fisetin
{{Short description|Plant chemical}}
{{Use American English|date=January 2025}}
{{Use dmy dates|date=January 2025}}
{{cs1 config|name-list-style=vanc|display-authors=3}}
{{chembox
| Watchedfields = changed
| verifiedrevid = 477167329
| Name = Fisetin
| ImageFile = Fisetin.svg
| ImageSize = 250px
| ImageAlt = Skeletal formula of fisetin
| ImageFile1 = Fisetin-3D-balls.png
| ImageAlt1 = Ball-and-stick model of the fisetin molecule
| ImageName = Fisetin structure
| IUPACName = 3,3′,4′,7-Tetrahydroxyflavone
| SystematicName = 2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-4H-1-benzopyran-4-one
| OtherNames = 2-(3,4-Dihydroxyphenyl)-3,7-dihydroxychromen-4-one
Cotinin (not to be confused with Cotinine)
5-Deoxyquercetin
Superfustel
Fisetholz
Fietin
Fustel
Fustet
Viset
Junger fustik
|Section1={{Chembox Identifiers
| IUPHAR_ligand = 5182
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4444933
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C10041
| InChI = 1/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
| InChIKey = XHEFDIBZLJXQHF-UHFFFAOYAQ
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 31574
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = XHEFDIBZLJXQHF-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 528-48-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = OO2ABO9578
| PubChem = 5281614
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB07795
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 42567
| SMILES = O=C1c3c(O/C(=C1/O)c2ccc(O)c(O)c2)cc(O)cc3
}}
|Section2={{Chembox Properties
| Formula = C15H10O6
| MolarMass = 286.2363 g/mol
| Density = 1.688 g/mL
| MeltingPtC = 330
| BoilingPt =
}}
}}
Fisetin (7,3′,4′-flavon-3-ol) is a plant flavonol from the flavonoid group of polyphenols.{{Cite journal|last1=Yousefzadeh|first1=Matthew J.|last2=Zhu|first2=Yi|last3=McGowan|first3=Sara J.|last4=Angelini|first4=Luise|last5=Fuhrmann-Stroissnigg|first5=Heike|last6=Xu|first6=Ming|last7=Ling|first7=Yuan Yuan|last8=Melos|first8=Kendra I.|last9=Pirtskhalava|first9=Tamar|last10=Inman|first10=Christina L.|last11=McGuckian|first11=Collin|date=2018-10-01|title=Fisetin is a senotherapeutic that extends health and lifespan|journal=eBioMedicine|language=en|volume=36|pages=18–28|doi=10.1016/j.ebiom.2018.09.015|issn=2352-3964|pmid=30279143|pmc=6197652|doi-access=free}} It occurs in many plants where it serves as a yellow pigment. It is found in many fruits and vegetables, such as strawberries, apples, persimmons, onions, and cucumbers.{{Cite journal | last1 = Arai | first1 = Y. | last2 = Watanabe | first2 = S. | last3 = Kimira | first3 = M. | last4 = Shimoi | first4 = K. | last5 = Mochizuki | first5 = R. | last6 = Kinae | first6 = N. | title = Dietary intakes of flavonols, flavones and isoflavones by Japanese women and the inverse correlation between quercetin intake and plasma LDL cholesterol concentration | journal = The Journal of Nutrition | volume = 130 | issue = 9 | pages = 2243–2250 | year = 2000 | pmid = 10958819| doi = 10.1093/jn/130.9.2243 | doi-access = free|url=https://www.sciencedirect.com/science/article/pii/S0022316622141702}}{{Cite journal | last1 = Viñas | first1 = P. | last2 = Martínez-Castillo | first2 = N. | last3 = Campillo | first3 = N. | last4 = Hernández-Córdoba | first4 = M. | title = Directly suspended droplet microextraction with in injection-port derivatization coupled to gas chromatography–mass spectrometry for the analysis of polyphenols in herbal infusions, fruits and functional foods | doi = 10.1016/j.chroma.2010.12.026 | journal = Journal of Chromatography A | volume = 1218 | issue = 5 | pages = 639–646 | year = 2011 | pmid = 21185565 |url=https://www.sciencedirect.com/science/article/abs/pii/S0021967310017024}}{{Cite journal | last1 = Fiorani | first1 = M. | last2 = Accorsi | first2 = A. | title = Dietary flavonoids as intracellular substrates for an erythrocyte trans-plasma membrane oxidoreductase activity | journal = The British Journal of Nutrition | volume = 94 | issue = 3 | pages = 338–345 | year = 2005 | pmid = 16176603| doi=10.1079/bjn20051504| url = https://zenodo.org/record/892052 | doi-access = free }}
Its chemical formula was first described by Austrian chemist Josef Herzig in 1891.{{cite journal |last1=Herzig |first1=J. |year=1891 |title=Studien über Quercetin und seine Derivate, VII. Abhandlung |trans-title=Studies on Quercetin and its Derivatives, Treatise VII |journal=Monatshefte für Chemie |volume=12 |issue=1 |pages=177–90 |doi=10.1007/BF01538594 |s2cid=197766725 |language=de|url=https://zenodo.org/record/2471924 }}
Sources
Fisetin occurs in many plants, such as the trees and shrubs of Fabaceae, acacias Acacia greggii,{{Cite web|author=Forbes TDA, Clement BA |title=Chemistry of Acacia's from South Texas |publisher=Texas A&M Agricultural Research and Extension Center at |url=http://uvalde.tamu.edu/pdf/chemtdaf.pdf |access-date=2010-04-14 |url-status=dead |archive-url=https://web.archive.org/web/20110515034950/http://uvalde.tamu.edu/pdf/chemtdaf.pdf |archive-date=May 15, 2011 }} and Acacia berlandieri, parrot tree (Butea frondosa), honey locust (Gleditsia triacanthos), members of the family Anacardiaceae such as the Quebracho colorado, and species of the genus Rhus, which contains the sumacs.{{cite journal |last1=Gábor |first1=M. |last2=Eperjessy |first2=E. |year=1966 |title=Antibacterial Effect of Fisetin and Fisetinidin |journal=Nature |volume=212 |issue=5067 |pages=1273 |doi=10.1038/2121273a0 |pmid=21090477|bibcode=1966Natur.212.1273G |s2cid=4262402 |doi-access=free }} Along with myricetin, fisetin provides the color of the traditional yellow dye young fustic, an extract from the Eurasian smoketree (Rhus cotinus).
Many fruits and vegetables contain fisetin. In one study, fisetin content was highest in strawberries, with content also observed in apples, grapes, onions, tomatoes, and cucumbers. Fisetin can be extracted from fruit juices, wines,{{Cite journal | last1 = De Santi | first1 = C. | last2 = Pietrabissa | first2 = A. | last3 = Mosca | first3 = F. | last4 = Pacifici | first4 = G. M. | title = Methylation of quercetin and fisetin, flavonoids widely distributed in edible vegetables, fruits and wine, by human liver | journal = International Journal of Clinical Pharmacology and Therapeutics | volume = 40 | issue = 5 | pages = 207–212 | year = 2002 | pmid = 12051572 |doi=10.5414/cpp40207}} and teas. It is also present in Pinophyta species such as the yellow cypress (Callitropsis nootkatensis).
The average intake of fisetin from foods in Japan is about 0.4 mg per day.
Biosynthesis
{{more references|section|date=January 2025}}
Fisetin is a flavonoid, which is a polyphenol subgroup.{{cite web |title=Flavonoids |url=https://lpi.oregonstate.edu/mic/dietary-factors/phytochemicals/flavonoids |publisher=Micronutrient Information Center, Linus Pauling Institute, Oregon State University |access-date=27 January 2025 |date=2025}} Flavonoid synthesis begins with the phenylpropanoid pathway, in which phenylalanine, an amino acid, is transformed into 4-coumaroyl-CoA. This is the compound that enters the flavonoid biosynthesis pathway. Chalcone synthase, the first enzyme of this pathway, produces chalcone from 4-coumaroyl-CoA. All flavonoids are derived from this chalcone backbone (this family being the so-called chalconoids).{{cn|date=January 2025}} The activity of different enzymes, including isomerases and hydroxylases, alter the backbone depending on the subclass of the flavonoid being produced.
Research
Although fisetin has been under laboratory research over several decades for its potential role in senescence or anticancer properties, among other possible effects, there is no clinical evidence that it provides any benefit to human health, as of 2018.