Competition between cis, trans and cyclopropane fatty acid formation and its impact on membrane fluidity

Engineering in Life Sciences

Volumn 7, Issue 1, 2007, Pages 67-74

  Loffhagen, Norbert ^a   Hartig C ^a   Geyer, W ^a   Voyevoda, M ^a   Harms, H ^a  

^a HELMHOLTZ CENTRE FOR ENVIRONMENTAL RESEARCH UFZ   (Germany)

Author keywords

Bacteria; Fatty acids; Membranes

Indexed keywords

BACTERIA; BIOLOGICAL MEMBRANES; CELL CULTURE; FLUIDITY; HYDROLYSIS; LIPIDS;

CELL HYDROLYZATES; LIPID EXTRACTS; MEMBRANE FLUIDITY;

FATTY ACIDS;

1,6 DIPHENYL 1,3,5 HEXATRIENE; CYCLOPROPANE; FATTY ACID; LIPID; LIPOSOME; UNSATURATED FATTY ACID;

BACTERIA; BIOLOGICAL MEMBRANES; CELL CULTURE; FATTY ACIDS; FLUIDITY; HYDROLYSIS; LIPIDS;

BACTERIUM; FATTY ACID; FLUIDIZATION; FTIR SPECTROSCOPY; GROWTH; MEMBRANE;

ANISOTROPY; ARTICLE; BACTERIAL GROWTH; BACTERIAL STRAIN; BACTERIUM CULTURE; COMAMONAS TESTOSTERONI; CONTROLLED STUDY; CORRELATION ANALYSIS; FATTY ACID SYNTHESIS; FLUORESCENCE ANALYSIS; HOMEOSTASIS; HYDROLYSIS; INFRARED SPECTROSCOPY; MEMBRANE FLUIDITY; NONHUMAN; NUTRITIONAL DEFICIENCY; PSEUDOMONAS PUTIDA; VISCOSITY;

COMAMONAS; COMAMONAS TESTOSTERONI; PSEUDOMONAS PUTIDA;

EID: 33847142732     PISSN: 16180240     EISSN: 16182863     Source Type: Journal    
DOI: 10.1002/elsc.200620168     Document Type: Article

References (30)

1. M. Sinensky, Homeoviscous adaptation: A homeostatic process that regulates the viscosity of membrane lipids in Escherichia coli, PNAS 1974, 71 (2), 522-525.
2. A. G. Marr, J. L. Ingraham, Effect of temperature on the composition of fatty acids in Escherichia coli, J. Bacteriol. 1962, 84, 1260-1267.
3. A. J. Fulco, Metabolic alterations of fatty acids, Annu. Rev. Biochem. 1974, 43, 215-241.
4. M. Suutari, S. Laakso, Changes in fatty acid branching and unsaturation of Streptomyces griseus and Brevibacterium fermentans as a response to growth temperature, Appl. Environ. Microbiol. 1992, 58, 2338-2340.
5. H. Okuyama, N. Okajima, S. Sasaki, S. Higashi, N. Murata, The cis/trans isomerization of the double bond of a fatty acid as a strategy for adaptation to changes in ambient temperature in the psychrophilic bacterium, Vibrio sp. strain ABE-1, Biochim. Biophys. Acta 1991, 1084, 13-20.
6. H. J. Heipieper, R. Diefenbach, H. Keweloh, 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. 1992, 58, 1847-1852.
7. H. J. Heipieper, F. Meinhardt, A. Segura, The cis-trans isomerase of unsaturated fatty acids in Pseudomonas and Vibrio: biochemistry, molecular biology and physiological function of a unique stress adaptive mechanism, FEMS Microbiol. Lett. 2003, 229, 1-7.
8. C. Härtig, N. Loffhagen, H. Harms, Formation of trans fatty acids is not involved in growth-linked membrane adaptation of Pseudomonas putida, Appl. Environ. Microbiol. 2005, 71, 1951-1922.
9. J. E. Cronan, W. D. Nunn, J. G. Batchelor, Studies on the biosynthesis of cyclopropane fatty acids in Escherichia coli, Biochim. Biophys. Acta 1974, 348, 63-75.
10. J. E. Cronan, Phospholipid modifications in bacteria, Curr. Opin. Microbiol. 2002, 5, 202-205.
11. C. Härtig, N. Loffhagen, W. Babel, Glucose stimulates a decrease of the fatty acid saturation degree in Acinetobacter calcoaceticus, Arch. Microbiol. 1999, 171, 166-172.
12. N. Loffhagen, C. Härtig, D. Benndorf, W. Babel, Effects of growth temperature and lipophilic carbon sources on the fatty acid composition and membrane lipid fluidity of Acinetobacter calcoaceticus 69V, Acta Biotechnol. 2002, 22, 235-243.
13. N. Loffhagen, C. Härtig, W. Babel, Fatty acid patterns of Acinetobacter calcoaceticus 69-V indicate sensitivity against xenobiotics, Appl. Microbiol. Biotechnol. 1995, 44, 526-531.
14. F. J. Weber, S. Isken, J. A. M. de Bont, Cis/trans isomerization of fatty acids as a defence mechanism of Pseudomonas putida strains to toxic concentrations of toluene, Microbiology 1994, 140, 2013-2017.
15. D.W. Grogan, J. E. Cronan, Jr., Cyclopropane ring formation in membrane lipids of bacteria, Microbiol. Mol. Biol. Rev. 1997, 61,429-441.
16. N. Loffhagen, C. Härtig, W. Babel, Pseudomonas putida NCTC 10936 balances membrane fluidity in response to physical and chemical stress by changing the saturation degree and the trans/cis ratio of fatty acids, Biosci. Biotechnol. Biochem. 2004, 68, 317-323.
17. I. S. Kim, J. H. Shim, Y. T. Suh, Changes in membrane fluidity and fatty acid composition of Pseudomonas putida CN-T19 in response to toluene, Biosci. Biotechnol. Biochem. 2002, 66, 1945-1950.
18. R. H. Müller, W. Babel, Glucose as an energy donor in acetate growing Acinetobacter calcoaceticus, Arch. Microbiol. 1986, 144, 62-66.
19. J. Folch, M. Lees, G. H. S. Stanley, A simple method for the isolation and purification of total lipids from animal tissues, J. Biol. Chem. 1957, 226, 497-509.
20. M. Shinitzky, Y. Barenholz, Fluidity parameters of lipid regions determined by fluorescence polarization, Biochim. Biophys. Acta 1978, 515, 367-394.
21. B. J. Litman, Y. Barenholz, Fluorescent probe: diphenylhexatriene, Methods Enzymol. 1982, 81, 678-685.
22. P. H. Calcott, J. D. Oliver, K. Dickey, K. Calcott, Cryosensitivity of Escherichia coli and the involvement of cyclopropane fatty acids, J. Appl. Bacteriol. 1984, 56, 165-172.
23. J. A. Couto, N. Rozes, T. Hogg, Ethanol-induced changes in the fatty acid composition of Lactobacillus hilgardii, J. Appl. Bacteriol. 1984, 81, 126-132.
24. S. I. Bakholdina, N. M. Sanina, I. N. Karsikova, O. B. Popova, T. F. Solov'eva, The impact of abiotic factors (temperature and glucose) on physicochemical properties of lipids from Yersinia pseudotubercolosis, Biochimie 2004, 86, 875-881.
25. F. R. Taylor, J. E. Cronan, Jr., Cyclopropane fatty acid synthase of Escherichia coli: Stabilization, purification, and interaction with phospholipids vesicles, Biochemistry 1979, 18, 3292-3300.
26. J. T. McGarrity, J. B. Armstrong, Phase transition behaviour of artificial liposomes composed of phosphatidylcholines acylated with cyclopropane fatty acids, Biochim. Biophys. Acta 1981, 640, 544-548.
27. J. R. Silvius, R. N. McElhaney, Effects of phospholipid acyl chain structure on thermotropic phase properties: 2: Phosphatidylcholines with unsaturated or cyclopropane acyl chains, Chem. Phys. Lipids 1979, 25, 125-134.
28. P. M. MacDonald, B. D. Sykes, R. N. McElhaney, Flourine-19 nuclear magnetic resonance studies of lipid fatty acyl chain order and dynamics in Acholeplasma laidlawii B membranes: A direct comparison of the effects of cis and trans cyclopropane ring and double-bond substituents on orientational order, Biochemistry 1985, 24, 4651-4659.
29. C. Roach, S. E. Feller, J. A. Ward, S. R. Shaikh, M. Zerouga, W. Stillwell, Comparison of cis and trans fatty acid containing phosphatidylcholines on membrane properties, Biochemistry 2004, 43, 6344-6351.
30. J. Munoz-Rojas, P. Bernal, E. Duque, P. Godoy, A. Segura, J. L. Ramos, Involvement of cyclopropane fatty acids in the response of Pseudomonas putida KT2440 to freeze-drying. Appl. Environ. Microbiol. 2006, 72, 472-477.