Laccase catalyzed synthesis of iodinated phenolic compounds with antifungal activity

PLoS ONE

Volumn 9, Issue 3, 2014, Pages

  Ihssen, Julian ^a   Schubert, Mark ^a   Thöny Meyer, Linda ^a   Richter, Michael ^a  

^a SWISS FEDERAL LABORATORIES FOR MATERIALS SCIENCE AND TECHNOLOGY   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

3 ETHOXY 4 HYDROXYBENZALDEHYDE; APOCYNIN; IODOETHYL VANILLIN; LACCASE; LIGNIN; METHYL VANILLATE; ORTHO VANILLIN; PHENOL DERIVATIVE; POTASSIUM IODIDE; UNCLASSIFIED DRUG; VANILLIC ACID; VANILLIN; VANILLIN DERIVATIVE; VANILLYL ALCOHOL; ANTIFUNGAL AGENT; IODINE;

ANTIFUNGAL ACTIVITY; ARTICLE; BIOCATALYSIS; CENTRIFUGATION; CONCENTRATION RESPONSE; DRUG DETERMINATION; DRUG OXIDATION; DRUG STRUCTURE; ENZYME MECHANISM; GREEN CHEMISTRY; GROWTH INHIBITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IODINATION; MASS SPECTROMETRY; NONHUMAN; STRUCTURE ANALYSIS; TRAMETES VERSICOLOR; CATALYSIS; CHEMISTRY; METABOLISM; OXIDATION REDUCTION REACTION; SYNTHESIS;

ANTIFUNGAL AGENTS; CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; IODINE; LACCASE; MASS SPECTROMETRY; OXIDATION-REDUCTION; PHENOLS;

EID: 84897042467     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0089924     Document Type: Article

References (53)

1. McDonnell G, Russell AD (1999) Antiseptics and disinfectants: Activity, action, and resistance. Clin Microbiol Rev 12: 147-179.
2. Gitchaiwat A, Kositchaiyong A, Sombatsompop K, Prapagdee B, Isarangkura K, et al. (2013) Assessment and characterization of antifungal and antialgal performances for biocide-enhanced linear low-density polyethylene. J Appl Polym Sci 128: 371-379.
3. Xu F (1996) Catalysis of novel enzymatic iodide oxidation by fungal laccase. Appl Biochem Biotech 59: 221-230.
4. Witayakran S, Ragauskas AJ (2009) Synthetic applications of laccase in green chemistry. Adv Synth Catal 351: 1187-1209.
5. Riva S (2006) Laccases: blue enzymes for green chemistry. Trends Biotechnol 24: 219-226.
6. Suzuki M, Eda Y, Ohsawa S, Kanesaki Y, Yoshikawa H, et al. (2012) Iodide oxidation by a novel multicopper oxidase from the Alphaproteobacterium strain Q-1. Appl Environ Microb 78: 3941-3949.
7. Kulys J, Bratkovskaja I, Vidziunaite R (2005) Laccase-catalysed iodide oxidation in presence of methyl syringate. Biotechnol Bioeng 92: 124-128. (Pubitemid 41657593)
8. Grover N, Borkar IV, Dinu CZ, Kane RS, Dordick JS (2012) Laccase- and chloroperoxidase-nanotube paint composites with bactericidal and sporicidal activity. Enzyme Microb Tech 50: 271-279.
9. Schubert M, Engel J, Thoeny-Meyer L, Schwarze FWMR, Ihssen J (2012) Protection of wood from microorganisms by laccase-catalyzed iodination. Appl Environ Microb 78: 7267-7275.
10. Seki M, Oikawa J, Taichi T, Ohnuki T, Muramatsu Y, et al. (2013) Laccase-catalyzed oxidation of iodide and formation of organically bound iodine in soils. Environ Sci Technol 47: 390-397.
11. Shimamoto YS, Takahashi Y, Terada Y (2011) Formation of organic iodine supplied as iodide in a soil-water system in Chiba, Japan. Environ Sci Technol 45: 2086-2092.
12. Herpoel I, Moukha S, Lesage-Meessen L, Sigoillot J, Asther M (2000) Selection of Pycnoporus cinnabarinus strains for laccase production. FEMS Microbiol Lett 183: 301-306. (Pubitemid 30079665)
13. Stalpers JA (1978) Identification of wood-inhabiting Aphyllophorales in pure culture. Baarn, Netherlands: Centraalbureau voor Schimmelcultures.
14. Camarero S, Ibarra D, Martinez MJ, Martinez AT (2005) Lignin-derived compounds as efficient laccase mediators for decolorization of different types of recalcitrant dyes. Appl Environ Microb 71: 1775-1784. (Pubitemid 40546092)
15. Piontek K, Antorini M, Choinowski T (2002) Crystal structure of a laccase from the fungus Trametes versicolor at 1.90-Angstrom resolution containing a full complement of coppers. J Biol Chem 277: 37663-37669.
16. Zakzeski J, Bruijnincx PCA, Jongerius AL, Weckhuysen BM (2010) The catalytic valorization of lignin for the production of renewable chemicals. Chem Rev 110: 3552-3599.
17. Pepper JM, Macdonald JA (1953) The synthesis of syringaldehyde from vanillin. Can J Chem 31: 476-483.
18. Lahtinen M, Heinonen P, Oivanen M, Karhunen P, Kruus K, et al. (2013) On the factors affecting product distribution in laccase-catalyzed oxidation of a lignin model compound vanillyl alcohol: experimental and computational evaluation. Org Biomol Chem 11: 5454-5464.
19. Nishimura RT, Giammanco CH, Vosburg DA (2010) Green, enzymatic syntheses of divanillin and diapocynin for the organic, biochemistry, or advanced general chemistry laboratory. J Chem Educ 87: 526-527.
20. Intra A, Nicotra S, Riva S, Danieli B (2005) Significant and unexpected solvent influence on the selectivity of laccase-catalyzed coupling of tetrahydro-2-naphthol derivatives. Adv Synth Catal 347: 973-977. (Pubitemid 40840017)
21. Iniesta J, Cooper HJ, Marshall AG, Heptinstall J, Walton DJ, et al. (2008) Specific electrochemical iodination of horse heart myoglobin at tyrosine 103 as determined by Fourier transform ion cyclotron resonance mass spectrometry. Arch Biochem Biophys 474: 1-7.
22. Tao JH, Xu JH (2009) Biocatalysis in development of green pharmaceutical processes. Curr Opin Chem Biol 13: 43-50.
23. Anastas P, Eghbali N (2010) Green Chemistry: Principles and Practice. Chem Soc Rev 39: 301-312.
24. Wohlgemuth R (2010) Biocatalysis - key to sustainable industrial chemistry. Curr Opin Biotech 21: 713-724.
25. Hofrichter M, Ullrich R (2006) Heme-thiolate haloperoxidases: versatile biocatalysts with biotechnological and environmental significance. Appl Microbiol Biot 71: 276-288.
26. Adimurthy S, Ramachandraiah G, Ghosh PK, Bedekar AV (2003) A new, environment friendly protocol for iodination of electron-rich aromatic compounds. Tetrahedron Lett 44: 5099-5101. (Pubitemid 36694920)
27. Ratto M, Ritschkoff AC, Viikari L (2004) Enzymatically polymerized phenolic compounds as wood preservatives. Holzforschung 58: 440-445.
28. Marjasvaara A, Janis J, Vainiotalo P (2008) Oxidation of a laccase mediator ABTS as studied by ESI-FTICR mass spectrometry. J Mass Spectrom 43: 470-477. (Pubitemid 351518667)
29. Martorana A, Sorace L, Boer H, Vazquez-Duhalt R, Basosi R, et al. (2013) A spectroscopic characterization of a phenolic natural mediator in the laccase biocatalytic reaction. J Mol Catal B-Enzym 97: 203-208.
30. Fernandez-Sanchez C, Tzanov T, Gubitz GM, Cavaco-Paulo A (2002) Voltammetric monitoring of laccase-catalysed mediated reactions. Bioelectro-chemistry 58: 149-156. (Pubitemid 35300092)
31. Xu F, Berka RM, Wahleithner JA, Nelson BA, Shuster JR, et al. (1998) Site-directed mutations in fungal laccase: effect on redox potential, activity and pH profile. Biochem J 334: 63-70. (Pubitemid 28420972)
32. Schubert M, Muffler A, Mourad S (2012) The use of a radial basis neural network and genetic algorithm for improving the efficiency of laccase-mediated dye decolourization. J Biotechnol 161: 429-436.
33. Sheldon RA (2007) Enzyme immobilization: The quest for optimum performance. Adv Synth Catal 349: 1289-1307.
34. Rekuc A, Bryjak J, Szymanska K, Jarzebski AB (2010) Very stable silica-gelbound laccase biocatalysts for the selective oxidation in continuous systems. Bioresource Technol 101: 2076-2083.
35. Voda K, Boh B, Vrtacnik M, Pohleven F (2003) Effect of the antifungal activity of oxygenated aromatic essential oil compounds on the white-rot Trametes versicolor and the brown-rot Coniophora puteana. Int Biodeter Biodegr 51: 51-59. (Pubitemid 35381126)
36. Bakkali F, Averbeck S, Averbeck D, Waomar M (2008) Biological effects of essential oils - A review. Food Chem Toxicol 46: 446-475. (Pubitemid 350297552)
37. Al-Adham ISI, Dinning AJ, Eastwood IM, Austin P, Collier PJ (1998) Cell membrane effects of some common biocides. J Ind Microbiol Biot 21: 6-10. (Pubitemid 28519879)
38. Russell AD, Chopra I (1996) Understanding antibacterial action and resistance. London: Ellis Horwood.
39. Xavier AMRB, Tavares APM, Ferreira R, Amado F (2007) Trametes versicolor growth and laccase induction with by-products of pulp and paper industry. Electron J Biotechn 10: 444-451.
40. Kiiskinen LL, Ratto M, Kruus K (2004) Screening for novel laccase-producing microbes. J Appl Microbiol 97: 640-646. (Pubitemid 39208207)
41. Wei DS, Houtman CJ, Kapich AN, Hunt CG, Cullen D, et al. (2010) Laccase and its role in production of extracellular reactive oxygen species during wood decay by the brown rot basidiomycete Postia placenta. Appl Environ Microb 76: 2091-2097.
42. Wymelenberg AV, Gaskell J, Mozuch M, Sabat G, Ralph J, et al. (2010) Comparative transcriptome and secretome analysis of wood decay fungi Postia placenta and Phanerochaete chrysosporium. Appl Environ Microb 76: 3599-3610.
43. Hammel KE, Kapich AN, Jensen KA, Ryan ZC (2002) Reactive oxygen species as agents of wood decay by fungi. Enzyme Microb Tech 30: 445-453. (Pubitemid 34310268)
44. Deng YH, Feng XJ, Zhou MS, Qian Y, Yu HF, et al. (2011) Investigation of aggregation and assembly of alkali lignin using iodine as a probe. Biomacromolecules 12: 1116-1125.
45. Mizrahi B, Domb AJ (2007) Mucoadhesive tablet releasing iodine for treating oral infections. J Pharm Sci 96: 3144-3150. (Pubitemid 350221209)
46. Zelzer M, Todd SJ, Hirst AR, McDonald TO, Ulijn RV (2013) Enzyme responsive materials: design strategies and future developments. Biomater Sci 1: 11-39.
47. Baier G, Cavallaro A, Vasilev K, Mailander V, Musyanovych A, et al. (2013) Enzyme responsive hyaluronic acid nanocapsules containing polyhexanide and their exposure to bacteria to prevent infection. Biomacromolecules 14: 1103-1112.
48. Said SS, El-Halfawy OM, El-Gowelli HM, Aloufy AK, Boraei NA, et al. (2012) Bioburden-responsive antimicrobial PLGA ultrafine fibers for wound healing. Eur J Pharm Biopharm 80: 85-94.
49. Wagner C, El Omari M, Konig GM (2009) Biohalogenation: Nature's way to synthesize halogenated metabolites. J Nat Prod 72: 540-553.
50. Gribble GW (1992) Naturally-occurring organohalogen compounds - a survey. J Nat Prod 55: 1353-1395.
51. Borrelli F, Campagnuolo C, Capasso R, Fattorusso E, Taglialatela-Scafati O (2004) Iodinated indole alkaloids from Plakortis simplex - New plakohypaphorines and an evaluation of their antihistamine activity. Eur J Org Chem: 3227-3232.
52. Hoegger PJ, Kilaru S, James TY, Thacker JR, Kues U (2006) Phylogenetic comparison and classification of laccase and related multicopper oxidase protein sequences. FEBS J 273: 2308-2326.
53. Reiss R, Ihssen J, Richter M, Eichhorn E, Schilling B, et al. (2013) Laccase versus laccase-like multi-copper oxidase: A comparative study of similar enzymes with diverse substrate spectra. PloS ONE 8: e65633.