibacterial activity.[Pubmed: 20839624]Nat Prod Commun. 2010 Aug;5(8):1225-32.Phenolic compounds are produced by secretory idioblasts and hypodermis, and by specialized cells of the epidermis and chlorenchyma of leaves of Alchornea triplinervia. Antioxidant and anti-inflammatory activities of quercetin 7-O-β-D-glucopyranoside from the leaves of Brasenia schreberi.[Pubmed: 21859349]J Med Food. 2011 Oct;14(10):1127-34.Brasenia schreberi Gmel. (Cabombaceae) is an aquatic plant that grows in eastern Asia, Australia, Africa, and North and Central America. B. schreberi leaf extracts were obtained by sequential solvent extraction with dichloromethane, methanol, and water. The antioxidant potential of each extract was assessed by using the oxygen radical absorbance capacity (ORAC) assay. Antioxidative flavonoids from leaves of Carthamus tinctorius.[Pubmed: 12135103]Arch Pharm Res. 2002 Jun;25(3):313-9.A total of eight flavonoids (1-8), including a novel quercetin-7-O-(6''-O-acetyl)-beta-D-glucopyranoside (6) and seven known flavonoids, luteolin (1), quercetin (2), luteolin 7-O-beta-D-glucopyranoside (3), luteolin-7-O-(6''-O-acetyl)-beta-D-glucopyranoside (4) Quercetin-7-O-beta-D-glucopyranoside (5), acacetin 7-O-beta-D-glucuronide (7) and apigenin-6-C-beta-D-glucopyrano syl-8-C-beta-D-glucopyranoside (8), have been isolated from the leaves of the safflower (Carthamus tinctorius L.) and identified on the basis of spectroscopic and chemical studies. |
| Structure Identification | Nat Prod Res. 2014;28(21):1859-63.A new flavonoid glycoside from the root bark of Morus alba L.[Pubmed: 25174266]
Food Funct. 2015 Jan;6(1):219-29.Quercetin 7-O-glucoside suppresses nitrite-induced formation of dinitrosocatechins and their quinones in catechin/nitrite systems under stomach simulating conditions.[Pubmed: 25375233]Foods of plant origin contain flavonoids. In the adzuki bean, (+)-catechin, quercetin 3-O-rutinoside (rutin), and Quercetin-7-O-beta-D-glucopyranoside(Q7G) are the major flavonoids. During mastication of foods prepared from the adzuki bean, the flavonoids are mixed with saliva and swallowed into the stomach. |
Quercetin-7-O-beta-D-glucopyranoside Dilution Calculator
Quercetin-7-O-beta-D-glucopyranoside Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.1534 mL | 10.767 mL | 21.5341 mL | 43.0682 mL | 53.8352 mL |
| 5 mM | 0.4307 mL | 2.1534 mL | 4.3068 mL | 8.6136 mL | 10.767 mL |
| 10 mM | 0.2153 mL | 1.0767 mL | 2.1534 mL | 4.3068 mL | 5.3835 mL |
| 50 mM | 0.0431 mL | 0.2153 mL | 0.4307 mL | 0.8614 mL | 1.0767 mL |
| 100 mM | 0.0215 mL | 0.1077 mL | 0.2153 mL | 0.4307 mL | 0.5384 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Antioxidant and anti-inflammatory activities of quercetin 7-O-beta-D-glucopyranoside from the leaves of Brasenia schreberi.[Pubmed:21859349]
J Med Food. 2011 Oct;14(10):1127-34.
Brasenia schreberi Gmel. (Cabombaceae) is an aquatic plant that grows in eastern Asia, Australia, Africa, and North and Central America. B. schreberi leaf extracts were obtained by sequential solvent extraction with dichloromethane, methanol, and water. The antioxidant potential of each extract was assessed by using the oxygen radical absorbance capacity (ORAC) assay. With this method, methanol and water extracts were found to be active with mean +/- standard deviation values of 7 +/- 2 and 5.1 +/- 0.5 mumol Trolox(R) equivalents (TE)/mg, respectively. Two major phenolic compounds, Quercetin-7-O-beta-D-glucopyranoside and gallic acid, were respectively isolated from the methanolic and water extracts. Both compounds exhibited antioxidant activities, in particular Quercetin-7-O-beta-D-glucopyranoside (ORAC value, 18 +/- 4 mumol TE/mumol). In contrast to its well-known antioxidant homologue quercetin, Quercetin-7-O-beta-D-glucopyranoside does not inhibit growth of human fibroblasts (WS-1) or murine macrophages (RAW 264.7). Some flavonoids have been reported to possess beneficial effects in cardiovascular and chronic inflammatory diseases associated with overproduction of nitric oxide. Quercetin-7-O-beta-D-glucopyranoside possesses anti-inflammatory activity, inhibiting expression of inducible nitric oxide synthase and release of nitric oxide by lipopolysaccharide-stimulated RAW 264.7 macrophages in a dose-dependent manner. Quercetin-7-O-beta-D-glucopyranoside also inhibited overexpression of cyclooxygenase-2 and granulocyte macrophage-colony-stimulating factor.
Antioxidative flavonoids from leaves of Carthamus tinctorius.[Pubmed:12135103]
Arch Pharm Res. 2002 Jun;25(3):313-9.
A total of eight flavonoids (1-8), including a novel quercetin-7-O-(6''-O-acetyl)-beta-D-glucopyranoside (6) and seven known flavonoids, luteolin (1), quercetin (2), luteolin 7-O-beta-D-glucopyranoside (3), luteolin-7-O-(6''-O-acetyl)-beta-D-glucopyranoside (4) quercetin 7-O-beta-D-glucopyranoside (5), acacetin 7-O-beta-D-glucuronide (7) and apigenin-6-C-beta-D-glucopyrano syl-8-C-beta-D-glucopyranoside (8), have been isolated from the leaves of the safflower (Carthamus tinctorius L.) and identified on the basis of spectroscopic and chemical studies. The antioxidative activity of these flavonoids was evaluated against 2-deoxyribose degradation and rat liver microsomal lipid peroxidation induced by hydroxyl radicals generated via a Fenton-type reaction. Among these flavonoids, luteolin-acetyl-glucoside (4) and quercetin-acetyl-glucoside (6) showed potent antioxidative activities against 2-deoxyribose degradation and lipid peroxidation in rat liver microsomes. Luteolin (1), quercetin (2), and their corresponding glycosides (3 & 5) also exhibited strong antioxidative activity, while acacetin glucuronide (7) and apigenin-6,8-di-C-glucoside (8) were relatively less active.
Phenolic compounds in leaves of Alchornea triplinervia: anatomical localization, mutagenicity, and antibacterial activity.[Pubmed:20839624]
Nat Prod Commun. 2010 Aug;5(8):1225-32.
Phenolic compounds are produced by secretory idioblasts and hypodermis, and by specialized cells of the epidermis and chlorenchyma of leaves of Alchornea triplinervia. Phytochemical investigation of these leaves led to the isolation of the known substances quercetin, Quercetin-7-O-beta-D-glucopyranoside, quercetin-3-O-beta-D-glucopyranoside, quercetin-3-O-beta-D-galactopyranoside, quercetin-3-O-alpha-L-arabinopyranoside, amentoflavone, brevifolin carboxylic acid, gallic acid, and methyl gallate from the methanolic extract, and stigmasterol, campesterol, sitosterol, lupeol, friedelan-3-ol, and friedelan-3-one from the chloroform extract. In studies of antibacterial activity and mutagenicity, the methanolic extract showed promising activity against Staphylococcus aureus (MIC = 62.5 microg/mL) and was slightly mutagenic in vitro and in vivo at the highest concentrations tested (1335 mg/kg b.w.).
A new flavonoid glycoside from the root bark of Morus alba L.[Pubmed:25174266]
Nat Prod Res. 2014;28(21):1859-63.
A new guibourtinidol glycoside, (2R,3S)-guibourtinidol-3-O-alpha-d-apiofuranosyl-(1 --> 6)-O-beta-D-glucopyranoside (1), and three known compounds, quercetin 7-O-beta-D-glucopyranoside (2), syringaresinol-4-O-beta-D-glucopyranoside (3) and dehydrodiconiferyl alcohol 4,9'-di-O-beta-D-glucopyranoside (4), were isolated from the root bark of Morus alba L. through repeated silica gel, octadecyl silica gel and Sephadex LH-20 column chromatography for the n-BuOH fraction. The chemical structure of the compounds was elucidated based on MS, infrared, 1D and 2D NMR spectroscopic data. Compounds 2-4 were also isolated for the first time from the root bark of M. alba L. in this study.
Quercetin 7-O-glucoside suppresses nitrite-induced formation of dinitrosocatechins and their quinones in catechin/nitrite systems under stomach simulating conditions.[Pubmed:25375233]
Food Funct. 2015 Jan;6(1):219-29.
Foods of plant origin contain flavonoids. In the adzuki bean, (+)-catechin, quercetin 3-O-rutinoside (rutin), and quercetin 7-O-beta-D-glucopyranoside (Q7G) are the major flavonoids. During mastication of foods prepared from the adzuki bean, the flavonoids are mixed with saliva and swallowed into the stomach. Here we investigated the interactions between Q7G and (+)-catechin at pH 2, which may proceed in the stomach after the ingestion of foods prepared from the adzuki bean. Q7G reacted with nitrous acid producing nitric oxide ( NO) and a glucoside of 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone. (+)-Catechin reacted with nitrous acid producing NO and 6,8-dinitrosocatechin. The production of the dinitrosocatechin was partly suppressed by Q7G, and the suppression resulted in the enhancement of Q7G oxidation. 6,8-Dinitrosocatechin reacted further with nitrous acid generating the o-quinone, and the quinone formation was effectively suppressed by Q7G. In the flavonoids investigated, the suppressive effect decreased in the order Q7G approximately quercetin>kaempferol>quercetin 4'-O-glucoside>rutin. Essentially the same results were obtained when (-)-epicatechin was used instead of (+)-catechin. The results indicate that nitrous acid-induced formation of 6,8-dinitrosocatechins and the o-quinones can be suppressed by flavonols in the stomach, and that both a hydroxyl group at C3 and ortho-hydroxyl groups in the B-ring are required for efficient suppression.
