Fisetin

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Contents

Fisetin
Fisetin structure Fisetin.svg
Fisetin structure
Fisetin-3D-balls.png
Names
IUPAC name
3,3′,4′,7-Tetrahydroxyflavone
Systematic IUPAC name
2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-4H-1-benzopyran-4-one
Other names
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
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.669 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: XHEFDIBZLJXQHF-UHFFFAOYSA-N Yes check.svgY
  • 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
    Key: XHEFDIBZLJXQHF-UHFFFAOYAQ
  • O=C1c3c(O/C(=C1/O)c2ccc(O)c(O)c2)cc(O)cc3
Properties
C15H10O6
Molar mass 286.2363 g/mol
Density 1.688 g/mL
Melting point 330 °C (626 °F; 603 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Fisetin (7,3′,4′-flavon-3-ol) is a plant flavonol from the flavonoid group of polyphenols. [1] 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. [2] [3] [4]

Its chemical formula was first described by Austrian chemist Josef Herzig in 1891. [5]

Sources

Fisetin occurs in many plants, such as the trees and shrubs of Fabaceae, acacias Acacia greggii , [6] and Acacia berlandieri , [6] 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. [7] 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. [2] In one study, fisetin content was highest in strawberries, with content also observed in apples, grapes, onions, tomatoes, and cucumbers. [2] Fisetin can be extracted from fruit juices, wines, [8] and teas. [3] 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. [1]

Plant sourceAmount of fisetin
(μg/g)
Toxicodendron vernicifluum [9] 15000
Strawberry [2] 160
Apple [2] 26
Persimmon [2] 10.6
Onion [2] 4.8
Lotus root [2] 5.8
Grape [2] 3.9
Kiwifruit [2] 2.0
Peach [2] 0.6
Cucumber [2] 0.1
Tomato [2] 0.1

Biosynthesis

Fisetin is a flavonoid, which is a polyphenol subgroup. [10] Flavonoid synthesis begins with the phenylpropanoid pathway, in which phenylalanine, an amino acid, is transformed into 4-coumaroyl-CoA. [10] 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).[ citation needed ] 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. [1]

References

  1. 1 2 3 Yousefzadeh MJ, Zhu Y, McGowan SJ, et al. (1 October 2018). "Fisetin is a senotherapeutic that extends health and lifespan". eBioMedicine. 36: 18–28. doi: 10.1016/j.ebiom.2018.09.015 . ISSN   2352-3964. PMC   6197652 . PMID   30279143.
  2. 1 2 3 4 5 6 7 8 9 10 11 12 13 Arai Y, Watanabe S, Kimira M, et al. (2000). "Dietary intakes of flavonols, flavones and isoflavones by Japanese women and the inverse correlation between quercetin intake and plasma LDL cholesterol concentration". The Journal of Nutrition. 130 (9): 2243–2250. doi: 10.1093/jn/130.9.2243 . PMID   10958819.
  3. 1 2 Viñas P, Martínez-Castillo N, Campillo N, et al. (2011). "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". Journal of Chromatography A. 1218 (5): 639–646. doi:10.1016/j.chroma.2010.12.026. PMID   21185565.
  4. ↑ Fiorani M, Accorsi A (2005). "Dietary flavonoids as intracellular substrates for an erythrocyte trans-plasma membrane oxidoreductase activity". The British Journal of Nutrition. 94 (3): 338–345. doi: 10.1079/bjn20051504 . PMID   16176603.
  5. ↑ Herzig J (1891). "Studien über Quercetin und seine Derivate, VII. Abhandlung" [Studies on Quercetin and its Derivatives, Treatise VII]. Monatshefte für Chemie (in German). 12 (1): 177–90. doi:10.1007/BF01538594. S2CID   197766725.
  6. 1 2 Forbes TDA, Clement BA. "Chemistry of Acacia's from South Texas" (PDF). Texas A&M Agricultural Research and Extension Center at. Archived from the original (PDF) on 15 May 2011. Retrieved 14 April 2010.
  7. ↑ Gábor M, Eperjessy E (1966). "Antibacterial Effect of Fisetin and Fisetinidin". Nature . 212 (5067): 1273. Bibcode:1966Natur.212.1273G. doi: 10.1038/2121273a0 . PMID   21090477. S2CID   4262402.
  8. ↑ De Santi C, Pietrabissa A, Mosca F, et al. (2002). "Methylation of quercetin and fisetin, flavonoids widely distributed in edible vegetables, fruits and wine, by human liver". International Journal of Clinical Pharmacology and Therapeutics. 40 (5): 207–212. doi:10.5414/cpp40207. PMID   12051572.
  9. ↑ Lee SO, Kim SJ, Kim JS, et al. (2 June 2021). "Comparison of the main components and bioactivity of Rhus verniciflua Stokes extracts by different detoxification processing methods". BMC Complementary and Alternative Medicine. 18 (1): 242. doi: 10.1186/s12906-018-2310-x . PMC   6118002 . PMID   30165848.
  10. 1 2 "Flavonoids". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 2025. Retrieved 27 January 2025.
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