Abstract
Members of the genus Rhodococcus produce biosurfactants in response to the presence of liquid hydrocarbons in the growth medium. These biosurfactants are predominantly cell-bound glycolipids containing trehalose as the carbohydrate. Physiological roles of these glycolipids are diverse and involve participation in the uptake of water-insoluble substrates, promotion of the cell adhesion to hydrophobic surfaces, and increased rhodococcal resistance to physicochemical influences. In terms of surfactant characteristics (e.g., surface and interfacial tension, critical micelle concentration, emulsifying activity), Rhodococcus biosurfactants compete favorably with other microbial and synthetic surfactants. Additionally, biological activities of trehalolipids from rhodococci were revealed, including immunomodulating and antitumor properties. Recently developed optimization procedures for their biosynthesis and recovery would broaden potential applications of Rhodococcus biosurfactants in new advanced technologies, such as environmental bioremediation, improved polymeric material construction, and biomedicine. The present chapter summarizes recent research on Rhodococcus biosurfactants, updating the comprehensive review of Lang and Philp (Antonie van Leeuwenhoek Int J Gen Mol Microbiol 74:59–70, 1998), and focuses on biosynthesis features, physicochemical and bioactive properties, and their application potential.
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References
Abdelhay A, Magnin J-P, Gondrexon N, Baup S, Willison J (2009) Adaptation of a Mycobacterium strain to phenanthrene degradation in a biphasic culture system: influence on interfacial area and droplet size. Biotechnol Lett 31:57–63
Alvarez HM, Silva RA, Cesari AC, Zamit AL, Peressutti SR, Reichelt R, Keller U, Malkus U, Rasch C, Maskow T, Mayer F, Steinbüchel A (2004) Physiological and morphological responses of the soil bacterium Rhodococcus opacus strain PD630 to water stress. FEMS Microbiol Ecol 50:75–86
Aranda FJ, Teruel JA, Espuny MJ, Marqués A, Manresa Á, Palacios-Lidon E, Ortiz A (2007) Domain formation by a Rhodococcus sp. biosurfactant trehalose lipid incorporated into phosphatidylcholine membranes. Biochem Biophys Acta 1768:2596–2604
Arenskötter M, Bröker D, Steinbüchel A (2004) Biology of the metabolically diverse genus Gordonia. Appl Env Microbiol 7:3195–3204
Banat IM, Makkar RS, Cameotra SS (2000) Potential commercial application of microbial surfactants. Appl Microbiol Biotechnol 53:495–508
Batrakov SG, Rozynov BV, Koronelli TV, Bergelson LD (1981) Two novel types of trehalose lipids. Chem Phys Lipids 29:241–266
Belisle JT, Vissa VD, Sievert T, Takayama K, Brennan PJ, Besra GS (1997) Role of the major antigen of Mycobacterium tuberculosis in cell wall biogenesis. Science 276:1420–1422
Bicca FC, Fleck LC, Ayub ZMA (1999) Production of biosurfactant bt hydrocarbon degrading Rhodococcus ruber and Rhodococcus erythropolis. Revista de Microbiologia 30:231–236
Billingsley KA, Backus SM, Wilson S, Singh A, Ward OP (2002) Remediation of PCBs in soil by surfactant washing and biodegradation in the wash by Pseudomonas sp. LB400. Biotechnol Lett 24:1827–1832
Bouchez-Naïtali M, Rakatozafy H, Marchal R, Leveau JY, Vandecasteele J-P (1999) Diversity of bacterial strains degrading hexadecane in relation to the mode of substrate uptake. J Appl Microbiol 86:421–428
Bryant F (1990) Improved method for the isolation of biosurfactant glycolipids from Rhodococcus sp. strain H13A. Appl Environ Microbiol 56:494–1496
Cameotra SS, Makkar RS (2004) Recent applications of biosurfactants as biological and immunological molecules. Curr Opin Microbiol 7:262–266
Choi K-S, Kim S-H, Lee T-H (1999) Purification and characterization of biosurfactant from Tsukamurella sp. 26A. J Microbiol Biotechnol 9:32–38
Christofi N, Ivshina IB (2002) Microbial surfactants and their use in field studies of soil remediation. J Appl Microbiol 93:915–929
Cooper DG, Zajic JE, Gerson DF (1979) Production of surface-active lipids by Corynebacterium lepus. Appl Environ Microbiol 37:4–10
Cunningham CJ, Ivshina IB, Lozinsky VI, Kuyukina MS, Philp JC (2004) Bioremediation of diesel contaminated soil by microorganisms immobilised in a polyvinyl alcohol cryogel. Int Biodeterior Biodegrad 54:167–174
De Smet KA, Weston A, Brown IN, Young DB, Robertson BD (2000) Three pathways for trehalose biosynthesis in mycobacteria. Microbiology 146:199–208
Desai JD, Banat IM (1997) Microbial production of surfactants and their commercial potential. Microbiol Mol Biol Rev 61:47–64
Deshpande S, Shiau BJ, Wade D, Sabatini DA, Harwell JH (1999) Surfactant selection for enhancing ex situ soil washing. Water Res 33:351–360
Espuny MJ, Egido S, Mercade ME, Manresa A (1995) Characterization of trehalose tetraester produced by a waste lube oil degrader Rhodococcus sp. Toxicol Environ Chem 48:83–88
Haba E, Bresco O, Ferrer C, Marqués A, Busquets M, Manresa A (2000) Isolation of lipase-secreting bacteria by deploying used frying oil as selective substrate. Enzyme Microb Technol 26:40–44
Haddadin MSY, Arqoub AAA, Reesh IA, Haddadin J (2009) Kinetics of hydrocarbon extraction from oil shale using biosurfactant producing bacteria. Energy Conver Manage 50:983–990
Hoq MM, Suzutani T, Toyoda T, Horiike G, Yoshida I, Azuma M (1997) Role of γδ TCRM lymphocytes in the augmented resistance of trehalose 6, 6-dimycolate-treated mice to influenza virus infection. J Gen Virol 78:1597–1603
Ivshina IB (2001) Operation and establishment of a Russian biological resource centre. WFCC Newsl 33:8–14
Ivshina IB, Kuyukina MS, Philp JC, Christo N (1998) Oil desorption from mineral and organic materials using biosurfactant complexes produced by Rhodococcus species. World J Microbiol Biotechnol 14:711–717
Iwabuchi N, Sunairi M, Anzai H, Nakajima M, Harayama S (2000) Relationships between colony morphotypes and oil tolerance in Rhodococcus rhodochrous. Appl Environ Microbiol 66:5073–5077
Kacem R, De Sousa-D’Auria C, Tropis M, Chami M, Gounon P, Leblon G, Houssin C, Daffé M (2004) Importance of mycoloyltransferases on the physiology of Corynebacterium glutamicum. Microbiology 150:73–84
Kamenskikh TN, Kuyukina MS, Ivshina IB (2004) Some features in preserving actinobacteria of the genus Rhodococcus. Perm University Herald Biol Iss 2:110–113
Kanga SA, Bonner JS, Page CA, Mills MA, Autenrieth RL (1997) Solubilization of naphthalene and methyl-substituted naphthalenes from crude oil using biosurfactant. Environ Sci Technol 31:556–561
Kim J-S, Powalla M, Lang S, Wagner F, Lunsdorf H, Wray V (1990) Microbial glycolipid production under nitrogen limitation and resting cell conditions. J Biotechnol 13:257–266
Kim SH, Lim EJ, Lee SO, Lee JD, Lee TH (2000) Purification and characterization of biosurfactants from Nocardia sp. L-417. Biotechnol Appl Biochem 31:249–253
Kitamoto D, Isoda H, Nakahara T (2002) Functions and potential applications of glycolipid biosurfactants – from energy-saving materials to gene delivery carriers. J Biosci Bioeng 94:187–201
Kosaric N (1992) Biosurfactants in industry. Pure Appl Chem 64:1731–1737
Kretschmer A, Wagner F (1983) Characterization of biosynthetic intermediates of trehalose dicorynomycolates from Rhodococcus erythropolis grown on n-alkanes. Appl Environ Microbiol 44:864–870
Kurane R, Hatamochi K, Kakuno T, Kiyohara M, Tajima T, Hirano M, Taniguchi Y (1995) Chemical structure of lipid bioflocculant produced by Rhodococcus erythropolis. Biosci Biotech Biochem 59:1652–1656
Kuyukina MS, Ivshina IB, Ritchkova MI, Chumakov OB (2000) Effect of cell lipid composition on the formation of non-specific antibiotic resistance in alkanotrophic rhodococci. Microbiology 69:51–57
Kuyukina MS, Ivshina IB, Philp JC, Christofi N, Dunbar SA, Ritchkova MI (2001) Recovery of Rhodococcus biosurfactants using methyl tertiary-butyl ether extraction. J Microbiol Methods 46:149–156
Kuyukina MS, Ivshina IB, Makarov SO, Litvinenko LV, Cunningham CJ, Philp JC (2005) Effect of biosurfactants on crude oil desorption and mobilization in a soil system. Environ Int 31:155–161
Kuyukina MS, Ivshina IB, Gavrin YuA, Podorozhko EA, Lozinsky VI, Jeffree CE, Philp JC (2006) Immobilization of hydrocarbon-oxidizing bacteria in poly(vinyl alcohol) cryogels hydrophobized using a biosurfactant. J Microbiol Methods 65:596–603
Kuyukina MS, Ivshina IB, Gein SV, Baeva TA, Chereshnev VA (2007) In vitro immunomodulating activity of biosurfactant glycolipid complex from Rhodococcus ruber. Bull Exp Biol Med 144:326–330
Lang S (2002) Biological amphiphiles microbial biosurfactants. Curr Opin Colloid Interf Sci 7:12–20
Lang S, Philp JC (1998) Surface-active lipids in rhodococci. Antonie van Leeuwenhoek Int J Gen Mol Microbiol 74:59–70
LeBlanc JC, Gonçalves ER, Mohn WW (2008) Global response to desiccation stress in the soil actinomycete Rhodococcus jostii RHA1. Appl Environ Microbiol 74:2627–2636
Maier RM (2003) Biosurfactants: evolution and diversity in bacteria. Adv Appl Microbiol 52:101–121
Makkar RS, Rockne KJ (2003) Comparison of synthetic surfactants and biosurfactants in enhancing biodegradation of polycyclic aromatic hydrocarbons. Environ Toxicol Chem 22:2280–2292
Marqués AM, Pinazo Farfan AM, Aranda FJ, Teruel JA, Ortiz A, Manresa A, Espuny MJ (2009) The physicochemical properties and chemical composition of trehalose lipids produced by Rhodococcus erythropolis 51T7. Chem Phys Lipids 158:110–117
Mulligan CN (2005) Environmental applications for biosurfactants. Environ Pollut 133:183–198
Neu TR (1996) Significance of bacterial surface-active compounds in interaction of bacteria with interfaces. Microbiol Rev 60:151–166
Nguyen L, Chinnapapagari S, Thompson CJ (2005) FbpA-dependent biosynthesis of trehalose dimycolate is required for the intrinsic multidrug resistance, cell wall structure, and colonial morphology of Mycobacterium smegmatis. J Bacteriol 187:6603–6611
Niescher VW, Lang S, Kaschabek SR, Schlömann M (2006) Identification and structural characterisation of novel trehalose dinocardiomycolates from n-alkane-grown Rhodococcus opacus 1CP. Appl Microbiol Biotechnol 70:605–611
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 94:195–212
Ortiz A, Teruel JA, Espuny MJ, Marqués A, Manresa A, Aranda FJ (2008) Interactions of a Rhodococcus sp. biosurfactant trehalose lipid with phosphatidylethanolamine membranes. Biochim Biophys Acta 1778:2806–2813
Ortiz A, Teruela JA, Espuny MJ, Marqués A, Manresa A, Aranda FJ (2009) Interactions of a bacterial biosurfactant trehalose lipid with phosphatidylserine membranes. Chem Phys Lipids 158:46–53
Page CA, Bonner JS, Kanga SA, Mills MA, Autenrieth RL (1999) Biosurfactant solubilization of PAHs. Environ Eng Sci 16:465–474
Pal MP, Vaidya BK, Desai KM, Joshi RM, Nene SN, Kulkarni BD (2009) Media optimization for biosurfactant production by Rhodococcus erythropolis MTCC 2794: artificial intelligence versus a statistical approach. J Ind Microbiol Biotechnol 36:747–756
Paria S (2008) Surfactant-enhanced remediation of organic contaminated soil and water. Adv Coll Interf Sci 138:24–58
Passeri A, Lang S, Wagner F, Wray V (1991) Marine biosurfactants, II. Production and characterization of an anionic trehalose tetraester from the marine bacterium Arthrobacter sp. EK 1. J Biosci 46:204–209
Peng F, Liu Z, Wang L, Shao Z (2007) An oil-degrading bacterium: Rhodococcus erythropolis strain 3C-9 and its biosurfactants. J Appl Microbiol 102:1603–1611
Peypoux F, Bonmatin JM, Wallach J (1999) Recent trends in the biochemistry of surfactin. Appl Microbiol Biotechnol 51:553–563
Philp JC, Kuyukina MS, Ivshina IB, Dunbar SA, Christofi N, Lang S, Wray V (2002) Alkanotrophic Rhodococcus ruber as a biosurfactant producer. Appl Microbiol Biotechnol 59:318–324
Pirog TP, Shevchuk TA, Voloshina IN, Karpenko EV (2004) Production of surfactants by Rhodococcus erythropolis strain EK-1, grown on hydrophilic and hydrophobic substrates. Appl Biochem Microbiol 40:470–475
Rapp P, Gabriel-Jürgens LHE (2003) Degradation of alkanes and highly chlorinated benzenes, and production of biosurfactants, by a psychrophilic Rhodococcus sp. and genetic characterization of its chlorobenzene dioxygenase. Microbiology 149:2879–2890
Rapp P, Bock H, Wray V, Wagner F (1979) Formation, isolation and characterization of trehalose dimycolates from Rhodococcus erythropolis grown on n-alkanes. J Gen Microbiol 115:491–503
Rapp P, Bock H, Urban E, Wagner F, Gebetsberger W, Schulz W (1977) Mikrobielle Bildung eines Trehaloselipids und seine Anwendung in Modellversuchen zum Tensidfluten von Erdollagerstatten. Dechema-Monographie Biotechnologie 81:177–186
Retzinger GS, Meredith SC, Takayama K, Hunter RL, Kezdy FJ (1981) The role of surface in the biological activities of trehalose 6, 6-dimicolate. J Biol Chem 256:8208–8216
Ristau E, Wagner F (1983) Formation of novel anionic trehalose tetraesters from Rhodococcus erythropolis under growth-limiting conditions. Biotechnol Lett 5:95–100
Ron EZ, Rosenberg E (2001) Natural roles of biosurfactants. Environ Microbiol 3:229–236
Ron EZ, Rosenberg E (2002) Biosurfactants and oil bioremediation. Curr Opin Biotechnol 13:249–252
Rosenberg E, Ron EZ (1999) High- and low-molecular-mass microbial surfactants. Appl Microbiol Biotechnol 52:154–162
Ryll R, Kumazawa Y, Yano I (2001) Immunological properties of trehalose dimycolate cord factor and other mycolic acid-containing glycolipids – a review. Microbiol Immunol 45:801–811
Sadouk Z, Hacene H, Tazerouti A (2008) Biosurfactants production from low cost substrate and degradation of diesel oil by a Rhodococcus strain. Oil Gas Sci Technol 63:747–753
Sakaguchi I, Ikeda N, Nakayama N, Kato Y, Yano I, Kaneda K (2000) Trehalose 6, 6-dimycolate cord factor neovascularization trough vascular endothelial growth factor production by neutrophiles and macrophages. Infect Immunity 68:2043–2052
Singer MEV, Finnerty WR (1990) Physiology of biosurfactant synthesis by Rhodococcus species H13-A. Can J Microbiol 36:741–745
Singh A, Van Hamme JD, Ward OP (2007) Surfactants in microbiology and biotechnology: Part 2. Application aspects. Biotechnol Adv 25:99–121
Sokolovska I, Rozenberg R, Riez C, Rouxhet PG, Agathos SN, Wattiau P (2003) Carbon source-induced modifications in the mycolic acid content and cell wall permeability of Rhodococcus erythropolis E1. Appl Environ Microbiol 69:7019–7027
Stainsby FM, Philp JC, Dunbar S, Ivshina IB, Kuyukina MS (2005) Microbial foaming and bulking in activated sludge plants. In: Lehr H, Keeley J, Lehr J, Kingery TB III (eds) Water encyclopedia: domestic, municipal, and industrial water supply and waste disposal. Wiley, New Jersey, pp 844–848
Sung N, Takayama K, Collins MT (2004) Possible association of GroES and Antigen 85 proteins with heat resistance of Mycobacterium paratuberculosis. Appl Environ Microbiol 70:1688–1697
Tokumoto Y, Nomura N, Uchiyama H, Imura T, Morita T, Fukuoka T, Kitamoto D (2009) Structural characterization and surface-active properties of succionyl trehalose lipid produced by Rhodococcus sp SD-74. J Oleo Sci 58:97–102
Tomiyasu I, Yoshinaga J, Kurano F, Kato Y, Kaneda K, Imaizumi S, Yano I (1986) Occurrence of a novel glycolipid, ‘trehalose 2,3,6′-trimycolate in a psychrophilic, acid-fast bacterium, Rhodococcus aurantiacus (Gordona aurantiaca). FEBS Lett 203:239–242
Tuleva B, Christova N, Cohen R, Stoev G, Stoineva I (2008) Production and structural elucidation of trehalose tetraesters (biosurfactants) from a novel alkanothrophic Rhodococcus wratislaviensis strain. J Appl Microbiol 104:1703–1710
Tzvetkov M, Klopprogge C, Zelder O, Liebl W (2003) Genetic dissection of trehalose biosynthesis in Corynebacterium glutamicum: inactivation of trehalose production leads to impaired growth and an altered cell wall lipid composition. Microbiology 149:1659–1673
Van der Geize R, Dijkhuizen L (2004) Harnessing the catabolic diversity of rhodococci for environmental and biotechnological applications. Cur Opin Microbiol 7:255–261
Van Hamme JD, Singh A, Ward OP (2006) Physiological aspects. Part 1 in a series of papers devoted to surfactants in microbiology and biotechnology. Biotechnol Adv 24:604–620
Whyte LG, Slagman SJ, Pietrantonio F, Bourbonniere L, Koval SF, Lawrence JR, Innis WE, Greer SW (1999) Physiological adaptations involved in alkane assimilation at a low temperature by Rhodococcus sp. strain Q15. Appl Environ Microbiol 65:2961–2968
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Kuyukina, M.S., Ivshina, I.B. (2010). Rhodococcus Biosurfactants: Biosynthesis, Properties, and Potential Applications. In: Alvarez, H. (eds) Biology of Rhodococcus. Microbiology Monographs, vol 16. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-12937-7_11
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