Oxidation of bisphenol A catalyzed by laccase hosted in reversed micelles in organic media

Okazaki, Shin Ya; Michizoe, Junji; Goto, Masahiro; Furusaki, Shintaro; Wariishi, Hiroyuki; Tanaka, Hiroo

doi:10.1016/s0141-0229(02)00104-7

Cited by 67 publications

(34 citation statements)

References 28 publications

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“…Therefore laccase might play a key role in BPA biodegradation. 6,26) Analysis of BPA Metabolites Using GC-MS The change in the amount of metabolites depending on the incubation period could be used to determine the degradation pathway. According to the above results, the two fungi appeared to degrade BPA.…”

Section: Resultsmentioning

confidence: 99%

Degradation of Bisphenol A by White Rot Fungi, Stereum hirsutum and Heterobasidium insulare, and Reduction of Its Estrogenic Activity

Lee

Koo

Choi

et al. 2005

Biological & Pharmaceutical Bulletin

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Two lignin-degrading basidiomycetes, Stereum hirsutum and Heterobasidium insulare, were used to degrade bisphenol A (BPA) in culture, and the estrogenic activity of the degradation products was examined using MCF-7 cell proliferation assays (E-screen) and analysis of pS2 mRNA expression in MCF 7 cells. Both S. hirsutum and H. insulare showed high resistance to BPA 100 ppm, and their mycelial growth was fully completed within 8 d of incubation at 30°C. It took 7 to 14 d to achieve complete degradation (ca. 99%) of BPA by both fungi. MCF-7 cells proliferated actively at a BPA concentration of 10 Ϫ5 M. However, cell line proliferation was significantly inhibited when the cells were incubated in BPA culture media containing S. hirsutum and H. insulare. Similar results were obtained regarding pS2 mRNA expression. The pS2 mRNA expression levels decreased by 1.5-fold in supernatant from BPA treated with S. hirsutum and H. insulare compared with those treated with BPA alone.Key words bisphenol A; biodegradation; Stereum hirsutum; Heterobasidium insulare; estrogenic activityResearch Institute using the Remazol Brilliant Blue R method and determination of ligninase activity. Both fungi were first grown in potato dextrose agar (PDA) medium at 30°C for 7 d, then transferred to a complex medium (YMPG), and kept at 4°C until use. The composition of the YMPG medium (per liter of distilled water) was 10 g of glucose, 10 g of malt extract, 2 g of peptone, 2 g of yeast extract, 1 g of asparagine, 2 g of KH 2 PO 4 , 1 g of MgSO 4 · 7H 2 O, 1 mg of thiamine, and 20 g of agar. Optimal growth temperature was determined by measuring the hyphal extension length on 2% malt extract agar medium after optimal pH determination. The 7-mm plugs of inoculum from the YMPG medium slant were transferred to plates containing 2% malt extract agar medium, which were kept at 17, 25, 30, and 34°C. Three replicates of each fungus at each temperature were prepared. Hyphal extension lengths were measured daily based on the usual colony diameter (unit: cm) in the longest perpendicular direction.Resistance to Various BPA Concentrations To determine BPA resistance, the inocula of both fungi were cultivated on YMPG medium, which contained BPA concentrations of 50, 100, and 500 ppm. The cultivated medium was incubated at 30°C for 14 d. Three replicates were prepared of each fungus at each concentration with control. The hyphal extension lengths of fungi were measured daily. Complete growth was assumed when the hyphal length reached 8.5 cm in the Petri dish.Analysis of Degradation Products Using HPLC and GC-MS Both fungi were incubated in shallow stationary culture (SSC medium) as previously described.17) The culture medium pH was adjusted to 4.5 using a 2,2-dimethylsuccinic acid buffer (1.46 g/l), and both fungi were incubated in flasks without shaking at 30°C. After full growth of the mycelium, BPA was added to the culture medium with an inoculated syringe to a final concentration of 100 mM to determine the degrading ability of the fungus. After each indicat...

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Section: Resultsmentioning

confidence: 99%

Degradation of Bisphenol A by White Rot Fungi, Stereum hirsutum and Heterobasidium insulare, and Reduction of Its Estrogenic Activity

Lee

Koo

Choi

et al. 2005

Biological & Pharmaceutical Bulletin

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“…9,14) The activity of laccase usually varies with environmental factors such as temperature, co-existing chemicals, and pH. 15) So far, the optimal oxidation conditions for the laccase-transformation of many contaminants such as hydroxy polychlorinated biphenyls, 13) chlorophenols, 16) bisphenol A 17) and the polymerization of catechol 18) have been well studied; however, little is known about benzo[a]pyrene oxidation, though it is a very hot contaminant.…”

Section: Introductionmentioning

confidence: 99%

Optimization of Laccase-mediated Benzo[a]pyrene Oxidation and the Bioremedial Application in Aged Polycyclic Aromatic Hydrocarbons-contaminated Soil

Lin

Yin

et al. 2010

JOURNAL OF HEALTH SCIENCE

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Laccase is a polyphenol oxidase with the ability to oxidize a broad range of persistent organic pollutants, including benzo[a]pyrene, the most carcinogenic, mutagenic and teratogenic polycyclic aromatic hydrocarbons (PAHs). In this study, the reaction conditions for benzo [a]pyrene oxidation by laccase from Trametes versicolor were optimized in a liquid medium by a series of single factor experiments. The maximal benzo[a]pyrene oxidation rate was observed at 40• C, pH 4, 10% of acetonitrile and an incubation time of more than 24 hr, and the benzo[a]pyrene oxidation was enhanced significantly by the addition of a mediator, 2,2-azino-bis-(3-ethylbenzothiazoline-6-sulfonicacid) (ABTS). Laccase was also applied to aged PAHs polluted soil to examine the efficiency of enzymatic bioremediation. The results showed that the enzyme was still effective in the degradation of anthracene, benzo[a]pyrene and benzo [a]anthracene in soil. Moreover, the degradation rate of most PAHs increased by the addition of ABTS. Our results indicated that the bioremediation of PAHs contaminated soil using laccase is feasible but a suboptimal pH might be a limiting factor in the enzymatic treatment of soil.

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“…Phenols such as hydroquinone, catechols, guaiacol and 2,6-dimethoxyphenol are good substrates for laccase in aqueous media. However, most phenolic compounds present a low solubility in water, such as bisphenol A (Okazaki et al, 2002). The presence of a cosolvent can increase the solubility of phenolic compounds, thus raising the capacity of a bioreactor and avoiding the appearance of two phases.…”

Section: Introductionmentioning

confidence: 99%

Ionic liquids as alternative co‐solvents for laccase: Study of enzyme activity and stability

Tavares

Rodrı́guez

Macedo

2008

Biotech & Bioengineering

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The activity and stability of commercial laccase (DeniLite base) in three different water soluble ionic liquids (ILs) (1-ethyl-3-methylimidazolium 2-(2-methoxyethoxy) ethylsulfate, [emim][[MDEGSO4], 1-ethyl-3-methylimidazolium ethylsulfate, [emim][EtSO4], and 1-ethyl-3-methylimidazolium methanesulfonate, [emim][MeSO3]) have been studied and compared to that in two organic solvents (acetonitrile and dimethyl sulfoxide). Initial enzyme activities were similar among the ILs if the same conditions were used. A high reduction on initial enzyme activity was found with acidic pH (5.0). The effect of pH and solvent concentration on enzyme stability were investigated in more detail for 1 week. The enzyme maintained a high stability at pH 9.0 for all ILs tested. [emim][MDEGSO4] was the most promising IL for laccase with an activity loss of about 10% after 7 days of incubation. The kinetic studies in the presence of ABTS as substrate allowed to calculate the Michaelis- Menten parameters. Good agreement was found between experimental data and calculated values using the Michaelis-Menten mechanism, with a total average relative deviation of 2.1%.

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Oxidation of bisphenol A catalyzed by laccase hosted in reversed micelles in organic media

Cited by 67 publications

References 28 publications

Degradation of Bisphenol A by White Rot Fungi, Stereum hirsutum and Heterobasidium insulare, and Reduction of Its Estrogenic Activity

Degradation of Bisphenol A by White Rot Fungi, Stereum hirsutum and Heterobasidium insulare, and Reduction of Its Estrogenic Activity

Optimization of Laccase-mediated Benzo[a]pyrene Oxidation and the Bioremedial Application in Aged Polycyclic Aromatic Hydrocarbons-contaminated Soil

Ionic liquids as alternative co‐solvents for laccase: Study of enzyme activity and stability

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