Genetic and chemical characterization of ibuprofen degradation by Sphingomonas Ibu-2

Murdoch, Robert W.

doi:10.1099/mic.0.062273-0

Cited by 80 publications

(76 citation statements)

References 66 publications

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“…This interaction may occur via the N-terminal DUF35/DUF35N domain of Shy, which is also present in the predicted proteins encoded by ipfE and bbsA in Sphingomonas sp. strain Ibu-2 and T. aromatica strain K172, respectively (42,44). Interestingly, in both cases, these proteins are thought to be required for the activity of the SCP-x-type enzyme (IbfD or BbsB).…”

Section: Discussionmentioning

confidence: 99%

The Essential Function of Genes for a Hydratase and an Aldehyde Dehydrogenase for Growth of Pseudomonas sp. Strain Chol1 with the Steroid Compound Cholate Indicates an Aldolytic Reaction Step for Deacetylation of the Side Chain

2013

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In the bacterial degradation of steroid compounds, the enzymes initiating the breakdown of the steroid rings are well known, while the reactions for degrading steroid side chains attached to C-17 are largely unknown. A recent in vitro analysis with Pseudomonas sp. strain Chol1 has shown that the degradation of the C 5 acyl side chain of the C 24 steroid compound cholate involves the C 22 intermediate 7␣,12␣-dihydroxy-3-oxopregna-1,4-diene-20S-carbaldehyde (DHOPDCA) with a terminal aldehyde group. In the present study, candidate genes with plausible functions in the formation and degradation of this aldehyde were identified. All deletion mutants were defective in growth with cholate but could transform it into dead-end metabolites. A mutant with a deletion of the shy gene, encoding a putative enoyl coenzyme A (CoA) hydratase, accumulated the C 24 steroid (22E)-7␣,12␣-dihydroxy-3-oxochola-1,4,22-triene-24-oate (DHOCTO). Deletion of the sal gene, formerly annotated as the steroid ketothiolase gene skt, resulted in the accumulation of 7␣,12␣,22-trihydroxy-3-oxochola-1,4-diene-24-oate (THOCDO). In cell extracts of strain Chol1, THOCDO was converted into DHOPDCA in a coenzyme A-and ATP-dependent reaction. A sad deletion mutant accumulated DHOPDCA, and expression in Escherichia coli revealed that sad encodes an aldehyde dehydrogenase for oxidizing DHOPDCA to the corresponding acid 7␣,12␣-dihydroxy-3-oxopregna-1,4-diene-20-carboxylate (DHOPDC) with NAD ؉ as the electron acceptor. These results clearly show that the degradation of the acyl side chain of cholate proceeds via an aldolytic cleavage of an acetyl residue; they exclude a thiolytic cleavage for this reaction step. Based on these results and on sequence alignments with predicted aldolases from other bacteria, we conclude that the enzyme encoded by sal catalyzes this aldolytic cleavage.

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Section: Discussionmentioning

confidence: 99%

The Essential Function of Genes for a Hydratase and an Aldehyde Dehydrogenase for Growth of Pseudomonas sp. Strain Chol1 with the Steroid Compound Cholate Indicates an Aldolytic Reaction Step for Deacetylation of the Side Chain

2013

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“…Murdoch and Hay (2013) found a Sphingomonas sp. strain in the phylum Proteobacteria capable of degrading IBP to yield catechols under aerobic conditions.…”

Section: Rhizodegradationmentioning

confidence: 99%

Phytoextraction, phytotransformation and rhizodegradation of ibuprofen associated with Typha angustifolia in a horizontal subsurface flow constructed wetland

Zhang

Zhu

et al. 2016

Water Research

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a b s t r a c tWidespread occurrence of trace pharmaceutical residues in aquatic environments is of great concerns due to the potential chronic toxicity of certain pharmaceuticals including ibuprofen on aquatic organisms even at environmental levels. In this study, the phytoextraction, phytotransformation and rhizodegradation of ibuprofen associated with Typha angustifolia were investigated in a horizontal subsurface flow constructed wetland system. The experimental wetland system consisted of a planted bed with Typha angustifolia and an unplanted bed (control) to treat ibuprofen-loaded wastewater (~107.2 mg L À1 ).Over a period of 342 days, ibuprofen was accumulated in leaf sheath and lamina tissues at a mean concentration of 160.7 ng g À1 , indicating the occurrence of the phytoextraction of ibuprofen. Root-uptake ibuprofen was partially transformed to ibuprofen carboxylic acid, 2-hydroxy ibuprofen and 1-hydroxy ibuprofen which were found to be 1374.9, 235.6 and 301.5 ng g À1 in the sheath, respectively, while they were 1051.1, 693.6 and 178.7 ng g À1 in the lamina. The findings from pyrosequencing analysis of the rhizosphere bacteria suggest that the Dechloromonas sp., the Clostridium sp. (e.g. Clostridium saccharobutylicum), the order Sphingobacteriales, and the Cytophaga sp. in the order Cytophagales were most probably responsible for the rhizodegradation of ibuprofen.

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“…Another example, albeit in an environmental setting, is ibuprofen, which can be metabolized by an environmental strain of Sphingomonas sp. Ibu2 ( Figure , Table 1 ). This mechanism provides a potential opportunity for bioremediation of pharmaceutical waste in the environment.…”

Section: Impact Of Microbiome On Drug Pharmacodynamics and Pharmacokimentioning

confidence: 99%

“…Studies that integrate human microbiome–gene–drug interactions are becoming increasingly popular, as evidence supporting the impact of the human microbiome, especially the gut microbiome, on drug response is growing . Other human‐associated environments, such as the skin, urogenital tract, and vagina, are also being documented …”

Section: Gut Microbiome Directly Influences Drug Efficacy and Toxicitymentioning

confidence: 99%

Pharmacomicrobiomics: The Holy Grail to Variability in Drug Response?

Sharma

Buschmann

Gilbert

2019

Clin Pharma and Therapeutics

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The human body, with 3.0 × 1013 cells and more than 3.8 × 1013 microorganisms, has nearly a one‐to‐one ratio of resident microbes to human cells. Initiatives like the Human Microbiome Project, American Gut, and Flemish Gut have identified associations between microbial taxa and human health. The study of interactions between microbiome and pharmaceutical agents, i.e., pharmacomicrobiomics, has revealed an instrumental role of the microbiome in modulating drug response that alters the therapeutic outcomes. In this review, we present our current comprehension of the relationship of the microbiome, host biology, and pharmaceutical agents such as cardiovascular drugs, analgesics, and chemotherapeutic agents to human disease and treatment outcomes. We also discuss the significance of studying diet–gene–drug interactions and further address the key challenges associated with pharmacomicrobiomics. Finally, we examine proposed models employing systems biology for the application of pharmacomicrobiomics and other ‐omics data, and provide approaches to elucidate microbiome–drug interactions to improve future translation to personalized medicine.

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Genetic and chemical characterization of ibuprofen degradation by Sphingomonas Ibu-2

Cited by 80 publications

References 66 publications

The Essential Function of Genes for a Hydratase and an Aldehyde Dehydrogenase for Growth of Pseudomonas sp. Strain Chol1 with the Steroid Compound Cholate Indicates an Aldolytic Reaction Step for Deacetylation of the Side Chain

The Essential Function of Genes for a Hydratase and an Aldehyde Dehydrogenase for Growth of Pseudomonas sp. Strain Chol1 with the Steroid Compound Cholate Indicates an Aldolytic Reaction Step for Deacetylation of the Side Chain

Phytoextraction, phytotransformation and rhizodegradation of ibuprofen associated with Typha angustifolia in a horizontal subsurface flow constructed wetland

Pharmacomicrobiomics: The Holy Grail to Variability in Drug Response?

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