Action of tyrosinase on ortho-substituted phenols: Possible influence on browning and melanogenesis

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 25, 2012, Pages 6447-6453

  Garcia Molina, Maria Del Mar ^a   Muñoz Muñoz, Jose Luis ^a   Garcia Molina, Francisco ^a   García Ruiz, Pedro Antonio ^a   Garcia Canovas, Francisco ^a  

^a UNIVERSITY OF MURCIA   (Spain)

Author keywords

carvacrol; melanogenesis; monophenols; thymol; tyrosinase

Indexed keywords

CARVACROL; MELANOGENESIS; MONOPHENOLS; THYMOL; TYROSINASE;

ALCOHOLS; AMINO ACIDS;

PHENOLS;

ENZYME INHIBITOR; FUNGAL PROTEIN; MONOPHENOL MONOOXYGENASE; PHENOL DERIVATIVE;

AGARICALES; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; ENZYME SPECIFICITY; ENZYMOLOGY; KINETICS;

AGARICALES; ENZYME INHIBITORS; FUNGAL PROTEINS; KINETICS; MOLECULAR STRUCTURE; MONOPHENOL MONOOXYGENASE; PHENOLS; SUBSTRATE SPECIFICITY;

EID: 84862878958     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf301238q     Document Type: Article

References (35)

1. Sanchez-Ferrer, A.; Rodriguez-Lopez, J. N.; Garcia-Canovas, F.; Garcia-Carmona, F. Tyrosinase: a comprehensive review of its mechanism Biochim. Biophys. Acta 1995, 1247, 1-11
2. Garcia-Carmona, F.; Garcia-Canovas, F.; Iborra, J. L.; Lozano, J. A. Kinetic study of the pathway of melanization between L-dopa and dopachrome Biochim. Biophys. Acta 1982, 717, 124-131
3. Garcia-Canovas, F.; Garcia-Carmona, F.; Vera, J.; Iborra, J. L.; Lozano, J. A. The role of pH in the melanin biosynthesis pathway J. Biol. Chem. 1982, 257, 8738-8744
4. Solano, F.; Martinez-Liarte, J. H.; Jimenez-Cervantes, C.; Garcia-Borron, J. C.; Lozano, J. A. Dopachrome tautomerase is a zinc-containing enzyme Biochem. Biophys. Res. Commun. 1994, 204, 1243-1250
5. Kim, J. M.; Marshall, M. R.; Cornell, J. A.; Preston, J. F.; Wei, C. I. Antibacterial activity of carvacrol, citral, and geraniol against Salmonella typhimurium in culture medium and on fish cubes J. Food Sci. 1995, 60, 1364-1368
6. Ultee, G.; Gorris, L. G.; Smid, E. J. Bactericidal activity of carvacrol towards the food-borne pathogen Bacillus cereus J. Appl. Microbiol. 1998, 85, 211-218
7. Walsh, S. E.; Maillard, J. Y.; Russell, A. D.; Catrenich, C. E.; Charbonneau, D. L.; Bartolo, R. G. Activity and mechanisms of action of selected biocidal agents on Gram-positive and -negative bacteria J. Appl. Microbiol. 2003, 94, 240-247
8. Aeschbach, R.; Löliger, J.; Scott, B. C.; Murcia, A.; Butler, J.; Halliwell, B.; Aruoma, O. I. Antioxidant actions of thymol, carvacrol, 6-gingerol, zingerone and hydroxytyrosol Food Chem. Toxicol. 1994, 32, 31-36
9. Jukic, M.; Milos, M. Catalytic oxidation and antioxidant properties of thyme essential oils (Thymus vulgarae L.) Croat. Chem. Acta. 2005, 78, 105-110
10. Yanishlieva, N. V.; Marinova, E. M.; Gordon, M. H.; Raneva, V. G. Antioxidant activity and mechanism of action of thymol and carvacrol in two lipid systems Food Chem. 1999, 64, 59-66
11. Satooka, H.; Kubo, I. Effects of thymol on mushroom tyrosinase-catalyzed melanin formation J. Agric. Food Chem. 2011, 59, 8908-8914
12. Jimenez, M.; Garcia-Carmona, F.; Garcia-Canovas, F.; Iborra, J. L.; Lozano, J. A.; Martinez, F. Chemical intermediates in dopamine oxidation by tyrosinase, and kinetic studies of the process Arch. Biochem. Biophys. 1984, 235, 438-448
13. Jimenez, M.; Garcia-Canovas, F.; Garcia-Carmona, F.; Tudela, J.; Iborra, J. L. Study of alpha-methyldopa oxidation by tyrosinase Int. J. Biochem. 1986, 18, 39-47
14. Jimenez, M.; Garcia-Canovas, F.; Garcia-Carmona, F.; Lozano, J. A.; Iborra, J. L. Kinetic study and intermediates identification of noradrenaline oxidation by tyrosinase Biochem. Pharmacol. 1984, 33, 3689-3697
15. Garcia-Carmona, F.; Cabanes, J.; Garcia-Canovas, F. Kinetic study of sinephrine oxidation by mushroom tyrosinase Biochem. Int. 1987, 14, 1003-1013
16. Jimenez, M.; Garcia-Carmona, F.; Garcia-Canovas, F.; Iborra, J. L.; Lozano, J. A. Isoproterenol oxidation by tyrosinase: intermediates characterization and kinetic study Biochem. Int. 1985, 11, 51-59
17. Rodriguez-Lopez, J. N.; Fenoll, L. G.; Garcia-Ruiz, P. A.; Varon, R.; Tudela, J.; Thorneley, R. N. F.; Garcia-Canovas, F. Stopped-flow and steady-state study of the diphenolase activity of mushroom tyrosinase Biochemistry 2000, 39, 10497-10506
18. Bradford, M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding Anal. Biochem. 1976, 72, 248-254
19. Garcia-Molina, F.; Muñoz, J. L.; Varon, R.; Rodriguez-Lopez, J. N.; Garcia-Canovas, F.; Tudela, J. A review on spectrophotometric methods for measuring the monophenolase and diphenolase activities of tyrosinase J. Agric. Food Chem. 2007, 55, 9739-9749
20. Ros, J. R.; Rodriguez-Lopez, J. N.; Garcia-Canovas, F. Tyrosinase: kinetic analysis of the transient phase and the steady state Biochim. Biophys. Acta 1994, 1204, 33-42
21. Muñoz-Muñoz, J. L.; Garcia-Molina, F.; Garcia-Ruiz, P. A.; Varon, R.; Tudela, J.; Rodriguez-Lopez, J. N.; Garcia-Canovas, F. Catalytic oxidation of o -aminophenols and aromatic amines by mushroom tyrosinase Biochim. Biophys. Acta 2011, 1814, 1974-1983
22. Espin, J. C.; Morales, M.; Varon, R.; Tudela, J.; Garcia-Canovas, F. Continuous spectrophotometric method for determining monophenolase and diphenolase activities of pear polyphenoloxidase J. Food Sci. 1996, 61, 1177-1201
23. Escribano, J.; Tudela, J.; Garcia-Carmona, F.; Garcia-Canovas, F. A kinetic study of the suicide inactivation of an enzyme measured through coupling reactions application to the suicide inactivation of tyrosinase Biochem. J. 1989, 262, 597-603
24. Pomerantz, S. H. The tyrosine hydroxylase activity of mammalian tyrosinase J. Biol. Chem. 1966, 241, 161-168
25. Rodriguez-Lopez, J. N.; Ros-Martinez, J. R.; Varon, R.; Garcia-Canovas, F. Calibration of a Clark-type oxygen electrode by tyrosinase-catalyzed oxidation of 4- tert -butylcatechol Anal. Biochem. 1992, 202, 356-360
26. Sigma Plot 9.0 for Windows; Jandel Scientific: Core Madera, CA, 2006.
27. Günther, H. Nuclear Magnetic Resonance of Fluorine-19 and Carbon-13. In NMR Spectroscopy; John Wiley & Sons: New York, 1980; pp 364-374.
28. N2 reactions of 9-substituted fluorenyl and α-cyano carbanions with benzyl chloride in dimethyl sulfoxide solution J. Org. Chem. 1983, 48, 2206-2215
29. Smith, N. P. M.; Pavel, S.; Riley, P. A. Mechanisms of control of the cytotoxicity of ortho -quinone intermediates of melanogenesis. In Role of Catechol Quinone Species in Cellular Toxicity; Creveling, C.R., Ed.; F. P. Graham Co.: Johnson City, TN, 2000; pp 191-246.
30. Krol, E. S.; Bolton, J. L. Oxidation of 4-alkylphenols and catechols by tyrosinase: ortho-substituents alter the mechanism of quinoid formation Chem.-Biol. Interact. 1997, 104, 11-27
31. Kahn, V.; Ben-Shalom, N. N -Acetyl- l -tyrosine (NAT) as a substrate for mushroom tyrosinase Pigm. Cell Res. 1998, 11, 24-33
32. Varon-Castellanos, R.; Garcia-Moreno, M.; Garcia-Sevilla, F.; Ruiz-Galea, M. M.; Garcia-Canovas, F. Computerized derivation of the steady-state equations of enzyme reactions. A5, ed.; Albacete, Spain, 1995.
33. Guazzaroni, M.; Crestini, C.; Saladino, R. Layer-by-layer coated tyrosinase: an efficient and selective synthesis of catechols Bioorg. Med. Chem. 2012, 20, 157-166
34. Rodriguez-Lopez, J. N.; Fenoll, L. G.; Peñalver, M. J.; Garcia-Ruiz, P. A.; Varon, R.; Martinez-Ortiz, F.; Garcia-Canovas, F.; Tudela, J. Tyrosinase action on monophenols: evidence for direct enzymatic release of o -diphenol Biochim. Biophys. Acta 2001, 1548, 238-256
35. Satooka, H.; Kubo, I. Effects of thymol on B16-F10 melanoma cells J. Agric. Food Chem. 2012, 60, 2746-2752