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Review
. 2015 Mar 3;16(3):4814-37.
doi: 10.3390/ijms16034814.

Chemical structure, property and potential applications of biosurfactants produced by Bacillus subtilis in petroleum recovery and spill mitigation

Jin-Feng Liu  1   2 , Serge Maurice Mbadinga  3   4 , Shi-Zhong Yang  5   6 , Ji-Dong Gu  7 , Bo-Zhong Mu  8   9
Affiliations
Review

Chemical structure, property and potential applications of biosurfactants produced by Bacillus subtilis in petroleum recovery and spill mitigation

Jin-Feng Liu et al. Int J Mol Sci. .

Abstract

Lipopeptides produced by microorganisms are one of the five major classes of biosurfactants known and they have received much attention from scientific and industrial communities due to their powerful interfacial and biological activities as well as environmentally friendly characteristics. Microbially produced lipopeptides are a series of chemical structural analogues of different families and, among them, 26 families covering about 90 lipopeptide compounds have been reported in the last two decades. This paper reviews the chemical structural characteristics and molecular behaviors of surfactin, one of the representative lipopeptides of the 26 families. In particular, two novel surfactin molecules isolated from cell-free cultures of Bacillus subtilis HSO121 are presented. Surfactins exhibit strong self-assembly ability to form sphere-like micelles and larger aggregates at very low concentrations. The amphipathic and surface properties of surfactins are related to the existence of the minor polar and major hydrophobic domains in the three 3-D conformations. In addition, the application potential of surfactin in bioremediation of oil spills and oil contaminants, and microbial enhanced oil recovery are discussed.

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Figures

Figure 1
Figure 1
Tandem MS of C15-surfactin-O-methyl ester (A) TOF MS/MS; (B) Fragment ions after simple cleavage; (C,D) fragment ions produced after the double hydrogen transfer of lipopeptides in TOF MS/MS. Reprinted from Process Biochem 44: 1144 [23]. Copyright (2009), with permission from Elsevier.
Figure 2
Figure 2
Basic chemical structure of C15-surfactin-O-methyl ester. Reprinted from Process Biochem 44:1144 [23]. Copyright (2009), with permission from Elsevier.
Figure 3
Figure 3
Snapshots of the representative arrangement of surfactin molecules at (a) 2.20 and (b) 1.20 nm2·molecule−1 (The atom coloring scheme is C, green; N, blue; O, red; and H, white). Reprinted with permission from Gang et al. [38]. Copyright (2011) American Chemical Society.
Figure 4
Figure 4
Normalized probability distribution of CC and NN magnitudes (a–d corresponds to the interfacial concentration of 2.20, 1.50, 1.20, and 0.95 nm2·molecule−1, respectively; CC, the vector connecting the β carbon atom of the fatty acid residue and the α carbon atom in Val4; NN, the vector connects the nitrogen atom of Leu2 and the nitrogen atom of Leu6). Reprinted with permission from Gang et al. [38]. Copyright (2011) American Chemical Society.
Figure 5
Figure 5
The S1 (top) and S2 (bottom) structure (only Glu1 and Asp5 residues have been represented, S1 and S2 exhibit a particular horse saddle folding mode (left) and acidic residues show a claw topology). Reprinted with permission from Bonmatin et al. [45]. Copyright (2004) John Wiley & Sons, Inc.
Figure 6
Figure 6
The 3-D structure (a) and Electrostatic potentials associated to solvent-accessible surfaces (b) of surfactin (The backbone is in blue, the two negatively charged side chains are in red, the FA8 fatty acid in yellow, and the other hydrophobic residues in green). Reprinted with permission from Tsan et al. [46]. Copyright (2007) American Chemical Society.
Figure 7
Figure 7
Surface tension of surfactins with different fatty acid chain length [51].
Figure 8
Figure 8
Micelle size distribution of surfactin-C13, -C14 and -C15 [51].
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References

    1. Desai J.D., Banat I.M. Microbial production of surfactants and their commercial potential. Microbiol. Mol. Biol. Rev. 1997;61:47–64. - PMC - PubMed
    1. Silva R.D.C.F.S., Almeida D.G., Rufino R.D., Luna J.M., Santos V.A., Sarubbo L.A. Applications of biosurfactants in the petroleum industry and the remediation of oil spills. Int. J. Mol. Sci. 2014;15:12523–12542. doi: 10.3390/ijms150712523. - DOI - PMC - PubMed
    1. Deleu M., Razafindralambo H., Popineau Y., Jacques P., Thonart P., Paquot M. Interfacial and emulsifying properties of lipopeptides from Bacillus subtilis. Colloids Surf. Physicochem. Eng. Asp. 1999;152:3–10. doi: 10.1016/S0927-7757(98)00627-X. - DOI
    1. Peypoux F., Bonmatin J.M., Wallach J. Recent trends in the biochemistry of surfactin. Appl. Microbiol. Biotechnol. 1999;51:553–563. doi: 10.1007/s002530051432. - DOI - PubMed
    1. Grgurina I. Lipopeptide secondary metabolites from the phytopathogenic bacterium Pseudomonas syringae. In: Upadhyay R., editor. Advances in Microbial Toxin Research and Its Biotechnological Exploitation. Springer US; New York, NY, USA: 2002. pp. 105–140.

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