Organic synthesis of new putative lycopene metabolites and preliminary investigation of their cell-signaling effects

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 4, 2011, Pages 1457-1463

  Reynaud, Eric ^a,b   Aydemir, Gamze ^c   Rühl, Ralph ^c   Dangles, Olivier ^a,b   Caris Veyrat, Catherine ^a,b  

^a UMR A 408 INRA University of Avignon   (France)

^b UNIVERSITY OF AVIGNON   (France)

^c UNIVERSITY OF DEBRECEN   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

COUPLING REACTION; DIETARY SOURCES; LYCOPENES; ORGANIC SYNTHESIS; PROTECTIVE EFFECTS; WADSWORTH-EMMONS;

METABOLISM; METABOLITES;

BIOMOLECULES;

14' APOLYCOPEN 14' OIC ACID; 14'-APOLYCOPEN-14'-OIC ACID; 4,9,13,17,21 PENTAMETHYLDOCOSA 2,4,6,8,10,12,14,16,20 NONAENOIC ACID; 4,9,13,17,21-PENTAMETHYLDOCOSA-2,4,6,8,10,12,14,16,20-NONAENOIC ACID; ACYL COENZYME A DESATURASE; BCO2 PROTEIN, HUMAN; BETA CAROTENE KETOLASE; BETA-CAROTENE KETOLASE; CAROTENOID; LYCOPENE; OXYGENASE; UNSATURATED FATTY ACID;

ANIMAL; ARTICLE; C57BL MOUSE; CHEMISTRY; DRUG EFFECT; ENZYMOLOGY; FRUIT; GENE EXPRESSION; GENETICS; MALE; METABOLISM; MOUSE; SIGNAL TRANSDUCTION; STEREOISOMERISM; SYNTHESIS; TESTIS; TOMATO;

ANIMALS; CAROTENOIDS; FATTY ACID DESATURASES; FATTY ACIDS, UNSATURATED; FRUIT; GENE EXPRESSION; LYCOPERSICON ESCULENTUM; MALE; MICE; MICE, INBRED C57BL; OXYGENASES; SIGNAL TRANSDUCTION; STEREOISOMERISM; TESTIS;

LYCOPERSICON ESCULENTUM;

EID: 79951731062     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf104092e     Document Type: Article

References (31)

1. Rao, A. V. R.; Agarwal, S. Role of antioxidant lycopene in cancer and heart disease J. Am. Coll. Nutr. 2000, 19, 563-569
2. Giovannucci, E. Tomato products, lycopene, and prostate cancer: a review of the epidemiological literature J. Nutr. 2005, 135, 2030S-2031S (Pubitemid 41099768)
3. Sesso, H. D.; Liu, S. M.; Gaziano, J. M.; Buring, J. E. Dietary lycopene, tomato-based food products and cardiovascular disease in women J. Nutr. 2003, 133, 2336-2341 (Pubitemid 36841562)
4. Sesso, H. D.; Buring, J. E.; Norkus, E. P.; Gaziano, J. M. Plasma lycopene, other carotenoids, and retinol and the risk of cardiovascular disease in women Am. J. Clin. Nutr. 2004, 79, 47-53 (Pubitemid 41132061)
5. Wang, X. D. Carotenoid Oxidative/Degradative Products and Their Biological Activities. In Carotenoids in Health and Disease; Krinsky, N. I.; Mayne, S. T.; Sies, H., Eds.; Marcel Dekker: New York, 2004; pp 313 - 335.
6. Lindshield, B. L.; Canene-Adams, K.; Erdman, J. W. Lycopenoids: Are lycopene metabolites bioactive? Arch. Biochem. Biophys. 2007, 458, 136-140 (Pubitemid 46215568)
7. Khachik, F.; Spangler, C. J.; Smith, J. C.; Canfield, L. M.; Steck, A.; Pfander, H. Identification, quantification, and relative concentrations of carotenoids and their metabolites in human milk and serum Anal. Chem. 1997, 69, 1873-1881
8. Ben-Aziz, A.; Britton, G.; Goodwin, T. W. Carotene epoxides of Lycopersicon esculentum Phytochemistry 1973, 12, 2759-2764
9. Märki-Fisher, E.; Eugster, C. H. Dyes from roses. 5. Isolation of 10′-apo-beta-carotene-10′-ol and (3 R)-10′-apo-beta-carotene- 3,10′-diol (galloxanthin) from rose flowers Helv. Chim. Acta 1987, 70, 1994-2002
10. Gajic, M.; Zaripheh, S.; Sun, F. R.; Erdman, J. W. Apo-8 ′-lycopenal and apo-12′-lycopenal are metabolic products of lycopene in rat liver J. Nutr. 2006, 136, 1552-1557 (Pubitemid 43765361)
11. Hu, K. Q.; Liu, C.; Ernst, H.; Krinsky, N. I.; Russell, R. M.; Wang, X. D. The biochemical characterization of ferret carotene-9′,10′- monooxygenase catalyzing cleavage of carotenoids in vitro and in vivo J. Biol. Chem. 2006, 281, 19327-19338 (Pubitemid 44035438)
12. 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
13. Tibaduiza, E. C.; Fleet, J. C.; Russell, R. M.; Krinsky, N. I. Excentric cleavage products of beta-carotene inhibit estrogen receptor positive and negative breast tumor cell growth in vitro and inhibit activator protein-1-mediated transcriptional activation J. Nutr. 2002, 132, 1368-1375 (Pubitemid 34606478)
14. Prakash, P.; Liu, C.; Hu, K. Q.; Krinsky, N. I.; Russell, R. M.; Wang, X. D. Beta-carotene and beta-apo-14′-carotenoic acid prevent the reduction of retinoic acid receptor beta in benzo a pyrene-treated normal human bronchial epithelial cells J. Nutr. 2004, 134, 667-673 (Pubitemid 38298514)
15. Mein, R.; Wang, X.-D. Oxidative Metabolites of Lycopene and Their Biological Functions. In Carotenoids. Physical, Chemical, and Biological Functions and Properties; Landrum, J. T., Ed.; CRC Press: Boca Raton, FL, 2010; pp 417 - 435.
16. Stahl, W.; von Laar, J.; Martin, H.-D.; Emmerich, T.; Sies, H. Stimulation of gap junctional communication: comparison of acyclo-retinoic acid and lycopene Arch. Biochem. Biophys. 2000, 373, 271-274 (Pubitemid 30046514)
17. Lian, F. Z.; Smith, D. E.; Ernst, H.; Russell, R. M.; Wang, X. D. Apo-10′-lycopenoic acid inhihits lung cancer cell growth in vitro, and suppresses lung tumorigenesis in the A/J mouse model in vivo Carcinogenesis 2007, 28, 1567-1574 (Pubitemid 47241807)
18. Lian, F. Z.; Wang, X. D. Enzymatic metabolites of lycopene induce Nrf2-mediated expression of phase II detoxifying/antioxidant enzymes in human bronchial epithelial cells Int. J. Cancer 2008, 123, 1262-1268
19. Linnewiel, K.; Ernst, H.; Caris-Veyrat, C.; Ben-Dor, A.; Kampf, A.; Salman, H.; Danilenko, M.; Levy, J.; Sharoni, Y. Structure activity relationship of carotenoid derivatives in activation of the electrophile/antioxidant response element transcription system Free Radical Biol. Med. 2009, 47, 659-667
20. Ben-Dor, A.; Steiner, M.; Gheber, L.; Danilenko, M.; Dubi, N.; Linnewiel, K.; Zick, A.; Sharoni, Y.; Levy, J. Carotenoids activate the antioxidant response element transcription system Mol. Cancer Ther. 2005, 4, 177-186 (Pubitemid 40268075)
21. Kiefer, C.; Hessel, S.; Lampert, J. M.; Vogt, K.; Lederer, M. O.; Breithaupt, D. E.; von Lintig, J. Identification and characterization of a mammalian enzyme catalyzing the asymmetric oxidative cleavage of provitamin A J. Biol. Chem. 2001, 276, 14110-14116
22. Hengartner, U.; Bernhard, K.; Meyer, K.; Englert, G.; Glinz, E. Synthesis, isolation, and NMR-spectroscopic characterization of 14 (Z)-isomers of lycopene and of some acetylenic didehydrolycopenes and tetradehydrolycopenes Helv. Chim. Acta 1992, 75, 1848-1865
23. Gottlieb, H. E.; Kotlyar, V.; Nudelman, A. NMR chemical shifts of common laboratory solvents as trace impurities J. Org. Chem. 1997, 62, 7512-7515
24. Caris-Veyrat, C.; Schmid, A.; Carail, M.; Bohm, V. Cleavage products of lycopene produced by in vitro oxidations: characterization and mechanisms of formation J. Agric. Food Chem. 2003, 51, 7318-7325
25. Paust, J. Recent progress in commercial retinoids and carotenoids Pure Appl. Chem. 1991, 63, 45-48
26. Ernst, H. Recent advances in industrial carotenoid synthesis Pure Appl. Chem. 2002, 74, 2213-2226
27. Muller, R. K.; Bernhard, K.; Giger, A.; Moine, G.; Hengartner, U. (E / Z)-Isomeric carotenes Pure Appl. Chem. 1997, 69, 2039-2046
28. Wegner, C.; John, M. U.S. Patent 6,423,873, 2002.
29. Takeda, T. Modern Carbonyl Olefination; Wiley-VCH: Weinheim, Germany, 2004; p 349.
30. Bachmann, H.; Desbarats, A.; Pattison, P.; Sedgewick, M.; Riss, G.; Wyss, A.; Cardinault, N.; Duszka, C.; Goralczyk, R.; Grolier, P. Feedback regulation of beta,beta-carotene 15,15′-monooxygenase by retinoic acid in rats and chickens J. Nutr. 2002, 132, 3616-3622 (Pubitemid 35435037)
31. Boulanger, A.; McLemore, P.; Copeland, N. G.; Gilbert, D. J.; Jenkins, N. A.; Yu, S. S.; Gentleman, S.; Redmond, T. M. Identification of beta-carotene 15,15′-monooxygenase as a peroxisome proliferator-activated receptor target gene FASEB J. 2003, 17, 1304-1306