Chlorinated Pharmaceutical and Personal Care Products

An expanding array of substances called 'Endocrine-disrupting compounds' (EDC) include chemicals of natural and anthropogenic origin. EDCs are widely distributed in the environment. They constitute a potential health risk to humans and aquatic life. Only a couple of EDCs are covered here. Triclosan is one such synthetic antimicrobial compound that is present in a wide range of health care products, such as tooth-paste, deodorant sticks and soaps. It has been detected in various environmental matrices due to its low degradation by conventional wastewater treatment processes. The fact, that triclosan shows remarkable toxicity towards bacteria, makes white rot fungi interesting candidates to test for biodegradation of this compound. Triclosan was degraded by seven strains of white rot fungi including P. chrysosporium ME 446, P. magnoliae, T. versicolor, I. lacteus, P. ostreatus, P. cinnabarinus, and D. squalens, while B. adusta was the only organism included in the screening that did not degrade triclosan (Cajthaml et al. 2009). I. lacteus and P. ostreatus were found to be the most efficient triclosan degraders with a degradation efficiency exceeding 90 and 80%, respectively.

In another study, triclosan was shown to inhibit the growth of T. versicolor over the first 3 d of incubation, but the ability of the fungus to transform triclosan to glucoside and xyloside conjugated forms and small amounts of 2,4-dichlorophenol lowered the toxicity due to triclosan and allowed the subsequent normal growth of the fungus (Hundt et al. 2000). The white rot fungus P. cinnabarinus also converted triclosan to the glucoside conjugate and additionally produced 2,4,4'-trichloro-2'-methoxydiphenyl (Hundt et al. 2000).

Several studies have focused on the applicability of purified laccases to oxidize and detoxify triclosan. The enzymatic transformation of triclosan by laccase was found to be optimal at pH 5 and 50°C and was negatively affected by the presence of sulfite, sulfide, cyanide, chloride, Fe(III) and Cu (II) ions that may be present in a wastewater matrix (Kim and Nicell 2006; Cabana et al. 2007). The use of polyethylene glycol (PEG) to prevent the inactivation of laccase resulted in an enhancement of triclosan degradation, but influenced negatively the toxicity of the treated solution (Kim and Nicell 2006). Immobilized laccase showed higher ability to degrade triclosan and had greater stability than free laccases (Cabana et al. 2009a, b). Degradation rates of triclosan by laccase were substantially improved through the use of laccase mediators (Murugesan et al. 2010). For example, * 90% triclosan degradation was observed in the presence of mediators, such as 1-hydroxybenzotriazole (HBT) and syringaldehyde (SYD). Other investigators did not see enhanced degradation of triclosan in the presence of mediators (Kim and Nicell 2006; Cabana et al. 2007). Two different mechanisms of triclosan degradation catalyzed by laccase were proposed. In the absence of redox mediators, laccase transformed triclosan to dimers, trimers and tetramers formed by oxidative coupling of the phenoxy radicals of triclosan (Cabana et al. 2007; Murugesan et al. 2010). Although the basic structure of triclosan was unaffected, laccase-mediated detoxification of triclosan was demonstrated using bacterial growth inhibition tests (Murugesan et al. 2010). In the presence of redox mediators HBT and SYD, the ether bond linkage of triclosan was cleaved producing 2,4-dichlorophenol, which was further dechlorinated through oligomerization reaction (in the case of HBT) or oxidative dechlorination to 2-chlorohydroquinone (in the case of SYD) (Murug-esan et al. 2010). Recently, direct dechlorination of triclosan resulting in the formation of dechlorinated oligomers was shown in the presence of laccases conjugated with chitosan (Cabana et al. 2010). MnP seems to be a more promising choice than laccase for triclosan degradation, evidenced from the higher degradation rates obtained with MnP than laccase only or laccase + HOBT (Inoue et al. 2010). However, the transformation products were not described. Algal and bacterial growth inhibition tests showed that triclosan treated with MnP results in greatly reduced toxicity in the effluent.

Clofibric acid (CA) is the pharmacologically active derivative of clofibrate and several other fibrates that are used as blood lipid regulators in human medicine. Limited removal of CA, that was observed in municipal wastewater treatment plants, deserves more attention because of the risk of CA passing later barriers in partly closed water cycles. Of the four white rot fungi screened for their ability to degrade CA, only T. versicolor was able to degrade nearly 90% of CA (8 mg l-1)

in defined liquid medium after 7 d (Marco-Urrea et al. 2009c); but three other fungi, P. chrysosporium, G. lucidum and I. lacteus, were unable to degrade CA under similar conditions. CA was not oxidized by the purified MnP or laccase even in the presence of redox mediators. However, CA degradation by T. versicolor cultures was inhibited by more than half in the presence of cytochrome P450 inhibitors piperonyl butoxide or 1-aminobenzotriazole, suggesting that P450 plays a role in CA degradation by this organism (Marco-Urrea et al. 2009c). Degradation of CA in cultures of T. versicolor was also attempted by inducing hydroxyl radicals, through the quinone redox cycling mechanism (Marco-Urrea et al. 2010). Based on time-course experiments, using 10 mg l-1 of CA, these cultures showed >80% degradations after 6 h of incubation. An intermediate showing hydroxyl-ation of the benzene ring of CA was detected early in the incubation, but it was not detectable in the cultures after 24 h (Marco-Urrea et al. 2010).

2.4 Conclusions

White rot fungi have become increasingly attractive as candidates for designing effective bioremediation strategies, because of the broad substrate specificity of the ligninolytic enzymes which enable these fungi to degrade or mineralize quite a broad spectrum of chloro-organics (and other environmental pollutants). Even though a large majority of the bioremediation studies to date were done with P. chrysosporium as the model, a greater number of other genera of white rot fungi have also been studied in recent years and this may help determine the right organism with the right characteristics for carrying out a desired bioremediation application. Basic studies designed to obtain a better understanding of the mechanisms of actions as well as the basic protein and gene structures of the major extracellular ligninolytic enzymes (LiP, MnP, VP, and laccase), that catalyze degradation of chloro-organics through free radical mediated reactions, have been described. Recent studies indicate that intracellular enzymes as exemplified by cytochrome P450 monooxygenases are widespread in white rot fungi and appear to be key players involved in the degradation of a number of the chloro-organic pollutants.

Although most studies on lab or field scale bioremediation were done using bacteria, white rot fungi are beginning to gain prominence in this area, because they offer a number of advantages over bacteria for biodegradation of chloro-organic environmental pollutants. For example, reductive dechlorination of toxic PCE and TCE by bacteria usually leads to accumulation of toxic cis-dichloro-ethylene and vinyl chloride in the environment, whereas white rot fungi not only can degrade PCE and TCE to less toxic intermediates, but also have the ability to mineralize TCE. Also, compared to most degradative enzymes of bacteria, the ligninolytic enzymes of white rot fungi are non-specific and allow these organisms to degrade several classes of organo-pollutants individually or in mixtures.

Most published studies on biodegradation of chloro-organo-pollutants have been carried out in defined or complex laboratory media or in small samples of autoclaved soils and the effect of temperature, pH, moisture, nutrient (mainly C, N and S) and oxygen concentration, and small molecular weight growth/enzyme inducers on the quantitative and qualitative production of degradative enzymes, and biochemical pathways for the degradation of various pollutants have been studied. However, less number of pilot scale or field scale studies have been done to date. Because of the great versatility of white rot fungi in degrading a broad array of environmental pollutants, it is important to study bioremediation applications on a larger scale using large bioreactors and contaminated soils, sediments, and effluent streams, and other pollutant sites. Some of these studies have been reviewed by Baldrian (2008) and he described some of the limitations for the practical applicability of white rot fungi for field scale bioremediations. The specific physico-chemical properties of some chloro-organics can also restrict the application of white rot fungi. For instance, some chloro-organics, such as PCE and TCE are highly volatile, have low solubility, and are denser than water and therefore, they accumulate in the form of pools in groundwater when released into the environment. In these environments, anoxic conditions are predominant and the white rot fungi which are aerobic would require oxygen and this may add to the costs. Successful use of immobilized enzymes of white rot fungi, such as LiP, MnP, and laccases for bioremediation would obviate some of the difficulties associated with the use of whole mycelia cells. In turn, this points to the importance of detailed characterization of the ligninolytic enzymes/isoenzymes produced by different strains or species of white rot fungi that offer the most promise for different bioremediation applications, because fungal strains vary a great deal in their repertoire of enzymes/isoenzymes. Recently, application of laccases immobilized on solid supports has been explored for the treatment of contaminated effluents in adapted bioreactors. In general, immobilization of laccase on solid supports allows enhanced enzyme stability and continuous utilization of the bio-catalyst for bioremediation applications. For successful bioremediation, white rot fungi should be able to survive and successfully compete with autochthonous soil flora for carbon, nitrogen, and other nutrient sources. Even though, woody materials are their natural substrates, recent studies indicate that several species of white rot fungi can survive in soil and their soil colonizing ability is comparable to those of soil-inhabiting basidiomycetes utilizing the available lignocellulosic and other substrates in soil. Also, some of the white rot fungi appear to compete well with the complex soil microbial flora.

White rot fungi are extraordinary in their versatility to degrade a large variety of complex and recalcitrant environmental pollutants that contaminate soil and groundwater ecosystems, constituting a potential danger to human and animal health. It is fairly well proven now that white rot (as well as some non-white rot fungi) have the ecological and biochemical capability to degrade important categories of toxic chloro-organic pollutants. There has been much progress in screening and identifying strains/species of white rot fungi isolated from different ecosystems that are increasingly more efficient than previously described organisms in degrading selected chloro-organic pollutants generated by different industrial processes. There has been also much advancement in our understanding of the basic physiology, biochemistry, and molecular biology of enzymes and enzyme systems involved in the degradation of chloro-organic pollutants by white rot fungi. Current genomics and proteomics tools offer significant opportunities to determine the role and interactions of known genes and for identifying new genes involved in degradation of chloro-organics by white rot fungi. This information would also be of great interest to monitor and better understand the behaviour of white rot fungi in soils and to use them more efficiently as the agents of biore-mediation in contaminated sites. More research is needed to obtain better understanding of the ecology, enzymology, genomics, and proteomics of some of the more important species of white rot fungi that appear more desirable from a bioremediation perspective. Despite of great promise of white rot fungi as biore-mediation agents, a number of challenges remain to be surmounted in translating the basic knowledge on these organisms into cost-effective practical bioremedia-tion applications.

Acknowledgments The authors wish to acknowledge past students, postdoctoral fellows, and visiting scientists in their labs who contributed to the research results presented in this chapter. C. A. Reddy is also grateful for the funding received from Department of Energy over the years that contributed in part to the research presented here.

References

Aranda E, Marco-Urrea E, Caminal G, Arias ME, Garcia-Romera I, Guillen F (2010) Advanced oxidation of benzene, toluene, ethylbenzene and xylene isomers (BTEX) by Trametes versicolor. J Hazard Mater 181:181-186 Aust SD (1990) Degradation of environmental pollutants by Phanerochaete chrysosporium.

Microb Ecol 20:197-209 Baldrian P (2008) Wood-inhabiting ligninolytic basidiomycetes in soils: ecology and constraints for applicability in bioremediation. Fungal Ecol 1:4-12 Barr DP, Shah MM, Grover TA, Aust SD (1992) Production of hydroxyl radical by lignin peroxidase from Phanerochaete chrysosporium. Arch Biochem Biophys 298:480-485 Bastos AC, Magan N (2009) Trametes versicolor: potential for atrazine bioremediation in calcareous clay soil, under low water availability conditions. Int Biodeter Biodegrad 63:389-394

Beaudette LA, Davies S, Fedorak PM, Ward OP, Pickard MA (1998) Comparison of gas chromatography and mineralization experiments for measuring loss of selected polychlori-nated biphenyl congeners in cultures of white rot fungi. Appl Environ Microbiol 64:2020-2025

Beaudette LA, Ward OP, Pickard MA, Fedorak PM (2000) Low surfactant concentration increases fungal mineralization of a polychlorinated biphenyl congener but has no effect on overall metabolism. Lett Appl Microbiol 30:155-160 Bending GD, Friloux M, Walker A (2002) Degradation of contrasting pesticides by white rot fungi and its relationship with ligninolytic potential. FEMS Microbiol Lett 212:59-63 Bumpus JA, Aust SD (1987) Biodegradation of DDT [1, 1, 1-trichloro-2, 2-bis(4-chloropheny-l)ethane] by the white rot fungus Phanerochaete chrysosporium. Appl Environ Microbiol 53:2001-2008

Bumpus JA, Tien M, Wright D, Aust SD (1985) Oxidation of persistent environmental pollutants by a white rot fungus. Science 228:1434-1436 Buswell JA, Odier E (1987) Lignin biodegradation. CRC Crit Rev Microbiol 15:141-168 Cabana H, Jiwan JL, Rozenberg R, Elisashvili V, Penninckx M, Agathos SN, Jones JP (2007) Elimination of endocrine disrupting chemicals nonylphenol and bisphenol A and personal care product ingredient triclosan using enzyme preparation from the white rot fungus Coriolopsis polyzona. Chemosphere 67:770-778 Cabana H, Alexandre C, Agathos SN, Jones JP (2009a) Immobilization of laccase from the white rot fungus Coriolopsis polyzona and use of the immobilized biocatalyst for the continuous elimination of endocrine disrupting chemicals. Biores Technol 100:3447-3458 Cabana H, Jones JP, Agathos SN (2009b) Utilization of cross-linked laccase aggregates in a perfusion basket reactor for the continuous elimination of endocrine-disrupting chemicals. Biotechnol Bioeng 102:1582-1592 Cabana H, Ahamed A, Leduc R (2010) Conjugation of laccase from the white rot fungus Trametes versicolor to chitosan and its utilization for the elimination of triclosan. Biores Technol. doi:10.1016/j.biotech.2010.09.080 Cajthaml T, Kresinova Z, Svobodova K, Moder M (2009) Biodegradation of endocrine-disrupting compounds and suppression of estrogenic activity by ligninolytic fungi. Chemo-sphere 75:745-750

Cameron MD, Aust SD (1999) Degradation of chemicals by reactive radicals produced by cellobiose dehydrogenase from Phanerochaete chrysosporium. Arch Biochem Biophys 367:115-121

Cañas AI, Camarero S (2010) Laccases and their natural mediators: biotechnological tools for sustainable eco-friendly processes. Biotechnol Adv 28:694-705 Chang YS (2008) Recent developments in microbial biotransformation and biodegradation of dioxins. J Mol Microbiol Biotechnol 15:152-171 De S, Perkins M, Dutta SK (2006) Nitrate reductase gene involvement in hexachlorobiphenyl dechlorination by Phanerochaete chrysosporium. J Hazard Mater 135:350-354 Dietrich D, Hickey WJ, Lamar R (1995) Degradation of 4,4'-dichlorobiphenyl, 3,3',4, 4'-tetrachlorobiphenyl, and 2,2',4,4',5,5'-hexachlorobiphenyl by the white rot fungus Phanerochaete chrysosporium. Appl Environ Microbiol 61:3904-3909 Doddapaneni H, Yadav JS (2004) Differential regulation and xenobiotic induction of tandem P450 monooxygenase genes pc-1 (CYP63A1) and pc-2 (CYP63A2) in the white rot fungus Phanerochaete chrysosporium. Appl Microbiol Biotechnol 65:559-565 Donnelly PK, Entry JA, Crawford DL (1993) Degradation of atrazine and 2, 4-dichlorophe-noxyacetic acid by mycorrhizal fungi at three nitrogen concentrations in vitro. Appl Environ Microbiol 59:2642-2647 Dosoretz CG, Reddy CA (2007) Lignin and lignin-modifying enzymes. In: Reddy CA, Beveridge TJ, Breznak JA, Marzluf GA, Schmidt TM, Snyder LJ (eds) Methods for general and molecular microbiology, 3rd edn. American Society for Microbiology, Washington, pp 611-620

Eaton DC (1985) Mineralization of polychlorinated biphenyls by Phanerochaete chrysosporium:

a ligninolytic fungus. Enzyme Microb Technol 7:194-196 Entry JA, Donnelly PK, Emmingham WH (1996) Mineralization of atrazine and 2, 4-D in soils inoculated with Phanerochaete chrysosporium and Trappea darkeri. Appl Soil Ecol 3:85-90 Fernando T, Aust SD, Bumpus JA (1987) Effects of culture parameters on DDT [1,1, 1-trichloro-2, 2-bis(4-chlorophenyl)ethane] biodegradation by Phanerochaete chrysosporium. Chemosphere 19:1387-1398

Fragoeiro S, Magan N (2005) Enzymatic activity, osmotic stress and degradation of pesticide mixtures in soil extract liquid broth inoculated with Phanerochaete chrysosporium and Trametes versicolor. Environ Microb 7:348-355 Fragoeiro S, Magan N (2008) Impact of Trametes versicolor and Phanerochaete chrysosporium on differential breakdown of pesticide mixtures in soil microcosms at two water potentials and associated respiration and enzyme activity. Int Biodeter Biodegrad 62:376-383

Fujihiro S, Higuchi R, Hisamatsu S, Sonoki S (2009) Metabolism of hydroxylated PCB congeners by cloned laccase isoforms. Appl Microbiol Biotechnol 82:853-860 Gold MH, Alic M (1993) Molecular biology of the lignin-degrading basidiomycete

Phanerochaete chrysosporium. Micorbiol Rev 57:605-622 Gold MH, Youngs HL, Sollewijin Gelpke MD (2000) Manganese peroxidase. In: Sigel A, Sigel H (eds) Manganese and its role in biological processes. Marcel Dekker, New York, pp 559-580

Gomez-Toribio V, Garcia-Martin AB, Martinez MJ, Martinez AT, Guillen F (2009a) Enhancing the production of hydroxyl radicals by Pleurotus eryngii via quinone redox cycling for pollutant removal. Appl Environ Microbiol 75:3954-3962 Gomez-Toribio V, Garcia-Martin AB, Martinez MJ, Martinez AT, Guillen F (2009b) Induction of extracellular hydroxyl radical production by white rot fungi through quinone redox cycling. Appl Environ Microbiol 75:3944-3953 Guillen F, Martinez MJ, Munoz C, Martinez AT (1997) Quinone redox cycling in the ligninolytic fungus Pleurotus eryngii leading to extracellular production of superoxide anion radical. Arch Biochem Biophys 339:190-199 Hakala TK, Hilden K, Maijala P, Olsson C, Hatakka A (2006) Differential regulation of manganese peroxidases and characterization of two variable MnP encoding genes in the white-rot fungus Physisporinus rivulosus. Appl Microbiol Biotechnol 73:839-849 Hammel KE, Kalyanaraman B, Kirk TK (1986) Oxidation of polycyclic aromatic hydrocarbons and dibenzo[p]-dioxins by Phanerochaete chrysosporium. J Biol Chem 261:16948-16952 Harper DB, Buswell JA, Kennedy JT, Hamilton JT (1990) Chloromethane, methyl donor in veratryl alcohol biosynthesis in Phanerochaete chrysosporium and other lignin-degrading fungi. Appl Environ Microbiol 56:3450-3457 Hickey WJ, Fuster DJ, Lamar RT (1994) Transformation of atrazine in soil by Phanerochaete chrysosporium. Soil Biol Biochem 26:1665-1671 Hilden K, Hakala TK, Maijala P, Lundell TK, Hatakka A (2007) Novel thermotolerant laccases produced by the white-rot fungus Physisporinus rivulosus. Appl Microbiol Biotechnol 77:301-309

Hofrichter M, Ullrich R, Pecyna MJ, Liers C, Lundell T (2010) New and classic families of secreted fungal heme peroxidases. Appl Microbiol Biotechnol 87:871-897 Hundt K, Martin D, Hammer E, Jonas U, Kindermann MK, Schauer F (2000) Transformation of triclosan by Trametes versicolor and Pycnoporus cinnabarinus. Appl Environ Microbiol 66:4157-4160

Inoue Y, Hata T, Kawai S, Okamura H, Nishida T (2010) Elimination and detoxification of triclosan by manganese peroxidase from white rot fungus. J Hazard Mater 180:764-767 Kamei I, Kondo R (2005) Biotransformation of dichloro-, trichloro-, and tetrachlorodibenzo-p-dioxin by the white rot fungus Phlebia lindtneri. Appl Microbiol Biotechnol 68:560-566 Kamei I, Suhara H, Kondo R (2005) Phylogenetical approach to isolation of white rot fungi capable of degrading polychlorinated dibenzo-p-dioxin. Appl Microbiol Biotechnol 69:358-366

Kamei I, Kogura R, Kondo R (2006a) Metabolism of 4,40-dichlorobiphenyl by white rot fungi Phanerochaete chrysosporium and Phanerochaete sp. MZ142. Appl Microbiol Biotechnol 72:566-575

Kamei I, Sonoki S, Haraguchi K, Kondo R (2006b) Fungal bioconversion of toxic polychlorinated biphenyls by white rot fungus, Phlebia brevispora. Appl Microbiol Biotechnol 73:932-940

Kamei I, Watanabe M, Harada K, Miyahara T, Suzuki S, Matsufuji Y, Kondo R (2009) Influence of soil properties on the biodegradation of 1, 3, 6, 8-tetrachlorodibenzo-p-dioxin and fungal treatment of contaminated paddy soil by white rot fungus Phlebia brevispora. Chemosphere 75:1294-1300

Kamei I, Takagi K, Kondo R (2010) Bioconversion of dieldrin by wood-rotting fungi and metabolite detection. Pest Manag Sci 66:888-891

Kasai N, Ikushiro S, Shinkyo R, Yasuda K, Hirosue S, Arisawa A, Ichinose H, Wariishi H, Sakaki T (2010) Metabolism of mono- and dichloro-dibenzo-p-dioxins by Phanerochaete chrysos-porium cytochromes P450. Appl Microbiol Biotechnol 86:773-780 Kennedy DW, Aust SD, Bumpus JA (1990) Comparative biodegradation of alkyl halide insecticides by the white rot fungus, Phanerochaete chrysosporium (BKM-F-1767). Appl Environ Microbiol 56:2347-2353 Kersten PJ, Kalyanaraman B, Hammel KE, Reinhammar B, Kirk TK (1990) Comparison of lignin peroxidase, horseradish peroxidase and laccase in the oxidation of methoxybenzenes. Biochem J 268:475-480 Keum YS, Li QX (2004) Fungal laccase-catalyzed degradation of hydroxy polychlorinated biphenyls. Chemosphere 56:23-30 Khindaria A, Grover TA, Aust SD (1995) Reductive dehalogenation of aliphatic halocarbons by lignin peroxidase of Phanerochaete chrysosporium. Environ Sci Technol 29:719-725 Kim YJ, Nicell JA (2006) Laccase-catalysed oxidation of aqueous triclosan. J Chem Technol

Biotechnol 81:1344-1352 Köhler A, Jäager A, Willershausen H, Graf H (1988) Extracellular ligninase of Phanerochaete chrysosporium has no role in the degradation of DDT. Appl Microbiol Biotechnol 29:618-620 Koller G, Moder M, Czihal K (2000) Peroxidative degradation of selected PCB: a mechanistic study. Chemosphere 41:1827-1834 Kordon K, Mikolasch A, Schauer F (2010) Oxidative dehalogenation of chlorinated hydroxybiphenyls by laccases of white rot fungi. Int Biodeter Biodegrad 64:203-209 Kremer SM, Wood PM (1992) Cellobiose oxidase from Phanerochaete chrysosporium as a source of Fenton's reagent. Biochem Soc Trans 20:110S Kubatova A, Erbanova P, Eichlerova I, Homolka L, Nerud F, Sasek V (2001) PCB congener selective biodegradation by the white rot fungus Pleurotus ostreatus in contaminated soil. Chemosphere 43:207-215 Lawton LA, Robertson PKJ (1999) Physico-chemical treatment methods for the removal of microcystins (cyanobacterial hepatotoxins) from potable waters. Chem Soc Rev 28:217-224 Lundell TK, Makela MR, Hilden K (2010) Lignin-modifying enzymes in filamentous basidiomycetes-ecological, functional and phylogenetic review. J Basic Microbiol 50:5-20 Majeau JA, Brar SK, Tyagi RD (2010) Laccase for removal opf recalcitrant and emerging pollutants. Biores Technol 101:2331-2350 Manji S, Ishihara A (2004) Screening of tetrachlorodibenzo-p-dioxin-degrading fungi capable of producing extracellular peroxidases under various conditions. Appl Microbiol Biotechnol 63:438-444

Marco-Urrea E, Gabarrell X, Sarra M, Caminal G, Vicent T, Reddy CA (2006) Novel aerobic perchloroethylene degradation by the white rot fungus Trametes versicolor. Environ Sci Technol 40:7796-7802

Marco-Urrea E, Gabarrell X, Caminal G, Vicent T, Reddy CA (2008a) Aerobic degradation by white rot fungi of trichloroethylene (TCE) and mixtures of TCE and perchloroethylene (PCE). J Chem Technol Biotechnol 83:1190-1196 Marco-Urrea E, Parella T, Gabarrell X, Caminal G, Vicent T, Adinarayana Reddy C (2008b) Mechanistics of trichloroethylene mineralization by the white rot fungus Trametes versicolor. Chemosphere 70:404-410 Marco-Urrea E, Aranda E, Caminal G, Guillen F (2009a) Induction of hydroxyl radical production in Trametes versicolor to degrade recalcitrant chlorinated hydrocarbons. Biores Technol 100:5757-5762 Marco-Urrea E, Perez-Trujillo M, Caminal G, Vicent T (2009b) Dechlorination of 1, 2, 3- and 1, 2, 4-trichlorobenzene by the white rot fungus Trametes versicolor. J Hazard Mater 166:1141-1147

Marco-Urrea E, Perez-Trujillo M, Vicent T, Caminal G (2009c) Ability of white rot fungi to remove selected pharmaceuticals and identification of degradation products of ibuprofen by Trametes versicolor. Chemosphere 74:765-772

Marco-Urrea E, Radjenovic J, Caminal G, Petrovic M, Vicent T, Barcelo D (2010) Oxidation of atenolol, propranolol, carbamazepine and clofibric acid by a biological Fenton-like system mediated by the white rot fungus Trametes versicolor. Water Res 44:521-532 Martinez D, Larrondo LF, Putnam N, Gelpke MD, Huang K, Chapman J, Helfenbein KG, Ramaiya P, Detter JC, Larimer F, Coutinho PM, Henrissat B, Berka R, Cullen D, Rokhsar D (2004) Genome sequence of the lignocellulose degrading fungus Phanerochaete chrysosporium strain RP78. Nat Biotechnol 22:695-700 Masaphy S, Levanon D, Vaya J, Henis Y (1993) Isolation and characterization of a novel atrazine metabolite produced by the fungus Pleurotus pulmonarius, 2-chloro-4-ethylamino-6-(1-Hydroxyisopropyl)amino-1, 3, 5-triazine. Appl Environ Microbiol 59:4342-4346 Masaphy S, Henis Y, Levanon D (1996a) Manganese-enhanced biotransformation of atrazine by the white rot fungus Pleurotus pulmonarius and its correlation with oxidation activity. Appl Environ Microbiol 62:3587-3593 Masaphy S, Levanon D, Henis Y (1996b) Degradation of atrazine by the lignocellulolytic fungus

Pleurotus pulmonarius during solid-state fermentation. Biores Technol 56:207-214 Mason MG, Nicholls P, Wilson MT (2003) Rotting by radicals-the role of cellobiose oxidoreductase? Biochem Soc Trans 31:1335-1336 Matheus DR, RV L, Machado KMG (2000) Biodegradation of hexachlorobenzene by basidiomycetes in soil contaminated with industrial residues. World J Microbiol Biotechnol 16:415-421

Moreira PR, Duez C, Dehareng D, Antunes A, Almeida-Vara E, Frère JM, Malcata FX, Duarte JC (2005) Molecular characterization of a versatile peroxidase from a Bjerkandera strain. J Biotechnol 118:339-352 Morel M, Ngadin AA, Droux M, Jacquot JP, Gelhaye E (2009) The fungal glutathione S-transferase system. Evidence of new classes in the wood-degrading basidiomycete Phanero-chaete chrysosporium. Cell Mol Life Sci 66:3711-3725 Mori T, Kondo R (2002a) Degradation of 2, 7-dichlorodibenzo-p-dioxin by wood-rotting fungi, screened by dioxin degrading ability. FEMS Microbiol Lett 213:127-131 Mori T, Kondo R (2002b) Oxidation of dibenzo-p-dioxin, dibenzofuran, biphenyl, and diphenyl ether by the white rot fungus Phlebia lindtneri. Appl Microbiol Biotechnol 60:200-205 Mougin C, Laugero C, Asther M, Dubroca J, Frasse P (1994) Biotransformation of the herbicide atrazine by the white rot fungus Phanerochaete chrysosporium. Appl Environ Microbiol 60:705-708

Mougin C, Pericaud C, Malosse C, Laugero C, Asther C (1996) Biotransformation of the insecticide lindane by the white rot basidiomycete Phanerochaete chrysosporium. Pest Sci 47:51-59

Mougin C, Pericaud C, Dubroca J, Asther C (1997a) Enhanced mineralization of lindane in soils supplemented with the white rot basidiomycete Phanerochaete chrysosporium. Soil Biol Biochem 29:1321-1324

Mougin C, Pericaud C, Dubroca J, Asther M (1997b) Enhanced mineralization of lindane in soils supplemented with the white rot basidiomycete Phanerochaete chrysosporium. Soil Biol Biochem 29:9-10

Murugesan K, Chang YY, Kim YM, Jeon JR, Kim EJ, Chang YS (2010) Enhanced transformation of triclosan by laccase in the presence of redox mediators. Water Res 44:298-308

Nwachukwu EO, Osuji JO (2007) Bioremedial degradation of some herbicides by indigenous white rot fungus, Lentinus subnudus. J Plant Sci 2:619-624 Pinedo-Rilla C, Aleu J, Collado IG (2009) Pollutants biodegradation by fungi. Curr Org Chem 13:1194-1214

Pointing SB (2001) Feasibility of bioremediation by white rot fungi. Appl Microbiol Biotechnol 57:20-33

Popp JL, Kirk TK (1991) Oxidation of methoxybenzenes by manganese peroxidase and by Mn3+. Arch Biochem Biophys 288:145-148

Purnomo AS, Kamei I, Kondo R (2008) Degradation of 1, 1, 1-trichloro-2, 2-bis (4-chlorophenyl)

ethane (DDT) by brown-rot fungi. J Biosci Bioeng 105:614-621 Purnomo AS, Mori T, Kamei I, Nishii T, Kondo R (2010) Application of mushroom waste medium from Pleurotus ostreatus for bioremediation of DDT-contaminated soil. Int Biodeter Biodegrad 64:397-402

Quintero JC, Moreira MT, Feijoo G, Lema JM (2008) Screening of white rot fungal species for their capacity to degrade lindane and other isomers of hexachlorocyclohexane (HCH). Cienc Inv Agr 35:123-132

Raghukumar C (2000) Fungi from marine habitats: an application in bioremediation. Mycol Res 104:1222-1226

Reddy CA (1995) The potential for white rot fungi in the treatment of pollutants. Curr Opin Biotechnol 6:320-328

Reddy CA, D'Souza TM (1994) Physiology and Molecularbiology of the lignin peroxidases of

Phanerochaete chrysosporium. FEMS Microbiol Rev 13:137-152 Reddy CA, Mathew Z (2001) Bioremediation potential of white rot fungi. In: Gadd GM (ed)

Fungi in bioremediation. Cambridge University Press, London, pp 52-78 Reddy GVB, Joshi DK, Aust SD (1997) Degradation of chlorophenoxyacetic acids by the lignin-

degrading fungus Dichomitus squalens. Microbiol 143:2353-2360 Rodgers CJ, Blanford CF, Giddens SR, Skamnioti P, Armstrong FA, Gurr SJ (2010) Designer laccases: a vogue for high-potential fungal enzymes? Trends Biotechnol 28:63-72 Ruiz-Aguilar GM, Fernández-Sánchez JM, Rodríguez-Vázquez R, Poggi-Varaldo H (2002) Degradation by white rot fungi of high concentrations of PCB extracted from a contaminated soil. Adv Environ Res 6:559-568 Ruiz-Dueñas FJ, Morales M, García E, Miki Y, Martínez MJ, Martínez AT (2009) Substrate oxidation sites in versatile peroxidase and other basidiomycete peroxidases. J Exp Bot 60:441-452

Ryan TP, Bumpus JA (1989) Biodegradation of 2, 4, 5-trichlorophenoxyacetic acid in liquid culture and in soil by the white rot fungus Phanerochaete chrysosporium. Appl Microbiol Biotechnol 31:302-307

Sanino F, Filazzola MT, Violante A, Gianfreda L (1999) Fate of herbicides influenced by biotic and abiotic interactions. Chemosphere 39:333-341 Sato A, Watanabe T, Watanabe Y, Harazono K, Fukatsu T (2002) Screening for basidiomycetous fungi capable of degrading 2, 7-dichlorodibenzo-p-dioxin. FEMS Microbiol Lett 213:213-217 Schultz A, Jonas U, Hammer E, Schauer F (2001) Dehalogenation of chlorinated hydroxybiphenyls by fungal laccase. Appl Environ Microbiol 67:4377-4381 Shah MM, Grover TA, Aust SD (1993) Reduction of CCl4 to the trichloromethyl radical by lignin peroxidase H2 from Phanerochaete chrysosporium. Biochem Biophys Res Commun 191:887-892

Singh BK, Kuhad RC (1999) Biodegradation of lindane (gamma-hexachlorocyclohexane) by the white rot fungus Trametes hirsutus. Lett Appl Microbiol 28:238-241 Singh BK, Kuhad RC (2000) Degradation of insecticide lindane (y-HCH) by white rot fungi

Cyathus bulleri and Phanerochaete sordida. Pest Manag Sci 56:142-146 Subramanian V, Yadav JS (2008) Regulation and heterologous expression of P450 enzyme system components of the white rot fungus Phanerochaete chrysosporium. Enzyme Microb Technol 43:205-213

Sugiura T, Yamagishi K, Kimura T, Nishida T, Kawagishi H, Hirai H (2009) Cloning and homologous expression of novel lignin peroxidase genes in the white-rot fungus Phanero-chaete sordida YK-624. Biosci Biotechnol Biochem 73:1793-1798 Suhara H, Daikoku C, Takata H, Suzuki S, Matsufuji Y, Sakai K, Kondo R (2003) Monitoring of white rot fungus during bioremediation of polychlorinated dioxin-contaminated fly ash. Appl Microbiol Biotechnol 62:601-607 Takada S, Nakamura M, Matsueda T, Kondo R, Sakai K (1996) Degradation of polychlorinated dibenzo-p-dioxins and polychlorinated dibenzofurans by the white rot fungus Phanerochaete sordida YK-624. Appl Environ Microbiol 62:4323-4328

ten Have R, Hartmans S, Teunissen PJ, Field JA (1998) Purification and characterization of two lignin peroxidase isozymes produced by Bjerkandera sp. strain BOS55. FEBS Lett 422:391-394

Thomas DR, Carswell KS, Georgiou G (1992) Mineralization of biphenyl and PCBs by the white rot fungus Phanerochaete chrysosporium. Biotechnol Bioeng 40:1395-1402 Thurston CF (1994) The structure and function of fungal laccases. Microbiol 140:19-26 Valli K, Wariishi H, Gold MH (1992) Degradation of 2,7-dichlorodibenzo-p-dioxin by the lignin-

degrading basidiomycete Phanerochaete chrysosporium. J Bacteriol 174:2131-2137 Vanden Wymelenberg V, Minges P, Sabat G, Martinez D, Aerts A, Salamov A, Grigoriev I, Shapiro H, Putnam N, Belinky P, Dosoretz C, Gaskell J, Kersten P, Cullen D (2006) Computational analysis of the Phanerochaete chrysosporium v2.0 genome data base and mass spectrometrry identification of peptides in ligninolytic cultures reveal complex mixtures of secreted proteins. Fungal Genet Biol 43:342-356 Vanden Wymelenberg V, Gaskell J, Mozuch M, Kersten P, Sabat G, Martinez D, Cullen D (2009) Transcriptome and secretome analyses of Phanerochaete chrysosporium reveal complex patterns of gene expression. Appl Environ Microbiol 75:4058-4068 Vyas BRM, Sasek V, Matucha M, Bubner M (1994) Degradation of 3,3',4,4'-tetrachlorobiphenyl by selected white rot fungi. Chemosphere 28:1127-1134 Wesenberg D, Kyriakides I, Agatho SN (2003) White rot fungi and their enzymes for the treatment of industrial dye effluents. Biotechnol Adv 22:161-187 Wong DW (2009) Structure and action mechanism of ligninolytic enzymes. Appl Biochem

Biotechnol 157:174-209 Yadav JS, Reddy CA (1992) Non-involvement of lignin peroxidases and manganese peroxidases in 2, 4, 5-trichlorophenoxyacetic acid degradation by Phanerochaete chrysosporium. Biotechnol Lett 14:1089-1092 Yadav JS, Reddy CA (1993) Mineralization of 2, 4-dichlorophenoxyacetic acid (2, 4-D) and mixtures of 2, 4-D and 2, 4, 5-trichlorophenoxyacetic acid by Phanerochaete chrysosporium. Appl Environ Microbiol 59:2904-2908 Yadav JS, Quensen JF, Tiedje JM, Reddy CA (1995a) Degradation of polychlorinated biphenyl mixtures (Aroclors 1242, 1254, and 1260) by the white rot fungus Phanerochaete chrysosporium as evidenced by congener-specific analysis. Appl Environ Microbiol 61:2560-2565

Yadav JS, Wallace RE, Reddy CA (1995b) Mineralization of mono- and dichlorobenzenes and simultaneous degradation of chloro- and methyl-substituted benzenes by the white rot fungus Phanerochaete chrysosporium. Appl Environ Microbiol 61:677-680 Yadav JS, Bethea C, Reddy CA (2000) Mineralization of trichloroethylene (TCE) by the white rot fungus Phanerochaete chrysosporium. Bull Environ Contam Toxicol 65:28-34 Yadav JS, Doddapaneni H, Subramanian V (2006) P450ome of the white rot fungus Phanerochaete chrysosporium: structure, evolution and regulation of expression of genomic P450 clusters. Biochem Soc Trans 34:1165-1169 Zhao Y, Yi X (2010) Effects of soil oxygen conditions and soil pH on remediation of DDT-contaminated soil by laccase from white rot fungi. Int J Environ Res Public Health 7:1612-1621

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