FISETIN

Possibly Marketed Outside US

First approved in 2023

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

Structure Search

SMILES

OC1=CC2=C(C=C1)C(=O)C(O)=C(O2)C3=CC(O)=C(O)C=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

HIDE SMILES / InChI

Molecular Formula	C15H10O6
Molecular Weight	286.2363
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29383865 | https://www.ncbi.nlm.nih.gov/pubmed/29396047 | https://www.ncbi.nlm.nih.gov/pubmed/24923846

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
Protein kinase C delta type 2 Target ID: Q05655 Gene ID: 5580.0 Gene Symbol: PRKCD Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/29396047	Binding Agent 1064

Conditions

Condition	Modality	Highest Phase	Product
Chronic obstructive pulmonary disease 174 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29396047	Primary	Basic research	Unknown Approved Use Unknown
Uveal melanoma 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29383865	Primary	Basic research	Unknown Approved Use Unknown
Diabetic complications 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24923846	Primary	Preclinical	Unknown Approved Use Unknown
Atherosclerosis 74 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24923846	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Antimicrobial constituents of Gomphrena martiana and Gomphrena boliviana.	1992 Apr	1608273
Phenolic compounds and flavonoids as plant growth regulators from fruit and leaf of Vitex rotundifolia.	2004 Jul-Aug	15813370
Chromosomal malsegregation and micronucleus induction in vitro by the DNA topoisomerase II inhibitor fisetin.	2005 Apr 4	15781213
Interactions of the plant flavonoid fisetin with macromolecular targets: insights from fluorescence spectroscopic studies.	2005 Aug 1	16038806
Structure-activity relationships of the inhibitory effects of flavonoids on P-glycoprotein-mediated transport in KB-C2 cells.	2005 Dec	16327165
Crystal structure of a human cyclin-dependent kinase 6 complex with a flavonol inhibitor, fisetin.	2005 Feb 10	15689157
Evaluation of the antioxidant activity of flavonoids by "ferric reducing antioxidant power" assay and cyclic voltammetry.	2005 Jan 18	15652192
Inhibition of P-glycoprotein by natural products in human breast cancer cells.	2005 Jul	16114498
Oral flavonoids delay recovery from experimental autoimmune encephalomyelitis in SJL mice.	2005 Jul 15	15946653
Synergistic effects of flavonoids and ascorbate on enhancement in DNA degradation induced by a bleomycin-Fe complex.	2005 Mar	15788228
A blend of polyphenolic compounds explains the stimulatory effect of red wine on human endothelial NO synthase.	2005 Mar	15740983
Production of cytokine and NO by RAW 264.7 macrophages and PBMC in vitro incubation with flavonoids.	2005 May	15974445
Determination of dissociation constants of flavonoids by capillary electrophoresis.	2005 May	15832299
Antiherpetic activities of flavonoids against herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) in vitro.	2005 Nov	16350858
Effects of naturally occurring compounds on fibril formation and oxidative stress of beta-amyloid.	2005 Nov 2	16248550
Flavonoids purified from Rhus verniciflua Stokes actively inhibit cell growth and induce apoptosis in human osteosarcoma cells.	2005 Nov 30	16213662
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 Oct	16298737
Mechanisms for the inhibition of DNA methyltransferases by tea catechins and bioflavonoids.	2005 Oct	16037419
Dietary flavonoids as intracellular substrates for an erythrocyte trans-plasma membrane oxidoreductase activity.	2005 Sep	16176603
Properties of normal and glycated human hemoglobin in presence and absence of antioxidant.	2005 Sep 2	16053921
Luteolin, a flavonoid, inhibits CD40 ligand expression by activated human basophils.	2006	16601352
Novel antiproliferative flavonoids induce cell cycle arrest in human prostate cancer cell lines.	2006	16314891
Nutraceutical inhibitors of urokinase: potential applications in prostate cancer prevention and treatment.	2006 Aug	16820913
Distinctive antioxidant and antiinflammatory effects of flavonols.	2006 Dec 27	17177504
Luteolin, a flavonoid, inhibits AP-1 activation by basophils.	2006 Feb 3	16343431
Improved cold preservation of kidney tubular cells by means of adding bioflavonoids to organ preservation solutions.	2006 Jan 27	16436967
Flavonoids protect human retinal pigment epithelial cells from oxidative-stress-induced death.	2006 Jul	16799064
Anti-platelet effects of bioactive compounds isolated from the bark of Rhus verniciflua Stokes.	2006 Jun 15	16431050
Effect of different flavonoids on collagen synthesis in human fibroblasts.	2006 Mar	16642409
Antioxidants from Rabdosia japonica.	2006 Mar	16521110
Dietary flavonoids: effects on xenobiotic and carcinogen metabolism.	2006 Mar	16289744
Characteristics and inhibition by flavonoids of 20alpha-hydroxysteroid dehydrogenase activity in mouse tissues.	2006 May 15	16376383
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Zinc neurotoxicity is dependent on intracellular NAD levels and the sirtuin pathway.	2006 Oct	17042794
A comparison of the neurotrophic activities of the flavonoid fisetin and some of its derivatives.	2006 Oct	17015255
Study of the complexation of fisetin with cyclodextrins.	2006 Sep 14	16956235
Interaction of flavonoids and intestinal facilitated glucose transporters.	2007 Apr	17511059
Effects of the flavonoids kaempferol and fisetin on thermotolerance, oxidative stress and FoxO transcription factor DAF-16 in the model organism Caenorhabditis elegans.	2007 Dec	17551714
Inhibition of the intestinal glucose transporter GLUT2 by flavonoids.	2007 Feb	17172639
Design and synthesis of compounds that extend yeast replicative lifespan.	2007 Feb	17156081
Flavonoids modulate monocarboxylate transporter-1-mediated transport of gamma-hydroxybutyrate in vitro and in vivo.	2007 Feb	17108059
Anti-inflammatory activity of fisetin in human mast cells (HMC-1).	2007 Jan	17079162
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 Jun	17387141
Flavonoids and related compounds as anti-allergic substances.	2007 Jun	17384531
Structure-activity relationship of flavonoids for inhibition of epidermal growth factor-induced transformation of JB6 Cl 41 cells.	2007 Jun	17219438
Interaction of flavonoids with red blood cell membrane lipids and proteins: antioxidant and antihemolytic effects.	2007 Jun 1	17239435
The small polyphenolic molecule kaempferol increases cellular energy expenditure and thyroid hormone activation.	2007 Mar	17327447
Comparative study of the photophysical behavior of fisetin in homogeneous media and in anionic and cationic reverse micelles media.	2007 May-Jun	17115801
Determination of flavonoid aglycones in several food samples by mixed micellar electrokinetic chromatography.	2007 Oct	17654618
Effects of various plant polyphenols on bladder carcinogen benzidine-induced mutagenicity.	2007 Oct	17560706

Patents

Sample Use Guides

In Vivo Use Guide

hepatocellular carcinoma group rats: 20 mg/kg b.w.

Route of Administration: Oral

In Vitro Use Guide

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.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 19:59:00 GMT 2023` Edited by `admin` on `Sat Dec 16 19:59:00 GMT 2023`
Record UNII	OO2ABO9578
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

FISETIN

Official Name

English

Fisetin [WHO-DD]

Common Name

English

5-DESOXYQUERCETIN

Common Name

English

FISETIN [MI]

Common Name

English

FISIDENOLON 1521

Common Name

English

FISETIN [INCI]

Common Name

English

3,3',4',7-TETRAHYDROXYFLAVONE

Systematic Name

English

C.I. NATURAL BROWN 1

Common Name

English

NSC-407010

Code

English

NSC-656275

Code

English

2-(3,4-DIHYDROXYPHENYL)-3,7-DIHYDROXY-4H-1-BENZOPYRAN-4-ONE

Systematic Name

English

C.I. 75620

Common Name

English

Classification Tree Code System Code

DSLD

2651 (Number of products:20)