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Synthesis of trans unsaturated fatty acids in Pseudomonas putida P8 by direct isomerization of the double bond of lipids

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Abstract

The phospholipids of Pseudomonas putida P8 contain monounsaturated fatty acids in the cis and trans configuration. Cells of this phenol-degrading bacterium change the proportions of these isomers in response to the addition or elimination of a membrane active compound such as 4-chlorophenol. This study undoubtedly reveals that the cis unsaturated fatty acids are directly converted into trans isomers without involvement of de novo synthesis of fatty acids. Oleic acid, which cannot be synthesized by this bacterium, was incorporated as a cis unsaturated fatty acid marker in the membrane lipids of growing cells. The conversion of this fatty acid into the corresponding trans isomer was demonstrated by gas chromatographic-mass spectrometric analysis and use of 14C-labeled oleic acid. Separation and isolation of the cellular membranes showed that the fatty acid isomerase is located in the cytoplasmic membrane of P. putida P8.

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Abbreviations

4-CP :

4-chlorophenol

References

  • Bettmann H, Rehm HJ (1984) Degradation of phenol by polymer entrapped microorganisms. Appl Microbiol Biotechnol 20: 285–290

    Google Scholar 

  • Bligh EG, Dyer WJ (1959) A rapid method of total lipid extraction and purification. Can J Biochem Physiol 37: 911–917

    CAS  Google Scholar 

  • Christie WW (1989) Isolation of fatty acids and identification by spectroscopic and chemical degradative techniques. In: Christie WW (ed) Gas chromatography and lipids. Oily Press, Ayr, pp 129–160

    Google Scholar 

  • Conrad RS, Wulf RG, Ankrom KA (1981) Fatty acids of Pseudomonas aeruginosa grown on media affecting polymyxin susceptibility. Current Microbiol 5: 231–234

    Google Scholar 

  • Cronan JE, Rock CO (1987) Biosynthesis of membrane lipids. In: Neidhardt FC (ed) Escherichia coli and Salmonella typhimurium cellular and molecular biology, vol 1. American Society for Microbiology, Washington DC

    Google Scholar 

  • Diefenbach R, Heipieper HJ, Keweloh H (1992) The conversion of cis into trans unsaturated fatty acids in Pseudomonas putida P8: evidence for a role in the regulation of membrane fluidity. Appl Microbiol Biotechnol 38: 382–387

    Google Scholar 

  • Golden NG, Powell GL (1972) Stringent and relaxed control of phospholipid metabolism in Escherichia coli. J Biol Chem 247: 6651–6658

    Google Scholar 

  • Grogan DW, Cronan JE (1986) Characterization of Escherichia coli mutants completely defective in synthesis of cyclopropane fatty acids. J Bacteriol 166: 872–877

    Google Scholar 

  • Guckert JB, Ringelberg DB, White DC (1987) Biosynthesis of trans fatty acids from acetate in the bacterium Pseudomonas atlantica. Can J Microbiol 33: 748–754

    Google Scholar 

  • Hamilton WA (1971) Membrane active antibacterial compounds. In: Hugo WB (ed) Inhibition and destruction of the microbial cell. Academic Press, London New York, pp 77–93

    Google Scholar 

  • Heipieper HJ, Keweloh H, Rehm HJ (1991) Influence of phenols on growth and membrane permeability of free and immobilized Escherichia coli. Appl Environ Microbiol 57: 1213–1217

    Google Scholar 

  • Heipieper HJ, Diefenbach R, Keweloh H (1992) Conversion of cis unsaturated fatty acids to trans, a possible mechanism for the protection of phenol-degrading Pseudomonas putida P8 from substrate toxicity. Appl Environ Microbiol 58: 1847–1852

    Google Scholar 

  • Kaluzny MA, Duncan LA, Merritt MV, Epps DE (1985) Rapid separation of lipid classes in high yield and purity using bonded phase columns. J Lipid Res 26: 135–140

    Google Scholar 

  • Keweloh H, Diefenbach R, Rehm HJ (1991) Increase of phenol tolerance of Escherichia coli by alterations of the fatty acid composition of the membrane lipids. Arch Microbiol 157: 49–53

    Google Scholar 

  • Kitagawa S, Kametani F, Tsuchiya K, Sakurai H (1990) ESR analysis with long-chain alkyl spin labels in bovine blood platelets — relationship between the increase in membrane fluidity by alcohols and phenolic compounds and their inhibitory effects on aggregation. Biochim Biophys Acta 1027: 123–129

    Google Scholar 

  • Magnuson K, Jackowski S, Rock CO, Cronan JE (1993) Regulation of fatty acid biosynthesis in Escherichia coli. Microbiol Rev 57: 522–542

    Google Scholar 

  • Melchior DL (1982) Lipid phase transitions and regulation of membrane fluidity in prokaryotes. In: Razin S, Rottem S (eds) Current topics in membranes and transport, vol 17. Academic Press, London, pp 263–316

    Google Scholar 

  • Morita N, Shibahara A, Yamamoto K, Shinkai K, Kajimoto G, Okuyama H (1993) Evidence for cis-trans isomerization of a double bond in the fatty acids of the psychrophilic bacterium Vibrio sp. strain ABE-1. J Bacteriol 175: 916–918

    Google Scholar 

  • Morrison WR, Smith LM (1964) Preparation of fatty acid methyl esters and dimethylacetals from lipids with boron fluoridemethanol. J Lipid Res 5: 600–608

    Google Scholar 

  • Okuyama H, Sasaki S, Higashi S, Murata N (1990) A trans-unsaturated fatty acid in a psychrophilic bacterium, Vibrio sp. strain ABE-1. J Bacteriol 172: 3515–3518

    Google Scholar 

  • Osborn MJ, Gander JE, Parisi E, Carson J (1972) Mechanism of assembly of the outer membrane of Salmonella typhimurium. J Biol Chem 247(12): 3962–3972

    Google Scholar 

  • Polakis SE, Guchhait RB, Lane MD (1973) Stringent control of fatty acid synthesis in Escherichia coli: possible regulation of acetyl coenzyme A carboxylase by ppGpp. J Biol Chem 248: 7957–7966

    Google Scholar 

  • Russell NJ, Fukunaga N (1990) A comparison of thermal adaptation of membrane lipids in psychrophilic and thermophilic bacteria. FEMS Microbiol Rev 75: 171–182

    Google Scholar 

  • Shinitzky M (1984) Membrane fluidity and cellular functions. In: Shinitzky M (ed) Physiology of membrane fluidity, vol 1. CRC Press, Boca Raton, pp 1–52

    Google Scholar 

  • Sinensky, M (1974) Homeoviscous adaptation — a homeostatic process that regulates the viscosity of membrane lipids in Escherichia coli. Proc Natl Acad Sci USA 71: 522–525

    Google Scholar 

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Diefenbach, R., Keweloh, H. Synthesis of trans unsaturated fatty acids in Pseudomonas putida P8 by direct isomerization of the double bond of lipids. Arch. Microbiol. 162, 120–125 (1994). https://doi.org/10.1007/BF00264384

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  • DOI: https://doi.org/10.1007/BF00264384

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