Biodegradation of phenolic environmental pollutants by a surfactant–laccase complex in organic media

Michizoe, Junji; Ichinose, Hirofumi; Kamiya, Noriho; Maruyama, Tatsuo; Goto, Masahiro

doi:10.1263/jbb.99.642

Cited by 55 publications

(27 citation statements)

References 24 publications

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“…For instance, an interesting study was performed by Fukuda et al [20], in which they demonstrated that the BPA was metabolized by laccase in two kinds of compounds: one kind composed by high molecular weight compounds and another kind composed by low molecular weight compounds, one of which was identified as 4-isopropenylphenol by means of gas chromatography-mass spectrophotometry. The 4-isopropenylphenol as oxidative degradation product has been identified using chromatography mass-spectrometry also in other works reported in literature [21,22].…”

Section: Introductionmentioning

confidence: 68%

Laccase biosensor based on screen-printed electrode modified with thionine–carbon black nanocomposite, for Bisphenol A detection

Portaccio

Tuoro

Arduini

et al. 2013

Electrochimica Acta

146

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a b s t r a c tThe relevance of Bisphenol A (BPA) in human health is well-known. For this reason we designed and developed a biosensor based on a bionanocomposite (laccase-thionine-carbon black)-modified screenprinted electrode. Thionine, a commercially available dye, was used as electrochemical mediator coupled with a nanostructured carbon black. By means of cyclic voltammetry, the interaction of thionine adsorbed on modified screen printed electrode with laccase/BPA reaction products has been studied. In addition, the immobilization of laccase by physical adsorption on the surface of thionine-carbon black modified screen printed electrodes was investigated. The response of the biosensor has been optimized in terms of enzyme loading, pH and applied potential reaching a linear concentration range of 0.5-50 M, a sensitivity of 5.0 ± 0.1 nA/M and a limit-of-detection (LOD) of 0.2 M. The developed biosensor has been also challenged in tomato juice samples contained in metallic cans where release of BPA due to the epoxy resin coating can be assumed. A satisfactory recovery value comprised between 92% and 120% was obtained.

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Section: Introductionmentioning

confidence: 68%

Laccase biosensor based on screen-printed electrode modified with thionine–carbon black nanocomposite, for Bisphenol A detection

Portaccio

Tuoro

Arduini

et al. 2013

Electrochimica Acta

146

View full text Add to dashboard Cite

show abstract

“…It is yet not clear whether such reactions are nonenzymatic. Interestingly, 4-isopropylphenol and 4-isopropenylphenol were detected when BPA was incubated with fungal manganese peroxidase and laccase (17,24). In these cases, ipso attacks by these lignin-degrading enzymes cannot be excluded.…”

Section: Discussionmentioning

confidence: 99%

“…Microbial degradation of BPA leads to metabolites such as 4,4Ј-dihydroxy-␣-methylstilbene, 2,2-bis (4-hydroxyphenyl)-1-propanol, 2,2-bis(4-hydroxyphenyl)propanoic acid, and 2-(3,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)propane (32,37). In fungi, lignin-degrading enzymes such as manganese peroxidase and laccase are mainly involved in the biodegradation of BPA to polymerization products 4-isopropylphenol, 4-isopropenylphenol, and hexestrol (17,24).…”

mentioning

confidence: 99%

Degradation Pathway of Bisphenol A: Does ipso Substitution Apply to Phenols Containing a Quaternary α-Carbon Structure in the para Position?

Kolvenbach

Schlaich

Raoui

et al. 2007

Appl Environ Microbiol

103

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The degradation of bisphenol A and nonylphenol involves the unusual rearrangement of stable carboncarbon bonds. Some nonylphenol isomers and bisphenol A possess a quaternary ␣-carbon atom as a common structural feature. The degradation of nonylphenol in Sphingomonas sp. strain TTNP3 occurs via a type II ipso substitution with the presence of a quaternary ␣-carbon as a prerequisite. We report here a new degradation pathway of bisphenol A. Consequent to the hydroxylation at position C-4, according to a type II ipso substitution mechanism, the C-C bond between the phenolic moiety and the isopropyl group of bisphenol A is broken. Besides the formation of hydroquinone and 4-(2-hydroxypropan-2-yl)phenol as the main metabolites, further compounds resulting from molecular rearrangements consistent with a carbocationic intermediate were identified. Assays with resting cells or cell extracts of Sphingomonas sp. strain TTNP3 under an 18 O 2 atmosphere were performed. One atom of 18 O 2 was present in hydroquinone, resulting from the monooxygenation of bisphenol A and nonylphenol. The monooxygenase activity was dependent on both NADPH and flavin adenine dinucleotide. Various cytochrome P450 inhibitors had identical inhibition effects on the conversion of both xenobiotics. Using a mutant of Sphingomonas sp. strain TTNP3, which is defective for growth on nonylphenol, we demonstrated that the reaction is catalyzed by the same enzymatic system. In conclusion, the degradation of bisphenol A and nonylphenol is initiated by the same monooxygenase, which may also lead to ipso substitution in other xenobiotics containing phenol with a quaternary ␣-carbon.

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“…7,8) It has been reported that biodegradation of alkylphenol ethoxylates and alkylphenols stimulates production of biomarkers of estrogenic activity in male fish. 5,9,10) Many researchers have a great interest in oxidoreductases such as tyrosinase, [11][12][13][14][15] laccase, [16][17][18] and peroxidase, [19][20][21][22][23] because their industrial potentials are recognized in degradation and detoxification of recalcitrant environmental pollutions. The potential advantages of the enzymatic treatment include operation at low concentrations over wide pH and temperature ranges and the easy control process.…”

mentioning

confidence: 99%

Removal ofp-Alkylphenols from Aqueous Solutions by Combined Use of Mushroom Tyrosinase and Chitosan Beads

Yamada

Inoue

Akiba

et al. 2006

Bioscience, Biotechnology, and Biochemistry

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Biodegradation of phenolic environmental pollutants by a surfactant–laccase complex in organic media

Cited by 55 publications

References 24 publications

Laccase biosensor based on screen-printed electrode modified with thionine–carbon black nanocomposite, for Bisphenol A detection

Laccase biosensor based on screen-printed electrode modified with thionine–carbon black nanocomposite, for Bisphenol A detection

Degradation Pathway of Bisphenol A: Does ipso Substitution Apply to Phenols Containing a Quaternary α-Carbon Structure in the para Position?

Removal ofp-Alkylphenols from Aqueous Solutions by Combined Use of Mushroom Tyrosinase and Chitosan Beads

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