Lecture 6 Lycopene what is Lycopene? General description Their Importance in Functional Foods

1. Lecture 6Lycopenewhat is Lycopene?General descriptionTheir Importance in Functional Foods

2. PBRC 2005

3. An Interesting Example PBRC 2005

4. Lycopene: General • Belongs to a class referred to as carotenoids • Carotenoids are yellow, orange, and red pigments synthesized by plants • The most common carotenoids in North American diets are α-carotene, β-carotene, β-cryptoxanthin, lutein, zeaxanthin, and lycopene. • In plants, their function is to absorb light in photosynthesis, protecting plants against photosensitization • The five principal carotenoids found in human plasma, as the result of ingesting plants, include alpha and beta-carotene, beta-cryptoxanthin, lutein, and lycopene, but over 700 have been identified to date PBRC 2005

5. Lycopene: General • plants. Fruit and vegetables provide most of the 40 to 50 carotenoids found in the human diet. • α-Carotene, β-carotene, β-cryptoxanthin, lutein, zeaxanthin, and lycopene are the most common dietary carotenoids. • α-Carotene, β-carotene and β-cryptoxanthin are provitamin A carotenoids, meaning they can be converted by the body to retinol. • Lutein, zeaxanthin, and lycopene are non-provitamin A carotenoids because they cannot be converted to retinol PBRC 2005

6. Lycopene: General • Lycopene is what gives tomatoes, pink grapefruit, watermelon, and guava their red color • It has been estimated that 80% of the lycopene in the diet comes from tomatoes and tomato products like tomato sauce, tomato paste, and catsup • Unlike Alpha-carotene, Beta-carotene, and Beta-cryptoxanthin, lycopene is not a provitamin A carotenoid, meaning that the body cannot convert lycopene into Vitamin A

7. Lycopene: General • Tomatoes and tomato products are the single best source of lycopene, with only a short list of other foods containing much lower amounts • In tomatoes, lycopene content is affected by specific variety and ripening stage • Deep red varieties contain up to 50 mg/kg, while yellow types may be as low as 5 mg/kg

8. Lycopene: General • American lycopene intake averages 3.1 to 3.7 mg/d, closely matching beta-carotene • In contrast, British intake averages 1.1 mg/d and that for Finns is even lower at 0.7 mg/d • Data for rest of the world is not available/authentic

9. Lycopene: General • Was largely ignored for decades because of its lack of provitamin A activity, long thought to be the distinguishing characteristic among carotenoids • In the 1960’s, during a case study which first documented lycopenemia, an accumulation of lycopene in the body tissues, the following was stated: “So far as is known, lycopene is neither toxic nor beneficial, but is only an adventitious visitor to the body. Its failure to form Vitamin A may account for its accumulation in the liver”

10. Lycopene: General • Recent studies of lycopene bioavailability have shown that cooking tomato products significantly increases lycopene bioavailability compared to raw products, as does the presence of a small amount of oil or fat • This is because the absorption of carotenoids depends on the presence of fat in the intestine • As little as 3-5 grams of fat in a meal appears sufficient to ensure carotenoid absorption PBRC 2005 PBRC 2005

11. Lycopene Content of Selected Foods PBRC 2005 PBRC 2005

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13. Absorption • The absorption of carotenoids is limited to a range of 10-30% • Of this amount, the majority is excreted in the feces • The low absorption and high excretion rate is partly due to the fact that the carotenoids are tightly bound to large molecules, forming protein complexes in foods • Separation of carotenoids from protein complexes or dispersion of carotenoid aggregates occurs upon heating these food items, which, as previously mentioned, increases their bioavailability PBRC 2005 PBRC 2005

14. Factors that Affect Absorption Rate of Carotenoids • Level of dietary fat intake Studies comparing carotenoid absorption rate with a 40% fat diet to a 20% showed a significant reduction in absorption • Level of carotenoids ingested Intestinal absorption decreases significantly as carotenoid intake increases PBRC 2005 PBRC 2005

15. Pathway of Carotenoids: • Absorption pathway is similar to that of dietary fat • Carotenoids are believed to passively diffuse from the micelles across the intestinal cell membrane into the mucosal cell • Once inside the intestinal cell, carotenoids may be converted to vitamin A, those that are provitamin A carotenoids, or taken up by chylomicrons which transport them to the bloodstream via the lymphatic system to the liver • From the liver, carotenoids reenter circulation carried by lipoproteins, in similar proportions as cholesterol among the various fractions PBRC 2005 PBRC 2005

16. Lycopene, which is more lipophilic because of its non-polar chemical structure, appears to be carried exclusively by LDL, residing deep within the core of the lipoprotein, lipid layer • Beta-carotene probably protrudes into the aqueous interface of the lipoprotein • The location of the carotenoid within the lipoprotein molecule may influence tissue uptake

17. Tissue Distribution: Of Lycopene • Because of its lipophilic nature, lycopene tends to accumulate in body tissues • It predominates in prostate, liver, adrenal glands, and testes, with lycopene accounting for up to 80% of total carotenoid in these latter two tissues • Lycopene concentration in the testes and adrenals is up to 9X’s higher than in the tissue with the second highest amount, the liver

18. Several factors can influence lycopene tissue concentrations • Higher carotenoid concentrations tend to occur in tissues with a large number of LDL-receptors and high uptake of lipoproteins the liver, adrenals, and testes • Other factors include body mass index and waist circumference, with both exhibiting an inverse relationship with lycopene concentration in adipose tissue • Gender- this same study reported up to 50% lower carotenoid adipose levels in men compared to women

19. Lycopene: Function • Far from being inert, by virtue of its unique chemical properties, studies have shown lycopene to possess superior antioxidant abilities in comparison to other carotenoids • It has the ability to quench singlet oxygen and prevent oxidative damage to other molecules and cellular structures because of its unique structure of: 11 conjugated double bonds and no cyclic groups • Because of this role, many researchers now believe that lycopene may profoundly influence the evolution of several chronic diseases in a tissue-specific manner PBRC 2005 PBRC 2005

20. Biological Activity • The general mechanism by which carotenoids are thought to influence the development of chronic disease is by preventing oxidative damage in biological systems, which includes damage to the cell membrane and other structures, DNA molecules, lipids, and proteins • This damage arises from exposure to free radicals • Free radicals are molecules with an unpaired electron in their outer atomic orbital, causing the molecule to be extremely reactive

21. Free Radicals • Environmental sources of free radicals include: • Environmental toxins and air pollutants- such as ozone and nitrogen dioxide • Sunlight • Ionizing radiation • Certain drugs • Cigarette smoke

22. Free Radicals • The body can also produce free radicals during normal aerobic respiration, the metabolism of fatty acids, and from an acute or chronic immune responses • From the usage of superoxide dismutase, glutathione peroxidase, and dietary intake of the antioxidant nutrients, Vitamins E and C, selenium, and the carotenoids, the body can help fight off oxidative damage

23. Lycopene and Chronic DiseasesResearch Findings Overview: • Digestive Tract Cancers • Prostate Cancer • Bladder, Cervical, Breast, Lung Cancers • Cardiovascular Disease • Diabetes

24. Lycopene and Chronic DiseasesResearch Findings • Most small-scale intervention studies found little-to-no benefit of lycopene supplements in reducing incidence or severity of prostate cancer in high-risk patients. • Test tube studies indicated that lycopene is one of the most effective quenchers of singlet oxygen among carotenoids. • Although some clinical trials have found that β-carotene supplementation improves several biomarkers of immune function, increasing intakes of lycopene and lutein — carotenoids without vitamin A activity — have not resulted in similar improvements in biomarkers of immune function. • risk of lung cancer was estimated to be 20% and 14% lower with the highest versus lowest intakes of β-cryptoxanthin and lycopene, respectively.

25. Lycopene and Chronic DiseasesResearch Findings • Several early prospective cohort studies have suggested that lycopene-rich diets were associated with significant reductions in the risk of prostatecancer, particularly more aggressive forms. • dietary lycopene had a 11 to 19% lower risk of prostate cancer • pooled data from two case-control and five nested case-control studies showed a 26% lower risk of prostate cancer in participants with the highest serum concentrations of lycopene. • pooled data from mostly case-control studies also suggested that higher intakes of individual carotenoids, especially β-cryptoxanthin and lycopene, might be associated with a reduced risk of cancers of the mouth, pharynx, and larynx

26. Lycopene and Chronic DiseasesResearch Findings • A higher ratio of plasma nonprovitamin A carotenoids (lutein, zeaxanthin, and lycopene) to vitamin A carotenoids (β-carotene, β-carotene, β-cryptoxanthin) was associated with a reduced risk of diabetic retinopathy in a cross-sectional analysis in 111 individuals with type 2 diabetes mellitus. • intakes of total and individual carotenoids (β-carotene, lycopene, and lutein/zeaxanthin) were positively associated with proximal femur BMD in men over a four-year period, while lycopene intake was positively linked to lumbar spine BMD in women

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