Lycopene is an open-chain unsaturated carotenoid that acts as antioxidants neutralize free radicals, which may damage the body's cells. It helps prevent degenerative diseases by donating its electrons to oxygen free radicals thus quenching and neutralising them before they can damage cells. Free radicals are molecules that have at least one unpaired electron. By donating an electron lycopene can stabilise the free molecule. In the body, lycopene is deposited in the liver, lungs, prostate gland, colon and skin. Its concentration in body tissues tends to be higher than all other carotenoids.
Lycopene is part of the carotenoid family of pigments. It is found in raw tomatoes, products prepared from tomatoes, sweet potatoes, carrots and pumpkins. Lycopene is a powerful antioxidant that has been shown to neutralize free radicals, especially those derived from oxygen, thereby conferring protection against prostate cancer, breast cancer, atherosclerosis, and associated coronary artery disease. It reduces LDL (low-density lipoprotein) oxidation and helps reduce cholesterol levels in the blood. In addition, preliminary research suggests lycopene may reduce the risk of macular degenerative disease, serum lipid oxidation, and cancers of the lung, bladder, cervix, and skin. The chemical properties of lycopene responsible for these protective actions are well-documented.
Lycopene is a phytochemical, synthesized by plants and microorganisms but not by animals. It is an acyclic isomer of beta-carotene. This highly unsaturated hydrocarbon contains 11 conjugated and 2 unconjugated double bonds, making it longer than any other carotenoid. As a polyene, it undergoes cis-trans isomerization induced by light, thermal energy, and chemical reactions. Lycopene obtained from plants tends to exist in an all-trans configuration, the most thermodynamically stable form. Humans cannot produce lycopene and must ingest fruits, absorb the lycopene, and process it for use in the body. In human plasma, lycopene is present as an isomeric mixture, with 50% as cis isomers.
Two important properties of lycopene are involved in its role of health. First, lycopene is the most efficient scavenger of single oxygen among the carotenoids found in our bodies. In other words, lycopene is a powerful antioxidant. With its free radical scavenging abilities, lycopene has been found in some studies to perform better than some of the other better known antioxidants such as beta carotene and the tocopherols (vitamin E). Second, lycopene efficiently increases gap-junctional communication between cells. Gap-junction communication between cells is lost during malignant transformation of cells.
During the 1980s, most interest in the anti-cancer effects of carotenoids revolved around beta-carotene. In the late 1980s, however, epidemiological reports began to be published that found a protective effect of serum lycopene on the incidence of cancer in patients with cervical intra-epithelial neoplasia. No association was found for the other carotenoids tested. In another study, a low level serum lycopene was observed in patients who subsequently developed bladder and pancreatic cancers. Almost simultaneously, published laboratory reports began to appear showing that lycopene was as effective as beta-carotene in preventing in vitro growth of cancer cells. Recently, a study compared the antiproliferative properties of lycopene with alpha- and beta-carotene. The results indicate that lycopene is much more potent than alpha and beta-carotene in inhibiting human endometrial, mammary, and lung cancer cell growth. The fifty-percent effective inhibitory dose of lycopene was found to be in the range of lycopene that can be achieved in human plasma. Importantly, normal human cells were found to be much less sensitive to lycopene that cancer cells were. These results caused the researchers to conclude that it may be possible to use lycopene as an anticancer compound without significantly affecting normal cells. Another finding in this paper is lycopene's interference with IGF-I induced growth. The importance of the IGF autocrine system in regulating the growth of endometrial and mammary cancer cells has been established previously. Lycopene's ability to inhibit both basal and ICF-I stimulated growth may point to an important anticancer function of lycopene's (and other carotenoids') interference with growth factor-related cancer stimulation.
Although best known as an antioxidant, both oxidative and non-oxidative mechanisms are involved in lycopene's bioprotective activity. The nutraceutical activities of carotenoids such as beta-carotene are related to their ability to form vitamin A within the body. Since lycopene lacks a beta-ionone ring structure, it cannot form vitamin A and its biological effects in humans have been attributed to mechanisms other than vitamin A. Lycopene's configuration enables it to inactivate free radicals. Because free radicals are electrochemically imbalanced molecules, they are highly aggressive, ready to react with cell components and cause permanent damage. Oxygen-derived free radicals are the most reactive species. These toxic chemicals are formed naturally as by-products during oxidative cellular metabolism. As an antioxidant, lycopene has a singlet-oxygen-quenching ability twice as high as that of beta-carotene (vitamin A relative) and ten times higher than that of alpha-tocopherol (vitamin E relative). One non-oxidative activity is regulation of gap-junction communication between cells. Lycopene participates in a host of chemical reactions hypothesized to prevent carcinogenesis and atherogenesis by protecting critical cellular biomolecules, including lipids, proteins, and DNA.
Lycopene is the most predominant carotenoid in human plasma, present naturally in greater amounts than beta-carotene and other dietary carotenoids. This perhaps indicates its greater biological significance in the human defense system. Its level is affected by several biological and lifestyle factors. Because of its lipophilic nature, lycopene concentrates in low-density and very-low-density lipoprotein fractions of the serum. Lycopene is also found to concentrate in the adrenal, liver, testes, and prostate. However, unlike other carotenoids, lycopene levels in serum or tissues do not correlate well with overall intake of fruits and vegetables.
CAS Number: 502-65-8
Molecular Formula: C40H56
Molecular Weight: 536.9
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