What is the Chemical Structure of Flavonoids?
Flavonoids, a diverse family of plant-based phytonutrients, are part of the larger polyphenol group. They share a common 15-carbon skeleton structure, typically in a C6-C3-C6 arrangement with two aromatic rings (A and B) linked by a three-carbon heterocyclic ring (C). Minor variations in this core structure result in the thousands of known flavonoids. In plants, they often exist as glycosides, bound to sugar molecules, which increases their water solubility and stability. After consumption, they are poorly absorbed and extensively metabolized, which affects their biological activity in humans.
Major Classes of Flavonoids
Structural differences divide flavonoids into several subclasses. The six primary dietary subclasses are:
- Flavonols: The most common in the diet, characterized by a ketone and hydroxyl group on the C ring. Examples include quercetin and kaempferol found in onions and tea.
- Flavones: Contain a double bond between carbons 2 and 3 and a ketone at position 4. Luteolin and apigenin are examples, found in parsley and celery.
- Flavanones: Lack the double bond found in flavones, common in citrus fruits like hesperidin and naringenin.
- Flavan-3-ols (Catechins): Lack both the double bond and ketone group. This group includes catechins found in green tea and berries.
- Anthocyanidins: The pigments behind red, purple, and blue colors in fruits and vegetables, like cyanidin in berries.
- Isoflavones: Distinct in structure with the B ring attached at position 3, primarily found in soy and legumes, examples include genistein.
Where Can You Find Flavonoids?
To boost flavonoid intake, consume a variety of colorful plant foods. High concentrations are present in:
- Berries: Rich in anthocyanidins.
- Citrus Fruits: Excellent sources of flavanones.
- Onions: Particularly rich in flavonols like quercetin.
- Tea: Green and black tea provide flavan-3-ols.
- Cocoa and Dark Chocolate: Known for high flavanol content.
- Soybeans and Legumes: Primary sources of isoflavones.
- Herbs: Parsley contains flavones.
What are the Health Benefits of Flavonoids?
Flavonoids are known for their potential health-promoting activities and are linked to reduced risk of chronic diseases. Their benefits come from mechanisms including:
- Antioxidant Effects: They scavenge free radicals, protecting against oxidative stress.
- Anti-inflammatory Effects: They can reduce the body's inflammatory response by inhibiting enzymes.
- Cardioprotective Properties: Associated with lower cardiovascular risk by improving blood vessel function.
- Neuroprotective Properties: Certain flavonoids may protect neurons and improve cognitive function.
- Anticancer Activities: Preclinical studies suggest some can inhibit cancer cell growth and induce cell death.
Flavonoids vs. Polyphenols
While often used interchangeably, flavonoids are a specific subclass of the broader polyphenol group. All flavonoids are polyphenols, but not all polyphenols are flavonoids. Polyphenols include other classes like phenolic acids. Flavonoids are distinguished by their specific C6-C3-C6 structure.
| Flavonoid Class | Key Compounds | Common Sources | Potential Benefit | Example Food | 
|---|---|---|---|---|
| Anthocyanidins | Cyanidin, Delphinidin | Berries, Red Grapes | Potent antioxidant, vascular health | Blueberries | 
| Flavan-3-ols | Catechins, Epicatechins | Teas, Apples, Cocoa | Cardiovascular and metabolic health | Green Tea | 
| Flavonols | Quercetin, Kaempferol | Onions, Kale, Berries | Antioxidant, anti-inflammatory, and anticancer properties | Onions | 
| Flavones | Apigenin, Luteolin | Parsley, Celery, Thyme | Anti-inflammatory and antioxidant effects | Parsley | 
| Flavanones | Hesperidin, Naringenin | Citrus fruits and juices | Antioxidant, anti-inflammatory, and cholesterol-lowering properties | Oranges | 
| Isoflavones | Genistein, Daidzein | Soybeans, Legumes | Support against hormone-dependent cancers | Soybeans | 
Bioavailability of Flavonoids
Flavonoids generally have low bioavailability in humans, meaning only a small amount is absorbed. They undergo extensive metabolism by gut bacteria into smaller, potentially more active compounds. This process varies depending on the flavonoid structure and individual gut microbiome. Soy isoflavones, for example, are relatively bioavailable compared to anthocyanins. The low and variable bioavailability is why consuming flavonoids from whole foods is often preferred over supplements.
Research and Future Prospects
Ongoing research continues to explore the therapeutic potential of flavonoids in various diseases, including neurodegenerative conditions and cancer. Lab studies often show promising results. A key focus for researchers is improving delivery systems to enhance bioavailability in humans and maximize the clinical use of flavonoids.
Conclusion
Flavonoids are a significant group of plant compounds, a subclass of polyphenols, providing plants with color and defense and offering humans numerous potential health benefits through antioxidant and anti-inflammatory actions. Found widely in plant foods, their bioavailability is a crucial factor influencing their effects. The best way to benefit from flavonoids is through a diet rich in whole foods like berries, citrus, and tea to support overall wellness.
For more detailed scientific information, you can refer to comprehensive articles on the National Institutes of Health website.(https://pmc.ncbi.nlm.nih.gov/articles/PMC8007671/)