Removal of estrogenic activities of bisphenol A and nonylphenol by oxidative enzymes from lignin-degrading basidiomycetes

Tsutsumi, Yuji; Haneda, Takashi; Nishida, Takahiro

doi:10.1016/s0045-6535(00)00081-3

Cited by 214 publications

(145 citation statements)

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“…7), indicating oxidative coupling of primary oxidation metabolites. Similarly, the formation of polymerization products was reported for nonylphenol and bisphenol A degradation by laccases and manganese peroxidases from white-rot fungi (Tsutsumi et al, 2001;Uchida et al, 2001), which led to the removal of the oestrogenic activities of the contaminants (Tsutsumi et al, 2001). In aquatic ecosystems, laccase-catalysed degradation of endocrine disruptors may lead to their removal from these environments by formation of bound residues with organic matter, as already proposed for oxidoreductasecatalysed degradation of chlorophenols in presence of stream fulvic acids (Sarkar et al, 1988).…”

Section: Discussionsupporting

confidence: 58%

Section: Introductionmentioning

confidence: 98%

“…Their substrate range can be considerably extended in the presence of small, diffusible compounds acting as redox mediators (Bourbonnais & Paice, 1990), particularly in white-rot fungi (Eggert et al, 1996;Johannes & Majcherczyk, 2000). The oxidation of nonylphenol and bisphenol A, another phenolic environmental pollutant with endocrine activity, by laccases from white-rot basidiomycetes (Fukuda et al, 2001;Tsutsumi et al, 2001;Uchida et al, 2001) and soil-derived ascomycetes (Saito et al, 2003) has previously been demonstrated. Both pollutants are also degraded by the extracellular ligninmodifying enzyme manganese peroxidase (EC 1.11.1.13) produced by white-rot fungi (Tsutsumi et al, 2001).…”

Section: Introductionmentioning

confidence: 99%

“…The oxidation of nonylphenol and bisphenol A, another phenolic environmental pollutant with endocrine activity, by laccases from white-rot basidiomycetes (Fukuda et al, 2001;Tsutsumi et al, 2001; Uchida et al, 2001) and soil-derived ascomycetes (Saito et al, 2003) has previously been demonstrated. Both pollutants are also degraded by the extracellular ligninmodifying enzyme manganese peroxidase (EC 1.11.1.13) produced by white-rot fungi (Tsutsumi et al, 2001).Here, we focus on the degradation of t-NP by a strain of the aquatic hyphomycete Clavariopsis aquatica, a species frequently observed in rivers and streams (Baldy et al, 2002;Krauss et al, 2001Krauss et al, , 2003aNikolcheva et al, 2003), and a strain of a mitosporic fungus isolated from river water containing t-NP as a contaminant. In addition, 4-n-NP was employed in some experiments as a structurally defined reference compound.…”

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confidence: 98%

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Degradation of the xenoestrogen nonylphenol by aquatic fungi and their laccases

et al. 2005

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Degradation of technical nonylphenol (t-NP), known as an endocrine-disrupting compound mixture, was assessed, using the mitosporic fungal strain UHH 1-6-18-4 isolated from nonylphenol-contaminated river water, and a strain of the aquatic hyphomycete Clavariopsis aquatica. GC-MS analysis could resolve 12 peaks attributable to nonyl chain-branched t-NP isomers. All were degraded, to individual extents. Analysis of degradation metabolites suggested intracellular hydroxylation of the nonyl moieties of individual t-NP isomers. Further metabolites also indicated shortening of branched nonyl chains, and 4-hydroxybenzoic acid was identified as a t-NP breakdown product in UHH 1-6-18-4. The t-NP degradation efficiency was higher in UHH 1-6-18-4 than in C. aquatica, and a lower specificity in degradation of individual t-NP constituents in UHH 1-6-18-4 than in C. aquatica was observed. Strain UHH 1-6-18-4 concomitantly produced extracellular laccase under degradation conditions. A mixture of CuSO 4 and vanillic acid considerably enhanced laccase production in both fungi. Laccase preparations derived from UHH 1-6-18-4 and C. aquatica cultures also converted t-NP. Laccase-catalysed transformation of t-NP led to the formation of products with higher molecular masses than that of the parent compound. These results emphasize a role of fungi occurring in aquatic ecosystems in degradation of water contaminants with endocrine activity, which has not previously been considered. Furthermore, the results are in support of two different mechanisms employed by fungi isolated from aquatic environments to initiate t-NP degradation: hydroxylation of individual t-NP isomers at their branched nonyl chains and further breakdown of the alkyl chains of certain isomers; and attack of t-NP by extracellular laccase, the latter leading to oxidative coupling of primary radical products to compounds with higher molecular masses. INTRODUCTIONNonylphenols have increasingly gained attention because of their potential to mimic the action of natural hormones in vertebrates (Ying et al., 2002). They result from incomplete biodegradation of nonylphenol polyethoxylates (NPEOs), which have been widely used as non-ionic surfactants in industrial processes and households (Braun et al., 2003;Ying et al., 2002). Both nonylphenols and NPEOs are discharged into the environment, mainly due to incomplete removal in wastewater treatment facilities (Ying et al., 2002). Nonylphenols are more resistant to biodegradation than their parent compounds and hence are found worldwide in wastewater treatment plant effluents and rivers in concentrations of up to the mg l 21 range (Heemken et al., 2001;Kolpin et al., 2002;Stachel et al., 2003;Ying et al., 2002). Due to their hydrophobicity, they tend to adsorb onto surface water particles and sediments and accumulate in aquatic organisms (Heemken et al., 2001;Ying et al., 2002). Consequently, nonylphenols represent a serious environmental and human health risk. The assessment of biodegradative processes affecting the environmental...

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Section: Discussionsupporting

confidence: 58%

Section: Introductionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 98%

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Degradation of the xenoestrogen nonylphenol by aquatic fungi and their laccases

et al. 2005

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“…In recent years, several research groups have explored the ability of free fungal laccases to remove a wide range of hormones: genistein, estrone, 17b-estradiol, estriol, and 17a-ethinylestradiol (Auriol et al 2008;Nicotra et al 2004;Tamagawa et al 2006;Lloret et al 2010). Crude and purified laccase from Trametes versicolor and Trametes villosa were used to degrade bisphenol A (Kim and Nicell 2006) and nonylphenol (Tsutsumi et al 2001).…”

Section: Introductionmentioning

confidence: 99%

Immobilisation of laccase on Eupergit supports and its application for the removal of endocrine disrupting chemicals in a packed-bed reactor

et al. 2011

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Laccase from Myceliophthora thermophila was covalently immobilised on Eupergit C and Eupergit C 250L yielding specific activities of up to 17 and 80 U/g, respectively. Due to its superior activity, Eupergit C 250L was chosen for further research. The somewhat lower catalytic efficiency (based on the ratio between the turnover number and the Michaelis constant, k cat /K M ) of the immobilised enzyme in comparison with that of the free enzyme was balanced by its increased stability and broader operational window related to temperature and pH. The feasibility of the immobilised laccase was tested by using a packed bed reactor (PBR) operating in consecutive cycles for the removal of Acid Green 27 dye as model substrate. High degrees of elimination were achieved (88, 79, 69 and 57% in 4 consecutive cycles), while the levels of adsorption on the support varied from 18 to 6%, proving that dye removal took place mainly due to the action of the enzyme. Finally, a continuous PBR with the solid biocatalyst was applied for the treatment of a solution containing the following endocrine disrupting chemicals: estrone (E1), 17b-estradiol (E2) and 17a-ethinylestradiol (EE2). At steady-state operation, E1 was degraded by 65% and E2 and EE2 were removed up to 80% and only limited adsorption of these compounds on the support, between 12 and 22%, was detected. In addition, a 79% decrease in estrogenic activity was detected in the effluent of the enzymatic reactor while only 14% was attained by inactivated laccase.

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