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Chemical Compound Review

LYCOPENE     (6E,8E,10E,12E,14E,16E,18E,20E ,22E,24E...

Synonyms: trans-Lycopene, Lycopene 7, Lycopene (VAN), CHEMBL501174, Lyco Vit, ...
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Disease relevance of trans-Lycopene

  • METHODS: Colitis was induced using the iodoacetamide rat model, and rats were divided into different dietary groups of 6 rats each: 1, normal chow diet (control); 2, diet supplemented with iron; 3, iron supplementation and lycopene; 4, iron and Beta-carotene; 5, 5-ASA; 6, 5-ASA and lycopene; 7, 5-ASA and iron; 8, 5-ASA, iron, and lycopene [1].

High impact information on trans-Lycopene

  • The cyclization of lycopene (psi, psi-carotene) is a key branch point in the pathway of carotenoid biosynthesis [2].
  • Furthermore, all-trans-lycopene supplementation in ferrets resulted in significant accumulation of cis-isomers of lycopene and the formation of apo-10'-lycopenol, as well as up-regulation of the CMO2 expression in lung tissues [3].
  • Ingestion of tomato paste was found to yield 2.5-fold higher total and all-trans-lycopene peak concentrations (P < 0.05 and P < 0.005, respectively) and 3.8-fold higher area under the curve (AUC) responses (P < 0.001) than ingestion of fresh tomatoes [4].
  • RESULTS: Synthetic and tomato-lycopene resulted in significant increases above baseline of serum total lycopene by 0.58 and 0.57 micro mol/L, trans-lycopene by 0.34 and 0.41 micro mol/L, and total-cis-lycopene by 0.24 and 0.16 micro mol/L, whereas no significant changes were found in the placebo treatment [5].
  • When the mutant cells cultured under dark conditions were irradiated, cis-isomers of carotenes were converted to all-trans lycopene [6].

Anatomical context of trans-Lycopene


Associations of trans-Lycopene with other chemical compounds


Gene context of trans-Lycopene

  • Water-soluble complexes of the dietary carotenoid psi,psi-carotene (lycopene 1) with cyclomaltohexaose (alpha-cyclodextrin, alphaCD) and cyclomaltoheptaose (beta-cyclodextrin, betaCD) have been prepared and characterized via multiangle light scattering (MALS), ionspray/electrospray ionization (IS/ESI) mass spectrometry (MS) and tandem MS [12].

Analytical, diagnostic and therapeutic context of trans-Lycopene


  1. 5-ASA and lycopene decrease the oxidative stress and inflammation induced by iron in rats with colitis. Reifen, R., Nissenkorn, A., Matas, Z., Bujanover, Y. J. Gastroenterol. (2004) [Pubmed]
  2. Functional analysis of the beta and epsilon lycopene cyclase enzymes of Arabidopsis reveals a mechanism for control of cyclic carotenoid formation. Cunningham, F.X., Pogson, B., Sun, Z., McDonald, K.A., DellaPenna, D., Gantt, E. Plant Cell (1996) [Pubmed]
  3. The biochemical characterization of ferret carotene-9',10'-monooxygenase catalyzing cleavage of carotenoids in vitro and in vivo. Hu, K.Q., Liu, C., Ernst, H., Krinsky, N.I., Russell, R.M., Wang, X.D. J. Biol. Chem. (2006) [Pubmed]
  4. Lycopene is more bioavailable from tomato paste than from fresh tomatoes. Gärtner, C., Stahl, W., Sies, H. Am. J. Clin. Nutr. (1997) [Pubmed]
  5. Synthetic and tomato-based lycopene have identical bioavailability in humans. Hoppe, P.P., Krämer, K., van den Berg, H., Steenge, G., van Vliet, T. European journal of nutrition. (2003) [Pubmed]
  6. Identification of a gene required for cis-to-trans carotene isomerization in carotenogenesis of the cyanobacterium Synechocystis sp. PCC 6803. Masamoto, K., Wada, H., Kaneko, T., Takaichi, S. Plant Cell Physiol. (2001) [Pubmed]
  7. Isomerization of lycopene in the gastric milieu. Re, R., Fraser, P.D., Long, M., Bramley, P.M., Rice-Evans, C. Biochem. Biophys. Res. Commun. (2001) [Pubmed]
  8. zeta-Carotene cis isomers as products and substrates in the plant poly-cis carotenoid biosynthetic pathway to lycopene. Breitenbach, J., Sandmann, G. Planta (2005) [Pubmed]
  9. Simple determination of retinol, alpha-tocopherol and carotenoids (lutein, all-trans-lycopene, alpha- and beta-carotenes) in human plasma by isocratic liquid chromatography. Bui, M.H. J. Chromatogr. B, Biomed. Appl. (1994) [Pubmed]
  10. Kinetic studies of lycopene isomerization in a tributyrin model system at gastric pH. Moraru, C., Lee, T.C. J. Agric. Food Chem. (2005) [Pubmed]
  11. Stability of individual carotenoids, retinol and tocopherols in human plasma during exposure to light and after extraction. Su, Q., Rowley, K.G., O'Dea, K. J. Chromatogr. B Biomed. Sci. Appl. (1999) [Pubmed]
  12. Non-covalent associations of cyclomaltooligosaccharides (cyclodextrins) with carotenoids in water. A study on the alpha- and beta-cyclodextrin/psi,psi-carotene (lycopene) systems by light scattering, ionspray ionization and tandem mass spectrometry. Mele, A., Mendichi, R., Selva, A., Molnar, P., Toth, G. Carbohydr. Res. (2002) [Pubmed]
  13. Quantitative analysis of lycopene isomers in human plasma using high-performance liquid chromatography-tandem mass spectrometry. Fang, L., Pajkovic, N., Wang, Y., Gu, C., van Breemen, R.B. Anal. Chem. (2003) [Pubmed]
  14. Supercritical fluid extraction of all-trans-lycopene from tomato. Gómez-Prieto, M.S., Caja, M.M., Herraiz, M., Santa-María, G. J. Agric. Food Chem. (2003) [Pubmed]
  15. Tomato consumption increases lycopene isomer concentrations in breast milk and plasma of lactating women. Alien, C.M., Smith, A.M., Clinton, S.K., Schwartz, S.J. Journal of the American Dietetic Association. (2002) [Pubmed]
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