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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H20O11
Molecular Weight 448.3777
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUERCITRIN

SMILES

C[C@@]1([H])[C@@]([H])([C@]([H])([C@]([H])([C@@]([H])(O1)Oc2c(=O)c3c(cc(cc3oc2-c4ccc(c(c4)O)O)O)O)O)O)O

InChI

InChIKey=OXGUCUVFOIWWQJ-HQBVPOQASA-N
InChI=1S/C21H20O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-18,21-26,28-29H,1H3/t7-,15-,17+,18+,21-/m0/s1

HIDE SMILES / InChI

Molecular Formula C21H20O11
Molecular Weight 448.3777
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Quercitrin is known as a bio flavonoid antioxidant and was investigated extensively in its antioxidant potential in streptrozotocin (STZ)-induced diabetic rats. Quercitrin is also a constituent of the dye quercitron. Quercitrin can be found in Tartary buckwheat and in oaks species such as white oak or European red oak. Quercitrin has potential anti-inflammation effect that is used to treat heart and vascular conditions. Quercitrin offers protection against brain injury in mice by inhibiting oxidative stress and inflammation. Quercitrin also prevented CCl4 induced cerebral function disorders associated with its ability to inhibit the activities of monoamine oxidase (MAO), acetylcholine esterase (AChE) and the N-methyl-d-aspartate receptor 2B subunit (NR2B). Quercitrin suppressed the release of pro-inflammatory cytokines such as tumor necrosis factor alpha (TNF-α) and interleukin-6 (IL-6). Quercitrin may be a potential candidate to be developed as a neuroprotective agent. Quercitrin has been used previously as an antibacterial agent and has been shown to inhibit the oxidation of low-density lipoproteins and prevent an allergic reaction. It was demonstrated that quercitrin exerts protective effects against H2O2-induced dysfunction in lung fibroblast cells. Quercitrin has antiproliferative and apoptotic effects on lung cancer cells by modulating the immune response. There were significant increases in caspase-3 activity, loss of MMP, and increases in the apoptotic cell population in response to quercitrin in DLD-1 colon cancer cells in a time- and dose-dependent manner. These results revealed that quercitrin has antiproliferative and apoptotic effects on colon cancer cells. Quercitrin activity supported with in vivo analyses could be a biomarker candicate for early colorectal carcinoma.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
7.77 µM [IC50]
0.17 µM [IC50]
0.67 mM [IC50]
Target ID: P18654
Gene ID: 110651.0
Gene Symbol: Rps6ka3
Target Organism: Mus musculus (Mouse)
5.8 µM [Kd]
Conditions

Conditions

PubMed

PubMed

TitleDatePubMed
Inhibition of HIV infection by flavanoids.
1993 Oct
Inhibition of HIV-1 integrase by flavones, caffeic acid phenethyl ester (CAPE) and related compounds.
1994 Aug 3
Application of the electrotopological state index to QSAR analysis of flavone derivatives as HIV-1 integrase inhibitors.
1996 Dec
St. John's wort induces hepatic drug metabolism through activation of the pregnane X receptor.
2000 Jun 20
[Studies on chemical constituents in herb of Myricaria bracteata].
2006 Mar
In silico prediction of pregnane X receptor activators by machine learning approaches.
2007 Jan
Doubly linked, A-type proanthocyanidin trimer and other constituents of Ixora coccinea leaves and their antioxidant and antibacterial properties.
2010 Dec
[Chemical constituents from Parthenocissus quinquefolia].
2010 Jun
Antioxidant and hepatoprotective activities of Egyptian moraceous plants against carbon tetrachloride-induced oxidative stress and liver damage in rats.
2010 Nov
Activity-guided isolation and identification of radical scavenging components in Gao-Cha tea.
2010 Oct
Assessment of DNA damage induced by extracts, fractions and isolated compounds of Davilla nitida and Davilla elliptica (Dilleniaceae).
2010 Sep 30
Antiplasmodial activity of flavonol quercetin and its analogues in Plasmodium falciparum: evidence from clinical isolates in Bangladesh and standardized parasite clones.
2012 Jun
Antimicrobial activity of Schinus lentiscifolius (Anacardiaceae).
2013 Jul 9
Polyacetylenes and anti-hepatitis B virus active constituents from Artemisia capillaris.
2014 Jun
Patents

Sample Use Guides

Balb/c mice were orally administered with 10 or 50 mg/kg of quercitrin for 7 days and followed by the injection with single dose of 300 mg/kg APAP. Quercitrin decreased APAP-caused elevation of alanine aminotransferase and aspartate aminotransferase levels, liver necrosis, the expression of pro-inflammatory factors including inducible nitric oxide synthase, cyclooxygenase 2 and inerleukin-1β, and phosphorylation of kinases including c-Jun N-terminal kinase and p38.
Route of Administration: Oral
Of the isolated eight compounds from A. victorialis leaf extracts tested, quercitrin exhibited the most pronounced inhibitory effects on AR activity (IC₅₀ value of 0.17 uM) and AGEs formation (IC₅₀ value of 4.20 uM).
Substance Class Chemical
Created
by admin
on Sat Jun 26 06:13:39 UTC 2021
Edited
by admin
on Sat Jun 26 06:13:39 UTC 2021
Record UNII
2Y8906LC5P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
QUERCITRIN
MI  
Common Name English
4H-1-BENZOPYRAN-4-ONE, 3-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-
Common Name English
QUERCETIN 3-O-.ALPHA.-L-RHAMNOPYRANOSIDE
Common Name English
C.I. 75720
Common Name English
QUERCITRIN [MI]
Common Name English
QUERCITROSIDE
Common Name English
QUERCITRIN (QUERCETIN-3-O- RHAMNOSIDE) (CONSTITUENT OF GINKGO) [DSC]
Common Name English
QUERCITRIN [HSDB]
Common Name English
QUERCETIN 3-O-.ALPHA.-RHAMNOPYRANOSIDE
Common Name English
QUERCETIN 3-RHAMNOSIDE
Common Name English
WA 17779
Code English
QUERCETIN 3-O-RHAMNOSIDE
Common Name English
QUERCETIN-3-O-.ALPHA.-RHAMNOSIDE
Common Name English
3,3',4',5,7-PENTAHYDROXYFLAVONE 3-L-RHAMNOSIDE
Common Name English
QUERCIMELIN
Common Name English
QUERCETIN 3-RHAMNOPYRANOSIDE
Common Name English
3-O-.ALPHA.-L-RHAMNOPYRANOSYLQUERCETIN
Common Name English
5,7,3',4'-TETRAHYDROXYFLAVONOL 3-O-RHAMNOSIDE
Common Name English
QUERCETIN 3-O-RHAMNOPYRANOSIDE
Common Name English
3-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-4H-1-BENZOPYRAN-4-ONE
Common Name English
QUERCETIN 3-L-RHAMNOSIDE
Common Name English
3-O-RHAMNOSYLQUERCETIN
Common Name English
QUERCETIN-3-L-RHAMNOSIDE
Common Name English
QUERCETIN 3-O-.ALPHA.-L-RHAMNOSIDE
Common Name English
THUJIN
Common Name English
NSC-9221
Code English
QUERCETIN 3-O-L-RHAMNOSIDE
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
208-322-5
Created by admin on Sat Jun 26 06:13:39 UTC 2021 , Edited by admin on Sat Jun 26 06:13:39 UTC 2021
PRIMARY
HSDB
4339
Created by admin on Sat Jun 26 06:13:39 UTC 2021 , Edited by admin on Sat Jun 26 06:13:39 UTC 2021
PRIMARY
CAS
522-12-3
Created by admin on Sat Jun 26 06:13:39 UTC 2021 , Edited by admin on Sat Jun 26 06:13:39 UTC 2021
PRIMARY
FDA UNII
2Y8906LC5P
Created by admin on Sat Jun 26 06:13:39 UTC 2021 , Edited by admin on Sat Jun 26 06:13:39 UTC 2021
PRIMARY
MESH
C012526
Created by admin on Sat Jun 26 06:13:39 UTC 2021 , Edited by admin on Sat Jun 26 06:13:39 UTC 2021
PRIMARY
MERCK INDEX
M9423
Created by admin on Sat Jun 26 06:13:39 UTC 2021 , Edited by admin on Sat Jun 26 06:13:39 UTC 2021
PRIMARY Merck Index
EPA CompTox
522-12-3
Created by admin on Sat Jun 26 06:13:39 UTC 2021 , Edited by admin on Sat Jun 26 06:13:39 UTC 2021
PRIMARY
PUBCHEM
5280459
Created by admin on Sat Jun 26 06:13:39 UTC 2021 , Edited by admin on Sat Jun 26 06:13:39 UTC 2021
PRIMARY
WIKIPEDIA
QUERCITRIN
Created by admin on Sat Jun 26 06:13:39 UTC 2021 , Edited by admin on Sat Jun 26 06:13:39 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT