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
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
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2074 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27827864 |
7.77 µM [IC50] | ||
Target ID: CHEMBL612426 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24622055 |
|||
Target ID: CHEMBL1900 |
0.17 µM [IC50] | ||
Target ID: CHEMBL1808 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23194768 |
0.67 mM [IC50] | ||
Target ID: P18654 Gene ID: 110651.0 Gene Symbol: Rps6ka3 Target Organism: Mus musculus (Mouse) Sources: https://www.ncbi.nlm.nih.gov/pubmed/23385462 |
5.8 µM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Sources: https://www.ncbi.nlm.nih.gov/pubmed/15533892 |
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Differential inhibitory effects of various flavonoids on the activities of reverse transcriptase and cellular DNA and RNA polymerases. | 1990 Jul 5 |
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Inhibition of HIV infection by flavanoids. | 1993 Oct |
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Inhibition of HIV-1 integrase by flavones, caffeic acid phenethyl ester (CAPE) and related compounds. | 1994 Aug 3 |
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Application of the electrotopological state index to QSAR analysis of flavone derivatives as HIV-1 integrase inhibitors. | 1996 Dec |
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St. John's wort induces hepatic drug metabolism through activation of the pregnane X receptor. | 2000 Jun 20 |
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Anti-human immunodeficiency virus-type 1 activity of constituents from Juglans mandshurica. | 2002 Aug |
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A pharmacophore for human pregnane X receptor ligands. | 2002 Jan |
|
The inhibitory effects of 12 medicinal plants and their component compounds on lipid peroxidation. | 2003 |
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Isolation and structure elucidation of the major individual polyphenols in carob fibre. | 2003 Dec |
|
The chemical constituents of Rhododendron ovatum Planch. | 2005 Feb |
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Antinociceptive action of the extract and the flavonoid quercitrin isolated from Bauhinia microstachya leaves. | 2005 Oct |
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Inhibition of human cytochrome CYP 1 enzymes by flavonoids of St. John's wort. | 2006 Jan 16 |
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[Studies on chemical constituents in herb of Myricaria bracteata]. | 2006 Mar |
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Phenolic constituents in the fruits of Cinnamomum zeylanicum and their antioxidant activity. | 2006 Mar 8 |
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[Studies on flavonoids from stems and leaves of Calophyllum inophyllum]. | 2007 Apr |
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In silico prediction of pregnane X receptor activators by machine learning approaches. | 2007 Jan |
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An unusual C6-C6" linked flavonoid from Miconia cabucu (Melastomataceae). | 2007 Jul |
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[Studies on chemical constituents from leaves of Lysidice brevicalyx]. | 2008 Nov |
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[Studies on the chemical constituents of Rumex crispus]. | 2009 Dec |
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[Chemical constituents of flowers from Polygonum orientale]. | 2009 Oct |
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Stability of lipid constituents in radiation processed fenugreek seeds and turmeric: role of phenolic antioxidants. | 2009 Oct 14 |
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Doubly linked, A-type proanthocyanidin trimer and other constituents of Ixora coccinea leaves and their antioxidant and antibacterial properties. | 2010 Dec |
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[Chemical constituents from Parthenocissus quinquefolia]. | 2010 Jun |
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Antioxidant and hepatoprotective activities of Egyptian moraceous plants against carbon tetrachloride-induced oxidative stress and liver damage in rats. | 2010 Nov |
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Activity-guided isolation and identification of radical scavenging components in Gao-Cha tea. | 2010 Oct |
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Assessment of DNA damage induced by extracts, fractions and isolated compounds of Davilla nitida and Davilla elliptica (Dilleniaceae). | 2010 Sep 30 |
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Antiplasmodial activity of flavonol quercetin and its analogues in Plasmodium falciparum: evidence from clinical isolates in Bangladesh and standardized parasite clones. | 2012 Jun |
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Antimicrobial activity of Schinus lentiscifolius (Anacardiaceae). | 2013 Jul 9 |
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Polyacetylenes and anti-hepatitis B virus active constituents from Artemisia capillaris. | 2014 Jun |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27428996
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24090434
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
Edited
Sat Jun 26 06:13:39 UTC 2021
by
admin
on
Sat Jun 26 06:13:39 UTC 2021
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Record UNII |
2Y8906LC5P
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Record Status |
Validated (UNII)
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Record Version |
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208-322-5
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4339
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522-12-3
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2Y8906LC5P
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C012526
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M9423
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522-12-3
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5280459
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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
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Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |