The microbial degradation of cyclohexanecarboxylic acid: a pathway involving aromatization to form <i>p</i>-hydroxybenzoic acid

Blakley, E. R.

doi:10.1139/m74-202

Cited by 57 publications

(32 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To date, there are no reports of any of these microorganisms being involved in NAdegradation. Achromobacter spp., which have been shown to degrade cyclohexanecarboxylic acid and carboxylated cycloalkane by others (Blakley, 1974(Blakley, , 1978, were in low abundance in our study. Similarly, Corynebacterium cyclohexanicum (Tokuyama and Kaneda, 1973) and Acinetobacter spp.…”

Section: Discussioncontrasting

confidence: 52%

“…However, pathways have been proposed for the biodegradation of aliphatic and alicyclic carboxylic acids and include b-oxidation (Blakley, 1978;Blakley and Papish, 1982;Alexander, 1999;Quagraine et al, 2005a), combined a-and b-oxidation (Beam and Perry, 1974;Rontani and Bonin, 1992) and aromatization (Blakley, 1974;Taylor and Trudgill, 1978;Trudgill, 1984). In this work, we sought to elucidate the initial steps involved in aromatic alkanoic acid metabolism.…”

Section: Discussionmentioning

confidence: 99%

“…Several microorganisms including: Acinetobacter anitratum, Alcaligenes faecalis and Pseudomonas putida have been shown to metabolize model NAs by aerobic b-oxidation pathways (Blakley, 1974;Rho and Evans, 1975;Blakley and Papish, 1982). Alcaligenes sp.…”

Section: Discussionmentioning

confidence: 99%

See 2 more Smart Citations

Microbial biodegradation of aromatic alkanoic naphthenic acids is affected by the degree of alkyl side chain branching

Johnson

Smith²,

Sutton

et al. 2010

The ISME Journal

View full text Add to dashboard Cite

Naphthenic acids (NAs) occur naturally in oil sands and enter the environment through natural and anthropogenic processes. NAs comprise toxic carboxylic acids that are difficult to degrade. Information on NA biodegradation mechanisms is limited, and there are no studies on alkyl branched aromatic alkanoic acid biodegradation, despite their contribution to NA toxicity and recalcitrance. Increased alkyl side chain branching has been proposed to explain NA recalcitrance. Using soil enrichments, we examined the biodegradation of four aromatic alkanoic acid isomers that differed in alkyl side chain branching: (4 0 -n-butylphenyl)-4-butanoic acid (n-BPBA, least branched); (4 0 -iso-butylphenyl)-4-butanoic acid (iso-BPBA); (4 0 -sec-butylphenyl)-4-butanoic acid (sec-BPBA) and (4 0 -tert-butylphenyl)-4-butanoic acid (tert-BPBA, most branched). n-BPBA was completely metabolized within 49 days. Mass spectral analysis confirmed that the more branched isomers iso-, sec-and tert-BPBA were transformed to their butylphenylethanoic acid (BPEA) counterparts at 14 days. The BPEA metabolites were generally less toxic than BPBAs as determined by Microtox assay. n-BPEA was further transformed to a diacid, showing that carboxylation of the alkyl side chain occurred. In each case, biodegradation of the carboxyl side chain proceeded through betaoxidation, which depended on the degree of alkyl side chain branching, and a BPBA degradation pathway is proposed. Comparison of 16S rRNA gene sequences at days 0 and 49 showed an increase and high abundance at day 49 of Pseudomonas (sec-BPBA), Burkholderia (n-, iso-, tert-BPBA) and Sphingomonas (n-, sec-BPBA).

show abstract

Section: Discussioncontrasting

confidence: 52%

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Microbial biodegradation of aromatic alkanoic naphthenic acids is affected by the degree of alkyl side chain branching

Johnson

Smith²,

Sutton

et al. 2010

The ISME Journal

View full text Add to dashboard Cite

show abstract

“…Both quinate (a substituted cycloalkane) and shikimate (a substituted cycloalkene) can be mineralized via the aromatic intermediate protocatechuate (43), and this pathway appears to be widespread among diverse microorganisms. Cyclohexanecarboxylic acid can be mineralized via the aromatic intermediates p-hydroxybenzoic acid and protocatechuic acid (7,16), and this pathway exists in diverse microorganisms but is used by a minority of those growing on cyclohexane carboxylic acid (42). Despite these precedents, microbial degradation of cycloalkanes via aromatic intermediates appears to be unusual.…”

Section: Discussionmentioning

confidence: 99%

Genetic Investigation of the Catabolic Pathway for Degradation of Abietane Diterpenoids by Pseudomonas abietaniphila BKME-9

Martin

Mohn

2000

J Bacteriol

View full text Add to dashboard Cite

We have cloned and sequenced the dit gene cluster encoding enzymes of the catabolic pathway for abietane diterpenoid degradation by Pseudomonas abietaniphila BKME-9. The dit gene cluster is located on a 16.7-kb DNA fragment containing 13 complete open reading frames (ORFs) and 1 partial ORF. The genes ditA1A2A3 encode the ␣ and ␤ subunits and the ferredoxin of the dioxygenase which hydroxylates 7-oxodehydroabietic acid to 7-oxo-11,12-dihydroxy-8,13-abietadien acid. The dioxygenase mutant strain BKME-941 (ditA1::Tn5) did not grow on nonaromatic abietanes, and transformed palustric and abietic acids to 7-oxodehydroabietic acid in cell suspension assays. Thus, nonaromatic abietanes are aromatized prior to further degradation. Catechol 2,3-dioxygenase activity of xylE transcriptional fusion strains showed induction of ditA1 and ditA3 by abietic, dehydroabietic, and 7-oxodehydroabietic acids, which support the growth of strain BKME-9, as well as by isopimaric and 12,14-dichlorodehydroabietic acids, which are diterpenoids that do not support the growth of strain BKME-9. In addition to the aromatic-ring-hydroxylating dioxygenase genes, the dit cluster includes ditC, encoding an extradiol ring cleavage dioxygenase, and ditR, encoding an IclR-type transcriptional regulator. Although ditR is not strictly required for the growth of strain BKME-9 on abietanes, a ditR::Km r mutation in a ditA3::xylE reporter strain demonstrated that it encodes an inducer-dependent transcriptional activator of ditA3. An ORF with sequence similarity to genes encoding permeases (ditE) is linked with genes involved in abietane degradation.The pulping of wood to extract fibers used to make paper produces toxic wastewaters (23). The majority of the acute toxicity can be attributed to resin acids found in these wastewaters (18). Resin acids, a class of diterpenoids found in wood extractives, can be grouped into abietanes and pimeranes. Abietane-type acids have an isopropyl chain at the C-13 carbon atom, while pimerane-type acids have methyl and vinyl substituents at this position. Although these compounds are abundant in nature, they are problematic in the pulp and paper industry because of their unnaturally high concentrations in wastewaters. Therefore, resin acids must be removed from wastewater prior to its discharge to the environment. Biological treatment using aerated lagoons is the most common method used for detoxifying the wastewater (19). Several bacteria isolated from such biotreatment systems have been reported to use resin acids as growth substrates, and this catabolic activity appears to be widespread (22,25).Pseudomonas abietaniphila BKME-9, a bacterium isolated from a pulp and paper wastewater treatment system, is able to use dehydroabietic acid, an abietane-type resin acid, as a sole source of carbon and reductant (4). A novel three-component aromatic-ring-hydroxylating dioxygenase from this strain has been cloned and expressed (21). In strain BKME-9, dehydroabietic acid is first oxidized by an unidentified enzyme at the C-7 positi...

show abstract

“…Although some bacteria can metabolize them (11)(12)(13), naphthenic acids can have negative effects on bacteria (14,15), algae (16,17), and cyanobacteria (18). Aromatic hydrocarbons are also known to be toxic to a variety of microbial processes (19,20) and to bacteria (21,22).…”

mentioning

confidence: 99%

Aerobic Biofilms Grown from Athabasca Watershed Sediments Are Inhibited by Increasing Concentrations of Bituminous Compounds

Yergeau

Lawrence

Sanschagrin

et al. 2013

Appl Environ Microbiol

View full text Add to dashboard Cite

Sediments from the Athabasca River and its tributaries naturally contain bitumen at various concentrations, but the impacts of this variation on the ecology of the river are unknown. Here, we used controlled rotating biofilm reactors in which we recirculated diluted sediments containing various concentrations of bituminous compounds taken from the Athabasca River and three tributaries. Biofilms exposed to sediments having low and high concentrations of bituminous compounds were compared. The latter were 29% thinner, had a different extracellular polysaccharide composition, 67% less bacterial biomass per m 2 , 68% less cyanobacterial biomass per m 2 , 64% less algal biomass per m 2 , 13% fewer protozoa per cm 2 , were 21% less productive, and had a 33% reduced content in chlorophyll a per mm 2 and a 20% reduction in the expression of photosynthetic genes, but they had a 23% increase in the expression of aromatic hydrocarbon degradation genes. Within the Bacteria, differences in community composition were also observed, with relatively more Alphaproteobacteria and Betaproteobacteria and less Cyanobacteria, Bacteroidetes, and Firmicutes in biofilms exposed to high concentrations of bituminous compounds. Altogether, our results suggest that biofilms that develop in the presence of higher concentrations of bituminous compounds are less productive and have lower biomass, linked to a decrease in the activities and abundance of photosynthetic organisms likely due to inhibitory effects. However, within this general inhibition, some specific microbial taxa and functional genes are stimulated because they are less sensitive to the inhibitory effects of bituminous compounds or can degrade and utilize some bitumen-associated compounds.

show abstract

The microbial degradation of cyclohexanecarboxylic acid: a pathway involving aromatization to form p-hydroxybenzoic acid

Cited by 57 publications

References 11 publications

Microbial biodegradation of aromatic alkanoic naphthenic acids is affected by the degree of alkyl side chain branching

Microbial biodegradation of aromatic alkanoic naphthenic acids is affected by the degree of alkyl side chain branching

Genetic Investigation of the Catabolic Pathway for Degradation of Abietane Diterpenoids by Pseudomonas abietaniphila BKME-9

Aerobic Biofilms Grown from Athabasca Watershed Sediments Are Inhibited by Increasing Concentrations of Bituminous Compounds

Contact Info

Product

Resources

About