Lycopene epoxides and apo-lycopenals formed by chemical reactions and autoxidation in model systems and processed foods

Journal of Food Science

Volumn 74, Issue 9, 2009, Pages

  Rodriguez, Evelyn B ^a   Rodriguez Amaya, Delia B ^b  

^a UNIVERSITY OF THE PHILIPPINES LOS BAÑOS   (Philippines)

^b UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

Apo lycopenals; Degradation; Lycopene; Lycopene epoxides; Oxidation

Indexed keywords

3 CHLOROPERBENZOIC ACID; 3-CHLOROPERBENZOIC ACID; ALDEHYDE; CAROTENOID; CHLOROBENZOIC ACID DERIVATIVE; EPOXIDE; LYCOPENE; PERMANGANATE POTASSIUM;

ARTICLE; BEVERAGE; CHEMICAL MODEL; CHEMISTRY; COMPARATIVE STUDY; FOOD ANALYSIS; FRUIT; GUAVA; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; ISOMERISM; OXIDATION REDUCTION REACTION; PH; TOMATO; ANALYSIS; PSIDIUM;

ALDEHYDES; BEVERAGES; CAROTENOIDS; CHLOROBENZOATES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; EPOXY COMPOUNDS; FOOD ANALYSIS; FRUIT; HYDROGEN-ION CONCENTRATION; ISOMERISM; LYCOPERSICON ESCULENTUM; MODELS, CHEMICAL; OXIDATION-REDUCTION; POTASSIUM PERMANGANATE; PSIDIUM;

LYCOPERSICON ESCULENTUM; PSIDIUM;

EID: 70449461327     PISSN: 00221147     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1750-3841.2009.01353.x     Document Type: Article

References (34)

1. Aust O, Ale-Agha N, Zhang L, Wollersen H, Sies H, Stahl W. 2003. Lycopene oxidation product enhances gap junctional communication. Food Chem Toxicol 41 : 1399 1407.
2. Ben-Aziz A, Britton G, Goodwin TW. 1973. Carotene epoxides of Lycopersicon esculentum. Phytochemistry 12 : 2759 2764.
3. Britton G. 1995. UV/visible spectroscopy. In : Britton G, Liaaen-Jensen S, Pfander H, editors. Carotenoids vol. 1B: spectroscopy. Basel, Switzerland : Birkhäuser Verlag. p 13 63.
4. Caris-Veyrat C, Schmid A, Carail M, Böhm V. 2003. Cleavage products of lycopene produced by in vitro oxidations: characterization and mechanisms of formation. J Agric Food Chem 51 : 7318 7325.
5. Clinton SK. 1998. Lycopene: chemistry, biology, and implications for human health and disease. Nutr Rev 56 : 35 51.
6. Di Mascio P, Kaiser S, Sies H. 1989. Lycopene as the most efficient biological carotenoid singlet oxygen quencher. Arch Biochem Biophys 274 : 532 538.
7. Eugster CH. 1995. Chemical derivatization: Microscale tests for the presence of common functional groups in carotenoids. In : Britton G, Liaaen-Jensen S, Pfander H, editors. Carotenoids vol. 1A: isolation and analysis. Basel, Switzerland : Birkhäuser Verlag. p 71 80.
8. Gerster HY. 1997. The potential role of lycopene for human health. J Am Coll Nutr 16 : 109 126.
9. Giovannucci E. 1999. Tomatoes, tomato-based products, lycopene, and cancer: review of the epidemiologic literature. J Natl Cancer Inst 91 : 317 331.
10. Gradelet S, Leclerc J, Siess M-H, Astorg PO. 1996. β-apo-8′- carotenal, but not β-carotene, is a strong inducer of liver cytochromes P4501A1 and 1A2 in rat. Xenobiotica 26 : 909 919.
11. Hadley CW, Miller EC, Schwartz SJ, Clinton SK. 2002. Tomatoes, lycopene, and prostate cancer: progress and promise. Exp Biol Med 227 : 869 880.
12. Henry LK, Puspitasari-Nienabe NL, Jarén-Galán M, van Bremen RB, Castignani GL, Schwartz SJ. 2000. Effects of ozone and oxygen on the degradation of carotenoids in an aqueous system. J Agric Food Chem 48 : 5008 5013.
13. Holden JM, Eldridge AL, Beecher GR, Buzzard IM, Bhagwat S, Davis CS, Douglass LW, Gebhardt S, Haytowitz D, Schakel S. 1999. Carotenoid content of U.S. foods: an update of the database. J Food Comp Anal 12 : 169 196.
14. Hurst JS, Saini MK, Jin G-F, Awasthi YC, van Kuijk FJGM. 2005. Toxicity of oxidized β-carotene to cultured human cells. Exp Eye Res 81 : 239 243.
15. Kanasawud P, Crouzet JC. 1990. Mechanism of formation of volatile compounds by thermal degradation of carotenoids in aqueous medium. 1. β-Carotene degradation. J Agric Food Chem 38 : 237 243.
16. Khachik F, Pfander H, Traber B. 1998a. Proposed mechanisms for the formation of synthetic and naturally occurring metabolites of lycopene in tomato products and human serum. J Agric Food Chem 46 : 4885 4890.
17. Khachik F, Steck A, Niggli UA, Pfander H. 1998b. Partial synthesis and structural elucidation of the oxidative metabolites of lycopene identified in tomato paste, tomato juice, and human serum. J Agric Food Chem 46 : 4874 4884.
18. Kim S-J, Nara E, Kobayashi H, Terão J, Nagao A. 2001. Formation of cleavage products by autoxidation of lycopene. Lipids 36 : 191 199.
19. King TJ, Khachik F, Bortkiewicz H, Fukushima LH, Morioka S, Bertram JS. 1997. Metabolites of dietary carotenoids as potential cancer preventive agents. Pure Appl Chem 69 : 2135 2140.
20. Marty C, Berset C. 1986. Degradation of trans-β-carotene during heating in sealed glass tubes and extrusion cooking. J Food Sci 51 : 698 702.
21. Marty C, Berset C. 1988. Degradation products of trans-β-carotene produced during extrusion cooking. J Food Sci 53 : 1880 1886.
22. Marty C, Berset C. 1990. Factors affecting the thermal degradation of all-trans-β-carotene. J Agric Food Chem 38 : 1063 1067.
23. Mercadante AZ, Steck A, Pfander H. 1999. Carotenoids from guava (Psidium guajava L.): isolation and structure elucidation. J Agric Food Chem 47 : 145 151.
24. Rao AV, Agarwal S. 1999. Role of lycopene as antioxidant carotenoid in the prevention of chronic diseases: a review. Nutr Res 19 : 305 323.
25. Rissanen T, Voutilainen S, Nyyssönen K, Salonen JT. 2002. Lycopene, atherosclerosis, and coronary heart disease. Exp Biol Med 227 : 900 907.
26. Rodriguez EB, Rodriguez-Amaya DB. 2007. Formation of apocarotenals and epoxycarotenoids from β-carotene by chemical reactions and by autoxidation in model systems and processed foods. Food Chem 101 : 563 572.
27. Rodriguez-Amaya DB. 1999. A guide to carotenoid analysis in foods. Washington, D.C. : ILSI Press.
28. Rodriguez-Amaya DB, Kimura M, Godoy HT, Amaya-Farfan J. 2008. Updated Brazilian database on food carotenoids: factors affecting carotenoid composition. J Food Comp Anal 21 : 445 463.
29. Schiedt K, Liaaen-Jensen S. 1995. Isolation and analysis. In : Britton G, Liaaen-Jensen S, Pfander H, editors. Carotenoids vol. 1A: isolation and analysis. Basel, Switzerland : Birkhäuser Verlag. p 81 108.
30. Siems W, Sommerburg O, Schild L, Augustin W, Langhans C-D, Wiswedel I. 2002. β-Carotene cleavage products induce oxidative stress in vitro by impairing mitochondrial respiration. FASEB J 16 : 1289 1291.
31. Singh P, Goyal GK. 2008. Dietary lycopene: its properties and anticarcinogenic effects. Comp Rev Food Sci Food Safety 7 : 255 270.
32. Stacewicz-Sapuntzakis M, Bowen PE. 2005. Role of lycopene and tomato products in prostate health. Biochim Biophys Acta 1740 : 202 205.
33. Weisburger JH. 2002. Lycopene and tomato products in health promotion. Exp Biol Med 227 : 924 927.
34. Wertz K, Siler U, Goralczyk R. 2004. Lycopene: modes of action to promote prostate health. Arch Biochem Biophys 430 : 127 134.