Oxidation of the flavonol quercetin by polyphenol oxidase

Journal of Agricultural and Food Chemistry

Volumn 47, Issue 1, 1999, Pages 56-60

  Jiménez, Mercedes ^a   García Carmona, Francisco ^a  

^a UNIVERSITY OF MURCIA   (Spain)

Author keywords

Flavonols; Polyphenol oxidase; Quercetin

Indexed keywords

CATECHOL OXIDASE; ENZYME INHIBITOR; FLAVONOL; QUERCETIN;

ARTICLE; CATALYSIS; ENZYME ACTIVATION; ENZYME MECHANISM; ENZYME SYNTHESIS; HYDROXYLATION; METABOLISM; OXIDATION REDUCTION REACTION; PH; PLANT SEED; REACTION ANALYSIS; SECRETION;

CATECHOL OXIDASE; ENZYME ACTIVATION; ENZYME INHIBITORS; HYDROGEN-ION CONCENTRATION; OXIDATION-REDUCTION; QUERCETIN;

PHASEOLUS (ANGIOSPERM); VICIA FABA;

EID: 0043051981     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf9805653     Document Type: Article

References (43)

1. Bordier, C. Phase separation of integral membrane proteins in Triton-X114 solution. J. Biol. Chem. 1981, 256, 1604-1607.
2. Bors, W.; Heller, W.; Michel, C.; Saran, M. Flavonoids as antioxidants: Determination of radical-scavenging efficiencies. Methods Enzymol. 1990, 186, 343-355.
3. Bradford, M. M. A rapid and sensitive method for the quantitation of microgram quantities of proteins utilizing the priciple of protein-dye binding. Anal. Biochem. 1976, 72, 248-254.
4. Brand-Williams, W.; Cuvelier, M. E.; Berset, C. Use of a free radical method to evaluate antioxidant activity. Lebensm. Wiss. -Technol. 1995, 28, 25-30.
5. Chazarra, S.; Cabanes, J.; Escribano, J.; García-Carmona, F. Partial purification and characterization of latent polyphenol oxidase in iceberg lettuce (Lactuca sativa L.) J. Agric. Food Chem. 1996, 44, 984-988.
6. Deschner, E. E.; Ruperto, J.; Wong, G.; Newmark, H. L. Quercetin and rutin as inhibitors of azoxymethanol-induced colonic neophasia. Carcinogenesis 1991, 12, 1193-1196.
7. Dick, D.; Redden, P.; DeMarco, A.; Lidster, P.; Grindley, T. Flavonoid glycosides of spartan apple peel. J. Agric. Food Chem. 1987, 35, 529-531.
8. Finger, A. In vitro studies on the effect of polyphenol oxidase and peroxidase on the formation of polyphenolic black tea constituents. J. Sci. Food Agric. 1994, 66, 293-305.
9. Frankos, V. H.; Schmitt, D. F.; Haws, L. C.; McEvily, A. J.; Iyengar, R.; Miller, S. A. Generally recognized as safe (GRAS) evaluation of 4-hexylresorcinol for use as a processing aid for prevention of melanosis in shrimp. Regul. Toxicol. Pharmacol. 1991, 14, 202-212.
10. Golbeck, J. H.; Cammarata, K. V. Spinach thylakoid polyphenol oxidase. Isolation, activation and properties of native chloroplast enzyme. Plant Physiol. 1981, 67, 977-984.
11. Gross, M.; Pfeiffer, M.; Martini, M.; Campbell, D.; Slavin, J.; Potter, J. The quantitation of metabolites of quercetin flavonols in hguman urine. Cancer Epidemiol., Biomarkers Prev. 1996, 5, 711-720.
12. Haenen, G. R.; Paquay, J. B.; Korthouwer; R. E.; Bast, A. Peroxynitrite scavenging by flavonoids. Biochem. Biophys. Res. Commun. 1997, 236, 591-593.
13. Halliwell, B. Free radicals, antioxidants, and human disease: Curiosity, cause, or consequence? Lancet 1994, 344, 721-724.
14. Hertog, M. G. L.; Hollman, P. C. H.; van de Putte, B. Content of potentially anticarcinogenic flavonoids of tea infusions, wines, and fruit juices. J. Agric. Food Chem. 1993, 41, 1242-1246.
15. Hollman, P. C.; Gaag, M.; Mengelers, M. J. B.; Trijp, J. M. P.; Vriers, J. H. M.; Katan, M. B. Absorption and disposition kinetics of the dietary antioxidant quercetin in man. Free Radicals Biol. Med. 1996, 21, 703-707.
16. Hutcheson, S. W.; Buchanan, B. B. Polyphenol oxidation by Vicia faba chloroplast membranes. Studies on the latent membrane-bound polyphenol oxidase and on the mechanism of photochemical polyphenol oxidation. Plant Physiol. 1980, 66, 1150-1154.
17. Iyengar, R.; Bohmont, C. W.; McEvily, A. 4-Hexylresorcinol and prevention of shrimp blackspot: residual analysis. J. Food Compos. Anal. 1991, 4, 148-157.
18. Jiménez, M.; García-Carmona, F. Kinetics of the slow pH-mediated transition of polyphenol oxidase. Arch. Biochem. Biophys. 1996a, 331, 15-22.
19. Jiménez, M.; García-Carmona, F. The effect of sodium dodecyl sulfate on polyphenol oxidase. Phytochemistry 1996b, 42, 1503-1509.
20. Jiménez, M.; García-Carmona, F. 4-Substituted resorcinols (sulfite alternatives) are slow-binding inhibitorsof tyrosinase catecholase activity. J. Agric. Food Chem. 1997, 45, 2061-2065.
21. Kenten, R. H. Latent polyphenol oxidase in extracts od broad bean (Vicia faba L.). 1. Activation by acid and alkali. Biochem. J. 1957, 67, 300-307.
22. King, R. S.; Flurkey, W. H. Effects of limited proteolysis on broad bean polyphenol oxidase. J. Sci. Food Agric. 1987, 41, 231-240.
23. Kinsella, J. E.; Frankel, E.; German, B.; Kanner, J. Possible mechanisms for the protective role of antioxidants in wine and plant foods. Food Technol. 1993, 47, 85-89.
24. Lee, Y.; Howard, L. R.; Villalón, B. Flavonids and antioxidant activity of fresh pepper (Capsicum annuum) cultivars. J. Food Sci. 1995, 60, 473-476.
25. McEvily, A. J.; Iyengar, R.; Otwell, W. S. Inhibition of enzymatic browning in foods and beverages. Crit. Rev. Food Sci. Nutr. 1992, 32, 253-273.
26. Merfort, I.; Heilmann, J.; Weiss, M.; Pietta, P.; Gardana, C. Radical scavenger activity of three flavonoid metabolites studied by inhibition of chemiluminescence in human PMNs. Planta Med. 1996, 62, 289-292.
27. Midddleton, E.; Kandaswami, C. The impact of plant flavonoids on mammalian biology: Implications for immunity, inflammation and cancer. In The Flavonoids: Advances in Research since 1986; Chapman and Hall: London, 1994; pp 619-652.
28. Moore, A. M.; Flurkey, W. H. Sodium dodecyl sulfate activation of a plant polyphenol oxidase. Effect of sodium dodecyl sulfate on an enzymatic and physical characteristics of purified broad bean polyphenol oxidase. J. Biol. Chem. 1990, 265, 4982-4990.
29. 84 cells. J. Nutr. 1993, 123, 259-268.
30. Nicolas, J.; Potus, J. Enzymatic oxidation phenomena and coupled oxidations. Effects of lypoxygenase in breadmaking and of polyphenoloxidase in fruit technology. Sci. Aliments 1994, 14, 627-642.
31. Okuda, T. Natural polyphenols as antioxidants and their potential use in cancer prevention. In Polyphenolic Phenomena; INRA: Paris, 1993; pp 221-235.
32. Sánchez-Ferrer, A.; Bru, R.; García-Carmona, F. Partial purification of athylakoid-bound enzyme using temperature-iduced phase partitioning. Anal. Biochem. 1990, 184, 279-282.
33. Sánchez-Ferrer, A.; Laveda, F.; García-Carmona, F. Substrate-dependent activation of latent potato leaf polyphenol oxidase by anionic surfactants. J. Agric. Food Chem. 1993, 41, 1583-1586.
34. Sánchez-Moreno, C.; Larrauri, J. A.; Saura-Calixto, F. A procedure to measure the antiradical efficiency of polyphenols. Journal 1998, 76, 270-276.
35. Saramet, A.; Danila, G.; Paduraru, I.; Petrariu, D.; Olinescu, R. Direct detection of the antioxidant activity of a new flavonic derivative using the chemiluminescence method. Arzneimittelforschung 1996, 46, 501-504.
36. Sarni-Manchado, P.; Cheynier, V.; Moutounet, M. Reactions of polyphenol oxidase generated caftaric acid o-quinone with malvidin 3-O-glucoside. Phytochemistry 1997, 45, 1365-1369.
37. Schrock, H. L.; Gennis, R. B. High affinity lipid binding sites on the peripheral membrane enzyme pyruvate oxidase. J. Biol. Chem. 1977, 252, 5990-5995.
38. Steinberg, D.; Parthasarathy, S.; Carew, T. E.; Khoo, J. C.; Witztum, J. L. Beyond cholesterol. Modification of low-density lipoproteins that increase its atherogenicity. New Engl. J. Med. 1989, 262, 3603-3608.
39. Strube, M.; Haenen, G. R. M. M.; Berg, H.; Bast, A. Pitfalls in a method for assesment of total antioxidant capacity. Free Radical Res. 1997, 26, 515-521.
40. Teissedre, P. L.; Frankel, E. N.; Waterhouse, A. L.; Peleg, H.; German, J. B. Inhibition of in vitro human LDL oxidation by phenolic antioxidants from grapes and wines. J. Sci. Food Agric. 1996, 70, 55-61.
41. Vamos-Vigyázó, L. Polyphenol oxidase and peroxidase in fruits and vegetables. CRC Crit. Rev. Food Sci. Nutr. 1981, 15, 49-127.
42. Weber, G.; Shen, F.; Prajda, N.; Yang, H.; Li, W.; Yeh, A.; Csokay, B.; Olah, E.; Look, K. Y. Regulation of the signal transduction program by drugs. Adv. Enzyme Regul. 1997, 37, 35-55.
43. Wesche-Ebeling, P.; Montgomery, M. W. Strawberry polyphenol oxidase: its role in anthocyanin degradation. J. Food Sci. 1990, 55, 731-734.