Effect of phenolic acids on manganese peroxidase-dependent peroxidation of linoleic acid and degradation of a non-phenolic lignin model compound

References

• Bao W, Fukushima Y, Jensen KA, Moen MA, Hammel KE. Oxidative degradation of non-phenolic lignin during lipid peroxidation by fungal manganese peroxidase. FEBS Lett 1994; 354: 297–300
   PubMedGoogle Scholar
• Cao G, Sofic A, Prior RL. Antioxidant and pro-oxidant behavior of flavonoids: Structure–activity relationships. Free Rad Biol Med 1997; 22: 749–760
   PubMed Web of Science ®Google Scholar
• Decker EA. Phenolics: Pro-oxidants or antioxidants?. Nutr Rev 1997; 55: 396–407
   PubMed Web of Science ®Google Scholar
• Eriksson K-EL, Blanchette RA, Ander P. Microbial and enzymatic degradation of wood and wood components. Springer-Verlag, Berlin 1990
   Google Scholar
• Evans CS, Gallagher IM, Atkey PT, Wood DA. Localisation of degradative enzymes in white-rot decay of lignocellulose. Biodegradation 1991; 2: 93–106
   Google Scholar
• Feussner I, Wasternack C. The lipoxygenase pathway. Annu Rev Plant Biol 2002; 53: 275–297
   PubMed Web of Science ®Google Scholar
• Flournoy DS, Paul JA, Kirk TK, Highley TL. Changes in the size and volume of pores in sweetgum wood during simultaneous rot by Phanerochaete chrysosporium. Holzforschung 1993; 47: 297–301
   Google Scholar
• Fukumoto LR, Mazza G. Assessing antioxidant and pro-oxidant activities of phenolic compounds. J Agric Food Chem 2000; 48: 3597–3604
   PubMed Web of Science ®Google Scholar
• Galati G, Sabzevari O, Wilson JX, O'Brien PJ. Pro-oxidant activity and cellular effects of the phenoxyl radicals of dietary flavonoids and other polyphenolics. Toxicology 2002; 177: 91–104
   PubMed Web of Science ®Google Scholar
• Gold MH, Youngs HL, Sollewijn Gelpke MD. Manganese peroxidase. Metal ions in biological systems, A Sigel, H Sigel. Marcel Dekker, New York and Basel 2000; 37: 559–586
   Google Scholar
• Grechkin A. Recent developments in biochemistry of the plant lipoxygenase pathway. Prog Lipid Res 1998; 37: 317–352
   PubMed Web of Science ®Google Scholar
• Halliwell B, Gutteridge JMC. Free radicals in biology and medicine. University Press, Oxford 1999
   Google Scholar
• Hammel KE, Kapich AN, Jensen KA, Ryan ZC. Reactive oxygen species as agents of wood decay by fungi. Enzyme Microb Technol 2002; 30: 445–453
   Web of Science ®Google Scholar
• Hatakka A. Lignin-modifying enzymes from selected white-rot fungi: Production and role in lignin degradation. FEMS Microbiol Rev 1994; 13: 125–135
   Web of Science ®Google Scholar
• Hatakka A. Biodegradation of lignin. Biopolymers. Biology, chemistry, biotechnology, applications. Vol 1. Lignin, humic substances and coal, M Hofrichter, A Steinbüchel. Wiley-VCH, WeinheimGermany 2001; 129–180
   Google Scholar
• Hatakka AI, Lundell TK, Tervilä-Wilo ALM, Brunow G. Metabolism of non-phenolic β-O-4 lignin model compounds by the white-rot fungus Phlebia radiata. Appl Microbiol Biotechnol 1991; 36: 270–277
   Google Scholar
• Higuchi T. Microbial degradation of lignin: Role of lignin peroxidase, manganese peroxidase, and laccase. Proc Jpn Acad Ser B 2004; 80: 204–214
   Web of Science ®Google Scholar
• Kapich AN, Jensen KA, Hammel KE. Peroxyl radicals are potential agents of lignin biodegradation. FEBS Lett 1999; 461: 115–119
   PubMedGoogle Scholar
• Kapich AN, Prior BA, Botha A, Galkin S, Lundell T, Hatakka A. Effect of lignocellulose-containing substrates on production of ligninolytic peroxidases in submerged cultures of Phanerochaete chrysosporium ME-446. Enzyme Microb Technol 2004; 34: 187–195
   Web of Science ®Google Scholar
• Kapich AN, Prior BA, Lundell T, Hatakka A. A rapid method to quantify pro-oxidant activity in cultures of wood-decaying white-rot fungi. J Microbiol Meth 2005a; 61: 261–271
   PubMedGoogle Scholar
• Kapich AN, Steffen K, Hofrichter M, Hatakka A. Involvement of lipid peroxidation in the degradation of a non-phenolic lignin model compound by manganese peroxidase of the litter-decomposing fungus Stropharia coronilla. Biochem Biophys Res Commun 2005b; 330: 371–377
   PubMedGoogle Scholar
• Martinez AT, Speranza M, Ruiz-Dueñas FJ, Ferreira P, Camarero S, Guillén F, Martinez MJ, Gutiérrez A, del Rio JC. Biodegradation of lignocellulosics: Microbial, chemical, and enzymatic aspects of the fungal attack of lignin. Int Microbiol 2005; 8: 195–204
   PubMed Web of Science ®Google Scholar
• Monties B, Fukushima K. Occurrence, function and biosynthesis of lignins. Biopolymers. Biology, chemistry, biotechnology, applications. Vol 1. Lignin, humic substances and coal, M Hofrichter, A Steinbüchel. Wiley-VCH, WeinheimGermany 2001; 1–64
   Google Scholar
• O'Brien PJ. Peroxidases. Chem Biol Interact 2000; 129: 113–139
   PubMed Web of Science ®Google Scholar
• Rice-Evans CA, Miller NJ, Paganga G. Structure–antioxidant activity relationships of flavonoids and phenolic acids. Free Rad Biol Med 1996; 20: 933–956
   PubMed Web of Science ®Google Scholar
• Ritov VB, Menshikova EV, Goldman R, Kagan VE. Direct oxidation of polyunsaturated cis-parinaric fatty acid by phenoxyl radicals generated by peroxidase/H2O2 in model systems and in HL-60 cells. Toxicol Lett 1996; 87: 121–129
   PubMedGoogle Scholar
• Sakihama Y, Cohen MF, Grace SC, Yamasaki H. Plant phenolic antioxidant and prooxidant activities: Phenolics-induced oxidative damage mediated by metals in plants. Toxicology 2002; 177: 67–80
   PubMed Web of Science ®Google Scholar
• Soobrattee MA, Neergheen VS, Luximon-Ramma A, Aruoma OI, Bahorun T. Phenolics as potential antioxidant therapeutic agents: Mechanism and actions. Mut Res 2005; 579: 200–213
   PubMed Web of Science ®Google Scholar
• Spiteller G. Linoleic acid peroxidation – the dominant lipid peroxidation process in low density lipoprotein – and its relationship to chronic diseases. Chem Phys Lipids 1998; 95: 105–162
   PubMed Web of Science ®Google Scholar
• Srebotnik E, Messner K, Foisner R. Penetrability of white-rot degraded pine wood by the lignin peroxidase of Phanerochaete chrysosporium. Appl Environ Microbiol 1988; 54: 2608–2614
   PubMedGoogle Scholar
• Wariishi H, Valli K, Gold MH. Manganese (II) oxidation by manganese peroxidase from the basidiomycete Phanerochaete chrysosporium. Kinetic mechanism and role of chelators. J Biol Chem 1992; 267: 23688–23695
   PubMed Web of Science ®Google Scholar
• Watanabe T, Katayama S, Enoki M, Honda Y, Kuwahara M. Formation of acyl radical in lipid peroxidation of linoleic acid by manganese-dependent peroxidase from Ceriporiopsis subvermispora and Bjerkandera adusta. Eur J Biochem 2000; 267: 4222–4231
   PubMedGoogle Scholar
• Zabel RA, Morrell JJ. Wood microbiology: decay and its prevention. Academic Press, San Diego, CA 1992
   Google Scholar