The Metabolism of Tryptophan and 7-Chlorotryptophan in<i>Pseudomonas pyrrocinia</i>and<i>Pseudomonas aureofaciens</i>

Lübbe, Claus; Pée, K.-H. Van; Salcher, Olga; Lingens, Franz

doi:10.1515/bchm2.1983.364.1.447

Cited by 18 publications

(6 citation statements)

References 11 publications

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“…Indole-3-carboxylic acid, an indolic compound derived from the bacterial metabolites of tryptophan ( Konopelski et al, 2019 ), was also found to be elevated in the plasma samples of AD patients. A branch of the tryptophan metabolic fate through the bacterial pathway is to be transaminated to indole-3-pyruvate, transformed to series downstream indole derivatives such as indole-3-acetaldehyde, indole-3-acetic acid, indole-3-carboxaldehyde, and indole-3-carboxylic acid, followed by spontaneous decarboxylation of indole-3-carboxylic acid to indole ( Lübbe et al, 1983 ; Agus et al, 2018 ). Our findings suggested a potential regulatory role of gut microbiota in dietary tryptophan metabolism in AD, possibly referring to the changes in gut permeability ( Leclercq et al, 2014 ; Zhu et al, 2021b ).…”

Section: Discussionmentioning

confidence: 99%

Combining Metabolomics and Interpretable Machine Learning to Reveal Plasma Metabolic Profiling and Biological Correlates of Alcohol-Dependent Inpatients: What About Tryptophan Metabolism Regulation?

Zhu

Huang

et al. 2021

Front. Mol. Biosci.

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Alcohol dependence (AD) is a condition of alcohol use disorder in which the drinkers frequently develop emotional symptoms associated with a continuous alcohol intake. AD characterized by metabolic disturbances can be quantitatively analyzed by metabolomics to identify the alterations in metabolic pathways. This study aimed to: i) compare the plasma metabolic profiling between healthy and AD-diagnosed individuals to reveal the altered metabolic profiles in AD, and ii) identify potential biological correlates of alcohol-dependent inpatients based on metabolomics and interpretable machine learning. Plasma samples were obtained from healthy (n = 42) and AD-diagnosed individuals (n = 43). The plasma metabolic differences between them were investigated using liquid chromatography-tandem mass spectrometry (AB SCIEX® QTRAP 4500 system) in different electrospray ionization modes with scheduled multiple reaction monitoring scans. In total, 59 and 52 compounds were semi-quantitatively measured in positive and negative ionization modes, respectively. In addition, 39 metabolites were identified as important variables to contribute to the classifications using an orthogonal partial least squares-discriminant analysis (OPLS-DA) (VIP > 1) and also significantly different between healthy and AD-diagnosed individuals using univariate analysis (p-value < 0.05 and false discovery rate < 0.05). Among the identified metabolites, indole-3-carboxylic acid, quinolinic acid, hydroxy-tryptophan, and serotonin were involved in the tryptophan metabolism along the indole, kynurenine, and serotonin pathways. Metabolic pathway analysis revealed significant changes or imbalances in alanine, aspartate, glutamate metabolism, which was possibly the main altered pathway related to AD. Tryptophan metabolism interactively influenced other metabolic pathways, such as nicotinate and nicotinamide metabolism. Furthermore, among the OPLS-DA-identified metabolites, normetanephrine and ascorbic acid were demonstrated as suitable biological correlates of AD inpatients from our model using an interpretable, supervised decision tree classifier algorithm. These findings indicate that the discriminatory metabolic profiles between healthy and AD-diagnosed individuals may benefit researchers in illustrating the underlying molecular mechanisms of AD. This study also highlights the approach of combining metabolomics and interpretable machine learning as a valuable tool to uncover potential biological correlates. Future studies should focus on the global analysis of the possible roles of these differential metabolites and disordered metabolic pathways in the pathophysiology of AD.

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Section: Discussionmentioning

confidence: 99%

Combining Metabolomics and Interpretable Machine Learning to Reveal Plasma Metabolic Profiling and Biological Correlates of Alcohol-Dependent Inpatients: What About Tryptophan Metabolism Regulation?

Zhu

Huang

et al. 2021

Front. Mol. Biosci.

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“…This enzyme was detected as a bromoperoxidase by the monochlorodimedone assay developed by Hager et al (2). Monochlorodimedone was not chlorinated by the chloroperoxidase from P. pyrrocinia; however, when indole was used as a substrate, it was chlorinated to 7-chloroindole (21), a substance which is known to be produced by P. pyrrocinia (8). Therefore, it was thought to be possible that the bromoperoxidase isolated from S. aureofaciens Tu24 could be a chloroperoxidase, too, but only if a more "natural" substrate than monochlorodimedone was used.…”

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confidence: 99%

Molecular cloning and high-level expression of a bromoperoxidase gene from Streptomyces aureofaciens Tü24

Pée

1988

J Bacteriol

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A bromoperoxidase gene was cloned from Streptomyces aureofaciens Tu24 into Streptomyces lividans TK64 by using the promoter-probe vector pIJ486. Subcloning of DNA from the original, unstable clone allowed the gene to be localized to a 1.7-kilobase (kb) fragment of DNA. Southern blotting showed that the cloned 1.7-kb insert hybridized to a 4.3-kb fragment in an SstI digest of S. aureofaciens Tu24 total DNA. The 1.7-kb insert was shown to code for a protein with the electrophoretic properties of the subunits of the nonheme bromoperoxidase isolated from S. aureofaciens Tu24.-The protein produced by S. lividans TK64 transformed with pHM621, which contained an 8.0-kb insert, was shown to be identical to the S. aureofaciens Tu24 bromoperoxidase in terms of its electrophoretic mobility on denaturing and nondenaturing polyacrylamide gels and its NH2-terminal amino acid sequence. The bromoperoxidase was overproduced (up to 180 times) by S.lividans TK64 containing pHM621. Based on the heat stability of the S. aureofaciens Tu24 bromoperoxidase, a new and simple purification procedure with very high yields was developed.Streptomyces aureofaciens Tu24 produces the antibiotic 7-chlorotetracycline. The incorporation of chlorine during the biosynthesis of 7-chlorotetracycline is believed to be catalyzed by a chloroperoxidase (12). However, only a brominating enzyme, a bromoperoxidase, could be isolated from this strain (18). Bromoperoxidases have been isolated from other chlorometabolite-producing bacteria as well (16,17,20). The only bacterial chloroperoxidase known until now was detected in Pseudomonas pyrrocinia (2). This enzyme was detected as a bromoperoxidase by the monochlorodimedone assay developed by Hager et al. (2). Monochlorodimedone was not chlorinated by the chloroperoxidase from P. pyrrocinia; however, when indole was used as a substrate, it was chlorinated to 7-chloroindole (21), a substance which is known to be produced by P. pyrrocinia (8). Therefore, it was thought to be possible that the bromoperoxidase isolated from S. aureofaciens Tu24 could be a chloroperoxidase, too, but only if a more "natural" substrate than monochlorodimedone was used. To check this, large amounts of the enzyme are needed, and thus I decided to try to clone the bromoperoxidase gene of S. aureofaciens Tu24. This report describes the cloning of the S. aureofaciens Tu24 bromoperoxidase gene in S. lividans TK64. MATERIALS AND METHODSBacterial strains and culture conditions. S. lividans TK64 and S. lividans TK24 containing the promoter-probe plasmid vector pIJ486 (19) were kindly supplied by D. A. Hopwood, Norwich, England, and S. aureofaciens Tu24 was provided by H. Zahner, Tubingen, Federal Republic of Germany (FRG). These strains were cultured on agar plates containing 2% (wt/vol) soybean flour and 2% (wt/vol) mannitol. This medium was also used as a liquid medium when cells were grown for the production of bromoperoxidase. Other media used were yeast extract-malt extract plus 34% (wt/vol) sucrose (YEME) (1); R2YE medium (14); P medium ...

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“…The only other bacterial bromoperoxidase thus far known showed its brominating activity only after partial purification too (18). The isolated bromoperoxidase probably is responsible for the formation of several brominated phenylpyrrole derivatives with antifungal activity and brominated indole derivatives which have been isolated from Pseudomonas aureofaciens (10,19). A comparison of bromoperoxidase from Pseudomonas aureofaciens with algal bromoperoxidases reveals some similarities and differences (Table 2).…”

Section: Resultsmentioning

confidence: 99%

“…However, to date, only one haloperoxidase has been detected in a halometabolite-producing procaryote (18). In this paper we report on the purification of a bromoperoxidase from Pseudomonas aureofaciens, a bacterium that produces several chlorineand bromine-containing metabolites (8,10,13,19).…”

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confidence: 99%

Purification of bromoperoxidase from Pseudomonas aureofaciens

Pée¹,

Lingens²

1985

J Bacteriol

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A Bromoperoxidase has been isolated and purified from Pseudomonas aureofaciens ATCC 15926 mutant strain ACN. The purified enzyme was homogeneous as determined by polyacrylamide gel electrophoresis and ultracentrifugation. This bromoperoxidase can utilize bromide ions in the presence of hydrogen peroxide and a halogen acceptor for the catalytic formation of carbon-halogen bonds. The homogeneous enzyme also has peroxidase and catalase activity. Based on the results from gel filtration and ultracentrifugation, the molecular weight of this procaryotic bromoperoxidase is 155,000 to 158,000. Sodium dodecyl sulfate-polyacrylamide gel electrophoresis shows a single band having the mobility of a 77,000-molecular-weight species. We thus conclude that this bromoperoxidase exists in solution as a dimeric species. The heme prosthetic group of bromoperoxidase is ferriprotoporphyrin IX. The spectral properties of the native and reduced enzyme are reported. This bromoperoxidase is the first halogenating enzyme purified from procaryotic sources.

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The Metabolism of Tryptophan and 7-Chlorotryptophan inPseudomonas pyrrociniaandPseudomonas aureofaciens

Cited by 18 publications

References 11 publications

Combining Metabolomics and Interpretable Machine Learning to Reveal Plasma Metabolic Profiling and Biological Correlates of Alcohol-Dependent Inpatients: What About Tryptophan Metabolism Regulation?

Combining Metabolomics and Interpretable Machine Learning to Reveal Plasma Metabolic Profiling and Biological Correlates of Alcohol-Dependent Inpatients: What About Tryptophan Metabolism Regulation?

Molecular cloning and high-level expression of a bromoperoxidase gene from Streptomyces aureofaciens Tü24

Purification of bromoperoxidase from Pseudomonas aureofaciens

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