Luteolin
[CAS# 491-70-3]

Identification

• Classification: API >> Respiratory medication >> Antitussive
• Name: Luteolin
• Synonyms: 3',4',5,7-Tetrahydroxyflavone; 5,7,3',4'-Tetrahydroxyflavone
• Molecular Formula: C₁₅H₁₀O₆
• Molecular Weight: 286.24
• CAS Registry Number: 491-70-3
• EC Number: 207-741-0
• SMILES: C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O)O

Properties

• Solubility: 35 mg/mL (DMSO)
• Density: 1.7±0.1 g/cm³, Calc.^*
• Melting point: 330 °C
• Index of Refraction: 1.768, Calc.^*
• Boiling Point: 616.1±55.0 °C (760 mmHg), Calc.^*
• Flash Point: 239.5±25.0 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety 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
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H336

Discovery and Applications

Luteolin is a naturally occurring flavonoid that has attracted considerable interest in the fields of nutrition, pharmacology, and biochemistry. Discovered in the early 19th century, luteolin was first isolated from the leaves of the plant species *Reseda luteola*, from which it derives its name. Over the years, researchers have identified luteolin in various other plant sources, including fruits, vegetables, and herbs, making it an important component of the human diet.

The chemical structure of luteolin is characterized by its flavone backbone, which consists of a 15-carbon skeleton with a chromone ring. This structural configuration is significant as it contributes to luteolin's diverse biological activities. The compound exhibits strong antioxidant properties, which are attributed to its ability to scavenge free radicals and chelate metal ions. These properties are critical in mitigating oxidative stress, a condition associated with various chronic diseases.

One of the primary applications of luteolin lies in its potential therapeutic benefits. Numerous studies have demonstrated its anti-inflammatory effects, making it a candidate for treating various inflammatory conditions such as arthritis and asthma. The mechanism behind this anti-inflammatory activity involves the inhibition of pro-inflammatory cytokines and enzymes, such as cyclooxygenase and lipoxygenase, which play crucial roles in the inflammatory response.

In addition to its anti-inflammatory properties, luteolin has been investigated for its neuroprotective effects. Research suggests that luteolin can cross the blood-brain barrier and exert protective effects on neuronal cells. It has shown promise in preventing neurodegenerative diseases such as Alzheimer’s and Parkinson’s by reducing neuroinflammation and oxidative damage. This neuroprotective potential has made luteolin a focus of interest in developing functional foods and nutraceuticals aimed at enhancing cognitive health.

Luteolin's anticancer properties are another area of significant research. Studies have indicated that luteolin can inhibit the proliferation of various cancer cell lines, including breast, colon, and prostate cancers. The compound induces apoptosis (programmed cell death) in cancer cells while sparing normal cells, which is a desirable trait in cancer therapeutics. Moreover, luteolin has been shown to enhance the effectiveness of conventional chemotherapy agents, making it a potential adjunct therapy in cancer treatment.

In addition to its therapeutic applications, luteolin is commonly used as a dietary supplement due to its health benefits. As an ingredient in herbal formulations and nutritional supplements, luteolin is marketed for its antioxidant, anti-inflammatory, and immune-modulating effects. Its presence in a variety of fruits and vegetables underscores the importance of a diet rich in flavonoids for maintaining health and preventing disease.

Recent advancements in nanotechnology have also paved the way for innovative delivery systems for luteolin, enhancing its bioavailability and therapeutic efficacy. Nanoparticle formulations have been developed to improve the solubility and stability of luteolin, facilitating its application in targeted drug delivery systems for various health conditions.

In summary, luteolin is a multifaceted flavonoid with a rich history and diverse applications in health and medicine. Its discovery has contributed significantly to our understanding of the role of dietary phytochemicals in human health, and ongoing research continues to explore its potential as a therapeutic agent in various health conditions.

References

2007. Luteolin sensitizes the anticancer effect of cisplatin via c-Jun NH2-terminal kinase-mediated p53 phosphorylation and stabilization. Molecular Cancer Therapeutics, 6(4).
DOI: 17431112

2005. Flavonoids: from cell cycle regulation to biotechnology. Biotechnology Letters, 27(6).
DOI: 15834800

2000. Flavonoids Inhibit Cell Growth and Induce Apoptosis in B16 Melanoma 4A5 Cells. Bioscience, Biotechnology, and Biochemistry, 64(9).
DOI: 11055382