Effect of surfactants on plasticizer biodegradation by Bacillus subtilis ATCC 6633
- 207 Downloads
- 3 Citations
Abstract
The biodegradation of plasticizers has been previously shown to result in the accumulation of metabolites that are more toxic than the initial compound. The present work shows that the pattern of degradation of di-2-ethylhexyl adipate by Bacillus subtilis can be significantly altered by the presence of biosurfactants, such as surfactin, or synthetic surfactants, such as Pluronic L122. In particular, this work confirms that the monoester, mono-2-ethylhexyl adipate, is a metabolite in the breakdown of the plasticizer. This metabolite was proposed but not observed in earlier studies. Toxicity measurements showed it to be significantly more toxic than the plasticizer. Thus, the effect of the surfactants was to significantly increase the accumulation of one or both of the two most toxic metabolites; i.e., the monoester and 2-ethylhexanol. It was proposed that the most likely cause of the effect of the surfactants was the sequestering of these two metabolites into mixed micelles, resulting in their reduced availability for further degradation.
Keywords
Biodegradation DEHA 2-Ethylhexanol Mono-2-ethylhexyl adipate Plasticizer SurfactantPreview
Unable to display preview. Download preview PDF.
Notes
Acknowledgement
The financial support of the EJLB Foundation is gratefully acknowledged.
References
- Ahimou F, Jacques P, Deleu M (2001) Surfactin and iturin A effects on Bacillus subtilis surface hydrophobicity. Enzyme Microbial Technol 27(10):749–754CrossRefGoogle Scholar
- Akhter MS, Al-Alawi SM (2000) Influence of alcohols on the critical micelle concentration of non-aqueous micellar solutions. Colloids and surfaces, A. Physicochem Eng Aspects 164(2–3):247–255CrossRefGoogle Scholar
- Al-Tahhan RA, Sandrin TR, Bodour AA, Maier RM (2000) Rhamnolipid-induced removal of lipopolysaccharide from Pseudomonas aeruginosa: effect on cell surface properties and interaction with hydrophobic substrates. Appl Environ Microbiol 66(8):3262–3268CrossRefGoogle Scholar
- Bauer MJ, Herrmann R (1997) Estimation of the environmental contamination by phthalic acid esters leaching from household wastes. Sci Total Environ 208(1, 2):49–57Google Scholar
- Bockstahl F, Duplatre G (2001) Effect of 1-pentanol on size and shape of sodium dodecyl sulfate micelles as studied by positron annihilation lifetime spectroscopy. J Phys Chem B 105(1):13–18CrossRefGoogle Scholar
- Bodour AA, Drees KP, Maier RM (2003) Distribution of biosurfactant-producing bacteria in undisturbed and contaminated arid southwestern soils. Appl Environ Microbiol 69(6):3280–3287CrossRefGoogle Scholar
- Bohnert T, Izadi R, Pitman S, Stanhope B (1999) Recent developments: benzoate esters in polyvinyl resilient flooring. J Vinyl Additive Technol 5(3):143–147CrossRefGoogle Scholar
- Bramwell D-AP, Laha S (2001) Effects of surfactant addition on the biomineralization and microbial toxicity of phenanthrene. Biodegradation 11(4):263–277CrossRefGoogle Scholar
- Brown WA (2001) The self-cycling fermentor – development, applications, and future opportunities. Recent Res Develop Biotechnol Bioeng 4:61–90Google Scholar
- Bulich AA, Greene MW, Isenberg DL (1981) Reliability of the bacterial luminescence assay for determination of the toxicity of pure compounds and complex effluents. ASTM Special Tech Publ 737(Aquatic Toxicology and Hazard Assessment):338–347Google Scholar
- Cadogan DF, Papez M, Poppe AC, Pugh DM, Scheubel J (1999) An assessment of the release, occurrence and possible effects of plasticizers in the environment. Prog Rubber Plastics Technol 10(1):1–19Google Scholar
- Caragheorgheopol A, Caldararu H, Dragutan I, Joela H, Brown W (1997) Micellization and micellar structure of a poly(ethylene oxide)/poly(propylene oxide)/poly(ethylene oxide) triblock copolymer in water solution, as studied by the spin probe technique. Langmuir 13(26):6912–6921CrossRefGoogle Scholar
- Cartwright CD, Thompson IP, Burns RG (2000) Degradation and impact of phthalate plasticizers on soil microbial communities. Environ Toxicol Chem 19(5):1253–1261CrossRefGoogle Scholar
- Cavalero DA, Cooper DG (2003) The effect of medium composition on the structure and physical state of sophorolipids produced by Candida bombicola ATCC 22214. J Biotechnol 103(1):31–41Google Scholar
- Christofi N, Ivshina IB (2002) Microbial surfactants and their use in field studies of soil remediation. J Appl Microbiol 93(6):915–929CrossRefGoogle Scholar
- Churchill PF, Dudley RJ, Churchill SA (1995) Surfactant-enhanced bioremediation. Waste Manage (New York) 15(5/6):371–377Google Scholar
- Cooper DG, Macdonald CR, Duff SJB, Kosaric N (1981) Enhanced production of surfactin from Bacillus subtilis by continuous product removal and metal cation additions. Appl Environ Microbiol 42(3):408–412Google Scholar
- Cornu MC, Lhuguenot JC, Brady AM, Moore R, Elcombe CR (1992) Identification of the proximate peroxisome proliferator(s) derived from di-(2-ethylhexyl) adipate and species differences in response. Biochem Pharmacol 43(10):2129–2134CrossRefGoogle Scholar
- Deschenes L, Lafrance P, Villeneuve JP, Samson R (1996) Adding sodium dodecyl sulfate and Pseudomonas aeruginosa UG2 biosurfactants inhibits polycyclic aromatic hydrocarbon biodegradation in a weathered creosote-contaminated soil. Appl Microbiol Biotechnol 46(5–6):638–646Google Scholar
- Ding W-H, Tzing S-H, Lo J-H (1999) Occurrence and concentrations of aromatic surfactants and their degradation products in river waters of Taiwan. Chemosphere 38(11):2597–2606CrossRefGoogle Scholar
- Ejlertsson J, Alnervik M, Jonsson S, Svensson BH (1997) Influence of water solubility, side-chain degradability, and side-chain structure on the degradation of phthalic acid esters under methanogenic conditions. Environ Sci Technol 31(10):2761–2764CrossRefGoogle Scholar
- European Union Commission (2001) Decision No. 2455/2001/EC of the European Parliament and of the Council of 20 November 2001 establishing the list of priority substances in the field of water policy and amending Directive 2000/60/EC. Official Journal of European Communities L 331 1Google Scholar
- Fromme H, Kuchler T, Otto T, Pilz K, Muller J, Wenzel A (2002) Occurrence of phthalates and bisphenol A and F in the environment. Water Res 36(6):1429–1438CrossRefGoogle Scholar
- Fujii M, Shinohara N, Lim A, Otake T, Kumagai K, Yanagisawa Y (2003) A study on emission of phthalate esters from plastic materials using a passive flux sampler. Atmos Environ 37(39–40):5495–5504CrossRefGoogle Scholar
- Fukuwatari T, Suzuki Y, Sugimoto E, Shibata K (2002) Identification of a toxic mechanism of the plasticizers, phthalic acid esters, which are putative endocrine disrupters: time-dependent increase in quinolinic acid and its metabolites in rats fed di(2-ethylhexyl)phthalate. Biosci Biotechnol Biochem 66(12):2687–2691CrossRefGoogle Scholar
- Gartshore J, Cooper DG, Nicell JA (2003) Biodegradation of plasticizers by Rhodotorula rubra. Environ Toxicol Chem 22(6):1244–1251CrossRefGoogle Scholar
- Graham PR (1973) Phthalate ester plasticizers. Why and how they are used. Environ Health Perspect 3:3–12CrossRefGoogle Scholar
- Guha S, Jaffe PR (1996) Biodegradation kinetics of phenanthrene partitioned into the micellar phase of nonionic surfactants. Environ Sci Technol 30(2):605–611CrossRefGoogle Scholar
- Hill SS, Shaw BR, Wu AHB (2003) Plasticizers, antioxidants, and other contaminants found in air delivered by PVC tubing used in respiratory therapy. Biomed Chromatogr 17(4):250–262CrossRefGoogle Scholar
- Horn OJ, Nalli S, Cooper DG, Nicell JA (2004) Plasticizer metabolites in the environment. Water Res 38(17):3693–3698CrossRefGoogle Scholar
- Ito S, Inoue S (1982) Sophorolipids from Torulopsis bombicola: possible relation to alkane uptake. Appl Environ Microbiol 43(6):1278–1283Google Scholar
- Jha BK, Patist A, Shah DO (1999) Effect of antifoaming agents on the micellar stability and foamability of sodium dodecyl sulfate solutions. Langmuir 15(9):3042–3044CrossRefGoogle Scholar
- Jianlong W, Lujun C, Hanchang S, Yi Q (2000) Microbial degradation of phthalic acid esters under anaerobic digestion of sludge. Chemosphere 41(8):1245–1248CrossRefGoogle Scholar
- Jonsson S, Ejlertsson J, Ledin A, Mersiowsky I, Svensson BH (2003) Mono- and diesters from o-phthalic acid in leachates from different European landfills. Water Res 37(3):609–617CrossRefGoogle Scholar
- Kim K, Yoo D, Kim Y, Lee B, Shin D, Kim EK (2002) Characteristics of sophorolipid as an antimicrobial agent. J Microbiol Biotechnol 12(2):235–241Google Scholar
- Kolpin DW, Furlong ET, Meyer MT, Thurman EM, Zaugg SD, Barber LB, Buxton HT (2002) Pharmaceuticals, hormones, and other organic wastewater contaminants in U.S. streams, 1999–2000: a national reconnaissance. Environ Sci Technol 36(6):1202–1211CrossRefGoogle Scholar
- Kurane R, Suzuki T, Takahara Y (1977) Microbial degradation of phthalate esters. Part I. Isolation of microorganisms growing on phthalate esters and degradation of phthalate esters by Pseudomonas acidovorans 256–1. Agric Biol Chem 41(11):2119–2123Google Scholar
- Lang J, Stanhope BE (2001) Benzoate plasticizer for flexible PVC injection molded toy applications. Plastics Additives Compounding 3(6):30–33CrossRefGoogle Scholar
- Lin S-C, Jiang H-J (1997) Recovery and purification of the lipopeptide biosurfactant of Bacillus subtilis by ultrafiltration. Biotechnol Techniq 11(6):413–416CrossRefGoogle Scholar
- Lin Y, Smith TW, Paschalis A (2002) Adsorption of amphiphilic copolymers on hydrophobic particles in aqueous media. J Dispersion Sci Technol 23(4):539–553 CrossRefGoogle Scholar
- Marangoni DG, Kwak JCT (1991) Solubilization of alcohols and ethoxylated alcohols in anionic and cationic micelles. Langmuir 7(10):2083–2088CrossRefGoogle Scholar
- Nalli S, Cooper DG, Nicell JA (2002) Biodegradation of plasticizers by Rhodococcus rhodochrous. Biodegradation 13(5):343–352CrossRefGoogle Scholar
- Nalli S, Horn OJ, Grochowalski AR, Cooper DG, Nicell JA (2005) Origin of 2-ethylhexanol as a VOC. Environ Pollut 140:181–185CrossRefGoogle Scholar
- Nerin C, Gancedo P, Cacho J (1992) Determination of bis(2-ethylhexyl) adipate in food products. J Agric Food Chem 40(10):1833–1835CrossRefGoogle Scholar
- Norback D, Wieslander G, Nordstrom K, Walinder R (2000) Asthma symptoms in relation to measured building dampness in upper concrete floor construction, and 2-ethyl-1-hexanol in indoor air. Int J Tuberculosis Lung Dis 4(11):1016–1025Google Scholar
- Noordman WH, Wachter JHJ, de Boer GJ, Janssen DB (2002) The enhancement by surfactants of hexadecane degradation by Pseudomonas aeruginosa varies with substrate availability. J Biotechnol 94(2):195–212CrossRefGoogle Scholar
- Oberbremer A, Mueller-Hurtig R, Wagner F (1990) Effect of the addition of microbial surfactants on hydrocarbon degradation in a soil population in a stirred reactor. Appl Microbiol Biotechnol 32(4):485–489CrossRefGoogle Scholar
- O’Grady DP, Howard PH, Werner AF (1985) Activated sludge biodegradation of 12 commercial phthalate esters. Appl Environ Microbiol 49(2):443–445Google Scholar
- Otake T, Yoshinaga J, Yanagisawa Y (2001) Analysis of organic esters of plasticizer in indoor air by GC-MS and GC-FPD. Environ Sci Technol 35(15):3099–3102CrossRefGoogle Scholar
- Patist A, Axelberd T, Shah DO (1998) Effect of long chain alcohols on micellar relaxation time and foaming properties of sodium dodecyl sulfate solutions. J Colloid Interface Sci 208(1):259–265CrossRefGoogle Scholar
- Peakall DB (1975) Phthalate esters: occurrence and biological effects. Residue Rev 54:1–41Google Scholar
- Popovici H, Chiriac A (1994) Co-surfactant effect of 2-ethylhexanol resulting from (bis 2-ethyl) sulfosuccinate sodium salt alkaline hydrolysis on surfactant micellar structure. Analele Universitatii de Vest din Timisoara. Seria Chimie 3:89–98Google Scholar
- Prak DJL, Pritchard PH (2002) Degradation of polycyclic aromatic hydrocarbons dissolved in Tween 80 surfactant solutions by Sphingomonas paucimobilis EPA 505. Can J Microbiol 48(2):151–158CrossRefGoogle Scholar
- Saeger VW, Tucker III ES (1973) Phthalate esters undergo ready biodegradation. Plastics Eng 29(8):46–49Google Scholar
- Schillen K, Bryskhe K, Mel’nikova YS (1999) Vesicles formed from a poly(ethylene oxide)–poly(propylene oxide)–poly(ethylene oxide) triblock copolymer in␣dilute aqueous solution. Macromolecules 32(20): 6885–6888CrossRefGoogle Scholar
- Schippers C, Gessner K, Muller T, Scheper T (2000) Microbial degradation of phenanthrene by addition of a sophorolipid mixture. J Biotechnol 83(3):189–198CrossRefGoogle Scholar
- Staples CA, Peterson DR, Parkerton TF, Adams WJ (1997) The environmental fate of phthalate esters: a literature review. Chemosphere 35(4):667–749CrossRefGoogle Scholar
- Startin JR, Sharman M, Rose MD, Parker I, Mercer AJ, Castle L, Gilbert J (1987) Migration from plasticized films into foods. 1. Migration of di-(2-ethylhexyl)adipate from PVC films during home-use and microwave␣cooking. Food Additives Contaminants 4(4):385–398Google Scholar
- Su Y-L, Wei X-F, Liu H-Z (2003) Influence of 1-pentanol on the micellization of poly(ethylene oxide)–poly(propylene oxide)–poly(ethylene oxide) block copolymers in aqueous solutions. Langmuir 19(7):2995–3000CrossRefGoogle Scholar
- Tepper LB (1973) Phthalic acid esters – an overview. Environ Health Perspect 3:179–182CrossRefGoogle Scholar
- Trotta M, Gasco MR, Pattarino F (1993) Effect of a series of alcohols on critical micellar concentration of hexyl phosphate: a quantitative structure-CMC relationship study. J Colloid Interface Sci 158(1):133–135CrossRefGoogle Scholar
- US Environmental Protection Agency (1999) Introduction to water policy standards. Office of Water, Washington, DCGoogle Scholar
- Willumsen PA, Arvin E (1999) Kinetics of degradation of surfactant-solubilized fluoranthene by a Sphingomonas paucimobilis. Environ Sci Technol 33(15):2571–2578CrossRefGoogle Scholar
- Wilson AS (1995) Plasticizers: principles and practice. Institute of Materials, LondonGoogle Scholar
- Zhang Y, Miller RM (1994) Effect of a Pseudomonas rhamnolipid biosurfactant on cell hydrophobicity and biodegradation of octadecane. Appl Environ Microbiol 60(6):2101–2106Google Scholar
- Zheng Z, Obbard JP (2001) Effect of non-ionic surfactants on elimination of polycyclic aromatic hydrocarbons (PAHs) in soil-slurry by Phanerochaete chrysosporium. J Chem Technol Biotechnol 76(4):423–429CrossRefGoogle Scholar
- Zhu L, Yang K, Lou B, Yuan B (2003) A multi-component statistic analysis for the influence of sediment/soil composition on the sorption of a nonionic surfactant (Triton X-100) onto natural sediments/soils. Water Res 37(19):4792–4800CrossRefGoogle Scholar