Degradation of Bisphenol A by the Lignin-Degrading Enzyme, Manganese Peroxidase, Produced by the White-rot Basidiomycete,<i>Pleurotus ostreatus</i>

Hirano, Toshitsugu; Honda, Yoshio; Watanabe, Takashi; Kuwahara, Masaaki

doi:10.1271/bbb.64.1958

Cited by 155 publications

(77 citation statements)

References 13 publications

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“…This finding requires more study in the future. Hirano et al 5) reported that the major metabolites of BPA treated with MnP from P. ostreatus were phenol, 4-isophenyl phenol, 4-isopropyl phenol, and hexestrol. Some phenolic compounds were also detected in this study, but the compounds were slightly different (data not shown).…”

Section: Resultsmentioning

confidence: 99%

“…It has been reported that MnP and laccase from Pleurotus osrteatus are able to degrade BPA and have the ability to ameliorate or eliminate the estrogenic activity of BPA. 5,6) However, studies on other lignin-degrading basidiomycetes for the degradation of BPA are few, and the reduction of the estrogenic activity of BPA by those fungi, if any, has not been clearly established.…”

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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%

mentioning

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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“…Yim et al (48) showed that in fungi BPA was metabolized to BPA-O-␤-D-glucopyranoside. Several investigators have also reported that lignin-degrading enzymes, including lignin peroxidase, manganese peroxidase, and/or laccase from basidiomycetes, react with BPA (6,9,34,44,45,46). However, it is not clear how these systems can degrade BPA into small molecules, because some of them also concomitantly produce polymerized BPA (34,45,46).…”

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Purification of Cytochrome P450 and Ferredoxin, Involved in Bisphenol A Degradation, from Sphingomonas sp. Strain AO1

Sasaki¹,

Akahira²,

Oshiman³

et al. 2005

Appl Environ Microbiol

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In a previous study (M. Sasaki, J. Maki, K. Oshiman, Y. Matsumura, and T. Tsuchido, Biodegradation 16:449-459, 2005), the cytochrome P450 monooxygenase system was shown to be involved in bisphenol A (BPA) degradation by Sphingomonas sp. strain AO1. In the present investigation, we purified the components of this monooxygenase, cytochrome P450 (P450 bisd ), ferredoxin (Fd bisd ), and ferredoxin reductase (Red bisd ). We demonstrated that P450 bisd and Fd bisd are homodimeric proteins with molecular masses of 102.3 and 19.1 kDa, respectively, by gel filtration chromatography analysis. Spectroscopic analysis of Fd bisd revealed the presence of a putidaredoxin-type [2Fe-2S] cluster. P450 bisd , in the presence of Fd bisd , Red bisd , and NADH, was able to convert BPA. The K m and k cat values for BPA degradation were 85 ؎ 4.7 M and 3.9 ؎ 0.04 min ؊1 , respectively. NADPH, spinach ferredoxin, and spinach ferredoxin reductase resulted in weak monooxygenase activity. These results indicated that the electron transport system of P450 bisd might exhibit strict specificity. Two BPA degradation products of the P450 bisd system were detected by high-performance liquid chromatography analysis and were thought to be 1,2-bis(4-hydroxyphenyl)-2-propanol and 2,2-bis(4-hydroxyphenyl)-1-propanol based on mass spectrometry-mass spectrometry analysis. This is the first report demonstrating that the cytochrome P450 monooxygenase system in bacteria is involved in BPA degradation.Bisphenol A (BPA) [2,2-bis(4-hydroxyphenyl)propane] is one of the industrially important compounds for production of polycarbonates, epoxy resins, and other plastics, and worldwide annual consumption of this compound is increasing. However, BPA is strongly suspected to be an endocrine disruptor (7,16,26) and exhibits slight or moderate toxicity in aquatic organisms (39). recently also reported that BPA is immunotoxic and reduces the nonspecific host defense to a level that causes acute toxicity in mice. Furthermore, Colborn and colleagues (4) reported that BPA is widely distributed in rivers, seas, streams, and soils. These reports have proposed that information about the biological conversion of BPA is useful for understanding the fate of this compound in the environment and also for establishing techniques to purge and remove BPA from the environment.Biological transformation of BPA has been reported by many researchers. In mammals, it has been established that BPA is converted to a glucuronide conjugate and a sulfate conjugate in rats (30, 31). In plants, cells of Eucalyptus perriniana and tobacco BY-2 metabolize BPA to its hydroxyl and/or glycosyl products (8, 24). However, it has been proposed that BPA in the environment is decomposed mainly by microorganisms (5, 39). Yim et al. (48) showed that in fungi BPA was metabolized to BPA-O-␤-D-glucopyranoside. Several investigators have also reported that lignin-degrading enzymes, including lignin peroxidase, manganese peroxidase, and/or laccase from basidiomycetes, react with BPA (6,9,34,44,45,46). However, i...

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“…; Atkinson et al 1995;Yokota et al 1999;Hirano et al 2000). However, little attention has been paid to the biological degradation of endocrine disrupting chemicals such as diphenyl compounds.…”

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confidence: 99%

Regioselective hydroxylation, reduction, and glycosylation of diphenyl compounds by cultured plant cells of Eucalyptus perriniana

Kondo

Shimoda

Miyahara

et al. 2006

Plant Biotechnology

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Degradation of Bisphenol A by the Lignin-Degrading Enzyme, Manganese Peroxidase, Produced by the White-rot Basidiomycete,Pleurotus ostreatus

Cited by 155 publications

References 13 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

Purification of Cytochrome P450 and Ferredoxin, Involved in Bisphenol A Degradation, from Sphingomonas sp. Strain AO1

Regioselective hydroxylation, reduction, and glycosylation of diphenyl compounds by cultured plant cells of Eucalyptus perriniana

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