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Fisetin

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Fisetin

Fisetin
Identifiers
CAS number 528-48-3 YesY
PubChem 5281614
ChemSpider 4444933 YesY
DrugBank DB07795
KEGG C10041 YesY
ChEBI CHEBI:42567 YesY
Jmol-3D images Image 1
Properties
Molecular formula C15H10O6
Molar mass 286.2363 g/mol
Density 1.688 g/mL
Melting point

330 °C

 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Fisetin is a flavonol, a structurally distinct chemical substance that belongs to the flavonoid group of polyphenols. It can be found in many plants, where it serves as a colouring agent. Its chemical formula was first described by Austrian chemist Josef Herzig in 1891.[1] Possible anti-aging, anti-inflammatory, anti-cancer, and anti-viral properties of fisetin are under active scientific investigation.

Biological activity

Fisetin is a potent sirtuin-activating compound (STAC),[2] an agent that modulates sirtuins. Therefore, it is a caloric restriction mimetic candidate, a drug that has been shown to be able to alleviate aging effects in certain model organisms, such as the yeast S. cerevisiae,[2] the nematode C. elegans[3] and the fruit fly Drosophila melanogaster.[3] Whether such effects can be replicated in humans and other mammals is currently still not entirely clear and remains an issue of scientific research and debate.

Aside from its effects on aging, various in vitro studies have shown fisetin to exert anti-inflammatory,[4][5] anti-carcinogenic,[6][7] and antiviral[8][9][10][11] effects in different lines of culture cells. However, because in vitro experiments do not or only incompletely mimic fisetin metabolism in the body, they may not accurately reflect the actual effects of fisetin in vivo. During absorption through the small intestine and passage through the liver, fisetin and other flavonoids undergo chemical modifications such that their form in circulating blood is different from that in the original dietary source.[12]

Similar to many other flavonoids, such as the structurally related flavonol

Biological sources

Fisetin can be found in a wide variety of plants. It is found in Eudicotyledons, such as trees and shrubs in the family Fabaceae, such as the acacias Acacia greggii[16] and Acacia berlandieri,[16] the parrot tree (Butea frondosa), the honey locust (Gleditsia triacanthos), members of the family Anacardiaceae such as the Quebracho colorado and species of the genus Rhus, which contains the sumacs.[17] Along with myricetin, fisetin provides the color of the traditional yellow dye young fustic, which was extracted from the Eurasian smoketree (Rhus cotinus). Many fruits and vegetables also contain fisetin,[18] including strawberries[15][19] apples,[19] and grapes.[19][20] Fisetin can be extracted from fruit and herbal sources in juices, wines,[21] and infusions such as teas.[20] It is also found in Monocotyledons such as onions.[19] It is also present in Pinopyta species such as the yellow cypress (Callitropsis nootkatensis).

Side effects

Fisetin was, among other flavonoids, found to be a strong topoisomerase inhibitor.[22] This effect may be responsible for both anticarcinogenic and carcinogenic potentials of the substance.[23] As DNA topoisomerase inhibitors, fisetin and other flavonoids may increase risk of infant acute myeloid leukemia, a rare disease.[24]

References

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