Cancer in the Red

The health benefits of tomatoes are supported in a recent study published in the Journal of Agricultural and Food Chemistry.1 In the study by Schwartz, Director of the Center for Advanced Functional Foods Research and Entrepreneurship at the Ohio State University, researchers identified and quantified lycopene (CAS Registry Number® (RN): 502-65-8) and apo-lycopenals in human plasma and food items such as tomatoes, grapefruit, watermelon, catsup, spaghetti sauce, pizza sauce, tomato soup, tomato paste, and tomato juice. Lycopene and apo-lycopenals antioxidant and anticancer properties help prevent cancer.

Lycopene is a carotenoid first identified in 1903 when carotenoid pigments from tomatoes and carrots were found to absorb light differently.2 The chemical structure of carotenoids influences what wavelengths of light are absorbed and reflected. Lycopene and β-carotene (CAS RN: 7235-40-7) have multiple double bonds and absorb lower energy green and blue light. This means that the red and orange portions of light are reflected, making tomatoes and carrots appear red and orange. The bright pigments of carotenoids protect plants from overexposure to light and absorb energy used for photosynthesis. These photo-protective properties also give lycopene its antioxidant and anticancer activities.  

Lycopene acts as an antioxidant by protecting cells from damage caused by reactive oxygen species (ROS).3, 4 These oxygen-containing molecules, such as a peroxide, form as by-products of metabolism. Increased ROS levels result in oxidative stress that can damage DNA, proteins, and lipids and lead to early cell death. Although the anticancer activity of lycopene is likely related to its role as an antioxidant, emerging evidence supports direct anticancer activity.3 For instance, lycopene has been shown to inhibit cancer by interfering with the proteins necessary for regulating cell growth and division.5 Lycopene can simultaneously affect multiple cells by increasing protein expression involved in coordinating communication between these adjacent cells.6

Lycopene cleavage and oxidation produce apo-lycopenals,7 such as those identified in food sources and human plasma by Schwartz. Although the function of apo-lycopenals is unclear, research on lycopene metabolism may help us understand the molecular mechanisms underlying the health benefits of lycopene-containing foods such as tomatoes.

Use SciFinder® and STN® to explore more information about apo-lycopenals and other antioxidants and anti-cancer agents to be found in the CAS databases.

Contributed by
Kathryn J. Kitzmiller, Ph.D.

  1. Kopec, R. E.; Riedl, K. M.; Harrison, E. H.; Curley, R. W.; Hruszkewycz, D. P.; Clinton, S. K.; Schwartz, S. J. Identification and Quantification of Apo-lycopenals in Fruits, Vegetables, and Human Plasma. J. Agric. Food Chem. 2010, 58, 3290-3296.
  2. Schunck, C. A. The Xanthophyll Group of Yellow Coloring Matters. Proc. Royal Soc. London, 1903, 72, 165-176.
  3. Clinton, S. K. Lycopene: Chemistry, Biology, and Implications for Human Health and Disease: a Review. Nutr. Res. 1998, 56, 35-51.
  4. Rao, A. V.; Agarwal, S. Role of Lycopene as Antioxidant Carotenoid in the Prevention of Chronic Diseases: a Review. Nutr. Res.1999, 19, 305-323.
  5. Levy, J.; Danilenko, M.; Karas, M.; Amir, H.; Nahum, A.; Giat, Y.; Sharoni, Y. Lycopene and Cancer: An Overview. In Functional Foods for Disease Prevention I; Shibamoto, T., Terao, J., Osawa, T., Eds.; ACS Symposium Series 701; American Chemical Society: Washington, DC, 1998; pp 34-41.
  6. Zhang, L.; Cooney, R. V.; Bertram, J. S. Carotenoids Up-Regulate Connexin43 Gene Expression Independent of Their Provitamin A or Antioxidant Properties. Cancer Res. 1992, 52, 5707-5712.
  7. Ferreira, A. L.; Yeum, K. J.; Russell, R. M.; Krinsky, N. I.; Tang, G. Enzymatic and Oxidative Metabolites of Lycopene. J. Nutr. 2003, 14, 531-540.

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