Rhamnolipids-Next generation surfactants?

Journal of Biotechnology

Volumn 162, Issue 4, 2012, Pages 366-380

  Müller, Markus Michael ^a   Kügler, Johannes H ^a   Henkel, Marius ^a   Gerlitzki, Melanie ^a   Hörmann, Barbara ^a   Pöhnlein, Martin ^a   Syldatk, Christoph ^a   Hausmann, Rudolf ^b  

^a KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

^b UNIVERSITY OF HOHENHEIM   (Germany)

Author keywords

Alkyl polyglycoside; Biosurfactant; Burkholderia; Pseudomonas; Rhamnolipid; Systems biotechnology

Indexed keywords

ALKYL POLYGLYCOSIDE; BIO SURFACTANT; BURKHOLDERIA; PSEUDOMONAS; RHAMNOLIPIDS; SYSTEMS BIOTECHNOLOGY;

BACTERIA; BIOCHEMISTRY; BIOCONVERSION; BIOMOLECULES; BIOREACTORS; BIOSYNTHESIS; BIOTECHNOLOGY; COMMERCE; GENE EXPRESSION; LIPIDS; OPTIMIZATION; PETROLEUM INDUSTRY; VEGETABLE OILS;

SURFACE ACTIVE AGENTS;

BETA HYDROXYFATTY ACID; FATTY ACID; RHAMNOLIPID; RHAMNOSE; UNCLASSIFIED DRUG;

ARTICLE; BIOCATALYSIS; BURKHOLDERIA; CARBOHYDRATE SYNTHESIS; CHEMICAL STRUCTURE; COMMERCIAL PHENOMENA; DOWNSTREAM PROCESSING; MICROCYSTIS AERUGINOSA; NONHUMAN; PRIORITY JOURNAL; SCREENING TEST;

BIOTECHNOLOGY; BURKHOLDERIA; GLYCOLIPIDS; PSEUDOMONAS; SURFACE-ACTIVE AGENTS;

BURKHOLDERIA; PSEUDOMONAS; PSEUDOMONAS AERUGINOSA;

EID: 84871670057     PISSN: 01681656     EISSN: 18734863     Source Type: Journal    
DOI: 10.1016/j.jbiotec.2012.05.022     Document Type: Article

References (198)

1. Abalos A., Maximo F., Manresa M.A., Bastida J. Utilization of response surface methodology to optimize the culture media for the production of rhamnolipids by Pseudomonas aeruginosa AT10. Journal of Chemical Technology and Biotechnology 2002, 77:777-784.
2. Abalos A., Pinazo A., Infante M., Casals M., García F., Manresa A. Physicochemical and antimicrobial properties of new rhamnolipids produced by Pseudomonas aeruginosa AT10 from soybean oil refinery wastes. Langmuir 2001, 17:1367-1371.
3. Abdel-Mawgoud A.M., Hausmann R., Lépine F., Müller M.M., Déziel E. Rhamnolipids: detection, analysis, biosynthesis, genetic regulation and bioengineering of production. Biosurfactants 2011, 13-55. Springer, Berlin. 1st edition, VII 216 pp.
4. Abdel-Mawgoud A.M., Lepine F., Deziel E. Rhamnolipids: diversity of structures, microbial origins and roles. Applied Microbiology and Biotechnology 2010, 86:1323-1336.
5. Alibaba.com, 2011. Global trade starts here: current market prices for sugar cane molasses, crude glycerol and soybean oil fatty acids. Hong Kong. (accessed 01.10.11). http://www.alibaba.com/.
6. Alper H., Moxley J., Nevoigt E., Fink G.R., Stephanopoulos G. Engineering yeast transcription machinery for improved ethanol tolerance and production. Science 2006, 314:1565-1568.
7. Andrä J., Rademann J., Howe J., Koch M., Heine H., Zähringer U., Brandenburg K. Endotoxin-like properties of a rhamnolipid exotoxin from Burkholderia (Pseudomonas) plantarii: immune cell stimulation and biophysical characterization. Biological Chemistry 2006, 387:301-310.
8. Arino S., Marchal R., Vandecasteele J.P. Identification and production of a rhamnolipidic biosurfactant by a Pseudomonas species. Applied Microbiology and Biotechnology 1996, 45:162-168.
9. Babu P.S., Vaidya A.N., Bal A.S., Kapur R., Juwarkar A., Khanna P. Kinetics of biosurfactant production by Pseudomonas aeruginosa strain BS2 from industrial wastes. Biotechnology Letters 1996, 18:263-268.
10. Banat I., Franzetti A., Gandolfi I., Bestetti G., Martinotti M., Fracchia L., Smyth T., Marchant R. Microbial biosurfactants production, applications and future potential. Applied Microbiology and Biotechnology 2010, 87:427-444.
11. Banat I.M., Makkar R.S., Cameotra S.S. Potential commercial applications of microbial surfactants. Applied Microbiology and Biotechnology 2000, 53:495-508.
12. Beyer, S., 2011. Nachwachsende Rohstoffe halten Einzug in die Chemie. Process. Vogel Business Media GmbH & Co.KG, Würzburg. (accessed 15.11.11). http://www.process.vogel.de/anlagen_apparatebau/articles/317189/index1.html.
13. Breucker C., Jordan V., Nitsche M., Gutsche B. Oleochemie - Chemieprodukte auf der Basis nachwachsender Rohstoffe. Chemie Ingenieur Technik 1995, 67:430-440.
14. Bujara M., Panke S. Engineering in complex systems. Current Opinion in Biotechnology 2010, 21:586-591.
15. Burger M., Glaser L., Burton R.M. The enzymatic synthesis of a rhamnose-containing glycolipid by extracts of Pseudomonas aeruginosa. Federation Proceedings 1963, 21:2595-2602.
16. Byrd M.S., Sadovskaya I., Vinogradov E., Lu H.P., Sprinkle A.B., Richardson S.H., Ma L.Y., Ralston B., Parsek M.R., Anderson E.M., Lam J.S., Wozniak D.J. Genetic and bioChem. analyses of the Pseudomonas aeruginosa Psl exopolysaccharide reveal overlapping roles for polysaccharide synthesis enzymes in Psl and LPS production. Molecular Microbiology 2009, 73:622-638.
17. Cabrera-Valladares N., Richardson A.P., Olvera C., Trevino L.G., Deziel E., Lepine F., Soberon-Chavez G. Monorhamnolipids and 3-(3-hydroxyalkanoyloxy)alkanoic acids (HAAs) production using Escherichia coli as a heterologous host. Applied Microbiology and Biotechnology 2006, 73:187-194.
18. Camilios-Neto D., Bugay C., de Santana-Filho A.P., Joslin T., de Souza L.M., Sassaki G.L., Mitchell D.A., Krieger N. Production of rhamnolipids in solid-state cultivation using a mixture of sugarcane bagasse and corn bran supplemented with glycerol and soybean oil. Applied Microbiology and Biotechnology 2011, 89:1395-1403.
19. Carr J.A., Bisht K.S. Enzyme-catalyzed regioselective transesterification of peracylated sophorolipids. Tetrahedron 2003, 59:7713-7724.
20. Cha M., Lee N., Kim M., Lee S. Heterologous production of Pseudomonas aeruginosa EMS1 biosurfactant in Pseudomonas putida. Bioresource Technology 2008, 99:2192-2199.
21. Chandrasekaran E.V., BeMiller J.N. Constituent analysis of glycosaminoglycans. Methods in Carbohydrate Chemistry 1980, 89-96. Academic Press, New York. R.L. Whistler, J.N. BeMiller (Eds.).
22. Chayabutra C., Wu J., Ju L. Rhamnolipid production by Pseudomonas aeruginosa under denitrification: effects of limiting nutrients and carbon substrates. Biotechnology and Bioengineering 2001, 72:25-33.
23. Chen C.Y., Baker S.C., Darton R.C. Batch production of biosurfactant with foam fractionation. Journal of Chemical Technology and Biotechnology 2006, 81:1923-1931.
24. Chen C.Y., Baker S.C., Darton R.C. The application of a high throughput analysis method for the screening of potential biosurfactants from natural sources. Journal of Microbiological Methods 2007, 70:503-510.
25. Chen S.-Y., Wei Y.-H., Chang J.-S. Repeated pH-stat fed-batch fermentation for rhamnolipid production with indigenous Pseudomonas aeruginosa S2. Applied Microbiology and Biotechnology 2007, 76:67-74.
26. Chen S.Y., Lu W.B., Wei Y.H., Chen W.M., Chang J.S. Improved production of biosurfactant with newly isolated Pseudomonas aeruginosa S2. Biotechnology Progress 2007, 23:661-666.
27. 13C NMR analysis of the products in wild-type and mutants. Journal of Biotechnology 2011, 151:30-42.
28. Choudhary S., Schmidt-Dannert C. Applications of quorum sensing in biotechnol. Applied Microbiology and Biotechnology 2009, 86:1267-1279.
29. Clal, 2011. CLAL S.r.l.: dry whey USA. Modena. (accessed 01.10.11). http://www.clal.it/en/index.php%3Fsection=dry_whey.
30. Cognis, 2004. Der Cognis Nachhaltigkeitsbericht. COGNIS GmbH, Düsseldorf, Germany.
31. Cooper D.G., Goldenberg B.G. Surface-active agents from two Bacillus species. Applied and Environment Microbiology 1987, 53:224-229.
32. Costa S., Lepine F., Milot S., Deziel E., Nitschke M., Contiero J. Cassava wastewater as a substrate for the simultaneous production of rhamnolipids and polyhydroxyalkanoates by Pseudomonas aeruginosa. Journal of Industrial Microbiology and Biotechnology 2009, 36:1063-1072.
33. Costa S.G.V.A.O., Déziel E., Lépine F. Characterization of rhamnolipid production by Burkholderia glumae. Letters in Applied Microbiology 2011, 53:620-627.
34. Cottingham M.G., Bain C.D., Vaux D.J.T. Rapid method for measurement of surface tension in multiwell plates. Laboratory Investigation 2004, 84:523-529.
35. Davies J.T. A quantitative kinetic theory of emulsion type. I: physical chemistry of the emulsifying agent. Gas/liquid and liquid/liquid interface. Proceedings of 2nd International Congress Surface Activity 1957, 426-438.
36. Deleu M., Paquot M. From renewable vegetables resources to microorganisms: new trends in surfactants. Comptes Rendus Chimie 2004, 7:641-646.
37. Desai J.D., Banat I.M. Microbial production of surfactants and their commercial potential. Microbiology and Molecular Biology Reviews 1997, 61:47-64.
38. Deziel E., Lepine F., Milot S., He J.X., Mindrinos M.N., Tompkins R.G., Rahme L.G. Analysis of Pseudomonas aeruginosa 4-hydroxy-2-alkylquinolines (HAQs) reveals a role for 4-hydroxy-2-heptylquinoline in cell-to-cell communication. Proceedings of the National Academy of Sciences of the United States of America 2004, 101:1339-1344.
39. Déziel E., Lepine F., Milot S., Villemur R. Mass spectrometry monitoring of rhamnolipids from a growing culture of Pseudomonas aeruginosa strain 57RP. Biochimica Et Biophysica Acta-Molecular and Cell Biology of Lipids 2000, 1485:145-152.
40. DMH, 2011. Deutsche Melasse Handelsgesellschaft mbH. Hamburg. (accessed 01.10.11). http://www.deutsche-melasse.de/.
41. Dubeau D., Deziel E., Woods D.E., Lepine F. Burkholderia thailandensis harbors two identical rhl gene clusters responsible for the biosynthesis of rhamnolipids. BMC Microbiology 2009, 9:263.
42. Dusane D.H., Nancharaiah Y.V., Zinjarde S.S., Venugopalan V.P. Rhamnolipid mediated disruption of marine Bacillus pumilus biofilms. Colloids and Surfaces B: Biointerfaces 2010, 81:242-248.
43. Dusane D.H., Zinjarde S.S., Venugopalan V.P., McLean R.J.C., Weber M.M., Rahman P.K.S.M. Quorum sensing: implications on rhamnolipid biosurfactant production. Biotechnology and Genetic Engineering Reviews 2010, vol. 27:159-184.
44. EBB, 2011. European Biodiesel Board: the EU biodiesel industry 2010. Brussels. (accessed 01.10.11). http://www.ebb-eu.org/stats.php%23.
45. Edwards J.R., Hayashi J.A. Structure of a rhamnolipid from Pseudomonas aeruginosa. Archives of Biochemistry and Biophysics 1965, 111:415.
46. EPO, 2011. European Patent Office: Espacenet Patent Search Platform. Munich, The Hague, Berlin, Vienna, Brussels. http://worldwide.espacenet.com/%3Flocale=en_EP.
47. FEDIOL, 2011. World production data for plant oils and fatty acids 2009. Brussels. (accessed 01.10.11). http://fediol.post-site.com/web/world%20production%20data/1011306087/list1187970075/f1.html.
48. Feist A.M., Herrgard M.J., Thiele I., Reed J.L., Palsson B.O. Reconstruction of bioChem. networks in microorganisms. Nature Reviews Microbiology 2009, 7:129-143.
49. Fernández D., Rodríguez E., Bassas M., Viñas M., Solanas A.M., Llorens J., Marqués A.M., Manresa A. Agro-industrial oily wastes as substrates for PHA production by the new strain Pseudomonas aeruginosa NCIB 40045: effect of culture conditions. Biochemical Engineering Journal 2005, 26:159-167.
50. Fiehn O. Metabolomics - the link between genotypes and phenotypes. Plant Molecular Biology 2002, 48:155-171.
51. Fish N.M., Allenby D.J., Lilly M.D. Oxidation of n-alkanes: growth of Pseudomonas putida. European Journal of Applied Microbiology and Biotechnology 1982, 14:259-262.
52. Frimmersdorf E., Horatzek S., Pelnikevich A., Wiehlmann L., Schomburg D. How Pseudomonas aeruginosa adapts to various environments: a metabolomic approach. Environmental Microbiology 2010, 12:1734-1747.
53. Giani C., Wullbrandt D., Rothert R., Meiwes J. Pseudomonas aeruginosa and its Use in a Process for the Biotechnological Preparation of l-rhamnose. US005658793A 1997, Hoechst Aktiengesellschaft, Frankfurt am Main, Germany.
54. Griffin W. Classification of surface-active agents by HLB. Journal of the Society of Cosmetic Chemists 1949, 1:311.
55. Griffin W. Calculation of HLB values of non-ionic surfactants. Journal of the Society of Cosmetic Chemists 1954, 5:235-249.
56. Gruber T. Verfahrenstechnische Aspekte der kontinuierlichen Produktion von Biotensiden am Beispiel der Rhamnolipide. Lehrstuhl für Bioprozesstechnik der Universität Stuttgart 1991, Universität Stuttgart, Stuttgart, p. 121.
57. Gruber T., Chmiel H., Käppeli O., Sticher P., Fiechter A. Integrated process for continuous rhamnolipid biosynthesis. Biosurfactants. Surfactant Science Series 1993, vol. 48. pp. 157-173.
58. Guerra-Santos L. Physiology of Pseudomonas aeruginosa Biosurfactant Production in Continuous Culture 1985, Institute of Biotechnol. Swiss Federal Institute of Technol., Zürich.
59. Guerra-Santos L., Kappeli O., Fiechter A. Pseudomonas aeruginosa biosurfactant production in continuous culture with glucose as carbon source. Applied and Environment Microbiology 1984, 48:301-305.
60. Guerra-Santos L.H., Käppeli O., Fiechter A. Dependence of Pseudomonas aeruginosa continuous culture biosurfactant production on nutritional and environmental factors. Applied Microbiology and Biotechnology 1986, 24:443-448.
61. Gutsmann T., Schromm A.B., Koch M.H.J., Kusumoto S., Fukase K., Oikawa M., Seydel U., Brandenburg K. Lipopolysaccharide-binding protein-mediated interaction of lipid A from different origin with phospholipid membranes. Physical Chemistry Chemical Physics 2000, 2:4521-4528.
62. Haba E., Pinazo A., Jauregui O., Espuny M.J., Infante M.R., Manresa A. PhysioChem. characterization and antimicrobial properties of rhamnolipids produced by Pseudomonas aeruginosa 47T2 NCBIM 40044. Biotechnology and Bioengineering 2003, 81:316-322.
63. Hauser G., Karnovsky M.L. Studies on the production of glycolipide by Pseudomonas aeruginosa. Journal of Bacteriology 1954, 68:645-654.
64. Hauser G., Karnovsky M.L. Rhamnose and rhamnolipid biosynthesis by Pseudomonas aeruginosa. Journal of Biological Chemistry 1957, 224:91-105.
65. Hauser G., Karnovsky M.L. Studies on the biosynthesis of l-rhamnose. Journal of Biological Chemistry 1958, 233:287-291.
66. Hembach T. Untersuchungen zur mikrobiellen Umsetzung von Maiskeimöl zu Rhamnolipid. Fakultät I Allgemeine und angewandte Naturwissenschaften der Universität Hohenheim 1994, Universität Hohenheim, Stuttgart, p. 105.
67. Heyd M., Franzreb M., Berensmeier S. Continuous rhamnolipid production with integrated product removal by foam fractionation and magnetic separation of immobilized Pseudomonas aeruginosa. Biotechnology Progress 2011, 27:706-716.
68. Heyd M., Franzreb M., Hausmann R., Syldatk C., Berensmeier S. Integral continuous microbial rhamnolipid production. Journal of Biotechnology 2007, 131:S77.
69. Heyd M., Kohnert A., Tan T.H., Nusser M., Kirschhofer F., Brenner-Weiss G., Franzreb M., Berensmeier S. Development and trends of biosurfactant analysis and purification using rhamnolipids as an example. Analytical and Bioanalytical Chemistry 2008, 391:1579-1590.
70. Hisatsuka K., Nakahara T., Sano N., Yamada K. Formation of rhamnolipid by Pseudomonas aeruginosa and its function in hydrocarbon fermentation. Agricultural and Biological Chemistry 1971, 35:686-692.
71. Hoang T.T., Schweizer H.P. Fatty acid biosynthesis in Pseudomonas aeruginosa: cloning and characterization of the fabAB operon encoding beta-hydroxyacyl-acyl carrier protein dehydratase (FabA) and beta-ketoacyl-acyl carrier protein synthase I (FabB). Journal of Bacteriology 1997, 179:5326-5332.
72. Hoang T.T., Schweizer H.P. Characterization of Pseudomonas aeruginosa enoyl-acyl carrier protein reductase (FabI): a target for the antimicrobial triclosan and its role in acylated homoserine lactone synthesis. Journal of Bacteriology 1999, 181:5489-5497.
73. Hodge J., Hofreiter B. Determination of reducing sugars and carbohydrates. Methods in Carbohydrate Chemistry 1962, 380-394. Academic, New York. R. Whistler, M. Wolfrom (Eds.).
74. Hörmann B., Müller M.M., Syldatk C., Hausmann R. Rhamnolipid production by Burkholderia plantarii DSM9509T. European Journal of Lipid Science and Technology 2010, 112:674-680.
75. Howe J., Bauer J., Andra J., Schromm A.B., Ernst M., Rossle M., Zahringer U., Rademann J., Brandenburg K. Biophysical characterization of synthetic rhamnolipids. FEBS Journal 2006, 273:5101-5112.
76. Islas D.J., Moreno S.A.M., Rodriguez J.N.G. Biosurfactant properties, applications and production: a review. Revista Internacional de Contaminación Ambiental 2010, 26:65-84.
77. Itoh S., Honda H., Tomita F., Suzuki T. Rhamnolipids produced by Pseudomonas aeruginosa grown on paraffin (mixture of C12, C13 and C14 fractions). Journal of Antibiotics 1971, 24:855.
78. Itoh S., Suzuki T. Effect of rhamnolipids on growth of Pseudomonas aeruginosa mutant deficient in n-paraffin-utilizing ability. Agricultural and Biological Chemistry 1972, 36:2233-2235.
79. Jain D.K., Collinsthompson D.L., Lee H., Trevors J.T. A drop-collapsing test for screening surfactant-producing microorganism. Journal of Microbiological Methods 1991, 13:271-279.
80. Jarvis F.G., Johnson M.J. A glyco-lipide produced by Pseudomonas aeruginosa. Journal of the American Chemical Society 1949, 71:4124-4126.
81. Jeong H., Lim D., Hwang S., Ha S., Kong J. Rhamnolipid production by Pseudomonas aeruginosa immobilized in polyvinyl alcohol beads. Biotechnology Letters 2004, 26:35-39.
82. Kanehisa M., Goto S. KEGG: Kyoto Encyclopedia of Genes and Genomes. Nucleic Acids Research 2000, 28:27-30.
83. Karmee S.K. Lipase catalyzed synthesis of ester-based surfactants from biomass derivatives. Biofuels Bioproducts and Biorefining: Biofpr 2008, 2:144-154.
84. Kennedy J.F., Kumar H., Panesar P.S., Marwaha S.S., Goyal R., Parmar A., Kaur S. Enzyme-catalyzed regioselective synthesis of sugar esters and related compounds. Journal of Chemical Technology and Biotechnology 2006, 81:866-876.
85. Klekner V., Kosaric N. Biosurfactants for cosmetics. Biosurfactants: Production - Properties - Applications 1993, 373-390. Marcel Dekker Inc., NY. N. Kosaric (Ed.).
86. Koch A.K., Reiser J., Kappeli O., Fiechter A. Genetic construction of lactose-utilizing strains of Pseudomonas aeruginosa and their application in biosurfactant production. Biotechnology 1988, 6:1335-1339.
87. Kosaric N. Biosurfactants and their application for soil bioremediation. Food Technology and Biotechnology 2001, 39:295-304.
88. Lang S. Biological amphiphiles (microbial biosurfactants). Current Opinion in Colloid and Interface Science 2002, 7:12-20.
89. Lang S., Trowitzsch-Kienast W. Biotenside 2002, B.G. Teubner, Stuttgart, Leipzig, Wiesbaden. 1st ed.
90. Laurila M.A. Biosurfactant Production by Mutant Strains of Pseudomonas aeruginosa 1985, Swiss Federal Institute of Technol., ETH Zürich, Zürich, p. 117.
91. Lee K.M., Hwang S., Ha S.D., Jang J., Lim D., Kong J. Rhamnolipid production in batch and fed-batch fermentation using Pseudomonas aeruginosa BYK-2 KCTC 18012P. Biotechnology and Bioprocess Engineering 2004, 9:267-273.
92. Lee S.Y., Lee D.Y., Kim T.Y. Systems biotechnology for strain improvement. Trends in Biotechnology 2005, 23:349-358.
93. Leighton, A., 2010. Adrem Biotech Inc.: method for treating rhinitis and sinusitis by rhamnolipids. WO2010/080406 A1.
94. Lin S.-C. Biosurfactants: recent advances. Journal of Chemical Technology and Biotechnology 1996, 66:109-120.
95. Lindahl M., Faris A., Wadstrom T., Hjerten S. A new test based on salting out to measure relative surface hydrophobicity of bacterial cells. Biochimica Et Biophysica Acta 1981, 677:471-476.
96. Lindhout T., Lau P.C.Y., Brewer D., Lam J.S. Truncation in the core oligosaccharide of lipopolysaccharide affects flagella-mediated motility in Pseudomonas aeruginosa PAO1 via modulation of cell surface attachment. Microbiology-(UK) 2009, 155:3449-3460.
97. Linhardt R.J., Bakhit R., Daniels L., Mayerl F., Pickenhagen W. Microbially produced rhamnolipid as a source of rhamnose. Biotechnology and Bioengineering 1989, 33:365-368.
98. LOHAS.de, 2011. Lifestyle of health and sustainability. Munich. (accessed 15.11.11). http://www.lohas.de/.
99. Lovaglio R.B., Costa S., Lima C.J.B., Cortezi M., Jonas C. Effect of C/N ratio and physicoChem. conditions on the production of rhamnolipids by Pseudomonas aeruginosa LBI. Research Journal of Biotechnology 2010, 5:19-24.
100. Maczek, J., Junne, S., Götz, P., 2007. Examining biosurfactant producing bacteria - an example for an automated search for natural compounds. , Application Note CyBio AG. http://www.cybio-ag.com/files.php%3Fdl_mg_id=1%26file=dl_mg_1177602301.pdf.
101. Magario I., Ma X., Neumann A., Syldatk C., Hausmann R. Non-porous magnetic micro-particles: comparison to porous enzyme carriers for a diffusion rate-controlled enzymatic conversion. Journal of Biotechnology 2008, 134:72.
102. Magario I., Viclhauer O., Neumann A., Hausmann R., Syldatk C. Kinetic analysis and modeling of the liquid-liquid conversion of emulsified di-rhamnolipids by naringinase from Penicillium decumbens. Biotechnology and Bioengineering 2009, 102:9-19.
103. Makkar R.S., Cameotra S.S. An update on the use of unconventional substrates for biosurfactant production and their new applications. Applied Microbiology and Biotechnology 2002, 58:428-434.
104. Maneerat S. Production of biosurfactants using substrates from renewable-resources. Songklanakarin Journal of Science and Technology 2005, 27:675-683.
105. Manresa M., Bastida J., Mercade M., Robert M., Deandres C., Espuny M., Guinea J. Kinetic studies on surfactant production by Pseudomonas aeruginosa 44T1. Journal of Industrial Microbiology 1991, 8:133-136.
106. Mata-Sandoval J., Karns J., Torrents A. High-performance liquid chromatography method for the characterization of rhamnolipid mixtures produced by Pseudomonas aeruginosa UG2 on corn oil. Journal of Chromatography A 1999, 864:211-220.
107. Matulovic, U., 1987. Verfahrensentwicklung zur Herstellung grenzflächenaktiver Rhamnolipide mit immobilisierten Zellen von Pseudomonas spec. DSM 2874. Thesis. Technische Universität Braunschweig.
108. Medina-Moreno S.A., Jimenez-Islas D., Gracida-Rodriguez J.N., Gutierrez-Rojas M., Diaz-Ramirez I.J. Modeling rhamnolipids production by Pseudomonas aeruginosa from immiscible carbon source in a batch system. International Journal of Environmental Science and Technology 2011, 8:471-482.
109. Mixich, J., Rapp, K., 1990. Process for producing rhamnose from rhamnolipids. DE4030262. Suedzucker AG, Germany.
110. Mixich J., Rothert R., Wullbrandt D. Process for the Quantitative Purification of Glycolipids. US005656747A 1997, Hoechst Aktiengesellschaft, Frankfurt am Main, Germany.
111. Monteiro S.A., Sassaki G.L., de Souza L.M., Meira J.A., de Araujo J.M., Mitchell D.A., Ramos L.P., Krieger N. Molecular and structural characterization of the biosurfactant produced by Pseudomonas aeruginosa DAUPE 614. Chemistry and Physics of Lipids 2007, 147:1-13.
112. Morikawa M., Hirata Y., Imanaka T. A study on the structure-function relationship of lipopeptide biosurfactants. Biochimica Et Biophysica Acta-Molecular and Cell Biology of Lipids 2000, 1488:211-218.
113. Müller M.M., Hausmann R. Regulatory and metabolic network of rhamnolipid biosynthesis: traditional and advanced engineering towards biotechnological production. Applied Microbiology and Biotechnology 2011, 91:251-264.
114. Müller M.M., Hörmann B., Kugel M., Syldatk C., Hausmann R. Evaluation of rhamnolipid production capacity of Pseudomonas aeruginosa PAO1 in comparison to the rhamnolipid over-producer strains DSM 7108 and DSM 2874. Applied Microbiology and Biotechnology 2011, 89:585-592.
115. Müller M.M., Hörmann B., Syldatk C., Hausmann R. Pseudomonas aeruginosa PAO1 as a model for rhamnolipid production in bioreactor cultivations. Applied Microbiology and Biotechnology 2010, 87:167-174.
116. Müller M.M., Hörmann B., Syldatk C., Hausmann R. Microbial rhamnolipids. Carbohydrate-Modifying Biocatalysts 2011, PanStanford Publishing Pte. Ltd., Singapore. P. Grunwald (Ed.).
117. Mulligan C., Gibbs B. Factors influencing the economics of biosurfactants. Biosurfactants: Production - Properties - Applications 1993, 329-371. Marcel Dekker Inc., NY. N. Kosaric (Ed.).
118. Mulligan C.N., Cooper D.G., Neufeld R.J. Selection of microbes producing biosurfactants in media without hydrocarbons. Journal of Fermentation Technology 1984, 62:311-314.
119. Mulligan C.N., Gibbs B.F. Correlation of nitrogen-metabolism with biosurfactant production by Pseudomonas aeruginosa. Applied and Environment Microbiology 1989, 55:3016-3019.
120. Mulligan C.N., Gibbs B.F. Recovery of biosurfactants by ultrafiltration. Journal of Chemical Technology and Biotechnology 1990, 47:23-29.
121. Nguyen T.T., Sabatini D.A. Characterization and emulsification properties of rhamnolipid and sophorolipid biosurfactants and their applications. International Journal of Molecular Sciences 2011, 12:1232-1244.
122. Nguyen T.T.L., Edelen A., Neighbors B., Sabatini D.A. Biocompatible lecithin-based microemulsions with rhamnolipid and sophorolipid biosurfactants: formulation and potential applications. Journal of Colloid and Interface Science 2010, 348:498-504.
123. Nitschke M., Costa S.G.V.A.O. Biosurfactants in food industry. Trends in Food Science and Technology 2007, 18:252-259.
124. Nogales J., Palsson B.O., Thiele I. A genome-scale metabolic reconstruction of Pseudomonas putida KT2440: iJN746 as a cell factory. BMC Systematic Biology 2008, 2:20.
125. Nunez A., Foglia T.A., Ashby R. Enzymatic synthesis of a galactopyranose sophorolipid fatty acid-ester. Biotechnology Letters 2003, 25:1291-1297.
126. Ochsner U.A., Fiechter A., Reiser J. Isolation, characterization and expression in Escherichia coli of the Pseudomonas aeruginosa rhlAB genes encoding a rhamnosyltransferase involved in rhamnolipid biosurfactant synthesis. Journal of Biological Chemistry 1994, 269:19787-19795.
127. Ochsner U.A., Hembach T., Fiechter A. Production of rhamnolipid biosurfactants. Advances in Biochemical Engineering/Biotechnology 1995, 89-118. Springer-Verlag, Berlin, Heidelberg, New York. A. Fiechter (Ed.).
128. Ochsner U.A., Reiser J., Fiechter A., Witholt B. Production of Pseudomonas aeruginosa rhamnolipid biosurfactants in heterologous hosts. Applied and Environmental Microbiology 1995, 61:3503-3506.
129. Olvera C., Goldberg J.B., Sanchez R., Soberon-Chavez G. The Pseudomonas aeruginosa algC gene product participates in rhamnolipid biosynthesis. FEMS Microbiology Letters 1999, 179:85-90.
130. OnVista.de, 2011. Real-time indications for soft commodities by Royal Bank of Scotland. Cologne, Frankfurt. (accessed 01.10.11). http://www.onvista.de/rohstoffe/rohstoffliste/soft-commodities/.
131. Orth J.D., Thiele I., Palsson B.O. What is flux balance analysis?. Nature Biotechnology 2010, 28:245-248.
132. Pacwa-Plociniczak M., Plaza G.A., Piotrowska-Seget Z., Cameotra S.S. Environmental applications of biosurfactants: recent advances. International Journal of Molecular Sciences 2010, 12:633-654.
133. Pajarron A.M., Dekoster C.G., Heerma W., Schmidt M., Haverkamp J. Structure identification of natural rhamnolipid mixtures by fast-atom-bombardment tandem mass-spectrometry. Glycoconjugate Journal 1993, 10:219-226.
134. Patel R.M., Desai A.J. Biosurfactant production by Pseudomonas aeruginosa GS3 from molasses. Letters in Applied Microbiology 1997, 25:91-94.
135. Patel R.M., Desai A.J. Surface-active properties of rhamnolipids from Pseudomonas aeruginosa GS3. Journal of Basic Microbiology 1997, 37:281-286.
136. Perumal D., Samal A., Sakharkar K.R., Sakharkar M.K. Targeting multiple targets in Pseudomonas aeruginosa PAO1 using flux balance analysis of a reconstructed genome-scale metabolic network. Journal of Drug Targeting 2011, 19:1-13.
137. Pham T.H., Webb J.S., Rehm B.H.A. The role of polyhydroxyalkanoate biosynthesis by Pseudomonas aeruginosa in rhamnolipid and alginate production as well as stress tolerance and biofilm formation. Microbiology-(UK) 2004, 150:3405-3413.
138. Pinzon N.M., Ju L.K. Analysis of rhamnolipid biosurfactants by methylene blue complexation. Applied Microbiology and Biotechnology 2009, 82:975-981.
139. Pinzon N.M., Ju L.K. Improved detection of rhamnolipid production using agar plates containing methylene blue and cetyl trimethylammonium bromide. Biotechnology Letters 2009, 31:1583-1588.
140. Plou F.J., Cruces M.A., Ferrer M., Fuentes G., Pastor E., Bernabe M., Christensen M., Comelles F., Parra J.L., Ballesteros A. Enzymatic acylation of di- and trisaccharides with fatty acids: choosing the appropriate enzyme, support and solvent. Journal of Biotechnology 2002, 96:55-66.
141. Potvin E., Sanschagrin F., Levesque R. Sigma factors in Pseudomonas aeruginosa. FEMS Microbiology Review 2008, 32:38-55.
142. Rahim R., Burrows L.L., Monteiro M.A., Perry M.B., Lam J.S. Involvement of the rml locus in core oligosaccharide and O polysaccharide assembly in Pseudomonas aeruginosa. Microbiology 2000, 146(Pt 11):2803-2814.
143. Rahim R., Ochsner U.A., Olvera C., Graninger M., Messner P., Lam J.S., Soberon-Chavez G. Cloning and functional characterization of the Pseudomonas aeruginosa rhlC gene that encodes rhamnosyltransferase 2, an enzyme responsible for di-rhamnolipid biosynthesis. Molecular Microbiology 2001, 40:708-718.
144. Ramana K.V., Karanth N.G. Production of biosurfactants by the resting cells of Pseudomonas aeruginosa CFTR-6. Biotechnology Letters 1989, 11(6):437-442.
145. Reddy P.G., Singh H.D., Pathak M.G., Bhagat S.D., Baruah J.N. Isolation and functional characterization of hydrocarbon emulsifying and solubilizing factors produced by a Pseudomonas species. Biotechnology and Bioengineering 1983, 25:387-401.
146. Rehm B.H.A., Mitsky T.A., Steinbuchel A. Role of fatty acid de novo biosynthesis in polyhydroxyalkanoic acid (PHA) and rhamnolipid synthesis by pseudomonads: establishment of the transacylase (PhaG)-mediated pathway for PHA biosynthesis in Escherichia coli. Applied and Environment Microbiology 2001, 67:3102-3109.
147. Reiling H.E., Thanei-Wyss U., Guerra-Santos L.H., Hirt R., Käppeli O., Fiechter A. Pilot plant production of rhamnolipid biosurfactant by Pseudomonas aeruginosa. Applied and Environment Microbiology 1986, 51:985-989.
148. Reis R.S., Pereira A.G., Neves B.C., Freire D.M.G. Gene regulation of rhamnolipid production in Pseudomonas aeruginosa - a review. Bioresource Technology 2011, 102:6377-6384.
149. Robert M., Mercadé M.E., Bosch M.P., Parra J.L., Espuny M.J., Manresa A., Guinea J. Effect of the carbon source on biosurfactant production by Pseudomonas aeruginosa 44T1. Biotechnology Letters 1989, 11:871-874.
150. Rodrigues L., Banat I.M., Teixeira J., Oliveira R. Biosurfactants: potential applications in medicine. Journal of Antimicrobial Chemotherapy 2006, 57:609-618.
151. Ron E.Z., Rosenberg E. Natural roles of biosurfactants. Environmental Microbiology 2001, 3:229-236.
152. Rosenberg M. Bacterial adherence to polystyrene - a replica method of screening for bacteria hydrophobicity. Applied and Environment Microbiology 1981, 42:375-377.
153. Rosenberg M. Microbial adhesion to hydrocarbons: twenty-five years of doing MATH. FEMS Microbiology Letters 2006, 262:129-134.
154. Rosenberg M., Gutnick D., Rosenberg E. Adherence of bacteria to hydrocarbons - a simple method for measuring cell-surface hydrophobicity. FEMS Microbiology Letters 1980, 9:29-33.
155. Salwa M.S., Asshifa M.N.N., Amirul A.A., Yahya A.R.M. Different feeding strategy for the production of biosurfactant from Pseudomonas aeruginosa USM AR2 in modified bioreactor. Biotechnology and Bioprocess Engineering 2009, 14:763-768.
156. Sarachat T., Pornsunthorntawee O., Chavadej S., Rujiravanit R. Purification and concentration of a rhamnolipid biosurfactant produced by Pseudomonas aeruginosa SP4 using foam fractionation. Bioresource Technology 2010, 101:324-330.
157. Sarney D.B., Vulfson E.N. Application of enzymes for the synthesis of surfactants. Trends in Biotechnology 1995, 13:164-172.
158. Satpute S.K., Banpurkar A.G., Dhakephalkar P.K., Banat I.M., Chopade B.A. Methods for investigating biosurfactants and bioemulsifiers: a review. Critical Reviews in Biotechnology 2010, 30:127-144.
159. Satpute S.K., Bhawsar B.D., Dhakephalkar P.K., Chopade B.A. Assessment of different screening methods for selecting biosurfactant producing marine bacteria. Indian Journal of Marine Sciences 2008, 37:243-250.
160. Sauer U. Metabolic networks in motion: C-13-based flux analysis. Molecular Systems Biology 2006, 2:62.
161. Schenk T., Schuphan I., Schmidt B. High-performance liquid-chromatographic determination of the rhamnolipids produced by Pseudomonas aeruginosa. Journal of Chromatography A 1995, 693:7-13.
162. Siegmund I., Wagner F. New method for detecting rhamnolipids excreted by Pseudomonas species during growth on mineral agar. Biotechnology Techniques 1991, 5:265-268.
163. Singh S.K., Felse A.P., Nunez A., Foglia T.A., Gross R.A. Regioselective enzyme-catalyzed synthesis of sophorolipid esters, amides, and multifunctional monomers. Journal of Organic Chemistry 2003, 68:5466-5477.
164. Smyth C.J., Jonsson P., Olsson E., Soderlind O., Rosengren J., Hjerten S., Wadstrom T. Differences in hydrophobic surface characteristics of porcine enteropathogenic Escherichia coli with or without K88 antigen as revealed by hydrophobic interaction chromatography. Infection and Immunity 1978, 22:462-472.
165. Soberón-Chávez G., Aguirre-Ramirez M., Ordonez L. Is Pseudomonas aeruginosa only " sensing quorum" ?. Critical Reviews in Microbiology 2005, 31:171-182.
166. Soberón-Chávez G., Lépine F., Déziel E. Production of rhamnolipids by Pseudomonas aeruginosa. Applied Microbiology and Biotechnology 2005, 68:718-725.
167. Sullivan E.R. Molecular genetics of biosurfactant production. Environmental Microbiology 1998, 9:263-269.
168. Syldatk C., Lang S., Matulovic U., Wagner F. Production of four interfacial active rhamnolipids from n-alkanes or glycerol by resting cells of Pseudomonas species DSM 2874. Zeitschrift fur Naturforschung Section C: Biosciences 1985, 40:61-67.
169. Syldatk C., Lang S., Wagner F., Wray V., Witte L. Chem. and physical characterization of four interfacial-active rhamnolipids from Pseudomonas spec. DSM 2874 grown on n-alkanes. Zeitschrift fur Naturforschung Section C: Biosciences 1985, 40:51-60.
170. Syldatk C., Matulovic U., Wagner F. Biotenside - Neue Verfahren zur mikrobiellen Herstellung grenzflächenaktiver anionischer Glykolipide. Biotech Forum 1984, 1:58-66.
171. Syldatk C., Schaub G., Schulze I., Ernst D., Neumann A. Existing Value Chains. Renewable Raw Materials 2011, Wiley-VCH Verlag GmbH & Co. KGaA, pp. 95-120.
172. Syldatk C., Wagner F. Production of biosurfactants. Biosurfactants and Biotechnology 1987, 25:89-120.
173. Ternes, Täufel, Tunger, Zobel, 2005. Lebensmittel-Lexikon. Behr's Verlag.
174. Thomson Reuters, 2011. ISI web of knowledge: web of science. http://apps.webofknowledge.com/.
175. Toribio J., Escalante A.E., Soberon-Chavez G. Rhamnolipids: production in bacteria other than Pseudomonas aeruginosa. European Journal of Lipid Science and Technology 2010, 112:1082-1087.
176. Trummler K., Effenberger F., Syldatk C. An integrated microbial/enzymatic process for production of rhamnolipids and l-(+)-rhamnose from rapeseed oil with Pseudomonas sp. DSM 2874. European Journal of Lipid Science and Technology 2003, 105:563-571.
177. U.S.DEC, 2011. U.S. dairy export council: dairy market. Arlington. (accessed 01.10.11). http://www.usdec.org/Products/.
178. Van Bogaert I.N.A., Saerens K., De Muynck C., Develter D., Soetaert W., Vandamme E.J. Microbial production and application of sophorolipids. Applied Microbiology and Biotechnology 2007, 76:23-34.
179. Van Gennip M., Christensen L.D., Alhede M., Phipps R., Jensen P.O., Christophersen L., Pamp S.J., Moser C., Mikkelsen P.J., Koh A.Y., Tolker-Nielsen T., Pier G.B., Hoiby N., Givskov M., Bjarnsholt T. Inactivation of the rhlA gene in Pseudomonas aeruginosa prevents rhamnolipid production, disabling the protection against polymorphonuclear leukocytes. Apmis 2009, 117:537-546.
180. Varma A., Palsson B.O. Stoichiometric flux balance models quantitatively predict growth and metabolic by-product secretion in wild-type Escherichia coli W3110. Applied and Environment Microbiology 1994, 60:3724-3731.
181. Vatsa P., Sanchez L., Clement C., Baillieul F., Dorey S. Rhamnolipid biosurfactants as new players in animal and plant defense against microbes. International Journal of Molecular Sciences 2010, 11:5095-5108.
182. Vaux, D., Cottingham, M., 2007. Method and apparatus for measuring surface configuration. WO 2007/039729 A1.
183. Velikonja J., Kosaric N. Biosurfactants in food applications. Biosurfactants: Production - Properties - Applications 1993, 419-446. Marcel Dekker Inc., NY. N. Kosaric (Ed.).
184. Wagner F., Behrendt U., Bock H., Kretschmer A., Lang S., Syldatk C. Production and chem. characterization of surfactants from Rhodococcus erythropolis and Pseudomonas sp. mub grown on hydrocarbons. Microbial Enhanced Oil recovery 1983, 55-60.
185. Walter V. New Approaches for the Economic Production of Rhamnolipid Biosurfactants from Renewable Resources. Fak. f. Chemieing. u. Verfahrenstech. Inst. f. Bio-u. Lebensmitteltech 2009, Karlsruhe Institute of Technol (KIT), Karlsruhe.
186. Walter V., Syldatk C., Hausmann R. Screening concepts for the isolation of biosurfactant producing microorganisms. Biosurfactants 2008, 1-13. R. Sen (Ed.).
187. Walter V., Syldatk C., Hausmann R., Flickinger M.C. Microbial Production of Rhamnolipid Biosurfactants. Encyclopedia of Industrial Biotechnology 2009, John Wiley & Sons, Inc. 10.1002/9780470054581.eib529.
188. Wang Q.H., Fang X.D., Bai B.J., Liang X.L., Shuler P.J., Goddard W.A., Tang Y.C. Engineering bacteria for production of rhamnolipid as an agent for enhanced oil recovery. Biotechnology and Bioengineering 2007, 98:842-853.
189. Wang Y., Chu J., Zhuang Y.P., Wang Y.H., Xia J.Y., Zhang S.L. Industrial bioprocess control and optimization in the context of systems. Biotechnology Advances 2009, 27:989-995.
190. Wei Y.-H., Chou C.-L., Chang J.-S. Rhamnolipid production by indigenous Pseudomonas aeruginosa J4 originating from petroChem. Wastewater Biochemical Engineering Journal 2005, 27:146.
191. Williams P., Camara M. Quorum sensing and environmental adaptation in Pseudomonas aeruginosa: a tale of regulatory networks and multifunctional signal molecules. Current Opinion in Microbiology 2009, 12:182-191.
192. Willumsen P.A., Karlson U. Screening of bacteria, isolated from PAH-contaminated soils, for production of biosurfactants and bioemulsifiers. Biodegradation 1997, 7:415-423.
193. Winsor G.L., Van Rossum T., Lo R., Khaira B., Whiteside M.D., Hancock R.E.W., Brinkman F.S.L. Pseudomonas genome database: facilitating user-friendly, comprehensive comparisons of microbial genomes. Nucleic Acids Research 2009, 37:D483-D488.
194. Witek-Krowiak A., Witek J., Gruszczynska A., Szafran R.G., Kozlecki T., Modelski S. Ultrafiltrative separation of rhamnolipid from culture medium. World Journal of Microbiology and Biotechnology 2011, 27:1961-1964.
195. Wittgens A., Tiso T., Arndt T., Wenk P., Hemmerich J., Muller C., Wichmann R., Kupper B., Zwick M., Wilhelm S., Hausmann R., Syldatk C., Rosenau F., Blank L. Growth independent rhamnolipid production from glucose using the non-pathogenic Pseudomonas putida KT2440. Microbial Cell Factories 2011, 10:80.
196. Yamaguchi M., Sato A. Microbial production of sugar-lipids. Chemistry and Industry 1976, 17:741-742.
197. Zhang L., Somasundaran P., Singh S.K., Felse A.P., Gross R. Synthesis and interfacial properties of sophorolipid derivatives. Colloids and Surfaces A: Physicochemical and Engineering Aspects 2004, 240:75-82.
198. Zhang Y.M., Miller R.M. Enhanced octadecane dispersion and biodegradation by a Pseudomonas rhamnolipid surfactant (biosurfactant). Applied and Environment Microbiology 1992, 58:3276-3282.