Chemical structure, surface properties and biological activities of the biosurfactant produced by Pseudomonas aeruginosa LBI from soapstock
01 Jan 2004-Antonie Van Leeuwenhoek International Journal of General and Molecular Microbiology (Kluwer Academic Publishers)-Vol. 85, Iss: 1, pp 1-8
TL;DR: Pseudomonas aeruginosa LBI isolated from petroleum-contaminated soil produced rhamnolipids (RLLBI) which showed good antimicrobial behaviour against bacteria and could be used in bioremediation treatment and in the food, cosmetic and pharmaceutical industries.
Abstract: Pseudomonas aeruginosa LBI isolated from petroleum-contaminated soil produced rhamnolipids (RLLBI) when cultivated on soapstock as the sole carbon source. HPLC–MS analysis of the purified culture supernatant identified 6 RL homologues (%): R2 C10 C10 28.9; R2 C10 C12:1 23.0; R1 C10 C10 23.4; R2 C10 C12 11.3; R2 C10 C12 7.9; R2 C10 C12 5.5. To assess the potential antimicrobial activity of the new rhamnolipid product, RLLBI, its physicochemical properties were studied. RLLBI had a surface tension of 24 mN m−1 and an interfacial tension of 1.31 mN m−1; the cmc was 120 mg l−1. RLLBI produced stable emulsions with hydrocarbons and vegetable oils. This product showed good antimicrobial behaviour against bacteria: MIC for Bacillus subtilis, Staphylococcus aureus and Proteus vulgaris was 8 mg l−1, for Streptococcus faecalis 4 mg l−1, and for Pseudomonas aeruginosa 32 mg l−1. RLLBI was active against phytopathogenic fungal species, MIC values of 32 mg l−1 being found against Penicillium, Alternaria, Gliocadium virens and Chaetonium globosum. Due to its physicochemical properties and antimicrobial behaviour, RLLBI could be used in bioremediation treatment and in the food, cosmetic and pharmaceutical industries.
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TL;DR: The current knowledge and the latest advances in biosurfactant applications and the biotechnological strategies being developed for improving production processes and future potential are reviewed.
Abstract: Microorganisms synthesise a wide range of surface-active compounds (SAC), generally called biosurfactants. These compounds are mainly classified according to their molecular weight, physico-chemical properties and mode of action. The low-molecular-weight SACs or biosurfactants reduce the surface tension at the air/water interfaces and the interfacial tension at oil/water interfaces, whereas the high-molecular-weight SACs, also called bioemulsifiers, are more effective in stabilising oil-in-water emulsions. Biosurfactants are attracting much interest due to their potential advantages over their synthetic counterparts in many fields spanning environmental, food, biomedical, and other industrial applications. Their large-scale application and production, however, are currently limited by the high cost of production and by limited understanding of their interactions with cells and with the abiotic environment. In this paper, we review the current knowledge and the latest advances in biosurfactant applications and the biotechnological strategies being developed for improving production processes and future potential.
1,248 citations
Cites background from "Chemical structure, surface propert..."
...…roseosporus (Baltz et al. 2005), viscosin, a cyclic lipopeptide from Pseudomonas (Neu et al. 1990; Saini et al. 2008), rhamnolipids produced by P. aeruginosa (Abalos et al. 2001; Benincasa et al. 2004) and sophorolipids produced by C. bombicola (Kim et al. 2002; Van Bogaert et al. 2007)....
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TL;DR: Biosurfactants utility as suitable anti-adhesive coating agents for medical insertional materials leading to a reduction in a large number of hospital infections without the use of synthetic drugs and chemicals is indicated.
Abstract: The use and potential commercial application of biosurfactants in the medical field has increased during the past decade. Their antibacterial, antifungal and antiviral activities make them relevant molecules for applications in combating many diseases and as therapeutic agents. In addition, their role as anti-adhesive agents against several pathogens indicates their utility as suitable anti-adhesive coating agents for medical insertional materials leading to a reduction in a large number of hospital infections without the use of synthetic drugs and chemicals. This review looks at medicinal and therapeutic perspectives on biosurfactant applications.
783 citations
Cites background from "Chemical structure, surface propert..."
...Antibacterial and antiphytoviral effects of various rhamnolipids have been described in the literature.(13,64) Seven different rhamnolipids were identified in cultures of Pseudomonas aeruginosa AT10 from soybean oil refinery wastes and these showed excellent antifungal properties against various fungi....
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TL;DR: A wide diversity of rhamnolipid congeners and homologues that are produced at different concentrations by various Pseudomonas species and by bacteria belonging to other families, classes, or even phyla are found.
Abstract: Rhamnolipids are glycolipidic biosurfactants produced by various bacterial species. They were initially found as exoproducts of the opportunistic pathogen Pseudomonas aeruginosa and described as a mixture of four congeners: α-L-rhamnopyranosyl-α-L-rhamnopyranosyl-β-hydroxydecanoyl-β-hydroxydecanoate (Rha-Rha-C10-C10), α-L-rhamnopyranosyl-α-L-rhamnopyranosyl-β-hydroxydecanoate (Rha-Rha-C10), as well as their mono-rhamnolipid congeners Rha-C10-C10 and Rha-C10. The development of more sensitive analytical techniques has lead to the further discovery of a wide diversity of rhamnolipid congeners and homologues (about 60) that are produced at different concentrations by various Pseudomonas species and by bacteria belonging to other families, classes, or even phyla. For example, various Burkholderia species have been shown to produce rhamnolipids that have longer alkyl chains than those produced by P. aeruginosa. In P. aeruginosa, three genes, carried on two distinct operons, code for the enzymes responsible for the final steps of rhamnolipid synthesis: one operon carries the rhlAB genes and the other rhlC. Genes highly similar to rhlA, rhlB, and rhlC have also been found in various Burkholderia species but grouped within one putative operon, and they have been shown to be required for rhamnolipid production as well. The exact physiological function of these secondary metabolites is still unclear. Most identified activities are derived from the surface activity, wetting ability, detergency, and other amphipathic-related properties of these molecules. Indeed, rhamnolipids promote the uptake and biodegradation of poorly soluble substrates, act as immune modulators and virulence factors, have antimicrobial activities, and are involved in surface motility and in bacterial biofilm development.
737 citations
Cites background from "Chemical structure, surface propert..."
...…found as mixtures of different RL congeners, as observed with the various strains of P. aeruginosa (Abalos et al. 2001; AbdelMawgoud et al. 2009; Benincasa et al. 2004; Haba et al. 2003a; Mata-Sandoval et al. 1999; Pornsunthorntawee et al. 2008), of P. chlororaphis (Gunther et al. 2005, 2006)…...
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...The group of Manresa has performed comprehensive investigations on the antimicrobial properties of mixtures of RL congeners produced by three different strains of P. aeruginosa grown on various types of vegetable oil wastes (Abalos et al. 2001; Benincasa et al. 2004; Haba et al. 2003b)....
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...They also found an excellent inhibitory activity against a range of fungal species, including the filamentous fungi Chaetomium globosum, Aureobacidium pullulans, and Gliocladium virens, and the phytopathogens Botrytis cinerea and Rhizoctonia solanii, but no significant effect on yeasts (Abalos et al. 2001; Benincasa et al. 2004; Haba et al. 2003b)....
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...aeruginosa grown on various types of vegetable oil wastes (Abalos et al. 2001; Benincasa et al. 2004; Haba et al. 2003b)....
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...…a range of fungal species, including the filamentous fungi Chaetomium globosum, Aureobacidium pullulans, and Gliocladium virens, and the phytopathogens Botrytis cinerea and Rhizoctonia solanii, but no significant effect on yeasts (Abalos et al. 2001; Benincasa et al. 2004; Haba et al. 2003b)....
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TL;DR: Practical approaches that have been adopted to make the biosurfactant production process economically attractive include the use of cheaper raw materials, optimized and efficient bioprocesses and overproducing mutant and recombinant strains for obtaining maximum productivity.
694 citations
TL;DR: Biosurfactants play an essential natural role in the swarming motility of microorganisms and participate in cellular physiological processes of signaling and differentiation as well as in biofilm formation.
449 citations
Cites background from "Chemical structure, surface propert..."
...With respect to novelty and variety within a single strain, Benincasa et al. (2004) described six rhamnolipid homologues produced by a single Pseudomonas sp....
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...Low molecular weight Rhamnolipids Pseudomonas aeruginosa, Serratia rubidea Benincasa et al., (2004)...
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References
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Journal Article•
TL;DR: Procedures are described for measuring protein in solution or after precipitation with acids or other agents, and for the determination of as little as 0.2 gamma of protein.
289,852 citations
TL;DR: In this paper, the authors described a simplified version of the method and reported the results of a study of its application to different tissues, including the efficiency of the washing procedure in terms of the removal from tissue lipides of some non-lipide substances of special biochemical interest.
59,550 citations
Book•
01 Jan 1978
TL;DR: In this paper, the Gibbs equation is used to calculate the area per Molecule at the interface by using the Gibbs Equation (GEE) of the Gibbs equilibrium. But the Gibbs equations are not applicable to surface-active agents.
Abstract: Preface. 1 Characteristic Features of Surfactants. A Conditions Under Which Interfacial Phenomena and Surfactants Become Significant. B General Structural Features and Behavior of Surfactants. 1 General Use of Charge Types. 2 General Effects of the Nature of the Hydrophobic Group. I Characteristic Features and Uses of Commercially Available Surfactants. I.A Anionics. 1 Carboxylic Acid Salts. 2 Sulfonic Acid Salts. 3 Sulfuric Acid Ester Salts. 4 Phosphoric and Polyphosphoric Acid Esters. 5 Fluorinated Anionics. I.B Cationics. 1 Long-Chain Amines and Their Salts. 2 Acylated Diamines and Polyamines and Their Salts. 3 Quaternary Ammonium Salts. 4 Polyoxyethylenated (POE) Long-Chain Amines. 5 Quaternized POE Long-Chain Amines. 6 Amine Oxides. I.C Nonionics. 1 POE Alkylphenols, Alkylphenol "Ethoxylates". 2 POE Straight-Chain Alcohols, Alcohol "Ethoxylates". 3 POE Polyoxypropylene glycols. 4 POE Mercaptans. 5 Long-Chain Carboxylic Acid Esters. 6 Alkanolamine "Condensates," Alkanolamides. 7 Tertiary Acetylenic Glycols and Their "Ethoxylates". 8 POE Silicones. 9 N-Alkylpyrrolidones. 10 Alkylpolyglycosides. I.D Zwitterionics. 1 pH-Sensitive Zwitterionics. 2 pH-Insensitive Zwitterionics. I.E Newer Surfactants Based Upon Renewable Raw Materials. 1 a-Sulfofatty Acid Methyl Esters (SME). 2 Acylated Aminoacids. 3 N-Acyl L-Glutamates (AG). 4 N-Acyl Glycinates. 5 N-Acyl DL-Alaninates. 6 Other Acylated Aminoacids. 7 Nopol Alkoxylates. II Environmental Effects of Surfactants. II.A Surfactant Biodegradability. II.B Surfactant Toxicity To and Bioconcentration in Marine Organisms. III Some Useful Generalizations. References. Problems. 2 Adsorption of Surface-Active Agents at Interfaces: The Electrical Double Layer. I The Electrical Double Layer. II Adsorption at the Solid-Liquid Interface. II.A Mechanisms of Adsorption and Aggregation. II.B Adsorption Isotherms. 1 The Langmuir Adsorption Isotherm. II.C Adsorption from Aqueous Solution Onto Adsorbents with Strongly Charged Sites. 1 Ionic Surfactants. 2 Nonionic Surfactants. 3 pH Change. 4 Ionic Strength. 5 Temperature. II.D Adsorption from Aqueous Solution Onto Nonpolar, Hydrophobic Adsorbents. II.E Adsorption from Aqueous Solution Onto Polar Adsorbents without Strongly Charged Sites. II.F Effects of Adsorption from Aqueous Solution on the Surface Properties of the Solid Adsorbent. 1 Substrates with Strongly Charged Sites. 2 Nonpolar Adsorbents. II.G Adsorption from Nonaqueous Solution. II.H Determination of the Specific Surface Areas of Solids. III Adsorption at the Liquid-Gas (L/G) and Liquid-Liquid (L/L) Interfaces. III.A The Gibbs Adsorption Equation 60 III.B Calculation of Surface Concentrations and Area per Molecule at the Interface By Use of the Gibbs Equation. III.C Effectiveness of Adsorption at the L/G and L/L Interfaces. III.D The Szyszkowski, Langmuir, and Frumkin Equations. III.E Efficiency of Adsorption at the L/G and L/L Interfaces. III.F Calculation of Thermodynamic Parameters of Adsorption at the L/G and L/L Interfaces. III.G Adsorption from Mixtures of Two Surfactants. References. Problems. 3 Micelle Formation by Surfactants. I The Critical Micelle Concentration (CMC). II Micellar Structure and Shape. II.A The Packing Parameter. II.B Surfactant Structure and Micellar Shape. II.C Liquid Crystals. III Micellar Aggregation Numbers. IV Factors Affecting the Value of the CMC in Aqueous Media. IV.A Structure of the Surfactant. 1 The Hydrophobic Group. 2 The Hydrophobic Group. 3 The Counterion in Ionic Surfactants: Degree of Binding to the Micelle 139 4 Empirical Equations. IV.B Electrolyte. IV.C Organic Additives. 1 Class I Materials. 2 Class II Materials. IV.D The Presence of a Second Liquid Phase. IV.E Temperature. V Micellization in Aqueous Solution and Adsorption at the Aqueous Solution-Air or Aqueous Solution-Hydrocarbon Interface. V.A. The CMC/C20 ratio. VI CMCs in Nonaqueous Media. VII Equations for the CMC Based on Theoretical Considerations. VIII Thermodynamic Parameters of Micellization. IX Mixed Micelle Formation in Mixtures of Two Surfactants. References. Problems. 4 Solubilization by Solutions of Surfactants: Micellar Catalysis. I Solubilization in Aqueous Media. I.A Locus of Solubilization. I.B Factors Determining the Extent of Solubilization. 1 Structure of the Surfactant. 2 Structure of the Solubilizate. 3 Effect of Electrolyte. 4 Effect of Monomeric Organic Additives. 5 Effect of Polymeric Organic Additives. 6 Mixed Anionic-Nonionic Micelles. 7 Effect of Temperature. 8 Hydrotropy. I.C Rate of Solubilization. II Solubilization in Nonaqueous Solvents. II.A Secondary Solubilization. III Some Effects of Solubilization. III.A Effect of Solubilization on Micellar Structure. III.B Change in the Cloud Points of Aqueous Solutions of Nonionic Surfactants. III.C Reduction of the CMC. III.D Miscellaneous Effects of Solubilization. IV Micellar Catalysis. References. Problems. 5 Reduction of Surface and Interfacial Tension by Surfactants. I Efficiency in Surface Tension Reduction. II Effectiveness in Surface Tension Reduction. II.A The Krafft Point. II.B Interfacial Parameter and Chemical Structural Effects. III Liquid-Liquid Interfacial Tension Reduction. III.A Ultralow Interfacial Tension. IV Dynamic Surface Tension Reduction. IV.A Dynamic Regions. IV.B Apparent Diffusion Coefficients of Surfactants. References. Problems. 6 Wetting and Its Modification by Surfactants. I Wetting Equilibria. I.A Spreading Wetting. 1 The Contact Angle. 2 Measurement of the Contact Angle. I.B Adhesional Wetting. I.C Immersional Wetting. I.D Adsorption and Wetting. II Modification of Wetting by Surfactants. II.A General Considerations. II.B Hard Surface (Equilibrium) Wetting. II.C Textile (Nonequilibrium) Wetting. II.D Effect of Additives. III Synergy in Wetting by Mixtures of Surfactants. IV Superspreading (Superwetting). References. Problems. 7 Foaming and Antifoaming by Aqueous Solutions of Surfactants. I Theories of Film Elasticity. II Factors Determining Foam Persistence. II.A Drainage of Liquid in the Lamellae. II.B Diffusion of Gas Through the Lamellae. II.C Surface Viscosity. II.D The Existence and Thickness of the Electrical Double Layer. III The Relation of Surfactant Chemical Structure to Foaming in Aqueous Solution. III.A Efficiency as a Foaming Agent. III.B Effectiveness as a Foaming Agent. III.C Low-Foaming Surfactants. IV Foam-Stabilizing Organic Additives. V Antifoaming. VI Foaming of Aqueous Dispersions of Finely Divided Solids. References. Problems. 8 Emulsification by Surfactants. I Macroemulsions. I.A Formation. I.B Factors Determining Stability. 1 Physical Nature of the Interfacial Film. 2 Existence of an Electrical or Steric Barrier to Coalescence on the Dispersed Droplets. 3 Viscosity of the Continuous Phase. 4 Size Distribution of Droplets. 5 Phase Volume Ratio. 6 Temperature. I.C Inversion. I.D Multiple Emulsions. I.E Theories of Emulsion Type. 1 Qualitative Theories. 2 Kinetic Theory of Macroemulsion Type. II Microemulsions. III Nanoemulsions. IV Selection of Surfactants as Emulsifying Agents. IV.A The HLB Method. IV.B The PIT Method. IV.C The HLD Method. V Demulsification. References. Problems. 9 Dispersion and Aggregation of Solids in Liquid Media by Surfactants. I Interparticle Forces. I.A Soft (electrostatic) and van der Waals Forces: DLVO Theory. 1 Limitations of the DLVO Theory. I.B Steric Forces. II Role of the Surfactant in the Dispersion Process. II.A Wetting of the Powder. II.B Deaggregation or Fragmentation of Particle Clusters. II.C Prevention of Reaggregation. III Coagulation or Flocculation of Dispersed Solids by Surfactants. III.A Neutralization or Reduction of the Potential at the Stern Layer of the Dispersed Particles. III.B Bridging. III.C Reversible Flocculation. IV The Relation of Surfactant Chemical Structure to Dispersing Properties. IV.A Aqueous Dispersions. IV.B Nonaqueous Dispersions. References. Problems. 10 Detergency and Its Modification by Surfactants. I Mechanisms of the Cleaning Process. I.A Removal of Soil from Substrate. 1 Removal of Liquid Soil. 2 Removal of Solid Soil. I.B Suspension of the Soil in the Bath and Prevention of Redeposition. 1 Solid Particulate Soils: Formation of Electrical and Steric Barriers Soil Release Agents. 2 Liquid Oily Soil. I.C Skin Irritation. I.D Dry Cleaning. II Effect of Water Hardness. II.A Builders. II.B Lime Soap Dispersing Agents. III Fabric Softeners. IV The Relation of the Chemical Structure of the Surfactant to Its Detergency. IV.A Effect of Soil and Substrate. 1 Oily Soil. 2 Particulate Soil. 3 Mixed Soil. IV.B Effect of the Hydrophobic Group of the Surfactant. IV.C Effect of the Hydrophilic Group of the Surfactant. IV.D Dry Cleaning. References. Problems. 11 Molecular Interactions and Synergism in Mixtures of Two Surfactants. I Evaluation of Molecular Interaction Parameters. I.A Notes on the Use of Equations 11.1-11.4. II Effect of Chemical Structure and Molecular Environment on Molecular Interaction Parameters. III Conditions for the Existence of Synergism. III.A Synergism or Antagonism (Negative Synergism) in Surface or Interfacial Tension Reduction Efficiency. III.B Synergism or Antagonism (Negative Synergism) in Mixed Micelle Formation in Aqueous Medium. III.C Synergism or Antagonism (Negative Synergism) in Surface or Interfacial Tension Reduction Effectiveness. III.D Selection of Surfactants Pairs for Optimal Interfacial Properties. IV The Relation between Synergism in Fundamental Surface Properties and Synergism in Surfactant Applications. References. Problems. 12 Gemini Surfactants. I Fundamental Properties. II Interaction with Other Surfactant. III Performance Properties. References. Problems. Answers to Problems. Index.
6,147 citations
"Chemical structure, surface propert..." refers result in this paper
...…of 23% and R C C (11.3%). that the efficiency of RL is similar to that of its2 10 12 LBI 23.4% of the mixture corresponded to the monorham- chemical counterparts, pC being in the range of 1–320 21nolipid R C C , which was described as RL1 by mg l (Rosen 1978).1 10 10 Syldatk et al. (1985)....
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TL;DR: Biosurfactants are more effective, selective, environmentally friendly, and stable than many synthetic surfactants, and the most promising applications are cleaning of oil-contaminated tankers, oil spill management, transportation of heavy crude oil, enhanced oil recovery, recovery of crude oil from sludge, and bioremediation of sites contaminated with hydrocarbons, heavy metals, and other pollutants.
Abstract: Many microorganisms, especially bacteria, produce biosurfactants when grown on water-immiscible substrates. Biosurfactants are more effective, selective, environmentally friendly, and stable than many synthetic surfactants. Most common biosurfactants are glycolipids in which carbohydrates are attached to a long-chain aliphatic acid, while others, like lipopeptides, lipoproteins, and heteropolysaccharides, are more complex. Rapid and reliable methods for screening and selection of biosurfactant-producing microorganisms and evaluation of their activity have been developed. Genes involved in rhamnolipid synthesis (rhlAB) and regulation (rhlI and rhlR) in Pseudomonas aeruginosa are characterized, and expression of rhlAB in heterologous hosts is discussed. Genes for surfactin production (sfp, srfA, and comA) in Bacillus spp. are also characterized. Fermentative production of biosurfactants depends primarily on the microbial strain, source of carbon and nitrogen, pH, temperature, and concentration of oxygen and metal ions. Addition of water-immiscible substrates to media and nitrogen and iron limitations in the media result in an overproduction of some biosurfactants. Other important advances are the use of water-soluble substrates and agroindustrial wastes for production, development of continuous recovery processes, and production through biotransformation. Commercialization of biosurfactants in the cosmetic, food, health care, pulp- and paper-processing, coal, ceramic, and metal industries has been proposed. However, the most promising applications are cleaning of oil-contaminated tankers, oil spill management, transportation of heavy crude oil, enhanced oil recovery, recovery of crude oil from sludge, and bioremediation of sites contaminated with hydrocarbons, heavy metals, and other pollutants. Perspectives for future research and applications are also discussed.
2,092 citations
"Chemical structure, surface propert..." refers background in this paper
...Increasing 1997; Desai and Banat 1997; Lang and Wullbrandt ecological concern has led to the proposal that biosur1999)....
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TL;DR: Biosurfactants are amphiphilic compounds of microbial origin with considerable potential in commercial applications within various industries and have advantages over their chemical counterparts in biodegradability and effectiveness at extreme temperature or pH and in having lower toxicity.
Abstract: Surfactants are surface-active compounds capable of reducing surface and interfacial tension at the interfaces between liquids, solids and gases, thereby allowing them to mix or disperse readily as emulsions in water or other liquids. The enormous market demand for surfactants is currently met by numerous synthetic, mainly petroleum-based, chemical surfactants. These compounds are usually toxic to the environment and non-biodegradable. They may bio-accumulate and their production, processes and by-products can be environmentally hazardous. Tightening environmental regulations and increasing awareness for the need to protect the ecosystem have effectively resulted in an increasing interest in biosurfactants as possible alternatives to chemical surfactants. Biosurfactants are amphiphilic compounds of microbial origin with considerable potential in commercial applications within various industries. They have advantages over their chemical counterparts in biodegradability and effectiveness at extreme temperature or pH and in having lower toxicity. Biosurfactants are beginning to acquire a status as potential performance-effective molecules in various fields. At present biosurfactants are mainly used in studies on enhanced oil recovery and hydrocarbon bioremediation. The solubilization and emulsification of toxic chemicals by biosurfactants have also been reported. Biosurfactants also have potential applications in agriculture, cosmetics, pharmaceuticals, detergents, personal care products, food processing, textile manufacturing, laundry supplies, metal treatment and processing, pulp and paper processing and paint industries. Their uses and potential commercial applications in these fields are reviewed.
1,501 citations
"Chemical structure, surface propert..." refers background in this paper
...These metabolites bon or other hydrophobic substrates, which makes are complex amphiphilic molecules whose hydropho- them available for cell metabolism (Banat et al. 2000; bic and polar domains depend on the carbon substrate Lin 1996; Lang and Wagner 1993; Maier and ´ ´and the bacterial strain....
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