Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C15H10O6 |
| Molecular Weight | 286.2363 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC2=C(C=C1)C(=O)C(O)=C(O2)C3=CC=C(O)C(O)=C3
InChI
InChIKey=XHEFDIBZLJXQHF-UHFFFAOYSA-N
InChI=1S/C15H10O6/c16-8-2-3-9-12(6-8)21-15(14(20)13(9)19)7-1-4-10(17)11(18)5-7/h1-6,16-18,20H
Fisetin, a natural flavonoid found in various fruits, vegetables, and nuts, has various biological properties, including anti-inflammatory, anti-oxidant, neuroprotective in cell culture and in animal models relevant to human diseases. Fisetin can be also a promising agent for the treatment of uveal melanoma. Besides, it is a therapeutic agent for respiratory inflammatory diseases such as chronic obstructive pulmonary disease (COPD), where fisetin inhibits the TNF-α-activated IKK/NF-κB cascade by targeting PKCδ. In vitro and in vivo experiments have revealed that fisetin possesses significant therapeutic effects against diabetic complications and atherosclerosis, where it can suppress vascular inflammatory processes.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Q05655 Gene ID: 5580.0 Gene Symbol: PRKCD Target Organism: Homo sapiens (Human) |
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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effects of the flavonoids kaempferol and fisetin on thermotolerance, oxidative stress and FoxO transcription factor DAF-16 in the model organism Caenorhabditis elegans. | 2007-12 |
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| Determination of flavonoid aglycones in several food samples by mixed micellar electrokinetic chromatography. | 2007-10 |
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| Effects of various plant polyphenols on bladder carcinogen benzidine-induced mutagenicity. | 2007-10 |
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| Interaction of flavonoids with red blood cell membrane lipids and proteins: antioxidant and antihemolytic effects. | 2007-06-01 |
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| Fisetin, an inhibitor of cyclin-dependent kinase 6, down-regulates nuclear factor-kappaB-regulated cell proliferation, antiapoptotic and metastatic gene products through the suppression of TAK-1 and receptor-interacting protein-regulated IkappaBalpha kinase activation. | 2007-06 |
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| Flavonoids and related compounds as anti-allergic substances. | 2007-06 |
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| Structure-activity relationship of flavonoids for inhibition of epidermal growth factor-induced transformation of JB6 Cl 41 cells. | 2007-06 |
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| Interaction of flavonoids and intestinal facilitated glucose transporters. | 2007-04 |
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| The small polyphenolic molecule kaempferol increases cellular energy expenditure and thyroid hormone activation. | 2007-03 |
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| Inhibition of the intestinal glucose transporter GLUT2 by flavonoids. | 2007-02 |
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| Design and synthesis of compounds that extend yeast replicative lifespan. | 2007-02 |
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| Flavonoids modulate monocarboxylate transporter-1-mediated transport of gamma-hydroxybutyrate in vitro and in vivo. | 2007-02 |
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| Anti-inflammatory activity of fisetin in human mast cells (HMC-1). | 2007-01 |
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| Distinctive antioxidant and antiinflammatory effects of flavonols. | 2006-12-27 |
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| Comparative study of the photophysical behavior of fisetin in homogeneous media and in anionic and cationic reverse micelles media. | 2006-11-23 |
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| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006-11 |
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| Zinc neurotoxicity is dependent on intracellular NAD levels and the sirtuin pathway. | 2006-10 |
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| A comparison of the neurotrophic activities of the flavonoid fisetin and some of its derivatives. | 2006-10 |
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| Study of the complexation of fisetin with cyclodextrins. | 2006-09-14 |
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| Nutraceutical inhibitors of urokinase: potential applications in prostate cancer prevention and treatment. | 2006-08 |
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| Flavonoids protect human retinal pigment epithelial cells from oxidative-stress-induced death. | 2006-07 |
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| Anti-platelet effects of bioactive compounds isolated from the bark of Rhus verniciflua Stokes. | 2006-06-15 |
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| Characteristics and inhibition by flavonoids of 20alpha-hydroxysteroid dehydrogenase activity in mouse tissues. | 2006-05-15 |
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| Effect of different flavonoids on collagen synthesis in human fibroblasts. | 2006-03 |
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| Antioxidants from Rabdosia japonica. | 2006-03 |
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| Dietary flavonoids: effects on xenobiotic and carcinogen metabolism. | 2006-03 |
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| Luteolin, a flavonoid, inhibits AP-1 activation by basophils. | 2006-02-03 |
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| Improved cold preservation of kidney tubular cells by means of adding bioflavonoids to organ preservation solutions. | 2006-01-27 |
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| Luteolin, a flavonoid, inhibits CD40 ligand expression by activated human basophils. | 2006 |
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| Novel antiproliferative flavonoids induce cell cycle arrest in human prostate cancer cell lines. | 2006 |
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| Structure-activity relationships of the inhibitory effects of flavonoids on P-glycoprotein-mediated transport in KB-C2 cells. | 2005-12 |
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| Flavonoids purified from Rhus verniciflua Stokes actively inhibit cell growth and induce apoptosis in human osteosarcoma cells. | 2005-11-30 |
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| Effects of naturally occurring compounds on fibril formation and oxidative stress of beta-amyloid. | 2005-11-02 |
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| Antiherpetic activities of flavonoids against herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) in vitro. | 2005-11 |
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| Neuroprotective properties of the natural phenolic antioxidants curcumin and naringenin but not quercetin and fisetin in a 6-OHDA model of Parkinson's disease. | 2005-10 |
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| Mechanisms for the inhibition of DNA methyltransferases by tea catechins and bioflavonoids. | 2005-10 |
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| Properties of normal and glycated human hemoglobin in presence and absence of antioxidant. | 2005-09-02 |
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| Dietary flavonoids as intracellular substrates for an erythrocyte trans-plasma membrane oxidoreductase activity. | 2005-09 |
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| Interactions of the plant flavonoid fisetin with macromolecular targets: insights from fluorescence spectroscopic studies. | 2005-08-01 |
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| Oral flavonoids delay recovery from experimental autoimmune encephalomyelitis in SJL mice. | 2005-07-15 |
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| Inhibition of P-glycoprotein by natural products in human breast cancer cells. | 2005-07 |
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| Production of cytokine and NO by RAW 264.7 macrophages and PBMC in vitro incubation with flavonoids. | 2005-05 |
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| Determination of dissociation constants of flavonoids by capillary electrophoresis. | 2005-05 |
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| Phenolic compounds and flavonoids as plant growth regulators from fruit and leaf of Vitex rotundifolia. | 2005-04-09 |
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| Chromosomal malsegregation and micronucleus induction in vitro by the DNA topoisomerase II inhibitor fisetin. | 2005-04-04 |
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| Synergistic effects of flavonoids and ascorbate on enhancement in DNA degradation induced by a bleomycin-Fe complex. | 2005-03 |
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| A blend of polyphenolic compounds explains the stimulatory effect of red wine on human endothelial NO synthase. | 2005-03 |
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| Crystal structure of a human cyclin-dependent kinase 6 complex with a flavonol inhibitor, fisetin. | 2005-02-10 |
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| Evaluation of the antioxidant activity of flavonoids by "ferric reducing antioxidant power" assay and cyclic voltammetry. | 2005-01-18 |
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| Antimicrobial constituents of Gomphrena martiana and Gomphrena boliviana. | 1992-04 |
Sample Use Guides
It was investigated the antiangiogenic efficacy and associated mechanisms of fisetin in human umbilical vein endothelial cells (HUVECs). Fisetin (10-50 μM) strongly inhibited the regular serum plus growth supplement- and vascular endothelial growth factor (VEGF)-induced growth (up to 92%, P < 0.001) and survival (up to 16%, P < 0.001) of HUVEC in a dose- and time-dependent manner. Fisetin also caused cell cycle arrest at G(1) (strong) and G(2)/M (moderate) phases together with a decrease in cyclin D1 and an increase in p53 levels. Fisetin-caused cell death was accompanied by decreased expression of survivin and an increase in cleaved levels of caspases-3 and -7 and poly-(ADP-ribose) polymerase along with an increased ratio of Bax to Bcl-2.
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DSLD |
2651 (Number of products:20)
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OO2ABO9578
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DTXSID4022317
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5281614
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DB07795
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C179571
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42567
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528-48-3
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656275
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407010
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C017875
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m5389
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FISETIN
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OO2ABO9578
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208-434-4
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100000172072
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ACTIVE MOIETY
METABOLITE ACTIVE (PARENT)
