Enzymatic and chemical oxidation of trihydroxylated phenols

Food Chemistry

Volumn 113, Issue 2, 2009, Pages 435-444

  Munoz Munoz J L ^a   Garcia Molina F ^a   Garcia Ruiz P A ^b   Arribas, E ^c   Tudela, J ^a   Garcia Canovas F ^a   Rodriguez Lopez J N ^a  

^a GENZ   (Spain)

^b UNIVERSITY OF MURCIA   (Spain)

^c UNIVERSITY OF CASTILLA LA MANCHA   (Spain)

Author keywords

Anti oxidant; Hydrogen peroxide; Peroxidase; Pro oxidant; Trihydroxylated compounds; Tyrosinase

Indexed keywords

CARBOXYLIC ACID; CATECHOL OXIDASE; GALLIC ACID; GALLIC ACID METHYL ESTER; HYDROXYL GROUP; PEROXIDASE; PHENOL DERIVATIVE; PYROGALLOL;

ANTIOXIDANT ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; ENZYME KINETICS; ENZYME SUBSTRATE; OXIDATION; PEROXIDATION;

EID: 54049141996     PISSN: 03088146     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.foodchem.2008.07.076     Document Type: Article

References (47)

1. Bradford M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Analytical Biochemistry 72 (1976) 248-254
2. Briganti S., Camera E., and Picardo M. Chemical and instrumental approaches to treat hyperpigmentation. Pigment Cell Research 16 (2003) 101-110
3. Cano A., Hernandez-Ruiz J., Garcia-Canovas F., Acosta M., and Arnao M.B. An end-point method for estimation of the total anti-oxidant activity in plant material. Phytochemical Analysis 9 (1998) 196-202
4. Davis R., Lovelace T.C., Martinez N.J., and Millar A. Decomposition of peracids and their salts with activated carbon. Catalysis Letters 31 (1995) 307-311
5. Deorkar N.V., and Tavlarides L.L. A chemically bonded adsorbent for separation of antimony, cooper and lead. Hydrometallurgy 46 (1997) 121-135
6. Dunford H.B. Heme peroxidases (1999), Wiley-VHC, New York 92-97
7. a values of some hydroxylated benzoic acids in methanol-water binary mixtures by LC methodology and potentiometry. Talanta 72 (2007) 489-496
8. Espin J.C., Varon R., Fenoll L.G., Gilabert M.A., Garcia-Ruiz P.A., Tudela J., et al. Kinetic characterization of the substrate specificity and mechanism of mushroom tyrosinase. European Journal of Biochemistry 267 (2000) 1270-1279
9. Fenoll L.G., Rodriguez-Lopez J.N., Garcia-Molina F., Garcia-Canovas F., and Tudela J. Michaelis constant of mushroom tyrosinase with respect to oxygen in the presence of monophenols and diphenols. International Journal of Biochemistry and Cell Biology 34 (2002) 332-336
10. Fenoll L.G., Garcia-Molina F., Gilabert M.A., Varon R., Garcia-Ruiz P.A., Tudela J., et al. Interpretation of the reactivity of peroxidase compound II with phenols and anilines using the Marcus equation. Biological Chemistry 386 (2005) 351-360
11. Funasaka Y., Komoto M., and Ichihashi M. Depigmenting effect of alpha-tocopheryl ferulate on normal human melanocytes. Pigment Cell Research 8 (2000) 170-174
12. Garcia-Molina F., Munoz J.L., Varon R., Rodríguez-Lopez J.N., Garcia-Canovas F., and Tudela J. A review on spectrophotometric methods for measuring the monophenolase and diphenolase activities of tyrosinase. Journal of Agricultural and Food Chemistry 55 (2007) 9739-9749
13. Garcia-Molina F., Peñalver M.J., Rodríguez-Lopez J.N., Garcia-Canovas F., and Tudela J. Enzymatic method with polyphenoloxidase for the determination of cysteine and N-acetylcysteine. Journal of Agricultural and Food Chemistry 53 (2005) 6183-6189
14. Gilabert M.A., Fenoll L.G., Garcia-Molina F., Tudela J., Garcia-Canovas F., and Rodríguez-López J.N. Kinetic characterization of phenol and anilines derivates as substrates of peroxidase. Biological Chemistry 385 (2004) 795-800
15. Gilabert M.A., Hiner A.N., Garcia-Ruiz P.A., Tudela J., Garcia-Molina F., Acosta M., et al. Differential substrate behaviour of phenol and aniline derivatives during oxidation by horseradish peroxidise: Kinetic evidence for a two-step mechanism. Biochimica Biophysica Acta 1699 (2004) 235-243
16. Habebb A.F.S.A. Reaction of protein sulfhydryl groups with reagent Ellman's. Methods Enzymology 25 (1972) 457-464
17. Hearing V. Biogenesis of pigment granules: A sensitive way to regulate melanocyte function. Journal of Dermatological Science 37 (2005) 3-14
18. Hotta H., Nagano S., Ueda M., Tsujino Y., Koyama J., and Osakai T. Higher radical scavenging activities of polyphenolic anti-oxidants can be ascribed to chemicals reactions following their oxidation. Biochimica et Biophysica Acta 1572 (2002) 123-132
19. ®. Core Madera, CA: Jandel Scientific.
20. Kim Y. Antimelanogenic and anti-oxidant properties of gallic acid. Biological and Pharmaceutical Bulletin 30 (2007) 1052-1055
21. Kim S.W., Han Y.W., Lee S.T., Jeong H.J., Kim S.H., Kim I.H., et al. A superoxide anion generator, pyrogallol, inhibits the growth of HeLa cells via cell cycle arrest and apoptosis. Molecular Carcinogenesis 47 (2008) 114-125
22. Kim Y.J., and Uyama H. Tyrosinase inhibitors from natural and synthetic sources: Structure, inhibition mechanism and perspective for the future. Cellular and Molecular Life Sciences 62 (2005) 1707-1723
23. Lee S.F., Liang Y.C., and Lin J.K. Inhibition of 1,2,4-benzenetriol-generated active oxygen species and induction of phase II enzymes by green tea polyphenols. Chemico-Biological Interactions 98 (1995) 283-301
24. Lee S.F., and Lin J.K. Generation of hydrogen peroxide, superoxide anion and the hydroxyl free radical from polyphenols and active benzene metabolites: Their possible role in mutagenesis. Journal of Biomedical Science 1 (1994) 125-130
25. Li Y., Tanaka T., and Kouno I. Oxidative coupling of the pyrogallol B-ring with a galloyl group during enzymatic oxidation of epigallocatechin 3-O-gallate. Phytochemistry 68 (2007) 1081-1088
26. Lin J.K., and Lee S.F. Enhancement of the mutagenicity of polyphenols by chlorination and nitrosation in Salmonella typhimurium. Mutation Research 269 (1992) 217-224
27. Locatelli C., Rosso R., Santos-Silva M.C., de Souza C.A., Licinio M.A., Leal P., et al. Ester derivatives of gallic acid with potential toxicity toward L1210 leukemia cells. Bioorganic and Medicinal Chemistry 16 (2008) 3791-3799
28. Lu Z., Nie G., Belton P.S., Tang H., and Zhao B. Structure-activity relationship analysis of anti-oxidant ability effect of gallic acid derivatives. Neurochemistry International 48 (2006) 263-274
29. Matsuo, Y., Yamada, Y., Tanaka, T., Kouno, I. (in press). Enzymatic oxidation of gallocatechin and epigallocatechin: Effects of C-ring configuration on the reaction products. Phytochemistry.
30. Muñoz J.L., Garcia-Molina F., Varon R., Rodríguez-Lopez J.N., Garcia-Canovas F., and Tudela J. Calculating molar absorptivities for quinones: Application to the measurements of tyrosinase activity. Analytical Biochemistry 351 (2006) 128-138
31. Muzolf M., Szymusiak H., Gliszczynska-Swiglo A., Rietjens I.M.C.M., and Tyrakowska B. pH-dependent radical scavenging capacity of green tea catechins. Journal of Agricultural and Food Chemistry 56 (2008) 816-823
32. Noguchi M., Yokoyama M., and Watanabe S. Inhibitory effect of the tea polyphenol, (-)-epigallocatechin gallate, on growth of cervical adenocarcinoma cell lines. Cancer Letters 234 (2006) 135-142
33. Rodríguez-López J.N., Fenoll L.G., Garcia-Ruiz P.A., Varon R., Tudela J., Thorneley R.N., et al. Stopped-flow and steady-state study of the diphenolase activity of mushroom tyrosinase. Biochemistry 39 (2000) 10497-10506
34. Rodríguez-López J.N., Gilabert M.A., Tudela J., Thorneley R.N.F., and García-Cánovas F. Reactivity of horseradish peroxidase compound II toward substrates: Kinetic evidence for a two-step mechanism. Biochemistry 39 (2000) 13201-13209
35. Rodríguez-López J.N., Ros J.R., Varon R., and Garcia-Canovas F. Oxygen Michaelis constant for tyrosinase. Biochemical Journal 293 (1993) 859-866
36. Rodríguez-López J.N., Ros-Martinez J.R., Varon R., and Garcia-Canovas F. Calibration of a Clark-type oxygen electrode by tyrosinase-catalyzed oxidation of a 4-tert-butylcatechol. Analytical Biochemistry 202 (1992) 356-360
37. Rodríguez-López J.N., Tudela J., Varon R., Garcia-Carmona F., and Garcia-Canovas F. Kinetic study on the effect of pH on the melanin biosynthesis pathway. Biochimica Biophysica Acta 1076 (1991) 379-386
38. Roth E.F., and Gilbert H. The pyrogallol assay for superoxide dismutase: Absence of a glutathione artifact. Analytical Biochemistry 137 (1984) 50-53
39. Seo S.Y., Sharma V.K., and Sharma N. Mushroom tyrosinase: A recent prospects. Journal of Agricultural and Food Chemistry 51 (2003) 2837-2853
40. Solomon E.I., Sundaran U.M., and Machonkin T.E. Multicopper oxidases and oxygenases. Chemical Reviews 96 (1996) 2563-2606
41. Sroka Z., and Cisowski W. Hydrogen peroxide scavenging, anti-oxidant and anti-radical activity of some phenolic acids. Food and Chemical Toxicology 41 (2003) 753-758
42. Tomita Y., Hariu A., Mizuno C., and Seiji M. Inactivation of tyrosinase by dopa. Journal of Investigative Dermatology 75 (1980) 379-382
43. Tomiyama S., Sakai S., Nihiyama T., and Yasmada F. Factors influencing the anti-oxidant activities of phenols by an ab initio study. Bulletin of the Chemical Society of Japan 66 (1993) 293-304
44. Vámos-Vigázó L. In: Lee C.Y., and Whitacker J.R. (Eds). Enzymatic browning and its prevention (1995), American Chemical Society, Washington, DC
45. Weidman S.W., and Kaiser E.T. The mechanism of the periodate oxidation of aromatic systems III. A kinetic study of the periodate oxidation of catechol. Journal of the American Chemical Society 88 (1966) 5820-5827
46. Yasui H., and Sakurai H. Age-dependent generation of reactive oxygen species in the skin of live hairless rats exposed to UVA light. Experimental Dermatology 12 (2003) 655-661
47. Zhao X., Tian H., Ma X., and Li L. Epigallocatechin gallate, the main ingredient of green tea induces apoptosis in breast cancer cell. Frontiers in Bioscience 11 (2006) 2428-2433