The Core Difference: Trans vs. Cis Isomers
Lycopene's structure, a long carbon chain with double bonds, allows for variations in shape, creating different isomers like the linear all-trans and bent cis forms. These structural differences influence properties like color, stability, and bioavailability. While raw plants primarily contain all-trans lycopene, processing and digestion convert it into the more easily absorbed cis isomers.
All-Trans Lycopene: The Stable Form in Raw Foods
All-trans-lycopene is the dominant and most stable form found in fresh, raw fruits like tomatoes and watermelon. Its linear shape leads to crystallization within plant cells, making it less bioavailable from unprocessed foods.
Cis-Lycopene: The Bioavailable Form for the Body
Cis-lycopene isomers have a bent shape, making them more soluble in lipids and easier to absorb in the small intestine. Conversion to cis-lycopene occurs through: heat processing of foods like tomatoes, digestion in the stomach, and naturally in some varieties like tangerine tomatoes which contain tetra-cis-lycopene (prolycopene). Absorbed cis-lycopene, particularly 5-cis-lycopene, accumulates more readily in blood and tissues.
Comparison of Lycopene Isomers
| Feature | All-Trans Lycopene | Cis-Lycopene Isomers | 
|---|---|---|
| Molecular Shape | Linear and rigid | Bent, twisted, and shorter | 
| Thermodynamic Stability | Most stable form | Less stable than all-trans | 
| Bioavailability | Lower absorption by the body | Higher absorption by the body, more soluble in bile micelles | 
| Common Dietary Sources | Raw red tomatoes, watermelon | Processed tomato products (sauce, paste) | 
| Prevalence in Foods | Predominant form in fresh foods | Proportion increases with heat processing | 
| Prevalence in Human Tissues | Lower proportion relative to diet | Higher proportion relative to diet | 
The Role of Isomerization in Lycopene Bioavailability
Effective lycopene utilization requires its release from food and incorporation into digestive micelles. The crystalline nature of all-trans-lycopene hinders this from raw foods. Heating foods like tomatoes breaks down cell walls and converts trans to more soluble cis isomers, significantly increasing bioavailability. Consuming lycopene-rich foods with dietary fat further aids absorption by stimulating bile acid release for micelle formation.
Supplementation Forms and Considerations
Lycopene supplements offer alternative options and are available in various forms, including synthetic lycopene with specific isomer ratios, extracted lycopene from natural sources, and standardized tomato extract containing other natural tomato nutrients.
Conclusion: Maximizing Lycopene Absorption
Understanding lycopene isomers highlights the importance of food source and preparation for maximizing benefits. While all-trans is stable in nature, cis isomers are better absorbed. A mix of raw and cooked lycopene-rich foods, consumed with healthy fats, is ideal for broad isomer intake. Cooked tomato products offer superior cis-lycopene absorption.
For more on lycopene bioavailability from different sources, see this study: Enhanced bioavailability of lycopene when consumed as cis-isomers from tangerine tomatoes.