Nondegraded Metabolites Arising From the Biodegradation of Commercial Linear Alkylbenzenesulfonate (Las) Surfactants in a Laboratory Trickling Filter

Kölbener, Pius; Baumann, Urs; Leisinger, Thomas; Cook, Alasdair M.

doi:10.1897/1552-8618(1995)14[561:nmaftb]2.0.co;2

Cited by 19 publications

(40 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We experienced ready degradation of commercial LAS (0.5 mM) as the sole source of carbon and energy in oxic laboratory trickling filters inoculated with sewage from all sources, corresponding to earlier reports (20), but we obtained no satisfactory degradation of 0.5 mM LAS, as determined by HPLC and by the continued foaming in enrichment cultures containing only suspended microorganisms. Similarly, enrichment cultures failed to degrade 0.25 or 0.5 mM commercial LADPEDS as the sole source of carbon and energy for growth with inocula from three sewage treatment plants.…”

Section: Enrichment Culturessupporting

confidence: 73%

“…A diode array detector was used (24). The two mobile phases were 0.11 M NaClO 4 and acetonitrile in a system adapted from our published method (20) to new column geometry. The column was equilibrated with 100% of the polar solvent at 0.5 ml/min.…”

mentioning

confidence: 99%

“…The LAS concentration routinely used in laboratory trickling filters was 0.5 mM (20), but experiments were often initiated with 0.1 mM LAS to avoid toxic effects of LAS on the inoculum. Strain DS-1 was tested for growth at different concentrations in suspended culture and was found to grow at the highest concentration tested, in 5 mM LAS-salts-glass wool medium.…”

mentioning

confidence: 99%

See 2 more Smart Citations

An α-Proteobacterium Converts Linear Alkylbenzenesulfonate Surfactants into Sulfophenylcarboxylates and Linear Alkyldiphenyletherdisulfonate Surfactants into Sulfodiphenylethercarboxylates

Schleheck

Dong

Denger

et al. 2000

Appl Environ Microbiol

Self Cite

View full text Add to dashboard Cite

The surfactant linear alkylbenzenesulfonate (LAS; 0.5 mM) or linear monoalkyldiphenyletherdisulfonate (LADPEDS; 0.5 mM) in salts medium was easily degraded in laboratory trickling filters, whereas carbonlimited, aerobic enrichment cultures in suspended culture with the same inocula did not grow. We took portions of the trickling filters which degraded LADPEDS, shook the organisms from the solid support (polyester), and found that growth in suspended culture in LADPEDS-salts medium occurred only in the presence of some solid support (polyester fleece or glass wool), though little biomass was immobilized on the support. The end products in suspended culture were identical with those from the trickling filters. There was low plating efficiency of LADPEDS-grown cultures on complex medium, and no picked colony or mixture of colonies grew in LADPEDS-salts-glass wool medium. However, selective plates containing LADPEDS-salts medium solidified with agarose yielded LADPEDS-dependent, pinpoint colonies which could be picked singly and subcultured in selective liquid medium. Isolate DS-1 was a bacterium which showed 93% sequence homology (16S ribosomal DNA) to its nearest phylogenetic neighbor, an ␣-proteobacterium. Strain DS-1 grew heterotrophically in LADPEDS-salts-glass wool medium and converted the set of aryl-substituted alkanes to the corresponding aryl-substituted carboxylic acids of shorter chain length. Similarly, strain DS-1 grew heterotrophically with commercial LAS, converting it to a set of sulfophenylcarboxylates. Growth with a single isomer of LAS [3-(4-sulfophenyl)dodecane] was concomitant with excretion of 4-(4-sulfophenyl)hexanoate, which was identified by matrix-assisted laser desorption ionization mass spectrometry. The growth yield (6.4 g of protein/mol of C) indicated mass balance, which, with the specific growth rate (0.05 h ؊1 ), indicated a specific utilization rate of LAS of 2.2 mkat/kg of protein.

show abstract

Section: Enrichment Culturessupporting

confidence: 73%

mentioning

confidence: 99%

mentioning

confidence: 99%

See 1 more Smart Citation

An α-Proteobacterium Converts Linear Alkylbenzenesulfonate Surfactants into Sulfophenylcarboxylates and Linear Alkyldiphenyletherdisulfonate Surfactants into Sulfodiphenylethercarboxylates

Schleheck

Dong

Denger

et al. 2000

Appl Environ Microbiol

Self Cite

View full text Add to dashboard Cite

show abstract

“…Whereas the degradation of LAS is well established (16,26,27,35,39,43), the mechanisms of its degradation are not (4).…”

mentioning

confidence: 99%

“…SPB is quantitatively converted to cell material, CO 2 , water, and sulfate by activated sludge (27), but none of the degradative mechanisms are known (4).…”

mentioning

confidence: 99%

Enantiomeric Degradation of 2-(4-Sulfophenyl)Butyrate via 4-Sulfocatechol inDelftia acidovoransSPB1

Schulz

Dong²,

Groth

et al. 2000

Appl Environ Microbiol

Self Cite

View full text Add to dashboard Cite

Enrichment cultures with enantiomeric 2-(4-sulfophenyl)butyrate (SPB) as the sole added source(s) of carbon and energy for growth yielded a pure culture of a degradative bacterium, which was identified as Delftia acidovorans SPB1. The organism utilized the enantiomers sequentially. R-SPB was utilized first (specific growth rate [] ‫؍‬ 0.28 h ؊1 ), with transient excretion of an unknown intermediate, which was identified as 4-sulfocatechol (4SC). Utilization of S-SPB was slower ( ‫؍‬ 0.016 h ؊1 ) and was initiated only after the first enantiomer was exhausted. Suspensions of cells grown in S-SPB excreted 4SC, so metabolism of the two enantiomers converged at 4SC. The latter was degraded by ortho cleavage via 3-sulfo-cis,cis-muconate. Strain SPB1 grew with 4SC and with 1-(4-sulfophenyl)octane (referred to herein as model LAS) but not with commercial linear alkylbenzenesulfonate (LAS) surfactant, which is subterminally substituted but nontoxic. It would appear that metabolism of the model LAS does not represent metabolism of commercial LAS.One of the major xenobiotic compounds degraded in sewage works worldwide is linear alkylbenzenesulfonate (LAS) surfactant, which has an annual production of about 2,500,000 tons (40). Whereas the degradation of LAS is well established (16,26,27,35,39,43), the mechanisms of its degradation are not (4).Commercial LAS (Fig. 1) is, ideally, a mixture of linear alkanes (C 10 to C 13 ) subterminally substituted with a single 4-sulfophenyl moiety (31): this means a mixture of 20 compounds, 18 of which are racemic mixtures. Although many different degradative reactions have been deduced from the intermediates which have been observed (38,43), the general opinion is that the major degradative pathway involves oxygenation of one or both of the terminal methyl groups by an unknown oxygenase (see also references 19 and 20) followed by rounds of ␤-oxidation to yield a large set of transient sulfophenyl(di)carboxylates ( Fig. 1) (9,14,17,38,43,47,49). On paper, seven sulfophenyl(di)carboxylates, representing a maximum number of ␤-oxidation steps, can be proposed: 2-(4-sulfophenyl)butyrate (SPB) (which is often observed during the degradation of commercial LAS [e.g., see reference 14]), 2-(4-sulfophenyl)propionate, 2-(4-sulfophenyl)malonate, 3-(4-sulfophenyl)butyrate, 2-(4-sulfophenyl)succinate, 3-(4-sulfophenyl)valerate and 3-(4-sulfophenyl)glutarate.Many of these sulfophenyl(di)carboxylates are optically active (24), which can be assumed to have consequences for their further degradation (25,50). SPB is quantitatively converted to cell material, CO 2 , water, and sulfate by activated sludge (27), but none of the degradative mechanisms are known (4).We now describe the isolation of Delftia acidovorans SPB1, which degrades both enantiomers of SPB via 4-sulfocatechol (4SC) and ortho ring cleavage (7, 13). MATERIALS AND METHODSMaterials. Racemic, R-and S-SPB were synthesized by reacting sulfuric acid with the corresponding phenylcarboxylic acid (45). Yields of about 30% were obtained at about 97%...

show abstract

Linear alkylbenzenesulfonate (LAS) surfactants in a simple test to detect refractory organic carbon (ROC): Attribution of recalcitrants to impurities in LAS

Kölbener

Baumann

Leisinger

et al. 1995

Enviro Toxic and Chemistry

View full text Add to dashboard Cite

The standard procedure to examine the biodegradability of a (group of) compound(s) in a trickling filter is a continuous‐flow system. In this test, nondegraded metabolites from a commercial linear alkylbenzenesulfonate (LAS) surfactant are detected (Kölbener, Baumann, Leisinger, and Cook; accompanying paper). This procedure has now been augmented by two phases in closed cycle to give a test for refractory organic carbon (ROC test). First, the concentration of nondegraded metabolites was increased by readdition of LAS to the solution being cycled through the filter. Second, the concentrated residues were further recycled till the net dissolved organic carbon (DOC) stabilised at a finite value and the net released CO2 stabilised at about zero. The organic compounds remaining at this phase of the experiment were considered recalcitrant and could be examined by global (e.g., DOC) and specific (e.g., HPLC) assays. Four different commercial preparations of LAS were examined, as were the (4‐sulfophenyl)undecane homologue (C11‐LAS), the (4‐sulfophenyl)dodecane homologue (C12‐LAS), and some related compounds. The four commercial LAS preparations contained different levels of impurities (2% to about 17%, according to the producers), which were largely dialkyltetralinesulfonates (DATS) and branched‐chain alkylbenzenesulfonates (bABS). The refractory organic carbon (ROC) remaining after biodegradation varied from 3 to 14%. The results were a characteristic of the LAS under study and were independent of the source of the biomass used in the experiment. Residues were examined by HPLC, and 50 to 100 peaks were observed, which were usually characteristic of the LAS studied. No peak has been conclusively identified. We consider the recalcitrants to represent carboxylated DATS and carboxylated bABS.

show abstract

Nondegraded Metabolites Arising From the Biodegradation of Commercial Linear Alkylbenzenesulfonate (Las) Surfactants in a Laboratory Trickling Filter

Cited by 19 publications

References 0 publications

An α-Proteobacterium Converts Linear Alkylbenzenesulfonate Surfactants into Sulfophenylcarboxylates and Linear Alkyldiphenyletherdisulfonate Surfactants into Sulfodiphenylethercarboxylates

An α-Proteobacterium Converts Linear Alkylbenzenesulfonate Surfactants into Sulfophenylcarboxylates and Linear Alkyldiphenyletherdisulfonate Surfactants into Sulfodiphenylethercarboxylates

Enantiomeric Degradation of 2-(4-Sulfophenyl)Butyrate via 4-Sulfocatechol inDelftia acidovoransSPB1

Linear alkylbenzenesulfonate (LAS) surfactants in a simple test to detect refractory organic carbon (ROC): Attribution of recalcitrants to impurities in LAS

Contact Info

Product

Resources

About