Fisetin
[CAS# 528-48-3]

Identification

• Classification: Biochemical >> Natural biochemical product
• Name: Fisetin
• Synonyms: 3,3',4',7-Tetrahydroxyflavone
• Molecular Formula: C₁₅H₁₀O₆
• Molecular Weight: 286.24
• CAS Registry Number: 528-48-3
• EC Number: 208-434-4
• SMILES: C1=CC(=C(C=C1C2=C(C(=O)C3=C(O2)C=C(C=C3)O)O)O)O

Properties

• Solubility: 100 mM (DMSO), 10 mM (ethanol) (Expl.)
• Density: 1.7±0.1 g/cm³, Calc.^*
• Melting point: 330 ºC (Expl.)
• Index of Refraction: 1.785, Calc.^*
• Boiling Point: 599.4±50.0 ºC (760 mmHg), Calc.^*
• Flash Point: 233.0±23.6 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

Fisetin is a naturally occurring flavonoid that belongs to the flavonoid class of compounds, which are widely distributed in plants. It is found in various fruits and vegetables, including strawberries, apples, grapes, onions, and cucumbers. Fisetin has attracted significant attention due to its diverse biological activities and potential therapeutic benefits. Its structure, which includes a flavone backbone with hydroxyl and methoxy groups, gives it a range of antioxidant, anti-inflammatory, and anticancer properties, making it a subject of increasing research interest.

The discovery of fisetin dates back to the early 19th century, when it was first isolated from plants. Over time, its presence in a variety of common fruits and vegetables was confirmed, but it was not until more recent decades that scientists began to investigate its potential health benefits. The compound is gaining popularity due to its versatile biological effects and its relatively low toxicity, which makes it an appealing candidate for various therapeutic applications.

One of the primary applications of fisetin is its potential as an antioxidant. Like many flavonoids, fisetin exhibits strong free radical-scavenging activity. Free radicals are highly reactive molecules that can cause oxidative stress, leading to cellular damage and contributing to the development of various diseases, including cardiovascular disease, cancer, and neurodegenerative disorders. Fisetin’s antioxidant properties help neutralize these free radicals, potentially reducing the risk of chronic diseases and promoting overall health.

In addition to its antioxidant effects, fisetin has been extensively studied for its anti-inflammatory properties. Chronic inflammation is a key factor in the development of many health conditions, including arthritis, heart disease, and cancer. Fisetin has been shown to inhibit the production of pro-inflammatory cytokines and enzymes, such as COX-2, which play a role in inflammatory processes. By modulating these pathways, fisetin may help alleviate inflammation and prevent the onset or progression of inflammatory diseases.

Fisetin is also gaining attention for its potential anticancer properties. Several studies have demonstrated that fisetin can inhibit the growth and spread of cancer cells in vitro and in animal models. It has been shown to target multiple cancer-related pathways, including cell cycle regulation, apoptosis, and angiogenesis. Fisetin has been found to induce apoptosis (programmed cell death) in various cancer cell lines, including those derived from breast, prostate, and colon cancers. Furthermore, fisetin appears to inhibit the ability of cancer cells to form new blood vessels (angiogenesis), which is a critical step in tumor growth and metastasis. While these findings are promising, more clinical trials are needed to determine fisetin’s efficacy in humans.

Another area where fisetin shows promise is in the realm of neuroprotection. Neurodegenerative diseases, such as Alzheimer's disease and Parkinson's disease, are characterized by the progressive degeneration of brain cells, often due to oxidative stress and inflammation. Fisetin has been found to exhibit neuroprotective effects in preclinical studies by reducing oxidative stress and inflammation in the brain. It has also been shown to improve cognitive function in animal models, suggesting its potential as a therapeutic agent for the prevention and treatment of neurodegenerative diseases. Some studies have suggested that fisetin may help reduce amyloid plaque formation, a hallmark of Alzheimer's disease, and protect neurons from damage.

In addition to its antioxidant, anti-inflammatory, and anticancer effects, fisetin has been studied for its potential role in cardiovascular health. Cardiovascular diseases, such as atherosclerosis and heart disease, are associated with oxidative stress and inflammation. Fisetin has been shown to improve endothelial function and reduce oxidative stress in the cardiovascular system. Some studies also suggest that fisetin may help regulate cholesterol levels and improve blood vessel health, further supporting its potential as a therapeutic agent for cardiovascular disease.

Fisetin's potential extends beyond human health applications to include cosmetic and skincare products. Due to its antioxidant and anti-inflammatory properties, fisetin is increasingly being incorporated into skincare formulations. It has been shown to help protect the skin from oxidative damage caused by UV radiation, which contributes to premature aging and skin damage. Additionally, fisetin's anti-inflammatory effects make it a useful ingredient in products designed to reduce skin irritation, redness, and swelling. It is also being explored for its potential to reduce the appearance of fine lines and wrinkles.

The growing body of research on fisetin has spurred interest in its use as a dietary supplement. While fisetin can be obtained through a diet rich in fruits and vegetables, supplementation may provide a more concentrated source of the compound. Several companies now offer fisetin supplements, which are marketed for their potential health benefits, including their antioxidant, anti-inflammatory, and neuroprotective effects. However, it is important to note that more clinical research is needed to fully understand the optimal dosage and long-term safety of fisetin supplements.

In conclusion, fisetin is a naturally occurring flavonoid with a broad range of biological activities that make it a promising candidate for various therapeutic applications. Its antioxidant, anti-inflammatory, anticancer, and neuroprotective properties make it a valuable compound for the prevention and treatment of numerous diseases. While research into fisetin's full therapeutic potential is still ongoing, it is clear that this compound holds promise as a natural remedy for improving health and preventing chronic diseases.

References

2018. Flavonoids-induced redox cycling of copper ions leads to generation of reactive oxygen species: A potential role in cancer chemoprevention. International Journal of Biological Macromolecules, 106.
DOI: 10.1016/j.ijbiomac.2017.08.049

2008. A plant flavonoid fisetin induces apoptosis in colon cancer cells by inhibition of COX2 and Wnt/EGFR/NF-kappaB-signaling pathways. Carcinogenesis, 30(2).
DOI: 10.1093/carcin/bgn269

1979. Antineoplastic Activity and Cytotoxicity of Flavones, Isoflavones, and Flavanones. Journal of Natural Products, 42(1).
DOI: 10.1021/np50001a002