Kinetic studies of lycopene isomerization in a tributyrin model system at gastric pH

Journal of Agricultural and Food Chemistry

Volumn 53, Issue 23, 2005, Pages 8997-9004

  Moraru, Catalin ^a,b   Lee, Tung Ching ^a  

^a RUTGERS UNIVERSITY   (United States)

^b International Food Network   (United States)

Author keywords

cis trans isomerization; Gastric pH; Kinetics; Lycopene; Tributyrin

Indexed keywords

CAROTENOID; LYCOPENE; TRIACYLGLYCEROL; TRIBUTYRIN;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; DRUG STABILITY; ISOMERISM; KINETICS; PH; STOMACH; TOMATO;

CAROTENOIDS; DRUG STABILITY; HYDROGEN-ION CONCENTRATION; ISOMERISM; KINETICS; LYCOPERSICON ESCULENTUM; MODELS, CHEMICAL; STOMACH; TRIGLYCERIDES;

LYCOPERSICON ESCULENTUM;

EID: 28444491144     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf051672h     Document Type: Article

References (27)

1. Zechmeister, L. Cis-Trans Isomeric Carotenoids, Vitamins A and Arylpolyenes; Springer-Verlag: Wien, 1962.
2. Boileau, T. W. M.; Boileau, A. C.; Erdman, J. W. Bioavailability of all-trans and cis-isomers of lycopene. Exp. Biol. Med. 2002, 227, 914-919.
3. Krinsky, N. I.; Russett, M. D.; Handelman, G. J.; Snodderly, D. M. Structural and geometrical isomers of carotenoids in human plasma. J. Nutr. 1990, 120, 1654-1662.
4. Boileau, A. C.; Merchen, N. R.; Wasson, K.; Atkinson, C. A.; Erdman, J. W. cis-Lycopene is more bioavailable than trans-lycopene in vitro and in vivo in lymph-cannulated ferrets. J. Nutr. 1999, 129, 1176-1181.
5. Stahl, W.; Sies, H. Uptake of lycopene and its geometrical isomers is greater from heat-processed than from unprocessed tomato juice in humans. J. Nutr. 1992, 122, 2161-2166.
6. Re, R.; Fraser, P. D.; Long, M.; Bramley, P. M.; Rice-Evans, C. Isomerization of lycopene in the gastric milieu. Biochem. Biophys. Res. Commun. 2001, 281, 576-581.
7. Shi, J.; Le Maguer, M. Lycopene in tomatoes: Chemical and physical properties affected by food processing. Crit. Rev. Food Sci. Nutr. 2000, 40, 1-42.
8. Böhm, V.; Puspitasari-Nienaber, N. L.; Ferruzzi, M. G.; Schwartz, S. J. Trolox equivalent antioxidant capacity of different geometrical isomers of alpha-carotene, beta-carotene, lycopene, and zeaxanthin. J. Agric. Food Chem. 2002, 50, 221-226.
9. Tyssandier, V.; Reboul, E.; Dumas, J. F.; Bougteloup-Demange, C.; Armand, M.; Marcand, J.; Sallas, M.; Borel, P. Processing of vegetable-borne carotenoids in the human stomach and duodenum. Am. J. Physiol. - Gastrointest. Liver Physiol. 2003, 284, G913-G923.
10. Arias, R.; Lee, T. C.; Specca, D.; Janes, H. Quality comparison of hydroponic tomatoes (Lycopersicon esculentum) ripened on and off vine. J. Food Sci. 2000, 65, 545-548.
11. Chandler, L. A.; Schwartz, S. J. HPLC Separation of cis - trans carotene isomers in fresh and processed fruits and vegetables. J. Food Sci. 1987, 52, 669-672.
12. Lee, M. T.; Chen, B. H. Separation of lycopene and its cis isomers by liquid chromatography. Chromatographia 2001, 54, 613-617.
13. Clinton, S. K. Lycopene: Chemistry, biology, and implications for human health and disease. Nutr. Rev. 1998, 56, 35-51.
14. Yeum, K. J.; Booth, S. L.; Sadowski, J. A.; Liu, C.; Tang, G.; Krinsky, N. I.; Russell, R. M. Human plasma carotenoid response to the ingestion of controlled diets high in fruits and vegetables. Am. J. Clin. Nutr. 1996, 64, 594-602.
15. Khachik, F.; Pfander, H.; Traber, B. Proposed mechanisms for the formation of synthetic and naturally occurring metabolites of lycopene in tomato products and human serum. J. Agric. Food Chem. 1998, 46, 4885-4890.
16. Snyder, L. R.; Kirkland, J. J. Introduction to Modern Liquid Chromatography, 2nd ed.; Wiley: New York, 1979.
17. Englert, G. NMR Spectroscopy. In Carotenoids. Volume 1B: Spectroscopy; Britton, G., Liaaen-Jensen, S., Pfander, H., Eds.; Birkhäuser Verlag Basle: Basel, 1995.
18. Hengartner, U.; Bernhard, K.; Meyer, K.; Englert, G.; Glinz, E. Synthesis, isolation and NMR-spectroscopic characterization of fourteen (Z)-isomers of lycopene and of some acetylenic dide-hydro- and tetradehydrolycopenes. Helv. Chim. Acta 1992, 75, 1848-1865.
19. Schierle, J.; Bretzel, W.; Buhler, I.; Faccin, N.; Hess, D.; Steiner, K.; Schuep, W. Content and isomeric ratio of lycopene in food and human blood plasma. Food Chem. 1997, 59, 459-465.
20. Ishida, B. K.; Ma, J.; Chan, B. A simple, rapid method for HPLC analysis of lycopene isomers. Phytochem. Anal. 2001, 12, 194-198.
21. Nguyen, M. L.; Schwartz, S. J. Lycopene: Chemical and biological properties. Food Technol. 1999, 53, 38-45.
22. Mortensen, A.; Skibsted, L. H. Kinetics and mechanism of the primary steps of degradation of carotenoids by acid in homogeneous solution. J. Agric. Food Chem. 2000, 48, 279-286.
23. Barreiro, J. A.; Milano, M.; Sandoval, A. J. Kinetics of colour change of double concentrated tomato paste during thermal treatment. J. Food Eng. 1997, 33, 359-371.
24. Henry, L. K.; Catignani, G. L.; Schwartz, S. J. Oxidative degradation kinetics of lycopene, lutein, and 9-cis and all-trans beta-carotene. J. Am. Oil Chem. Soc. 1998, 75, 823-829.
25. Shi, J.; Le Maguer, M.; Bryan, M.; Kakuda, Y. Kinetics of lycopene degradation in tomato puree by heat and light irradiation. J. Food Proc. Eng. 2003, 25, 485-498.
26. van Boekel, M. A. J. S. Statistical aspects of kinetic modeling for food science problems. J. Food Sci. 1996, 61, 477-485.
27. Siegle, D. Critical Values of the Pearson Product-Moment Correlation Coefficient. Available online at http://www.gifted.uconn.edu/siegle/research/ Correlation/corrchrt.htm, accessed on May 14, 2004.