17793
Quercetin 3-β-D-glucoside
≥90% (HPLC)
Synonym(s):
3,3′,4′,5,7-Pentahydroxyflavone 3-β-glucoside, Isoquercitrin
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About This Item
Empirical Formula (Hill Notation):
C21H20O12
CAS Number:
Molecular Weight:
464.38
UNSPSC Code:
12352205
NACRES:
NA.25
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
100989
Quality Level
assay
≥90% (HPLC)
application(s)
metabolomics
vitamins, nutraceuticals, and natural products
storage temp.
−20°C
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
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
InChI key
OVSQVDMCBVZWGM-QSOFNFLRSA-N
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.
Storage Class
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)
Prasanna K Dadi et al.
International journal of biological macromolecules, 45(1), 72-79 (2009-04-21)
We have studied the inhibitory effect of five polyphenols namely, resveratrol, piceatannol, quercetin, quercetrin, and quercetin-3-beta-D glucoside on Escherichia coli ATP synthase. Recently published X-ray crystal structures of bovine mitochondrial ATP synthase inhibited by resveratrol, piceatannol, and quercetin, suggest that
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