Gentisate pathway in<i>Salmonella typhimurium</i>: metabolism of<i>m</i>-hydroxybenzoate and gentisate

Goetz, Frederick E.; Harmuth, Lorna J.

doi:10.1111/j.1574-6968.1992.tb05437.x

Cited by 20 publications

(3 citation statements)

References 22 publications

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“…Studies show that, homogentisate is the route for the aerobic catabolism of L-tyrosine, L-phenylalanine, and 3- and 4-hydroxyphenylacetate [ 32 – 34 ]. Similarly, m -hydroxybenzoate, 3-hydroxybenzoate, 2, 5-xylenol, and m -cresol degradation result in gentisate intermediate [ 35 – 37 ], while phenylalanine and styrene result in phenylacetyl-CoA intermediate [ 38 ] of central catabolism. These non-catechol hydroxyl-substituted aromatic carboxylic acids are the central intermediates formed from the upper pathways that begin with oxidation by either monooxygenase or dioxygenase in the aerobic condition [ 39 , 40 ].…”

Section: Resultsmentioning

confidence: 99%

Comparative genome analysis among Variovorax species and genome guided aromatic compound degradation analysis emphasizing 4-hydroxybenzoate degradation in Variovorax sp. PAMC26660

et al. 2022

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Background While the genus Variovorax is known for its aromatic compound metabolism, no detailed study of the peripheral and central pathways of aromatic compound degradation has yet been reported. Variovorax sp. PAMC26660 is a lichen-associated bacterium isolated from Antarctica. The work presents the genome-based elucidation of peripheral and central catabolic pathways of aromatic compound degradation genes in Variovorax sp. PAMC26660. Additionally, the accessory, core and unique genes were identified among Variovorax species using the pan genome analysis tool. A detailed analysis of the genes related to xenobiotic metabolism revealed the potential roles of Variovorax sp. PAMC26660 and other species in bioremediation. Results TYGS analysis, dDDH, phylogenetic placement and average nucleotide identity (ANI) analysis identified the strain as Variovorax sp. Cell morphology was assessed using scanning electron microscopy (SEM). On analysis of the core, accessory, and unique genes, xenobiotic metabolism accounted only for the accessory and unique genes. On detailed analysis of the aromatic compound catabolic genes, peripheral pathway related to 4-hydroxybenzoate (4-HB) degradation was found among all species while phenylacetate and tyrosine degradation pathways were present in most of the species including PAMC26660. Likewise, central catabolic pathways, like protocatechuate, gentisate, homogentisate, and phenylacetyl-CoA, were also present. The peripheral pathway for 4-HB degradation was functionally tested using PAMC26660, which resulted in the growth using it as a sole source of carbon. Conclusions Computational tools for genome and pan genome analysis are important to understand the behavior of an organism. Xenobiotic metabolism-related genes, that only account for the accessory and unique genes infer evolution through events like lateral gene transfer, mutation and gene rearrangement. 4-HB, an aromatic compound present among lichen species is utilized by lichen-associated Variovorax sp. PAMC26660 as the sole source of carbon. The strain holds genes and pathways for its utilization. Overall, this study outlines the importance of Variovorax in bioremediation and presents the genomic information of the species.

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Section: Resultsmentioning

confidence: 99%

Comparative genome analysis among Variovorax species and genome guided aromatic compound degradation analysis emphasizing 4-hydroxybenzoate degradation in Variovorax sp. PAMC26660

et al. 2022

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“…The central pathway for the catabolism of benzoates, phenolic compounds, and PAHs is oxidation through gentisate by gentisate 1.2-dioxygenase [45][46][47][48]. Three sequences encoding gentisate 1.2-dioxygenase were found in the genome of D. tsuruhatensis strain ULwDis3.…”

Section: Discussionmentioning

confidence: 99%

Characterization and Genomic Analysis of the Naphthalene-Degrading Delftia tsuruhatensis ULwDis3 Isolated from Seawater

et al. 2023

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Strains of the genus Delftia are poorly studied microorganisms. In this work, the complete genome of the naphthalene-degrading Delftia tsuruhatensis strain ULwDis3 isolated from seawater of the Gulf of Finland of the Baltic Sea was assembled. For the first time, genes encoding naphthalene cleavage pathways via salicylate and gentisate were identified in a strain of the genus Delftia. The genes are part of one operon (nag genes). Three open reading frames (ORFs) were found in the genome of D. tsuruhatensis strain ULwDis3 that encode gentisate 1.2-dioxygenase. One of the ORFs is part of the nag operon. The physiological and biochemical characteristics of the strain ULwDis3 when cultured in mineral medium with naphthalene as the sole source of carbon and energy were also studied. It was found that after 22 h of growth, the strain stopped consuming naphthalene, and at the same time, naphthalene 1.2-dioxygenase and salicylate 5-hydroxylase activities were not detected. Later, a decrease in the number of living cells and the death of the culture were observed. Gentisate 1.2-dioxygenase activity was detected from the time of gentisate formation until culture death.

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“…To the best of our knowledge, this is the first time that mycothiol biosynthesis was found to be essential for cell growth when aromatic compounds are provided as carbon sources, and that a mycothiol-dependent maleylpyruvate isomerase was identified. Gentisate and substituted gentisates are key intermediates during aerobic degradation of many aromatic compounds, such as 3-hydroxybenzoate (26,33,34), 3,5-or 2,5-xylenol (35,36), salicylate (37-39), 3,6-dichloro-2-methoxybenzoate (40), and naphthalene (41)(42)(43). In the gentisate pathway, isomerization of maleylpyruvate to fumarylpyruvate is catalyzed by either a GSH-dependent maleylpyruvate isomerase (26,27,34), a mycothiol-dependent maleylpyruvate isomerase (this study), or a maleylpyruvate isomerase as in B. megaterium that does not rely on glutathione or mycothiol (22).…”

Section: Discussionmentioning

confidence: 99%

The Gene ncgl2918 Encodes a Novel Maleylpyruvate Isomerase That Needs Mycothiol as Cofactor and Links Mycothiol Biosynthesis and Gentisate Assimilation in Corynebacterium glutamicum

Feng

Che

Milse

et al. 2006

Journal of Biological Chemistry

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Data mining of the Corynebacterium glutamicum genome identified 4 genes analogous to the mshA, mshB, mshC, and mshD genes that are involved in biosynthesis of mycothiol in Mycobacterium tuberculosis and Mycobacterium smegmatis. Individual deletion of these genes was carried out in this study. Mutants mshC ؊ and mshD ؊ lost the ability to produce mycothiol, but mutant mshB ؊ produced mycothiol as the wild type did. The phenotypes of mutants mshC ؊ and mshD ؊ were the same as the wild type when grown in LB or BHIS media, but mutants mshC ؊ and mshD ؊ were not able to grow in mineral medium with gentisate or 3-hydroxybenzoate as carbon sources. C. glutamicum assimilated gentisate and 3-hydroxybenzoate via a glutathione-independent gentisate pathway. In this study it was found that the maleylpyruvate isomerase, which catalyzes the conversion of maleylpyruvate into fumarylpyruvate in the glutathione-independent gentisate pathway, needed mycothiol as a cofactor. This mycothiol-dependent maleylpyruvate isomerase gene (ncgl2918) was cloned, actively expressed,andpurifiedfromEscherichiacoli.Thepurifiedmycothioldependent isomerase is a monomer of 34 kDa. The apparent K m and V max values for maleylpyruvate were determined to be 148.4 ؎ 11.9 M and 1520 ؎ 57.4 mol/min/mg, respectively (mycothiol concentration, 2.5 M). Previous studies had shown that mycothiol played roles in detoxification of oxidative chemicals and antibiotics in streptomycetes and mycobacteria. To our knowledge, this is the first demonstration that mycothiol is essential for growth of C. glutamicum with gentisate or 3-hydroxybenzoate as carbon sources and the first characterization of a mycothiol-dependent maleylpyruvate isomerase.Mycothiol (1), also known as MSH and chemically 1D-myo-inosityl-2-(N-acetyl-L-cysteinyl)amido-2-deoxy-␣-D-glucopyranoiside, is the major low-molecular mass thiol in mycobacteria and streptomycetes (2). Some investigations showed that mycothiol is associated with protection of Mycobacterium tuberculosis and Mycobacterium smegmatis against antibiotics such as rifampin (3, 4) and also helped these pathogens to detoxify reactive oxygen species produced by host cells (5).Thus, mycothiol is a potential target for medical treatment and has raised interest from both academia and industry. In addition, mycothiol also has the ability to protect cells against a range of toxic compounds. For example, in Amycolatopsis methanolica and Rhodococcus erythropolis, mycothiol detoxifies formaldehyde by acting as a cofactor for a formaldehyde dehydrogenase (6) and detoxifies alkylating agents such as monobromobimane by converting them to S-conjugates of mycothiol (7, 8). To date, the understanding of the physiological function of mycothiol is limited to detoxification and the protection of living cells (9), whereas essential metabolic roles for cell growth have not been reported.A survey on the distribution of low-molecular mass thiols in microorganisms showed that Corynebacterium diphtheriae produced mycothiol (2). However, the occurrence of mycoth...

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Gentisate pathway inSalmonella typhimurium: metabolism ofm-hydroxybenzoate and gentisate

Cited by 20 publications

References 22 publications

Comparative genome analysis among Variovorax species and genome guided aromatic compound degradation analysis emphasizing 4-hydroxybenzoate degradation in Variovorax sp. PAMC26660

Comparative genome analysis among Variovorax species and genome guided aromatic compound degradation analysis emphasizing 4-hydroxybenzoate degradation in Variovorax sp. PAMC26660

Characterization and Genomic Analysis of the Naphthalene-Degrading Delftia tsuruhatensis ULwDis3 Isolated from Seawater

The Gene ncgl2918 Encodes a Novel Maleylpyruvate Isomerase That Needs Mycothiol as Cofactor and Links Mycothiol Biosynthesis and Gentisate Assimilation in Corynebacterium glutamicum

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