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Quercetin-7-O-glucoside

$807

  • Brand : BIOFRON

  • Catalogue Number : BD-P0856

  • Specification : 98.0%(HPLC)

  • CAS number : 491-50-9

  • PUBCHEM ID : 5282160

  • Volume : 25mg

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Catalogue Number

BD-P0856

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC)

Storage

2-8°C

Molecular Weight

Appearance

Yellow crystalline powder

Botanical Source

Ginkgo biloba L./Occurs in numerous plant spp.

Structure Type

Flavonoids

Category

Standards;Natural Pytochemical;API

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

Synonyms

Quercimeritroside/gossypitrin/Quercetin-7-D-glucoside/2-(3,4-Dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-yl β-D-glucopyranoside/quercetin 7-O-beta-D-glucoside/4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-7-(β-D-glucopyranosyloxy)-3,5-dihydroxy-/Quercetin-7-O-β-D-glucopyranoside/Quercimeritrin (6CI,7CI,8CI)/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/Quercetin-7-glucoside/2-(3,4-Dihydroxyphenyl)-7-(b-D-glucopyranosyloxy)-3,5-dihydroxy-4H-1-benzopyran-4-one/Quercetin-7-O-Beta-D-glucopyranoside/quercimetrin/Quercimeritrin/3,3',4',5,7-Pentahydroxyflavone-7-D-Glucoside/Quercetin 7-O-glucoside

IUPAC 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

Applications

Antioxidant Activity of Quercetin and Its Glucosides from Propolis: A Theoretical Study. PUMID/DOI:DOI: 10.1038/s41598-017-08024-8 Sci Rep. 2017 Aug 8;7(1):7543. Among the multiple components of propolis, flavonoids contribute greatly to the antioxidant activities of propolis. Flavonoids mainly exist in the form of sugar-conjugated derivatives. Quercetin glycosides represent the predominant flavonoid fraction in propolis. In this work, density functional theory (DFT) calculations were applied to analyze the antioxidative properties of quercetin and its glucosides in the gas and in the liquid phase (ethanol, water). Three main antioxidant mechanisms, hydrogen atom transfer (HAT), single electron transfer followed by proton transfer (SET-PT) and sequential proton loss electron transfer (SPLET) were used to analyze the antioxidative capacity of the investigated compounds. Solvent effects dominantly affect SET-PT and SPLET. Thus, the thermodynamically preferred mechanism can be altered. HAT and SPLET are the thermodynamically dominant mechanisms in gas and solvent phases, respectively. Therefore, in the gas phase, the sequence of the antioxidative capacity is similar with the bond dissociation enthalpy values: quercetin?>?quercetin-5-O-glucoside?>?quercetin-7-O-glucoside?>?quercetin-3-O-glucoside?>?quercetin-3'-O-glucoside?>?quercetin-4'-O-glucoside. While, in the solvent phases, the sequence is similar with the proton affinity values: quercetin-4'-O-glucoside?>?quercetin-5-O-glucoside?>?quercetin?>?quercetin-3-O-glucoside?>?quercetin-7-O-glucoside?>?quercetin-3'-O-glucoside. OH groups in B-ring and C-ring contribute mainly to the antioxidative activities of quercetin and glucosides compared with A-ring. Probing the impact of quercetin-7-O-glucoside on influenza virus replication influence. PUMID/DOI:DOI: 10.1016/j.phymed.2016.06.001 Phytomedicine. 2016 Aug 15;23(9):958-67. BACKGROUND:Influenza virus is still at large and seriously affects social welfare and health. Dianthus superbus is a well-known medicinal plant widely used in Mongolian and Chinese traditional medicine for anti-inflammatory purposes.PURPOSE:To investigate the influence of this novel herbal medicinal product over virus infection and virus-induced symptomsMETHOD:Quercetin-7-O-glucoside was isolated by bioassay (anti-influenza)-guided fractionation. The structural elucidation was made with 1H-NMR and 13C-NMR. Influenza A/Vic/3/75 (H3N2), A/PR/8/34 (H1N1), B/Maryland/1/59 and B/Lee/40 viruses were used for the evaluation of the antiviral activity. Virus-induced reactive oxygen species and autophagy formation levels were studied. The antiviral mechanism was elucidated via time-dependent, pre-, post-incubation assay methods. The viral RNA replication inhibition of Q7G was analyzed using quantitative RT-PCR method. The blocking of polymerase basic protein subunits of influenza viral RNA polymerase by Q7G was detected by in silico molecular docking assays using AutoDock Vina program with m(7)GTP. Additionally, Q7G was tested against M-MuLV RNA polymerase.RESULTS:Q7G was not cytotoxic (CC50>100?g/ml) in MDCK cells and it showed 3.1?g/ml, 6.61?g/ml, 8.19?g/ml and 5.17?g/ml IC50 values against influenza A/PR/8/34, A/Vic/3/75, B/Lee/40 and B/Maryland/1/59 virus strains, respectively. Treatment of Q7G highly reduced ROS and autophagy formation induced by influenza virus infection. Q7G did not reduce NA activity and did not directly interact with the virus particles. Since viral RNA synthesis was blocked by treatment of Q7G. We targeted viral RNA polymerase for further probing. Interestingly, the binding energy of Q7G on viral PB2 protein was -9.1kcal/mol and was higher than m(7)GTP recorded as -7.5kcal/mol. It also was observe to block M-MuLV RNA polymerase.CONCLUSION:Isolated compound Q7G showed strong inhibition activity against influenza A and B viruses. It also reduced virus-induced ROS and autophagy formation. Q7G does not directly bind to the virus particles and did not affect NA activity. These results indicated that Q7G inhibits viral RNA polymerase, and that it occupies the binding site of m(7)GTP on viral PB2 protein. Phytochemical and biological investigations of Onopordum alexandrinum seeds PUMID/DOI: Abdallah W E, Elsayed W M, Hassanein H D, et al. Phytochemical and biological investigations of Onopordum alexandrinum seeds[J]. Research Journal of Pharmaceutical Biological & Chemical Sciences, 2015, 6(2):361-374. The investigation of the ethyl acetate fraction from Onopordum alexandrinum seeds resulted in the isolation of ?sitosterol compound and arctiin; a lignan glucoside compound. Whereas, the study of flavonoidal constituents of the alcoholic extract from Onopordum alexandrinum seeds resulted in the isolation of caffeic acid and three flavonoidal compounds, which were identified as 7- methoxy luteolin, Quercetin 7- O- glucoside and kampferol 7- O- glucoside. These compounds were isolated and identified for the first time from the genus Onopordum. Fractionation of Onopordum alexandrinum constituents was performed by applying column chromatography. Moreover, further purification was achieved using successive chromatographic techniques, viz: preparative thin layer chromatography (PTLC), paper chromatography (PPC), as well as sephadex LH-20 column chromatography. Identification of the isolated compounds was carried out through chromatographic means and spectroscopic analyses (viz: UV, MS and NMR). Different extracts of Onopordum alexandrinum seeds (ethyl acetate, methanol and the isolated compounds) were studied for their hepatoprotective activity using hepatocytes monolayer culture from rat. The cells were exposed to certain hepatotoxic doses of paracetamol, which was capable of inducing the IC50 of cultured isolated cells. The results showed that the ethyl acetate fraction of Onopordum alexandrinum showed hepatoprotective activity against paracetamol cytotoxicity at concentration 12.5 礸/mL, while its IC50 were >1000 礸/mL. Consequently, these fractions were assumed to be promising with regard to their hepatoprotective and hepatotoxic activities. The antioxidant activity of the seed extracts showed that the ethyl acetate fraction of Onopordum seeds exhibited the highest antioxidant activity followed by the alcoholic extract. Also, Compound 3 (caffeic acid) and compound 5 (quercetin-7- O- glucoside) showed high antioxidant activity as well as hepatoprotective activity and very low toxicity on liver cells.

Density

1.8±0.1 g/cm3

Solubility

Methanol

Flash Point

302.8±27.8 °C

Boiling Point

859.2±65.0 °C at 760 mmHg

Melting Point

InChl

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

InChl Key

BBFYUPYFXSSMNV-HMGRVEAOSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:491-50-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

25375233

Abstract

Foods of plant origin contain flavonoids. In the adzuki bean, (+)-catechin, quercetin 3-O-rutinoside (rutin), and quercetin 7-O-β-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≈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.

Title

Quercetin 7-O-glucoside suppresses nitrite-induced formation of dinitrosocatechins and their quinones in catechin/nitrite systems under stomach simulating conditions.

Author

Morina F1, Takahama U, Yamauchi R, Hirota S, Veljovic-Jovanovic S.

Publish date

2015 Jan

PMID

27387404

Abstract

BACKGROUND:
Influenza virus is still at large and seriously affects social welfare and health. Dianthus superbus is a well-known medicinal plant widely used in Mongolian and Chinese traditional medicine for anti-inflammatory purposes.

PURPOSE:
To investigate the influence of this novel herbal medicinal product over virus infection and virus-induced symptoms

METHOD:
Quercetin-7-O-glucoside was isolated by bioassay (anti-influenza)-guided fractionation. The structural elucidation was made with 1H-NMR and 13C-NMR. Influenza A/Vic/3/75 (H3N2), A/PR/8/34 (H1N1), B/Maryland/1/59 and B/Lee/40 viruses were used for the evaluation of the antiviral activity. Virus-induced reactive oxygen species and autophagy formation levels were studied. The antiviral mechanism was elucidated via time-dependent, pre-, post-incubation assay methods. The viral RNA replication inhibition of Q7G was analyzed using quantitative RT-PCR method. The blocking of polymerase basic protein subunits of influenza viral RNA polymerase by Q7G was detected by in silico molecular docking assays using AutoDock Vina program with m(7)GTP. Additionally, Q7G was tested against M-MuLV RNA polymerase.

RESULTS:
Q7G was not cytotoxic (CC50>100µg/ml) in MDCK cells and it showed 3.1µg/ml, 6.61µg/ml, 8.19µg/ml and 5.17µg/ml IC50 values against influenza A/PR/8/34, A/Vic/3/75, B/Lee/40 and B/Maryland/1/59 virus strains, respectively. Treatment of Q7G highly reduced ROS and autophagy formation induced by influenza virus infection. Q7G did not reduce NA activity and did not directly interact with the virus particles. Since viral RNA synthesis was blocked by treatment of Q7G. We targeted viral RNA polymerase for further probing. Interestingly, the binding energy of Q7G on viral PB2 protein was -9.1kcal/mol and was higher than m(7)GTP recorded as -7.5kcal/mol. It also was observe to block M-MuLV RNA polymerase.

CONCLUSION:
Isolated compound Q7G showed strong inhibition activity against influenza A and B viruses. It also reduced virus-induced ROS and autophagy formation. Q7G does not directly bind to the virus particles and did not affect NA activity. These results indicated that Q7G inhibits viral RNA polymerase, and that it occupies the binding site of m(7)GTP on viral PB2 protein.

Copyright © 2016 Elsevier GmbH. All rights reserved.

KEYWORDS

Autophagy; Dianthus superbus; Influenza virus; Viral PB2 subunit; Virus induced ROS

Title

Probing the impact of quercetin-7-O-glucoside on influenza virus replication influence.

Author

Gansukh E1, Kazibwe Z1, Pandurangan M1, Judy G1, Kim DH2.

Publish date

2016 Aug 15