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Key Documents

17793

Sigma-Aldrich

Quercetin 3-β-D-glucoside

≥90% (HPLC)

Synonyme(s) :

3,3′,4′,5,7-Pentahydroxyflavone 3-β-glucoside, Isoquercitrin

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About This Item

Formule empirique (notation de Hill):
C21H20O12
Numéro CAS:
Poids moléculaire :
464.38
Numéro Beilstein :
100989
Numéro MDL:
Code UNSPSC :
12352205
ID de substance PubChem :
Nomenclature NACRES :
NA.25

Niveau de qualité

Pureté

≥90% (HPLC)

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

OVSQVDMCBVZWGM-QSOFNFLRSA-N

Informations sur le gène

mouse ... Hexa(15211)

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Description générale

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

Actions biochimiques/physiologiques

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.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)


Certificats d'analyse (COA)

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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
Zhongxiang Zhao et al.
Journal of natural products, 70(10), 1683-1686 (2007-10-10)
Five new flavan-4-ol glycosides, abacopterins E-I ( 5- 9), and seven known flavonoid glycosides ( 3 and 10- 15) were isolated from the aerial parts of the fern Abacopteris penangiana. Their structures were elucidated on the basis of extensive spectroscopic
Teresa Mencherini et al.
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Mahendra Thapa et al.
Bioorganic & medicinal chemistry letters, 22(1), 353-356 (2011-11-26)
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Protocoles

HPLC Analysis of Polyphenols in Nero d'Avola Red Wine on Discovery® HS C18 (UV 280 nm)

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