17793
Quercetin 3-β-D-glucoside
≥90% (HPLC)
Synonyme(s) :
3,3′,4′,5,7-Pentahydroxyflavone 3-β-glucoside, Isoquercitrin
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A propos de cet article
Formule empirique (notation de Hill) :
C21H20O12
Numéro CAS:
Poids moléculaire :
464.38
UNSPSC Code:
12352205
NACRES:
NA.25
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
100989
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Laissez-nous vous aiderInChI
1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15-,17+,18-,21+/m1/s1
SMILES string
OC[C@H]1O[C@@H](OC2=C(Oc3cc(O)cc(O)c3C2=O)c4ccc(O)c(O)c4)[C@H](O)[C@@H](O)[C@@H]1O
InChI key
OVSQVDMCBVZWGM-QSOFNFLRSA-N
assay
≥90% (HPLC)
application(s)
metabolomics
vitamins, nutraceuticals, and natural products
storage temp.
−20°C
Quality Level
Gene Information
mouse ... Hexa(15211)
General description
Quercetin 3-β-D-glucoside (Q3G), also known as isoquercitrin, is one of the major glycosidic forms of quercetin. It is a mono-glucoside, first isolated from the seed pods of Cercis canadensis L., it is also found in various plants, vegetables, and fruits. Q3G has the basic chemical structure of a flavonoid, with a glucose molecule attached to the C-3 of quercetin.
Application
Quercetin 3-β-D-glucoside has been used:
- as a dietary flavonoid supplement to check its binding capacity with human small ubiquitin-related modifier 1 (SUMO1) protein using surface plasmon resonance (SPR)
- as an inhibitor for Escherichia coli adenosine triphosphate (ATP) synthase
- as an anti-aggregation agent to test its activity against β-amyloid, green fluorescent protein (GFP), and chymotrypsinogen proteins
Biochem/physiol Actions
Quercetin 3-β-D-glucoside possesses strong antioxidant and anti-inflammatory activities. Being a potent oxygen-radical scavenger, it is a neuroprotective agent that improves Alzheimer′s disease (AD) condition in mice models. It has shown antiproliferative activity against colon, lung, and hepatocellular cell lines and MCF-7 human breast cancer cells in combination with apple extracts.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Classe de stockage
11 - Combustible Solids
wgk
WGK 3
ppe
Eyeshields, Gloves, type N95 (US)
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Quercetin and quercetin-3-beta-d-glucoside improve cognitive and memory function in Alzheimer?s disease mouse
Kim J H, et al.,
Applied Biological Chemistry, 721-728 (2016)
Hyun Ju You et al.
Journal of agricultural and food chemistry, 58(20), 10886-10892 (2010-10-05)
The flavonol quercetin in plants and foods occurs predominantly in the form of glycoside whose sugar moiety affects the bioavailability and the mechanism of its biological activities. The antiproliferative activities of quercetin derivatives such as quercetin aglycone, quercetin-3-β-D-glucoside (Q3G), and
Jun Yang et al.
Journal of agricultural and food chemistry, 57(18), 8581-8586 (2009-08-22)
Breast cancer is the most frequently diagnosed cancer in women. An alternative strategy to reduce the risk of cancer is through dietary modification. Although phytochemicals naturally occur as complex mixtures, little information is available regarding possible additive, synergistic, or antagonistic
Kateřina Valentová et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 68, 267-282 (2014-04-01)
The flavonoid isoquercitrin (quercetin-3-O-β-d-glucopyranoside) is commonly found in medicinal herbs, fruits, vegetables and plant-derived foods and beverages. This article reviews the occurrence, preparation, bioavailability, pharmacokinetics, toxicology and biological activity of isoquercitrin and "enzymatically modified (α-glucosylated) isoquercitrin" (EMIQ). Pure isoquercitrin can
Ali Reza A Ladiwala et al.
Biotechnology and bioengineering, 109(7), 1869-1874 (2012-02-15)
Protein aggregation is a common problem during the purification and formulation of therapeutic proteins. Here we report that polyphenolic disaccharides are unusually effective at preventing protein aggregation. We find that two polyphenolic glycosides-naringin and rutin-endow diverse proteins with the ability
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