Fisetin

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Fisetin
Skeletal formula of fisetin
Ball-and-stick model of the fisetin molecule
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 Edit this at Wikidata
IUPHAR/BPS
KEGG
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 checkY
    Key: XHEFDIBZLJXQHF-UHFFFAOYSA-N checkY
  • 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).
checkY verify (what is checkY☒N ?)

Fisetin (7,3′,4′-

flavonol from the flavonoid group of polyphenols.[1] It can be found in many plants, where it serves as a yellow/ochre colouring agent. It is also found in many fruits and vegetables, such as strawberries, apples, persimmons, onions and cucumbers.[2] Its chemical formula was first described by Austrian chemist Josef Herzig in 1891.[3]

The

polyphenols
it has many activities.

Biological sources

Fisetin can be found in a wide variety of plants. It is found in

yellow cypress
(Callitropsis nootkatensis).

Plant source Amount of Fisetin
(μg /g)
Toxicodendron vernicifluum[11] 15000
Strawberry[8] 160
Apple[8] 26
Persimmon[8] 10.6
Onion[8] 4.8
Lotus root[8]
 5.8
Grapes[8]
 3.9
Kiwifruit[8] 2.0
Peach[8] 0.6
Cucumber[8] 0.1
Tomato[8] 0.1

Biosynthesis

Fisetin is a

Transferases help control changes in the flavonoid's solubility and reactivity by catalyzing the addition of things such as methyl groups and sugars. This allows for controlled fluctuations in physiological activities.[12]

Flavonoid biosynthesis gene regulation occurs through the interaction of different transcription factors. Depending on the combination of transcription factor interactions, the structural genes involved in flavonoid biosynthesis are expressed in specific locations of the plant and at specific times. Many myeloblastosis (MYB) transcription factors have been identified in a variety of fruits and plants, including strawberries, maize, and arabidopsis, as being important in the regulation of flavonoid biosynthesis and accumulation. These transcription factors continue to be studied in plant model organisms such as maize and Arabidopsis.[12]

The environment of the plant has also been shown to affect the flavonoid biosynthesis pathway. Shorter wavelengths of light, ranging from blue to UV light, allow for higher production and accumulation of flavonoids in fruits. These wavelengths activate enzymes that are involved in the phenylpropanoid and flavonoid biosynthesis pathways, stimulating the production of flavonoids. The level of stimulation can vary between individual fruits.[13]

Biological activity

Fisetin is a sirtuin-activating compound[14] and has been shown in laboratory studies to extend the life of yeast, worms, flies, and mice.[15][16] Like the other compounds, it has also been shown to be reactive in many different assays of biological activities, raising the possibility that any drug generated from fisetin would have too many side effects to be useful.[15][17]

Fisetin has shown anti-cancer activity in studies on cells and model animals conducted in laboratories, and appears to block the PI3K/AKT/mTOR pathway,[18] along with other mechanisms to induce apoptosis activation, and prevent apoptosis resistance.[19]

In lab studies fisetin has been shown to be an

anti-proliferative agent, interfering with the cell cycle in several ways.[20] Like some other flavonoids, it has been found in lab studies to be a topoisomerase inhibitor, which may turn out to be a carcinogenic activity or an anti-cancer activity; further research is needed.[21]

Fisetin has been shown to be an effective senolytic agent in wild-type mice, with effects of increased lifespan, reduced senescence markers in tissues, and reduced age-related pathologies.[22] Studies of cell cultures of senescent human umbilical vein endothelial cells have shown that fisetin induces apoptosis by inhibition of the anti-apoptotic protein Bcl-xL.[23] Fisetin has roughly twice the senolytic potency as quercetin.[24] A clinical trial in the U.S. was under way as of October 2018 to show effectiveness in humans.[25]

In studies conducted on cells in a laboratory, fisetin inhibits the activity of several pro-inflammatory

tumor necrosis factor alpha, interleukin 6, and nuclear factor kappa B (NF-κB).[20] The anti-inflammatory action is due to deacylation of the pro-inflammatory transcription factor NF-κB by sirtuin 1.[26]

Fisetin has been shown in lab studies to upregulate

hydroxyl groups on one ring and a hydroxyl group on another.[27]

In vitro screening has identified fisetin as an antimitotic compound.[28]

Health benefits claims

Manufacturers, promoters and sellers of fisetin dietary supplements make various claims of supposed health benefits for humans.

Medical research on humans is at a very early stage, and health claims are therefore not well supported. In vitro results or animal studies may and often do seriously differ from actual performance in human metabolism observed in double blind randomized reviewed studies.

References

  1. ^
    PMID 31109072
    .
  2. PMID 25184746
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  3. S2CID 197766725
    .
  4. ^ a b 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 May 15, 2011. Retrieved 2010-04-14.
  5. S2CID 4262402
    .
  6. PMID 16176603
    .
  7. PMID 21738623
    .
  8. ^
    PMID 10958819
    .
  9. ^
    PMID 21185565
    .
  10. PMID 12051572
    .
  11. PMID 30165848
    .
  12. ^
    PMID 23060891
    .
  13. PMID 25346743
    .
  14. S2CID 25896400
    .
  15. ^
    PMID 19897059
    .
  16. PMID 30279143
    .
  17. PMID 15213022
    .
  18. PMID 23293889
    .
  19. PMID 31064104
    .
  20. ^
    PMID 24946050
    .
  21. PMID 20939813
    .
  22. PMID 30279143
    .
  23. PMID 32686219
    .
  24. PMID 32752135
    .
  25. ^ "Alleviation by Fisetin of Frailty, Inflammation, and Related Measures in Older Women - Full Text View - ClinicalTrials.gov". Retrieved 2018-10-12.
  26. PMID 32848804
    .
  27. ^
    PMID 23121441
    .
  28. PMID 19395653
    .
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