scholarly journals Novel Ring Cleavage Products in the Biotransformation of Biphenyl by the Yeast Trichosporon mucoides

2001 ◽  
Vol 67 (9) ◽  
pp. 4158-4165 ◽  
Author(s):  
Rabea Sietmann ◽  
Elke Hammer ◽  
Michael Specht ◽  
Carl E. Cerniglia ◽  
Frieder Schauer
Keyword(s):  
Acetic Acid ◽  
Carboxylic Acid ◽  
High Performance ◽  
Fission Products ◽  
Transformation Product ◽  
Gas Chromatography Mass Spectrometry ◽  
Ring Cleavage ◽  
Aromatic Rings ◽  
Dead End ◽  
Ring Fission

ABSTRACT The yeast Trichosporon mucoides, grown on either glucose or phenol, was able to transform biphenyl into a variety of mono-, di-, and trihydroxylated derivatives hydroxylated on one or both aromatic rings. While some of these products accumulated in the supernatant as dead end products, the ortho-substituted dihydroxylated biphenyls were substrates for further oxidation and ring fission. These ring fission products were identified by high-performance liquid chromatography, gas chromatography-mass spectrometry, and nuclear magnetic resonance analyses as phenyl derivatives of hydroxymuconic acids and the corresponding pyrones. Seven novel products out of eight resulted from the oxidation and ring fission of 3,4-dihydroxybiphenyl. Using this compound as a substrate, 2-hydroxy-4-phenylmuconic acid, (5-oxo-3-phenyl-2,5-dihydrofuran-2-yl)acetic acid, and 3-phenyl-2-pyrone-6-carboxylic acid were identified. Ring cleavage of 3,4,4′-trihydroxybiphenyl resulted in the formation of [5-oxo-3-(4′-hydroxyphenyl)-2,5-dihydrofuran-2-yl]acetic acid, 4-(4′-hydroxyphenyl)-2-pyrone-6-carboxylic acid, and 3-(4′-hydroxyphenyl)-2-pyrone-6-carboxylic acid. 2,3,4-Trihydroxybiphenyl was oxidized to 2-hydroxy-5-phenylmuconic acid, and 4-phenyl-2-pyrone-6-carboxylic acid was the transformation product of 3,4,5-trihydroxybiphenyl. All these ring fission products were considerably less toxic than the hydroxylated derivatives.

scholarly journals Biotransformation of Biphenyl by Paecilomyces lilacinus and Characterization of Ring Cleavage Products

2001 ◽  
Vol 67 (4) ◽  
pp. 1551-1557 ◽  
Author(s):  
Manuela Gesell ◽  
Elke Hammer ◽  
Michael Specht ◽  
Wittko Francke ◽  
Frieder Schauer
Keyword(s):  
Acetic Acid ◽  
Carboxylic Acid ◽  
Fission Products ◽  
Paecilomyces Lilacinus ◽  
Proton Nuclear Magnetic Resonance ◽  
Ring Cleavage ◽  
Resonance Spectroscopy ◽  
Muconic Acid ◽  
Initial Oxidation ◽  
Gas Chromatography Mass Spectroscopy

ABSTRACT We examined the pathway by which the fungicide biphenyl is metabolized in the imperfect fungus Paecilomyces lilacinus. The initial oxidation yielded the three monohydroxylated biphenyls. Further hydroxylation occurred on the first and the second aromatic ring systems, resulting in the formation of five di- and trihydroxylated metabolites. The fungus could cleave the aromatic structures, resulting in the transformation of biphenyl viaortho-substituted dihydroxybiphenyl to six-ring fission products. All compounds were characterized by gas chromatography-mass spectroscopy and proton nuclear magnetic resonance spectroscopy. These compounds include 2-hydroxy-4-phenylmuconic acid and 2-hydroxy-4-(4′-hydroxyphenyl)-muconic acid, which were produced from 3,4-dihydroxybiphenyl and further transformed to the corresponding lactones 4-phenyl-2-pyrone-6-carboxylic acid and 4-(4′-hydroxyphenyl)-2-pyrone-6-carboxylic acid, which accumulated in large amounts. Two additional ring cleavage products were identified as (5-oxo-3-phenyl-2,5-dihydrofuran-2-yl)-acetic acid and [5-oxo-3-(4′-hydroxyphenyl)-2,5-dihydrofuran-2-yl]-acetic acid. We found that P. lilacinus has a high transformation capacity for biphenyl, which could explain this organism's tolerance to this fungicide.

scholarly journals Differential Degradation of Bicyclics with Aromatic and Alicyclic Rings by Rhodococcus sp. Strain DK17

2011 ◽  
Vol 77 (23) ◽  
pp. 8280-8287 ◽  
Author(s):  
Dockyu Kim ◽  
Miyoun Yoo ◽  
Ki Young Choi ◽  
Beom Sik Kang ◽  
Tai Kyoung Kim ◽  
...  
Keyword(s):  
Gas Chromatography Mass Spectrometry ◽  
Ring Cleavage ◽  
Content Type ◽  
Aromatic Hydroxylation ◽  
Dead End ◽  
Nuclear Magnetic Resonance Spectrometry ◽  
Magnetic Resonance Spectrometry ◽  
Differential Degradation ◽  
Unique Ability ◽  
Rhodococcus Sp

ABSTRACTThe metabolically versatileRhodococcussp. strain DK17 is able to grow on tetralin and indan but cannot use their respective desaturated counterparts, 1,2-dihydronaphthalene and indene, as sole carbon and energy sources. Metabolite analyses by gas chromatography-mass spectrometry and nuclear magnetic resonance spectrometry clearly show that (i) themeta-cleavage dioxygenase mutant strain DK180 accumulates 5,6,7,8-tetrahydro-1,2-naphthalene diol, 1,2-indene diol, and 3,4-dihydro-naphthalene-1,2-diol from tetralin, indene, and 1,2-dihydronaphthalene, respectively, and (ii) when expressed inEscherichia coli, the DK17o-xylene dioxygenase transforms tetralin, indene, and 1,2-dihydronaphthalene into tetralincis-dihydrodiol, indan-1,2-diol, andcis-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene, respectively. Tetralin, which is activated by aromatic hydroxylation, is degraded successfully via the ring cleavage pathway to support growth of DK17. Indene and 1,2-dihydronaphthalene do not serve as growth substrates because DK17 hydroxylates them on the alicyclic ring and further metabolism results in a dead-end metabolite. This study reveals that aromatic hydroxylation is a prerequisite for proper degradation of bicyclics with aromatic and alicyclic rings by DK17 and confirms the unique ability of the DK17o-xylene dioxygenase to perform distinct regioselective hydroxylations.

scholarly journals Degradation of Benzo[a]pyrene by Mycobacterium vanbaalenii PYR-1

2004 ◽  
Vol 70 (1) ◽  
pp. 340-345 ◽  
Author(s):  
Joanna D. Moody ◽  
James P. Freeman ◽  
Peter P. Fu ◽  
Carl E. Cerniglia
Keyword(s):  
High Performance ◽  
Culture Media ◽  
Optical Purity ◽  
Fission Products ◽  
Reversed Phase ◽  
Environmental Pollutant ◽  
Ring Fission ◽  
Uv Visible ◽  
Derivatives Of ◽  
Absolute Stereochemistry

ABSTRACT Metabolism of the environmental pollutant benzo[a]pyrene in the bacterium Mycobacterium vanbaalenii PYR-1 was examined. This organism initially oxidized benzo[a]pyrene with dioxygenases and monooxygenases at C-4,5, C-9,10, and C-11,12. The metabolites were separated by reversed-phase high-performance liquid chromatography (HPLC) and characterized by UV-visible, mass, nuclear magnetic resonance, and circular dichroism spectral analyses. The major intermediates of benzo[a]pyrene metabolism that had accumulated in the culture media after 96 h of incubation were cis-4,5-dihydro-4,5-dihydroxybenzo[a]pyrene (benzo[a]pyrene cis-4,5-dihydrodiol), cis-11,12-dihydro-11,12-dihydroxybenzo[a]pyrene (benzo[a]pyrene cis-11,12-dihydrodiol), trans-11,12-dihydro-11,12-dihydroxybenzo[a]pyrene (benzo[a]pyrene trans-11,12-dihydrodiol), 10-oxabenzo[def]chrysen-9-one, and hydroxymethoxy and dimethoxy derivatives of benzo[a]pyrene. The ortho-ring fission products 4-formylchrysene-5-carboxylic acid and 4,5-chrysene-dicarboxylic acid and a monocarboxylated chrysene product were formed when replacement culture experiments were conducted with benzo[a]pyrene cis-4,5-dihydrodiol. Chiral stationary-phase HPLC analysis of the dihydrodiols indicated that benzo[a]pyrene cis-4,5-dihydrodiol had 30% 4S,5R and 70% 4R,5S absolute stereochemistry. Benzo[a]pyrene cis-11,12-dihydrodiol adopted an 11S,12R conformation with 100% optical purity. The enantiomeric composition of benzo[a]pyrene trans-11,12-dihydrodiol was an equal mixture of 11S,12S and 11R,12R molecules. The results of this study, in conjunction with those of previously reported studies, extend the pathways proposed for the bacterial metabolism of benzo[a]pyrene. Our study also provides evidence of the stereo- and regioselectivity of the oxygenases that catalyze the metabolism of benzo[a]pyrene in M. vanbaalenii PYR-1.

A New Intermediate in the Mineralization of 3,4-Dichloroaniline by the White Rot FungusPhanerochaete chrysosporium

1998 ◽  
Vol 64 (9) ◽  
pp. 3305-3312 ◽  
Author(s):  
Heinrich Sandermann ◽  
Werner Heller ◽  
Norbert Hertkorn ◽  
Enamul Hoque ◽  
Dietmar Pieper ◽  
...  
Keyword(s):  
High Performance Liquid Chromatography ◽  
Liquid Chromatography ◽  
Mass Spectroscopy ◽  
High Performance ◽  
Culture Media ◽  
White Rot ◽  
Ring Cleavage ◽  
Resonance Spectroscopy ◽  
Dead End ◽  
C And N

ABSTRACT Phanerochaete chrysosporium ATCC 34541 has been reported to be unable to mineralize 3,4-dichloroaniline (DCA). However, high mineralization is now shown to occur when a fermentation temperature of 37° and gassing with oxygen are used. Mineralization did not correlate with lignin peroxidase activity. The latter was high under C limitation and low under N limitation, whereas the reverse was true for mineralization. The kinetics of DCA metabolism was studied in low-N and low-C and C- and N-rich culture media by metabolite analysis and 14CO2determination. In all cases, DCA disappeared within 2 days, and a novel highly polar conjugate termed DCAX accumulated in the growth medium. This metabolite was a dead-end product under C and N enrichment. In oxygenated low-C medium and in much higher yield in oxygenated low-N medium, DCAX was converted to DCA-succinimide and then mineralized. DCAX was purified by high-performance liquid chromatography and identified asN-(3,4-dichlorophenyl)-α-ketoglutaryl-δ-amide by high-performance liquid chromatography and mass spectroscopy, gas chromatography and mass spectroscopy, and nuclear magnetic resonance spectroscopy. The formation of conjugate intermediates is proposed to facilitate mineralization because the sensitive amino group of DCA needs protection so that ring cleavage rather than oligomerization can occur.

scholarly journals Identification of New Metabolites of Bacterial Transformation of Indole by Gas Chromatography-Mass Spectrometry and High Performance Liquid Chromatography

2014 ◽  
Vol 2014 ◽  
pp. 1-5 ◽  
Author(s):  
Pankaj Kumar Arora ◽  
Hanhong Bae
Keyword(s):  
Mass Spectrometry ◽  
Gas Chromatography ◽  
High Performance Liquid Chromatography ◽  
Acetic Acid ◽  
Liquid Chromatography ◽  
High Performance ◽  
Glyoxylic Acid ◽  
Gas Chromatography Mass Spectrometry ◽  
Chromatography Mass Spectrometry ◽  
Indole 3 Acetic Acid

Arthrobactersp. SPG transformed indole completely in the presence of an additional carbon source. High performance liquid chromatography and gas chromatography-mass spectrometry detected indole-3-acetic acid, indole-3-glyoxylic acid, and indole-3-aldehyde as biotransformation products. This is the first report of the formation of indole-3-acetic acid, indole-3-glyoxylic acid, and indole-3-aldehyde from indole by any bacterium.

scholarly journals Anaerobic Naphthalene Degradation by a Sulfate-Reducing Enrichment Culture

2000 ◽  
Vol 66 (7) ◽  
pp. 2743-2747 ◽  
Author(s):  
Rainer U. Meckenstock ◽  
Eva Annweiler ◽  
Walter Michaelis ◽  
Hans H. Richnow ◽  
Bernhard Schink
Keyword(s):  
Mass Spectra ◽  
Phenylacetic Acid ◽  
Enrichment Culture ◽  
Fission Products ◽  
Substrate Utilization ◽  
Gas Chromatography Mass Spectrometry ◽  
Ring Cleavage ◽  
Sulfate Reducing ◽  
Naphthalene Degradation ◽  
Naphthoic Acid

ABSTRACT Anaerobic naphthalene degradation by a sulfate-reducing enrichment culture was studied by substrate utilization tests and identification of metabolites by gas chromatography-mass spectrometry. In substrate utilization tests, the culture was able to oxidize naphthalene, 2-methylnaphthalene, 1- and 2-naphthoic acids, phenylacetic acid, benzoic acid, cyclohexanecarboxylic acid, and cyclohex-1-ene-carboxylic acid with sulfate as the electron acceptor. Neither hydroxylated 1- or 2-naphthoic acid derivatives and 1- or 2-naphthol nor the monoaromatic compounds ortho-phthalic acid, 2-carboxy-1-phenylacetic acid, and salicylic acid were utilized by the culture within 100 days. 2-Naphthoic acid accumulated in all naphthalene-grown cultures. Reduced 2-naphthoic acid derivatives could be identified by comparison of mass spectra and coelution with commercial reference compounds such as 1,2,3,4-tetrahydro-2-naphthoic acid and chemically synthesized decahydro-2-naphthoic acid. 5,6,7,8-Tetrahydro-2-naphthoic acid and octahydro-2-naphthoic acid were tentatively identified by their mass spectra. The metabolites identified suggest a stepwise reduction of the aromatic ring system before ring cleavage. In degradation experiments with [1-13C]naphthalene or deuterated D8-naphthalene, all metabolites mentioned derived from the introduced labeled naphthalene. When a [13C]bicarbonate-buffered growth medium was used in conjunction with unlabeled naphthalene, 13C incorporation into the carboxylic group of 2-naphthoic acid was shown, indicating that activation of naphthalene by carboxylation was the initial degradation step. No ring fission products were identified.

Biodegradation of carbazole byRalstoniasp. RJGII.123 isolated from a hydrocarbon contaminated soil

2000 ◽  
Vol 46 (3) ◽  
pp. 269-277 ◽  
Author(s):  
Joanne Schneider ◽  
Robert J Grosser ◽  
Koka Jayasimhulu ◽  
Weiling Xue ◽  
Brian Kinkle ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Mass Spectroscopy ◽  
Contaminated Soils ◽  
High Performance ◽  
Coal Gasification ◽  
Ring Cleavage ◽  
Gasification Plant ◽  
Gas Chromatography Mass Spectroscopy ◽  
Hazardous Compounds ◽  
High Resolution Mass Spectroscopy

The use of microorganisms for bioremediation of contaminated soils may be enhanced with an understanding of the pathways involved in their degradation of hazardous compounds. Ralstonia sp. strain RJGII.123 was isolated from soil located at a former coal gasification plant, based on its ability to mineralize carbazole, a three-ring N-heterocyclic pollutant. Experiments were carried out with strain RJGII.123 and14C-carbazole (2 mg/L and 500 mg/L) as the sole organic carbon source. At 15 days, 80% of the 2 mg/L carbazole was recovered as CO2, and <1% remained as undegraded carbazole, while 24% of the 500 mg/L carbazole was recovered as CO2and ~70% remained as undegraded carbazole. Several stable intermediates were formed during this time. These intermediates were separated by high performance liquid chromatography (HPLC) and were characterized using high resolution mass spectroscopy (HR-MS) and gas chromatography - mass spectroscopy (GC-MS). At least 10 ring cleavage products of carbazole degradation were identified; four of these were confirmed as anthranilic acid, indole-2-carboxylic acid, indole-3-carboxylic acid, and (1H)-4-quinolinone by comparison with standards. These data indicate that strain RJGII.123 shares aspects of carbazole degradation with previously described Pseudomonas spp., and may be useful in facilitating the bioremediation of NHA from contaminated soils.Key words: mineralization, biodegradation, N-heterocyclic aromatic hydrocarbons, carbazole.

Cometabolism of 1,1-Dichloro-2,2-Bis(4-Chlorophenyl)Ethylene by Pseudomonas acidovorans M3GY Grown on Biphenyl

1998 ◽  
Vol 64 (6) ◽  
pp. 2141-2146 ◽  
Author(s):  
Anthony G. Hay ◽  
Dennis D. Focht
Keyword(s):  
Sole Carbon Source ◽  
Gas Chromatography Mass Spectrometry ◽  
Infrared Spectrometry ◽  
Breakdown Product ◽  
Fourier Transform Infrared Spectrometry ◽  
Dead End ◽  
Ring Fission ◽  
Balance Analysis ◽  
Pseudomonas Acidovorans ◽  
Mass Balance Analysis

ABSTRACT 1,1-Dichloro-2,2-bis(4-chlorophenyl)ethylene (DDE), a toxic breakdown product of 1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane (DDT), has traditionally been viewed as a dead-end metabolite: there are no published reports detailing enzymatic ring fission of DDE by bacteria in either soil or pure culture. In this study, we investigated the ability of Pseudomonas acidovorans M3GY to transform DDE and its unchlorinated analog, 1,1-diphenylethylene (DPE). While strain M3GY could grow on DPE, cells grown on DPE as a sole carbon source could not degrade DDE. Cells grown on biphenyl, however, did degrade DDE. Mass balance analysis of [14C]DDE showed transformation of more than 40% of the recoverable radioactivity. Nine chlorinated metabolites produced from DDE were identified by gas chromatography-mass spectrometry–Fourier-transform infrared spectrometry (GC-MS-FTIR) from cultures grown on biphenyl. Recovery of these metabolites demonstrates that biphenyl-grown cells degrade DDE through a meta-fission pathway. This study provides a possible model for biodegradation of DDE in soil by biphenyl-utilizing bacteria.

Aromatic Degradation in Yeast Rhodotorula rubra

1992 ◽  
Vol 26 (3-4) ◽  
pp. 773-781 ◽  
Author(s):  
K. Katayama-Hirayama ◽  
S. Tobita ◽  
K. Hirayama
Keyword(s):  
High Performance ◽  
Hplc Analysis ◽  
Protocatechuic Acid ◽  
Gas Chromatography Mass Spectrometry ◽  
Ring Cleavage ◽  
Cell Free Extract ◽  
Muconic Acid ◽  
Yeast Strains ◽  
Metabolic Sequence ◽  
Aromatic Degradation

Aromatic degradation by two yeast strains of Rhodotorula (R.) rubra was examined. Separation and identification of phenol and protocatechuic acid (PCA) metabolites were carried out using high performance liquid chromatography (HPLC) and gas chromatography/mass spectrometry (GC/MS). For HPLC analysis of β -ketoadipic acid, 2,4-dinitrophenylhydrazone derivative was prepared. For GC/MS analysis, metabolites in the cultured broth were extracted with ethyl acetate and trimethylsilylated by N-o-bis(trimethylsilyl)acetoamide. Based on HPLC and GC/MS analyses, phenol metabolites were identified as catechol, eis, cis-muconic acid, muconolactone, β -ketoadipate enol-lactone and β -ketoadipic acid. β -Ketoadipic acid was also found in the PCA metabolites by crude cell-free extract. From the results obtained in this study, a metabolic sequence for aromatic degradation is proposed. Phenol may be hydroxylated to form catechol prior to ring cleavage, and catechol may be further oxidized to eis, cis-muconic acid, muconolactone, β -ketoadipate enol-lactone and β -ketoadipic acid. Catechol branch as well as protocatechuate branch in β -ketoadipate pathway may exist in R. rubra.

scholarly journals Use of Whole Cells of Pseudomonas aeruginosa for Synthesis of the Antioxidant Hydroxytyrosol via Conversion of Tyrosol

2004 ◽  
Vol 70 (4) ◽  
pp. 2105-2109 ◽  
Author(s):  
N. Allouche ◽  
M. Damak ◽  
R. Ellouz ◽  
S. Sayadi
Keyword(s):  
Pseudomonas Aeruginosa ◽  
Acetic Acid ◽  
High Performance ◽  
Sole Source ◽  
Gas Chromatography Mass Spectrometry ◽  
Growth State ◽  
Whole Cells ◽  
Resting Cell ◽  
Alternative Approach ◽  
First Time

ABSTRACT For the first time, a soil bacterium, designated Pseudomonas aeruginosa, was isolated based on its ability to grow on tyrosol as a sole source of carbon and energy. During growth on tyrosol, this strain was capable of promoting the formation of a significant amount of hydroxytyrosol and trace quantities of parahydroxyphenyl acetic acid and 3,4-dihydroxyphenyl acetic acid. The products were confirmed by high-performance liquid chromatography and gas chromatography-mass spectrometry analyses. Using an optimized tyrosol concentration of 2 g liter−1, the maximal hydroxytyrosol yield (80%) was achieved after a 7-h reaction in a growth experiment. To enhance the formation of hydroxytyrosol and prevent its degradation, a resting-cell method using P. aeruginosa was performed. The growth state of the culture utilized for biomass production, the carbon source on which the biomass was grown, the concentration of the biomass, and the amount of tyrosol that was treated were optimized. The optimal yield of hydroxytyrosol (96%) was obtained after a 7-h reaction using 4 g of tyrosol liter−1 and 5 g of cells liter−1 pregrown on tyrosol and harvested at the end of the exponential phase. This proposed procedure is an alternative approach to obtain hydroxytyrosol in an environmentally friendly way. In addition, the reaction is easy to perform and can be adapted to a bioreactor for industrial purposes.

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