Comparison of the characteristics of fungal and plant tyrosinases

Journal of Biotechnology

Volumn 130, Issue 4, 2007, Pages 471-480

  Selinheimo, Emilia ^a   NiEidhin, Deirdre ^b   Steffensen, Charlotte ^c   Nielsen, Jacob ^c   Lomascolo, Anne ^d   Halaouli, Sonia ^d   Record, Eric ^d   O'Beirne, David ^b   Buchert, Johanna ^a   Kruus, Kristiina ^a  

^a VTT TECHNICAL RESEARCH CENTRE OF FINLAND   (Finland)

^b UNIVERSITY OF LIMERICK   (Ireland)

^c DANISH INSTITUTE OF AGRICULTURAL SCIENCES   (Denmark)

^d AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Crosslinking; Fungal; Inhibition; Plant; Specificity; Tyrosinase

Indexed keywords

BIOCHEMISTRY; CROSSLINKING; HYDROXYLATION; KETONES; PARAMAGNETIC RESONANCE; PLANTS (BOTANY);

SPECIFICITY; TYROSINASE;

ENZYMES;

FUNGAL ENZYME; MONOPHENOL MONOOXYGENASE; SEMIQUINONE;

AGARICUS BISPORUS; ARTICLE; ELECTRON SPIN RESONANCE; ENZYME INHIBITION; ENZYME SPECIFICITY; NONHUMAN; PRIORITY JOURNAL; PROTEIN CROSS LINKING; TRICHODERMA REESEI;

ENZYME ACTIVATION; ENZYME STABILITY; FUNGAL PROTEINS; FUNGI; MONOPHENOL MONOOXYGENASE; PLANT PROTEINS; PLANTS; SUBSTRATE SPECIFICITY;

AGARICUS BISPORUS; BASIDIOMYCOTA; FUNGI; HYPOCREA JECORINA; MALUS X DOMESTICA; PYCNOPORUS SANGUINEUS; SOLANUM TUBEROSUM;

EID: 34347391249     PISSN: 01681656     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jbiotec.2007.05.018     Document Type: Article

References (80)

1. Åberg C.M., Chen T., Olumide A., Raghavan S.R., and Payne G.F. Enzymatic grafting of peptides from casein hydrolysate to chitosan. Potential for value-added byproducts from food-processing wastes. J. Agric. Food Chem. 52 (2004) 788-793
2. Abdel-Raheem A., and Shearer C.A. Extracellular enzyme production by freshwater ascomycetes. Fungal Divers. 11 (2002) 1-19
3. Anhgileri A., Lantto R., Kruus K., Arosio C., and Freddi G. Tyrosinase-catalyzed grafting of sericin peptides onto chitosan and production of protein-polysaccharide bioconjugates. J. Biotechnol. 127 (2007) 508-519
4. Bittner S. When quinones meet amino acids: chemical, physical and biological consequences. Amino Acids 30 (2006) 205-224
5. Boss P.K., Gardner R.C., Janssen B.J., and Ross G.S. An apple polyphenol oxidase cDNA is up-regulated in wounded tissues. Plant Mol. Biol. 27 (1995) 429-433
6. Chen T., Small D.A., Wu L.-Q., Rubloff G.W., Ghodssi R., Vazquez-Duhalt R., Bentley W.E., and Payne G.F. Nature-inspired creation of protein-polysaccharide conjugate and its subsequent assembly onto a patterned surface. Langmuir 19 (2003) 9382-9386
7. Conrad J.S., Dawso S.R., Hubbard E.R., and Strothkamp K.G. Inhibitor binding to the binuclear active site of tyrosinase: temperature, pH and solvent deuterium isotope effects. Biochemistry 33 (1994) 5739-5744
8. Cooksey C.J., Garratt P.J., Land E.J., Pavel S., Ramsden C.A., Riley P.A., and Smit N.P. Evidence of the indirect formation of the catecholic intermediate substrate responsible for the autoactivation kinetics of tyrosinase. J. Biol. Chem. 272 (1997) 26226-26235
9. Cuff M.E., Miller K.I., van Holde K.E., and Hendrickson W.A. Crystal structure of a functional unit from Octopus dofleini hemocyanin. J. Mol. Biol. 278 (1998) 855-870
10. Decker H., Schweikardt T., and Tuczek F. The first crystal structure of tyrosinase: all questions answered?. Angew. Chem. Intl. Ed. 45 (2006) 4546-4550
11. Della-Cioppa, G., Garger, S.J., Holtz, R.B., McCulloch, M.J., Sverlow, G.G., 1998a. Method for making stable extracellular tyrosinase and synthesis of polyphenolic polymers therefrom. US5801047.
12. Della-Cioppa, G., Garger, S.J., Sverlow, G.G., Turpen, T.H., Grill, L.K., Chedekal, M.R., 1998b. Melanin production by Streptomyces. US5814495.
13. del Marmol V., and Beermann F. Tyrosinase and related proteins in mammalian pigmentation. FEBS Lett. 381 (1996) 165-168
14. Dickinson E. Enzymic crosslinking as a tool for food colloid rheology control and interfacial stabilization. Trends Food Sci. Technol. 8 (1997) 334-339
15. Echigo, T., Ohno, R., 1997. Process for producing high-molecular weight compounds of phenolic compounds, etc. and use thereof. EP 919628.
16. Espín J.C., García-Ruiz P.A., Tudela J., and García-Cánovas F. Study of stereospecificity in mushroom tyrosinase. Biochem. J. 331 (1998) 547-551
17. Espín J.C., Morales M., Varón R., Tudela J., and García-Cánovas F.A. Continuous spectrophotometric method for determining the monophenolase and diphenolase activities of apple polyphenol oxidase. Anal. Biochem. 231 (1995) 237-246
18. Espín J.C., Morales M., Varón R., Tudela J., and García-Cánovas F. Monophenolase activity of polyphenol oxidase from Verdedoncella apple. J. Agric. Food Chem. 43 (1995) 2807-2812
19. Espín J.C., Morales M., Varón R., Tudela J., and García-Cánovas F. Monophenolase activity of polyphenol oxidase from Blanquilla pear. Phytochemistry 44 (1997) 17-22
20. Espín J.C., Ochoa M., Tudela J., and García-Cánovas F. Monophenolase activity of polyphenol oxidase from Chandler strawberry. Phytochemistry 45 (1997) 667-670
21. Espín J.C., Trujano M.F., Tudela J., and García-Cánovas F. Monophenolase activity of polyphenol oxidase from Haas avocado. J. Agric. Food Chem. 45 (1997) 1091-1096
22. Espín J.C., Tudela J., and García-Cánovas F. Monophenolase activity of polyphenol oxidase from artichoke (Cynara scolymus, L.) heads. Food Sci. Technol.-London 30 (1997) 819-825
23. Espín J.C., and Wichers H.J. Activation of a latent mushroom (Agaricus bisporus) tyrosinase isoform by sodium dodecyl sulfate (SDS). Kinetic properties of the SDS-activated isoform. J. Agric. Food Chem. 47 (1999) 3518-3525
24. Freddi G., Anghileri A., Sampaio S., Buchert J., Monti P., and Taddei P. Tyrosinase-catalyzed modification of Bombyx mori silk fibroin: grafting of chitosan under heterogenous reaction conditions. J. Biotechnol. 125 (2006) 281-294
25. Garcia-Molina F., Penalver M.J., Rodriguez-Lopez J.N., Garcia-Canovas F., and Tudela J. Enzymatic method with polyphenol oxidase for the determination of cysteine and N-acetylcysteine. J. Agric. Food Chem. 53 (2005) 6183-6189
26. Gary J.W., Lax A.R., and Flurkey W.H. Cloning and characterization of cDNAs coding for Vicia faba polyphenol oxidase. Plant Mol. Biol. 20 (1992) 245-253
27. Greggio E., Bergantino E., Carter D., Ahmad R., Costin G.E., Hearing V.J., Clarimon J., Singleton A., Eerola J., Hellstrom O., Tienari P.J., Miller D.W., Beilina A., Bubacco L., and Cookson M.R. Tyrosinase exacerbates dopamine toxicity but is not genetically associated with Parkinson's disease. J. Neurochem. 93 (2005) 246-256
28. Halaouli S., Asther Mi., Kruus K., Guo L., Hamdi M., Sigoillot J.-C., Asther M., and Lomascolo A. Characterization of a new tyrosinase from Pycnoporus species with high potential for food technological applications. J. Appl. Microbiol. 98 (2005) 332-343
29. Halaouili S., Asther M., Sigoillot J.-C., Hamdi M., and Lomascolo A. Fungal tryrosinases: new prospects in molecular characteristics, bioengineering and biotechnological applications. J. Appl. Microbiol. 100 (2006) 219-232
30. Halaouli S., Record E., Casalot L., Hamdi M., Sigoillot J.-C., Asther1 M., and Lomascolo A. Cloning and characterization of a tyrosinase gene from the white-rot fungus Pycnoporus sanguineus, and overproduction of the recombinant protein in Aspergillus niger. Appl. Microbiol. Biotechnol. 70 (2006) 580-589
31. Hearing V.J., and Tsukamoto K. Enzymatic control of pigmentation in mammals. FASEB J. 5 (1991) 2902-2909
32. Hernández-Romero D., Sanchez-Amat A., and Solano F. A tyrosinase with an abnormally high tyrosine hydroxylase/dopa oxidase ratio-role of the seventh histidine and accessibility to the active site. FEBS J. 273 (2006) 257-270
33. Hind G., Marshak D.R., and Coughlan S.J. Spinach thylakoid polyphenol oxidase: cloning, characterization, and relation to a putative protein kinase. Biochemistry 34 (1995) 8157-8164
34. Hunt M.D., Eanetta N.T., Yu H., Newman S.M., and Steffens J.C. cDNA cloning and expression of potato polyphenol oxidase. Plant Mol. Biol. 21 (1993) 59-68
35. Jiménez M., and García-Carmona F. The effect of sodium dodecyl sulfate onpolyphenol oxidase. Phytochemistry 4 (1996) 1503-1509
36. Jordan A.M., Khan T.H., Malkin H., Osborn H.M., Photiou A., and Riley P.A. Melanocyte-directed enzyme prodrug therapy (MDEPT). Development of second generation prodrugs for targeted treatment of malignant melanoma. Bioorg. Med. Chem. 9 (2001) 1549-1558
37. Jordan A.M., Khan T.H., Osborn H.M., Photiou A., and Riley P.A. Melanocytedirected enzyme prodrug therapy (MDEPT): development of a targeted treatment for malignant melanoma. Bioorg. Med. Chem. 7 (1999) 1775-1780
38. Kalyanaraman B. Characterization of o-semiquinone radicals in biological systems. Methods Enzymol. 186 (1990) 333-343
39. Kato A., Wada T., Kobayashi K., Seguro K., and Motoki M. Ovomucin-food protein conjugates prepared through the transglutaminase reaction. Agric. Biol. Chem. 55 (1991) 1027-1031
40. Klabunde T., Eicken C., Sacchettini J.C., and Krebs B. Crystal structure of a plant catechol oxidase containg a dicopper center. Nat. Struct. Biol. 5 (1998) 1084-1090
41. Kubo I., Nihei K., and Tsujimoto K. Methyl p-coumarate, a melanin formation inhibitor in B16 mouse melanoma cells. Bioorg. Med. Chem. 12 (2004) 5349-5354
42. Kwon B.S., Haq A.K., Pomerantz S.H., and Halaban R. Isolation and sequence of a cDNA clone for human tyrosinase that maps at the mouse c-albino locus. Proc. Natl. Acad. Sci. U.S.A. 84 (1987) 7473-7477
43. Kwon B.S., Wakulchik M., Haq A.K., Halaban R., and Kestler D. Sequence analysis of mouse tyrosinase cDNA and the effect of melanotropin on its gene expression. Biochem. Biophys. Res. Commun. 153 (1988) 1301-1309
44. Land E.J., Ramsden C.A., and Riley P.A. Quinone chemistry and melanogenesis. Methods Enzymol. 378 (2004) 88-109
45. Lantto R., Puolanne E., Kruus K., Buchert J., and Autio K. Tyrosinase-aided protein crosslinking: effects on gel formation of chicken breast myofibrils and texture and water-holding of chicken breast meat homogenate gels. J. Agric. Food Chem. 55 (2007) 1248-1255
46. Lerch K. Neurosopra tyrosinase: structural, spectroscopic and catalytic properties. Mol. Cell Biochem. 52 (1983) 125-138
47. Lerch K., Huber M., Schneider H., Drexel R., and Linzen B. Different origins of metal binding sites in binuclear copper proteins, tyrosinase and hemocyanin. J. Inorg. Biochem. 26 (1986) 213-217
48. Lim J.Y., Ishiguro K., and Kubo I. Tyrosinase inhibitory p-coumaric acid from ginseng leaves. Phytother. Res. 13 (1999) 371-375
49. Martínez M.V., and Whitaker J.R. The biochemistry and control of enzymatic browning. Trends Food Sci. Technol. 6 (1995) 195-200
50. Marusek C.M., Trobaugh N.M., Flurkey W.H., and Inlow J.K. Comparative analysis of polyphenol oxidase from plant and fungal species. J. Inorg. Biochem. 100 (2006) 108-123
51. Matoba Y., Kumagai T., Yamamoto A., Yoshitsu H., and Sugiyama M. Crystallographic evidence that the dinuclear copper center of tyrosinase is flexible during catalysis. J. Biol. Chem. 281 (2006) 8981-8990
52. Mayer A.M. Polyphenol oxidases in plant and fungi: going places? A review. Phytochemistry 67 (2006) 2318-2331
53. Mayer A.M. Polyphenol oxidases in plant-recent progress. Phytochemistry 26 (1987) 11-20
54. Mayer A.M., and Harel E. Polyphenol oxidases in plants. Phytochemistry 18 (1979) 193-215
55. McMahon A.M., Doyle E.M., Brooks S.J., and O'Connor K.E. Biochemical characterisation of the coexisting tyrosinase and laccase in the soil bacterium Pseudomonas putida F6. Enzyme Microb. Technol. 40 (2007) 1435-1441
56. Moore B.M., and Flurkey W.H. Sodium dodecyl sulfate activity of plant polyphenoloxidase. J. Biol. Chem. 265 (1990) 482-488
57. Moridani M.Y., Scobie H., Salehi P., and O'Brien P.J. Catechin metabolism: glutathione conjugate formation catalyzed by tyrosinase, peroxidase, and cytochrome p450. Chem. Res. Toxicol. 14 (2001) 841-848
58. Morrison M.E., Yagi M.J., and Cohen G. In vitro studies of 2,4-dihydroxyphenylalanine, a prodrug targeted against malignant melanoma cells. Proc. Natl. Acad. Sci. U.S.A. 82 (1985) 2960-2964
59. Newman S.M., Eannetta N.T., Yu H., Prince J.P., Carmen de Vicente M., Tanksley S.D., and Steffens J.C. Organisation of the tomato polyphenol oxidase gene family. Plant Mol. Biol. 21 (1993) 1035-1051
60. Ni Eidhin D.M., Murphy E., and O'Beirne D. Polyphenol oxidase from apple (Malus domestica Borkh. cv Bramley's Seedling): purification strategies and characterization. J. Food Sci. 71 1 (2006) C51-C58
61. 2+-independent microbial tyrosinase. Biosci. Biotechnol. Biochem. 60 1 (1996) 131-133
62. Piquemal J.-P., Madddaluno J., and Giessner-Prettre C. Theoretical study of phenol and 2-aminophenol docking at a model of tyrosinase active site. New J. Chem. 27 (2003) 909-913
63. Ramirez E.C., Whitaker J.R., and Virador V.M. Polyphenol oxidase. In: Whitaker J.R., Voragen A.G.J., and Wong D.W.S. (Eds). Handbook of Food Enzymology (2003), Marcel Dekker, Inc., New York 509-523
64. Robb D.A. Tyrosinase. In: Lontie R. (Ed). Copper Proteins and Copper Enzymes vol. 2 (1984), CRC Press Inc., Boca Raton, FL 207-240
65. Rodriguez-Lopez J.N., Tudela J., Varon R., Garcia-Carmona F., and Garcia-Canovas F. Analysis of a kinetic model for melanin biosynthesis pathway. J. Biol. Chem. 267 (1992) 3801-3810
66. Selinheimo E., Saloheimo M., Ahola E., Westerholm-Parvinen A., Kalkkinen N., Buchert J., and Kruus K. Production and characterization of a secreted, C-terminally processed tyrosinase from the filamentous fungus Trichoderma reesei. FEBS J. 273 (2006) 4322-4335
67. Seo S.-Y., Sharma V.K., and Sharma N. Mushroom tyrosinase: recent prospects. J. Agric. Food Chem. 51 10 (2003) 2837-2853
68. Solomon E.I., Sundaram U.M., and Machonkin T.E. Multicopper oxidases and oxygenases. Chem. Rev. 96 (1996) 2563-2606
69. Sugumaran M. Comparative biochemistry of eumelanogenesis and the protective roles of phenoloxidase and melanin in insects. Pigment Cell Res. 15 (2002) 2-9
70. Takase M., Miura I., Nakata A., Takeuchi T., and Nishioka M. Cloning and sequencing of the cDNA encoding tyrosinase of the Japanese pond frog, Rana nigromaculata. Gene 121 (1992) 359-363
71. Thalmann C., and Lötzbeyer T. Enzymatic crosslinking of proteins with tyrosinase. Eur. Food Res. Technol. 214 (2002) 276-281
72. Thygesen P.W., Dry I.B., and Robinson S.P. Polyphenol oxidase in potato. A multigene family that exhibits differential expression patterns. Plant Physiol. 109 (1995) 525-531
73. Tomsovsky M., and Homolka L. Tyrosinase activity discovered from Trametes spp. World J. Microbiol. Biotechnol. 20 (2004) 529-530
74. van Gelder C.W., Flurkey W.H., and Wichers H.J. Sequence and structural features of plant and fungal tyrosinases. Phytochemistry 45 (1997) 1309-1323
75. Walker J.R., and Ferrar P.H. Diphenol oxidases, enzyme-catalysed browning and plant disease resistance. Biotechnol. Genet. Eng. Rev. 15 (1998) 457-498
76. Wichers H.J., Gerritse Y.A., and Chapelon C.G.J. Tyrosinase isoforms from the fruitbodies of Agaricus bisporus. Phytochemistry 43 (1996) 333-337
77. Wichers H.J., Recourt K., Hendriks M., Ebbelaar C.F.M., Biancone G., Hoeberichts F.A., Mooibroek H., and Soler-Rivas C. Cloning, expression and characterisation of two tyrosinase cDNAs from Agaricus bisporus. Appl. Microbiol. Biotechnol. 61 (2003) 336-341
78. Winkler M.E., Lerch K., and Solomon E. I. Competitive inhibitor binding to the binuclear copper active site in tyrosinase. J. Am. Chem. Soc. 103 (1981) 7001-7003
79. 2-peroxidase system. FEBS Lett. 422 (1998) 377-380
80. Yamada, Y., Tawara, Y., Yoshika, H., 1983. Production of heat-resistant polyphenol oxidase. JP 60062980.