• This record comes from PubMed

Degradation of antibacterial 1-octylpyrrolidin-2-one by bacterial pairs isolated from river water and soil

. 2022 Jun ; 29 (30) : 45292-45302. [epub] 20220210

Language English Country Germany Media print-electronic

Document type Journal Article

Grant support
IGA/FT/2018/009 Univerzita Tomáše Bati ve Zlíně
IGA/FT/2019/011 Univerzita Tomáše Bati ve Zlíně

Links

PubMed 35146604
DOI 10.1007/s11356-022-19121-1
PII: 10.1007/s11356-022-19121-1
Knihovny.cz E-resources

The study of bacterial degradation of 1-octylpyrrolidin-2-one (NOP) by river water and soil bacteria was the main aim of the research. Although the compound demonstrated bacteriostatic as well as bactericidal effects against Gram-positive and certain Gram-negative bacteria at concentrations ranging from 100 to 1000 mg L-1, its concentration of 100 mg L-1 was successfully degraded by microbial communities of both river water and alluvial soil; removal efficiencies reached 87.2 and 88.4% of dissolved organic carbon, respectively. Isolation of the strains responsible for the process showed that bacterial degradation was initiated by the octane-utilising bacteria of the genus Phenylobacterium, which used four carbon atoms of the NOP octyl chain and oxidised terminal carbon atom of the remaining chain. The structure of the intermediate produced by phenylobacteria was elucidated following the results obtained from the detailed electrospray mass spectrometry (ESI-MS) analysis; these experiments showed that it is a 4-(2-oxopyrrolidin-1-yl)butanoic acid. This intermediate was further degraded by other bacterial members of appropriate microbial communities, namely Bordetella petrii and Arthrobacter sp. Further tests proved that these bacteria were able to assimilate the nitrogen atom of the lactam ring and thus complete the degradation process.

See more in PubMed

Binazadeh M, Karimi IA, Li Z (2009) Fast biodegradation of long chain n-alkanes and crude oil at high concentrations with Rhodococcus sp. Moj-3449. Enzyme Microb Tech 45:195–202. https://doi.org/10.1016/j.enzmictec.2009.06.001 DOI

Cycon M, Mrozik A, Piotrowska-Seget Z (2017) Bioaugmentation as a strategy for the remediation of pesticide-polluted soil: A review. Chemosphere 172:52–71. https://doi.org/10.1016/j.chemosphere.2016.12.129 DOI

ECHA (2021) https://echa.europa.eu/cs/brief-profile/-/briefprofile/100.100.541 Accessed 22 December 2021

Fitzpatrick FP (2018) The enzymes of microbial nicotine metabolism. Beilstein J Org Chem 14:2295–2307. https://doi.org/10.3762/bjoc.14.204 DOI

Guo X, Xie C, Wang L, Li Q, Wang Y (2019) Biodegradation of persistent environmental pollutants by Arthrobacter sp. Environ Sci Pollut R 26:8429–8443. https://doi.org/10.1007/s11356-019-04358-0 DOI

Holcapek M, Jirasko R, Lisa M (2010) Basic rules for the interpretation of atmospheric pressure ionization mass spectra of small molecules. J Chromatogr A 1217:3908–3921. https://doi.org/10.1016/j.chroma.2010.02.049 DOI

Kabra BP (2008) 2-pyrrolidone derivatives for preservation of ophthalmic, otic and nasal compositions. US Patent application publication No. 2008/0095863 A1

Khasaeva F, Vasilyuk N, Terentyev P, Troshina M, Lebedev AT (2011) A novel soil bacterial strain degrading pyridines. Environ Chem Lett 9:439–445. https://doi.org/10.1007/s10311-010-0299-6 DOI

Kim MN, Park ST (2010) Degradation of poly(l-lactide) by a mesophilic bacterium. J Appl Polym Sci 117:67–74. https://doi.org/10.1002/app.31950 DOI

Klasek A, Lycka A, Rouchal M, Bartosik R (2020) Reaction of 1-substituted 3-(2-hydroxyethylamino)quinolone-2,4-(1H,3H)-diones with isothiocyanic acid. Chem Heterocycl Comp 56:566–571. https://doi.org/10.1007/s10593-020-02701-9 DOI

Levsen K, Schiebel HM, Terlouw JK, Jobst KJ, Elend M, Preiß A, Thiele H, Ingendoh A (2007) Even-electron ions: a systematic study of the neutral species lost in the dissociation of quasi-molecular ions. J Mass Spectrom 42:1024–1044. https://doi.org/10.1002/jms.1234 DOI

Lingens F, Blecher R, Blecher H, Blobel F, Eberspächer J, Fröhner C, Görisch H, Layh G (1985) Phenylobacterium immobile gen. nov., sp. nov., a Gram-negative bacterium that degrades the herbicide chloridazon. Int J Syst Bacteriol 35:26–39. https://doi.org/10.1099/00207713-35-1-26 DOI

Login RB (1995) Pyrrolidone-based surfactants (a literature review). J Am Oil Chem Soc 72:759–771 DOI

Merkova M, Zalesak M, Ringlova E, Julinova M, Ruzicka J (2018) Degradation of the surfactant Cocamidopropyl betaine by two bacterial strains isolated from activated sludge. Int Biodeter Biodegr 127:236–240. https://doi.org/10.1016/j.ibiod.2017.12.006 DOI

Narayanan KS, Chaudhuri RK (1993) N-alkyl pyrrolidone requirement for stable water based microemulsions. In: Devisetty BN, Chasin DG, Berger, PD (eds) Pesticide formulation and application systems: 12th volume. American Society for Testing and Materials, Special Technical Publication 1146:85–104

Narayanan KS, Jon D, Prettypaul D (2000) Emulsion concentrates of fungicides, and aqueous use formulations thereof for wood preservation. US Patent No. 6,033,681.US Patent No. 6,033,681

Odukkathil G, Vasudevan N (2015) Biodegradation of endosulfan isomers and its metabolite endosulfate by two biosurfactant producing bacterial strains of Bordetella petrii. J Environ Sci Heal B 50:81–89. https://doi.org/10.1080/03601234.2015.975596 DOI

Rajadhyaksha VJ (1978) Physiological vehicle compositions containing higher alkyl substituted azacyclopentan-2-ones. US Patent No. 4,122,170

Singleton D, Adrion AC, Aitken MD (2016) Surfactant-induced bacterial community changes correlated with increased polycyclic aromatic hydrocarbon degradation in contaminated soil. Appl Microbiol Biot 100:10165–10177. https://doi.org/10.1007/s00253-016-7867-z DOI

von Wintzingerode F, Schattke A, Siddiqui RA, Rösick U, Göbel U, Gross R (2001) Bordetella petrii sp. nov., isolated from an anaerobic bioreactor, and amended description of the genus Bordetella. Int J Syst Evol Micr 51:1257–1265. https://doi.org/10.1099/00207713-51-4-1257 DOI

Wagner P (2006) Inert Reassessments: Two Exemptions from the Requirement of a Tolerance for N-(n-dodecyl)-2-pyrrolidone (CAS Reg. No. 2687-96-9) and N-(n-octyl)-2-pyrrolidone (CAS Reg. No. 2687-94-7). Action memorandum, US EPA.  http://www.epa.gov/sites/production/files/2015-04/documents/pyrrolidone.pdf . Accessed 9 Dec 2020

Weisburg WG, Barns SM, Pelletier DA, Lane DJ (1991) 16S Ribosomal DNA amplification for phylogenetic study. J Bacteriol 173:697–703. https://doi.org/10.1128/jb.173.2.697-703.1991 DOI

Yang S, Wen X, Zhao L, Shi Y, Jin H (2014) Crude oil treatment leads to shift of bacterial communities in soils from the deep active layer and upper permafrost along the China-Russia crude oil pipeline route. PLoS ONE 9:e96552. https://doi.org/10.1371/journal.pone.0096552 DOI

Yoneto K, Ghanem AH, Higuchi WI, Peck KD, Li SK (1995) Mechanistic studies of the 1-alkyl-2-pyrrolidones as skin permeation enhancers. J Pharm Sci 84:312–317. https://doi.org/10.1002/jps.2600840310 DOI

Find record

Citation metrics

Loading data ...

Archiving options

Loading data ...