Disposition of selected flavonoids in fruit tissues of various tomato (Lycopersicon esculentum Mill.) genotypes

Journal of Agricultural and Food Chemistry

Volumn 53, Issue 24, 2005, Pages 9536-9543

  Torres, Carolina A ^a   Davies, Neal M ^a   Yañez, Jaime A ^a   Andrews, Preston K ^a  

^a WASHINGTON STATE UNIVERSITY   (United States)

Author keywords

Enantiomer; Enzymatic hydrolysis; HPLC; Kaempferol; Maturity stage; Naringenin; Naringin; Quercetin

Indexed keywords

BETA GLUCOSIDASE; ENZYME; FLAVANONE DERIVATIVE; FLAVONOID; KAEMPFEROL; KAEMPFEROL DERIVATIVE; NARINGENIN; QUERCETIN;

ARTICLE; CHEMISTRY; FRUIT; GENETICS; GENOTYPE; HYDROLYSIS; METABOLISM; MUTATION; PH; TOMATO;

BETA-GLUCOSIDASE; ENZYMES; FLAVANONES; FLAVONOIDS; FRUIT; GENOTYPE; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; KAEMPFEROLS; LYCOPERSICON ESCULENTUM; MUTATION; QUERCETIN;

LYCOPERSICON ESCULENTUM;

EID: 28944441556     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf051176t     Document Type: Article

References (39)

1. Kliebenstein, D. J.; Lim, J. E.; Landry, L. G.; Last, R. L. Arabidopsis UVR8 regulates ultraviolet-B signal transduction and tolerance and contains sequence similarity to human regulator of chromatin condensation 1. Plant Physiol. 2002, 130, 234-243.
2. Li, J.; Ou-Lee, T. M.; Raba, R.; Amundson, R. G.; Last, R. L. Arabidopsis flavonoids mutants are hypersensitive to UV-B irradiation. Plant Cell 1993, 5, 171-179.
3. Ryan, K. G.; Swinny, E. E.; Winefield, C.; Markham, K. R. Flavonoids and UV photoprotection in Arabidopsis mutants. Z. Naturforsch. C 2001, 56, 745-754.
4. Bear, W. L.; Teel, R. W. Effects of Citrus flavonoids on the mutagenicity of heterocyclic amines and on cytochrome P450 1A2. Anticancer Res. B 2000, 20, 3609-3614.
5. Hódek, P.; Trefil, P.; Stiborova, M. Flavonoids: potent and versatile biologically active compounds interacting with cytochromes P450. Chem. Biol. Interact. 2002, 139, 1-21.
6. Middletown, E., Jr.; Kandaswami, C. The impact of plant flavonoids on mammalian biology: implications for immunity, inflammation and cancer. In The Flavonoids: Advances in Research since 1986; Harborne, J. B., Ed.; Chapman & Hall: London, U.K., 1993; pp 619-652.
7. Steinmetz, K. A.; Potter, J. D. Vegetables, fruit, and cancer prevention: a review. J. Am. Diet. Assoc. 1996, 96, 1027-1039.
8. Frydman, A.; Weisshaus, O.; Bar-Peled, M.; Huhman, D. V.; Sumner, L. W.; Marin, M.; Lewinsohn, E.; Flhur, R.; Gressel, J.; Eyal, Y. Citrus fruit bitter flavors: isolation and functional characterization of the gene Cm1, 2RhaT encoding a 1,2 rhamnosyltransferase, a key enzyme in the biosynthesis of the bitter flavonoids of citrus. Plant J. 2004, 40, 88-100.
9. Stewart, A. J.; Bozonnet, S.; Mullen, W.; Jenkins, G. I.; Lean, M. E. J.; Crozier, A. Occurrence of flavonols in tomatoes and tomato-based products. J. Agric. Food Chem. 2000, 48, 2663-2669.
10. Crozier, A.; Lean, M. E. J.; McDonald, M. S.; Black, C. Quantitative analysis of the flavonoids content of commercial tomatoes, onions, lettuce, and celery. J. Agric. Food Chem. 1997, 43, 590-595.
11. Le Gall, G.; DuPont, M. S.; Mellon, F. A.; Davis, A. L.; Collins, G. J.; Verhoeyen, M. E.; Colquhoun, I. J. Characterization and content of flavonoids glycosides in genetically modified tomato (Lycopersicon esculentum) fruits. J. Agric. Food Chem. 2003, 51, 2438-2446.
12. Kawaii, S.; Tomono, Y.; Katase, E.; Ogawa, K.; Yano, M. Quantitation of flavonoids constituents in Citrus fruits. J. Agric. Food Chem. 1999, 47, 3565-3571.
13. Davies, J. N.; Graeme, E. H. The constituents of tomato fruit: the influence of environment, nutrition, and genotype. Crit. Rev. Food Sci. Nutr. 1982, 15, 205-280.
14. Minoggio, M.; Bramati, L.; Simonetti, P.; Gardana, C.; Lemoli, L.; Santangelo, E.; Mauri, P. L.; Spigno, P.; Soressi, G. P.; Pietta, P. G. Polyphenol pattern and antioxidant activity of different tomato lines and cultivars. Ann. Nutr. Metab. 2003, 47, 64-69.
15. Paganga, G.; Miller, N.; Rice-Evans, C. The polyphenolic content of fruit and vegetable and their antioxidant activities. What does a serving constitute? Free Radical Res. 1999, 30, 153-162.
16. Schmidtlein, H.; Hermann, K. Bildung von Naringenin bei der Reife von Tomaten. Z. Naturforsch. C 1975, 30, 549-553.
17. Wu, M.; Burrell, R. C. Flavonoid pigment of the tomato (Lycopersicon esculentum Mill.). Arch. Biochem. Biophys. 1958, 74, 114-117.
18. Wardale, D. A. Effect of phenolic compounds in Lycopersicon esculentum on the synthesis of ethylene. Phytochemistry 1973, 12, 1523-1530.
19. Fuhrman, B.; Volkova, N.; Rosenblat, M.; Aviram, M. Lycopene synergistically inhibits LDL oxidation in combination with vitamin E, glabridin, rosmarinic acid, carnosic acid, or garlic. Antioxid. Redox Signaling 2001, 2, 491-506.
20. Kerckhoffs, L. H. J.; De Groot, N. A. M. A.; Van Tuinen, A.; Schreuder, M. E. L.; Nagatani, A.; Koornneef, M.; Kendrick, R. E. Physiological characterization of exaggerated-photoresponse mutants of tomato. J. Plant Phys. 1997, 150, 578-587.
21. Yañez, J. A.; Davies, N. M. Stereospecific high-performance liquid chromatographic analysis of naringenin in urine. J. Pharm. Biomed. Anal. 2005, 39, 164-169.
22. Bugianesi, R.; Catasta, G.; Spigno, P.; D'Uva, A.; Maiani, G. Naringenin from cooked tomato paste is bioavailable in men. J. Nutr. 2002, 132, 3349-3352.
23. Hertog, M. G. L.; Hollman, P. C. H.; Venema, D. P. Optimization of a quantitative HPLC determination of potentially anticarcinogenic flavonoids in vegetables and fruits. J. Agric. Food Chem. 1992, 40, 1591-1598.
24. Justesen, U.; Knuthsen, P.; Leth, T. Quantitative analysis of flavonols, flavones, and flavanones in fruits, vegetables and beverages by high-performance liquid chromatography with photo-diode array and mass spectrometric detection. J. Chromatogr. A 1998, 799, 101-110.
25. Kim, D.-O.; Padilla-Zakour, O. I.; Griffiths, P. D. Flavonoids and antioxidant capacity of various cabbage genotypes at juvenile stage. J. Food Sci. 2004, 69, 685-689.
26. Martinez-Valverde, I.; Periago, M. J.; Provan, G.; Chesson, A. Phenolic compounds, lycopene and antioxidant activity in commercial varieties of tomato (Lycopersicon esculentum). J. Sci. Food Agric. 2002, 82, 323-330.
27. Bovy, A.; de Vos, R.; Kemper, M.; Schijlen, E.; Almenar Pertejo, M.; Muir, S.; Collins, G.; Robinson, S.; Verhoeyen, M.; Hughes, S.; Santos-Buelga, C.; van Tunen, A. High-flavonol tomatoes resulting from the heterologous expression of the maize transcription factor genes LC and C1. Plant Cell. 2002, 14, 2509-2526.
28. Caris-Veyrat, C.; Amiot, M.-J.; Tyssandier, V.; Grasselly, D.; Buret, M.; Mikolajczak, M.; Guilland, J.-C.; Bouteloup-Demange, C.; Borel, P. Influence of organic versus conventional agricultural practice on the antioxidant microconstituent content of tomatoes and derived purees; consequences on antioxidant plasma status in humans. J. Agric. Food. Chem. 2004, 52, 6503-6509.
29. Muir, S. R.; Collins, G. J.; Robinson, S.; Hughes, S.; Bovy, A.; Ric De Vos, C. H.; van Tunen, A. J.; Verhoeyen, M. E. Overexpression of petunia chalcone isomerase in tomato results in fruit containing increased levels of flavonols. Nat. Biotechnol. 2001, 19, 470-474.
30. Andersson, T. Single-isomer drugs: true therapeutic advances. Clin. P. 2004, 43, 279-285.
31. U.S. Department of Agriculture. USDA Database for the Flavonoid Content of Selected Foods; Agricultural Research Service, Beltsville Human Nutrition Research Center: Beltsville, MD, 2003; 78 pp.
32. Ryan, K. G.; Swinny, E. E.; Winefield, C.; Markham, K. R. Flavonoids and UV protection in Arabidopsis mutants. Z. Naturforsch. C 2001, 56, 745-754.
33. Philouze, J. Description of isogenic lines, except for one, or two, mongenically controlled morphological traits in tomato, Lycopersicon esculentum Mill. Euphytica 1991, 56, 121-131.
34. Andrews, P. K.; Fahy, D. A.; Foyer, C. H. Relationships between fruit exocarp antioxidants in the tomato (Lycopersicon esculentum L.) high pigment-1 mutant during development. Physiol. Plant. 2004, 120, 1-10.
35. Baker, L. R.; Tomes, M. L. Carotenoids and chlorophylls in two tomato mutants and their hybrid. Proc. Am. Soc. Hortic. Sci. 1964, 85, 507-513.
36. Jarret, R. L.; Sayama, H.; Tigchelaar, E. C. Pleiotropic effects associated with the chlorophyll intensifier mutations of high pigment and dark green in tomato. J. Am. Soc. Hortic. Sci. 1984, 109, 873-878.
37. Stevens, M. A.; Rick, C. M. Genetics and breeding. In The Tomato Crop. A Scientific Basis for Improvement; Atherton, J. G., Rudish, J. Eds.; Chapman and Hall: London, U.K., 1986; pp 33-109.
38. Torres, C. A. Biochemical and physiological responses of tomato fruit to natural photooxidative conditions. Doctoral thesis, Washington State University, Pullman, WA, 2005.
39. Von Wettstein-Knowles, P. Mutations affecting anthocyanin synthesis in the tomato. I. Genetics, histology, and biochemistry. Hereditas 1968, 60, 317-346.