Fisetin (Fustel; CCRIS-9034; NSC-407010)

Alias:
Cat No.:V0435 Purity: ≥98%
Fisetin (Fustel; CCRIS9034; NSC40701; 3, 7, 3′, 4′-tetrahydroxyflavone) is a naturally occuring and dietary flavonoid isolated from/found in a variety of fruits and vegetables (i.
Fisetin (Fustel; CCRIS-9034; NSC-407010) Chemical Structure CAS No.: 528-48-3
Product category: Sirtuin
This product is for research use only, not for human use. We do not sell to patients.
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500mg
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Fisetin (Fustel; CCRIS9034; NSC40701; 3, 7, 3′, 4′-tetrahydroxyflavone) is a naturally occuring and dietary flavonoid isolated from/found in a variety of fruits and vegetables (i.e. strawberries, apples, persimmons, onions and cucumbers). It has many important biological activity including anti-inflammatory, anti-oxidant, anti-diabetic, anti-invasive, anti-tumorigenic, neuroprotective, anti-angiogenic, and cardioprotective effects in cell culture and in animal models relevant to human diseases. It is a potent sirtuin activating compound (STAC) and an agent that modulates sirtuins. It also acts as a tubulin inhibitor/stabilizer. Fisetin is a structurally distinct chemical belonging to the flavonoid class of polyphenols.

Biological Activity I Assay Protocols (From Reference)
ln Vitro
Fisetin reduces lipid accumulation and lowers PPARγ expression in 3T3-L1 cells. Fisetin suppresses early phases of preadipocyte development and stimulates Sirt1 expression. Fisetin stimulates Sirt1-mediated deacetylation of PPARγ and FoxO1, boosts the binding of Sirt1 to the PPARγ promoter, consequently decreasing PPARγ transcriptional activity, thereby inhibiting adipogenesis [1]. Fisetin binds tubulin and stabilizes microtubules, having binding properties substantially superior to those of paclitaxel. Fisetin treatment of human prostate cancer cells resulted in substantial overexpression of microtubule-associated proteins (MAP)-2 and -4. Fisetin strongly suppresses PCa cell growth, migration and invasion. Nudc, a protein linked with the microtubule motor dynein/dynamin complex that governs microtubule dynamics, is inhibited by Fisetin therapy [2].
ln Vivo
Treatment with fisetin decreased inflammatory cell infiltration and proliferation in mice exposed to UVB rays. Additionally, treating with fisetin lowers the levels of inflammatory mediators like COX-2, PGE2 and its receptors (EP1–EP4), and MPO activity. Moreover, fisetin lowers UVB-exposed skin's concentrations of the inflammatory cytokines TNFα, IL-1β, and IL-6. Increased expression of the proteins p53 and p21 indicates that fisetin treatment also reduces DNA damage and markers of cell proliferation [3].
Animal Protocol
topical treatment of Fisetin 250 nmol/0.2 mL acetone/mouse
Mice: The mice are divided into six groups of eight animals each. The mice in the first group are topically treated with 0.2 mL acetone and used as vehicle control. The mice in the second and third groups receive topical treatment of Fisetin 250 nmol/0.2 mL acetone/mouse and 500 nmol/0.2 mL acetone/mouse respectively on their dorsal skin and serves as agent controls. The mice in the fourth, fifth and sixth groups are exposed to UVB. The mice in the fourth group receive a topical application of 0.2 mL acetone after 15 min of UVB exposure designated as vehicle control. The mice in the fifth and sixth groups are treated with topical application of Fisetin 250 nmol/0.2 mL acetone/mouse and 500 nmol/0.2 mL acetone/mouse respectively on to their dorsal skin after 15 min of UVB exposure
References
[1]. Kim SC, et al. Fisetin induces Sirt1 expression while inhibiting early adipogenesis in 3T3-L1 cells. Biochem Biophys Res Commun. 2015 Nov 27;467(4):638-44.
[2]. Mukhtar E, et al. Dietary flavonoid fisetin binds to β-tubulin and disrupts microtubule dynamics in prostate cancer cells. Cancer Lett. 2015 Oct 28;367(2):173-83
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H10O6
Molecular Weight
286.24
CAS #
528-48-3
Related CAS #
Fisetin quarterhydrate;Fisetin (Standard);528-48-3
SMILES
O1C2C([H])=C(C([H])=C([H])C=2C(C(=C1C1C([H])=C([H])C(=C(C=1[H])O[H])O[H])O[H])=O)O[H]
InChi Key
XHEFDIBZLJXQHF-UHFFFAOYSA-N
InChi Code
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
Chemical Name
2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-4H-chromen-4-one
Synonyms

Fisetholz; Fisetin; CCRIS 9034; CCRIS9034; CCRIS-9034; NSC 407010; NSC407010; NSC-656275

Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 57 mg/mL (199.1 mM)
Water:<1 mg/mL
Ethanol: 3 mg/mL (10.5 mM)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.4936 mL 17.4679 mL 34.9357 mL
5 mM 0.6987 mL 3.4936 mL 6.9871 mL
10 mM 0.3494 mL 1.7468 mL 3.4936 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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