Initial oxidative and subsequent conjugative metabolites produced during the metabolism of phenanthrene by fungi

Casillas, Robert P.; Crow, Sidney A.; Heinze, Thomas M.; Deck, Joanna; Cerniglia, Carl E.

doi:10.1007/bf01570023

Cited by 55 publications

(33 citation statements)

References 30 publications

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“…In nonligninolytic conditions, metabolites from Phe were identified as phenanthrene trans-9,10-dihydrodiol, phenanthrene trans-3,4-dihydrodiol, 9-phenanthrol, 3-phen-anthrol, 4-phenanthrol, suggesting the involvement of monooxygenase and epoxide hydrolase activity in the initial oxidation and hydration of Phe by P. chrysosporium since peroxidases were not detected in the culture medium [Sutherland et al, 1991]. Casillas et al [1996] reported 1-phenanthrol, 2-phenanthrol, and phenanthrene trans-9,10-dihydrodiol as major metabolites from the metabolism of Phe by A. niger . Other authors have reported that Phe was metabolized by A. niger into small amounts of 1-and 2-phenanthrol, and also as major metabolite in the ethyl acetate extract, 1-methoxyphenanthrene; its RT was of 36.7 min, indicating a metabolite less polar than Phe [Sack et al, 1997].…”

Section: Discussionmentioning

confidence: 99%

Heterologous Expression of Manganese Peroxidase in Aspergillus niger and Its Effect on Phenanthrene Removal from Soil

Cortés-Espinosa¹,

Absalón²,

Sanchez³

et al. 2011

Microb Physiol

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A strain of Aspergillus niger, previously isolated from sugarcane bagasse because of its capacity to degrade phenanthrene in soil by solid culture, was used to express a manganese peroxidase gene (mnp1) from Phanerochaete chrysosporium, aiming at increasing its polycyclic aromatic hydrocarbons degradation capacity. Transformants were selected based on their resistance to hygromycin B and the discoloration induced on Poly R-478 dye by the peroxidase activity. The recombinant A. niger SBC2-T3 strain developed MnP activity and was able to remove 95% of the initial phenanthrene (400 ppm) from a microcosm soil system after 17 days, whereas the wild strain removed 72% under the same conditions. Transformation success was confirmed by PCR amplification using gene-specific primers, and a single fragment (1,348 bp long, as expected) of the recombinant mnp1 was amplified in the DNA from transformants, which was absent from the parental strain.

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Section: Discussionmentioning

confidence: 99%

Heterologous Expression of Manganese Peroxidase in Aspergillus niger and Its Effect on Phenanthrene Removal from Soil

Cortés-Espinosa¹,

Absalón²,

Sanchez³

et al. 2011

Microb Physiol

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“…The oxidative products are hydrated by epoxide hydrolase to the corresponding trans-dihydrodiols or isomerized to phenols (Bruice et al 1976;Cerniglia and Heitkamp 1989;Sutherland et al 1991). Formation of the trans-dihydrodiols and phenols has also been found in most cases of phenanthrene metabolism by fungi (Casillas et al 1996;Sutherland et al 1993), although involvement of fungal P450s was only demonstrated in a few species (Bezalel et al 1997).…”

Section: Introductionmentioning

confidence: 96%

Novel evidence of cytochrome P450-catalyzed oxidation of phenanthrene in Phanerochaete chrysosporium under ligninolytic conditions

et al. 2010

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The presence of cytochrome P450 and P450-mediated phenanthrene oxidation in the white rot fungus Phanerochaete chrysosporium under ligninolytic condition was first demonstrated in this study. The carbon monoxide difference spectra indicated induction of P450 (130 pmol mg(-1) in the microsomal fraction) by phenanthrene. The microsomal P450 degraded phenanthrene with a NADPH-dependent activity of 0.44 ± 0.02 min(-1). One of major detectable metabolites of phenanthrene in the ligninolytic cultures and microsomal fractions was identified as phenanthrene trans-9,10-dihydrodiol. Piperonyl butoxide, a P450 inhibitor which had no effect on manganese peroxidase activity, significantly inhibited phenanthrene degradation and the trans-9,10-dihydrodiol formation in both intact cultures and microsomal fractions. Furthermore, phenanthrene was also efficiently degraded by the extracellular fraction with high manganese peroxidase activity. These results indicate important roles of both manganese peroxidase and cytochrome P450 in phenanthrene metabolism by ligninolytic P. chrysosporium.

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“…Probably they are of importance for the detoxification of some specific lignin degradation products (14,15,17). Furthermore, they seem to be involved in the detoxification of xenobiotics, like polycyclic aromatic hydrocarbons (4,5,32) and dibenzothiophen derivatives (12), or 2-chlorobenzylalcohol (1) and 2,4-dichlorophenol (28). From unhalogenated diphenyl ether and some halogenated derivatives, ring cleavage products, like 6-carboxy-4-phenoxy-2-pyrone, are formed by T. versicolor after several hydroxylations (10,11).…”

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confidence: 99%

Transformation of Triclosan by Trametes versicolor and Pycnoporus cinnabarinus

Hundt

Martin

Hammer

et al. 2000

Appl Environ Microbiol

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We investigated the ability of Trametes versicolor and Pycnoporous cinnabarinus to metabolize triclosan. T. versicolor produced three metabolites, 2-O-(2,4,4-trichlorodiphenyl ether)-␤-D-xylopyranoside, 2-O-(2,4,4-trichlorodiphenyl ether)-␤-D-glucopyranoside, and 2,4-dichlorophenol. P. cinnabarinus converted triclosan to 2,4,4-trichloro-2-methoxydiphenyl ether and the glucoside conjugate known from T. versicolor. The conjugates showed a distinctly lower cytotoxic and microbicidal activity than triclosan did.Triclosan (2,4,4Ј-trichloro-2Ј-hydroxydiphenyl ether; synonym, Irgasan DP 300) has been used as an antimicrobial compound in deodorants (6), soaps, and dentifrices (2, 8, 36) for many years. The mode of action of triclosan has, however, remained unclear. Recently, it was shown that triclosan blocks one step in bacterial fatty acid synthesis (20,24,25). Due to its widespread use, triclosan and some of its derivatives can be detected in the environment (22,26,27). The chemical structure of triclosan is related to many compounds which are wellknown as xenobiotics, such as halogenated diphenyl ethers. Though some reports on the transformation of halogenated diphenyl ether compounds by bacteria are available (21, 30), triclosan itself was not metabolized by the strains tested (31) or by Rhodococcus chlorophenolicus, which can methylate several other chlorinated hydroxydiphenyl ethers (34). Several hydroxylated metabolites, as well as 2,4-dichlorophenol and 4-chlorocatechol, are formed from triclosan by rats (33), while guinea pigs mostly form glucuronide conjugates (3). No reports exist concerning the degradation of triclosan by fungi. The white rot fungi Trametes versicolor and Pycnoporus cinnabarinus are capable of transforming diphenyl ethers, like 4-chlorodiphenyl ether, up to ring cleavage (10, 11). Hydroxylated biarylic ethers are transformed to oligomerization products by laccases secreted by these strains (13). In this paper we describe some biotransformation reactions of triclosan by the white rot fungi T. versicolor and P. cinnabarinus.The strains T. versicolor SBUG-M 1050, T. versicolor DSM 11269, T. versicolor DSM 11309, and P. cinnabarinus SBUG-M 1044 were cultivated in a nitrogen-rich (8 mM) medium. The cultures for transformation were prepared with 0.25 mM (wt/ vol) triclosan (Mallinckrodt-Baker, Griesheim, Germany) and inoculated and incubated as described previously (10, 11).Cell extracts were prepared from a 3-day culture of T. versicolor, harvested by centrifugation, and washed twice with 50 mM ice-cold Tris-HCl buffer (pH 7.5). Cells were broken at 1,000 lb/in 2 using a French press (SLM Amnico, Rochester, N.Y.) and were immediately resuspended in Tris-HCl buffer. The cell extracts (4 ml, approximately 5 mg of protein ml Ϫ1 ) were incubated at 30°C for 24 h with 2.88 mg of triclosan and 1 mg each of UDP-xylose, UDP-glucose, and UDP-glucuronic acid (Sigma, Deisenhofen, Germany).Analysis of metabolites in culture supernatants and purification of intermediates were done by high-performance liquid ...

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Initial oxidative and subsequent conjugative metabolites produced during the metabolism of phenanthrene by fungi

Cited by 55 publications

References 30 publications

Heterologous Expression of Manganese Peroxidase in Aspergillus niger and Its Effect on Phenanthrene Removal from Soil

Heterologous Expression of Manganese Peroxidase in Aspergillus niger and Its Effect on Phenanthrene Removal from Soil

Novel evidence of cytochrome P450-catalyzed oxidation of phenanthrene in Phanerochaete chrysosporium under ligninolytic conditions

Transformation of Triclosan by Trametes versicolor and Pycnoporus cinnabarinus

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