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Biosurfactants from Bacillus licheniformis: structural analysis and characterization

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Summary

The surface-active compounds of the strain Bacillus licheniformis were isolated and their structure was elucidated. The high surface-active capacity of the crude extract was basically due to traces of long-chain saturated fatty acids, especially of palmitic and stearic acids, to a mixture of small amounts of hydrocarbons with chain lengths of 20 and 22 carbons, and mainly to appreciable amounts of four slightly different lipopeptides. The lipopeptides were found to be a mixture of four closely related compounds. The lipophilic part consisting of i-, n-C14 or i-, ai-C15 β-OH fatty acids was linked to the hydrophilic peptide moiety, which contained seven amino acids (Glu, Asp, Val, three Leu and Ile) by a lactone linkage. Fifteen milligrams per litre of the purified lipopeptide product decreased the surface tension of water from 72 mN m−1 to 27 mN m−1, characterizing the product as a powerful surface-active agent that compares favourably to other (bio)surfactants. Antibiotic activity was demonstrated against bacteria and yeasts.

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References

  • Arima K (1969) Confirmation of the structure of surfactin by mass spectrometry. Agric Biol Chem 33:1669–1671

    Google Scholar 

  • Asselineau C, Asselineau J (1984) Fatty acids and complex lipids. In: Odham G, Larsson L, Mardh P-A (eds) Gas chromatography — mass spectrometry, applications in microbiology. Plenum Press, New York, pp 57–103

    Google Scholar 

  • Aveldano MI, Horrocks LA (1983) Quantitative release of fatty acids from lipids by a simple hydrolysis procedure. J Lipid Res 24:1101–1105

    Google Scholar 

  • Bernheimer AW, Avigad L (1970) Nature and properties of a cytolytic agent produced by Bacillus subtilis. J Gen Microbiol 61:361–369

    Google Scholar 

  • Biemann K, Martin SA (1987) Mass spectrometric determination of the amino acid sequence of peptides and proteins. Mass Spectrom Rev 6:1–76

    Google Scholar 

  • Christie WW (9) Lipid Analysis. Pergamon Press, pp 51–60

  • Cooper DG, Goldenberg BG (1987) Surface-active agents from two Bacillus species. Appl Environ Microbiol 53:224–229

    Google Scholar 

  • Cooper DG, Zajic JE (1980) Surface-active compounds from microorganisms. Adv Appl Microbiol 26:229–253

    Google Scholar 

  • Cooper DG, MacDonald CR, Duff SJB, Kosaric N (1981a) Enhanced production of surfactin from Bacillus subtilis by continuous product removal and metal cation additions. Appl Environ Microbiol 42:408–412

    Google Scholar 

  • Cooper DG, Zajic JE, Denis C (1981b) Surface active properties of a biosurfactant from Corynebacterium lepus. J Am Oil Chem Soc 58:77–80

    Google Scholar 

  • Donaldson EC, Clark JB (1982) Proceedings of 1982: International Conference on Microbial Enhancement of Oil Recovery. May 16–21, 1982, Shangri-La, Afton, Oklahoma. Published by Bartlesville Energy Technology Center, Bartlesville, Oklahoma, USA

    Google Scholar 

  • Finnerty WR (1989) Microbial lipid metabolism. In: Ratledge C, Wilkinson SG (eds) Microbial lipids, vol 2. Academic Press, London, pp 525–566

    Google Scholar 

  • Folch J, Lees M, Stainley GHS (1957) A simple method for the isolation and purification of total lipids from animal tissues. J Biol Chem 226:497–509

    Google Scholar 

  • Gutnick DL, Rosenberg E (1977) Oil tankers and pollution: a microbiological approach. Annu Rev Microbiol 31:379–395

    Google Scholar 

  • Haferberg D, Hommel R, Claus R, Kleber H-P (1986) Extracellular microbial lipids as biosurfactants. Adv Bio Eng 33:53–93

    Google Scholar 

  • Harvey DJ (1982) Picolinyl esters as derivatives for the structural determination of long chain branched and unsaturated fatty acids. Biomed Mass Spectrum 9:33–38

    Google Scholar 

  • Harvey S, Elashvili I, Valdes JJ, Kamely D, Chakravarty AM (1990) Enhanced removal of Exxon Valdez spilled oil from Alaskan gravel by a microbial surfactant. Biotechnology 8:228–230

    Google Scholar 

  • Hiramoto M, Okada K, Nagai S (1969) The revised structure of viscosin, a peptide antibiotic. Antibiot Chemother 3:1239–1242

    Google Scholar 

  • Hommel R, Stüwer O, Stuber W, Haferburg D, Kleber H-P (1987) Production of water-soluble surface-active exolipids by Torulopsis apicola. Appl Microbiol Biotechnol 26:199–205

    Google Scholar 

  • Hosono K, Suzuki H (1983) Acylpeptides, the inhibitor of cyclic adenosine 3',5'-monophosphate phosphodiesterase: I. Purification, physicochemical properties and structure of fatty acid residues. II. Amino acid sequence and location of lactone linkage. J Antibiot 36:194–196, 667–673, 674–678

    Google Scholar 

  • Inoue S (1988) Biosurfactants in cosmetic applications. In: Applewhite ThH (ed) Proceedings of the World Conference on Biotechnology for the Fats and Oil Industry. American Oil Chemists' Society, pp 206–210

  • Itoh S, Honda H, Tomita F, Suzuki T (1971) Rhamnolipids produced by Pseudomonas aeruginosa grown on n-paraffin (mixture of C12, C13 and C14 fractions). J Antibiot 24:855–859

    Google Scholar 

  • Javaheri M, Jenneman GE, McInerney MJ, Knapp RM (1985) Anaerobic production of a biosurfactant by Bacillus licheniformis JF-2. Appl Environ Microbiol 50:698–700

    Google Scholar 

  • Jenneman GE, McInerney MJ, Knapp RM, Clark JB, Feero JM (1983) A halotolerant biosurfactant producing Bacillus species potentially useful for EOR. Dev Ind Microbiol 24:485–492

    Google Scholar 

  • Kachholz T, Schlingmann M (1987) Possible food and agriculture application of microbial surfactants: an assessment. In: Kosaric N, Cairns WL, Gray NCC (eds) Surfactant sciences series: biosurfactants and biotechnology, vol 25. Dekker, Basel, pp 183–210

    Google Scholar 

  • Kaneda T (1977) Fatty acids of the genus Bacillus: an example of branched-chain preference. Bacterial Rev 41:391–418

    Google Scholar 

  • Kleinkauf H, Döhren VH (1986) Peptide antibiotics. In: Rehm H-J, Reed G (eds) Biotechnology — a comprehensive treatise. Verlag Chemie, Weinheim, pp 283–307

    Google Scholar 

  • Kleinkauf H, Döhren von (1987) Biosynthesis of peptide antibiotics. Annu Rev Microbiol 41:259–289

    Google Scholar 

  • Kluge B, Vater J, Salnikow J, Eckart K (1988) Studies on the biosynthesis of surfactin, a lipopeptide antibiotic from Bacillus subtilis ATCC 21 332. FEBS Lett 231:107–110

    Google Scholar 

  • Kudo S (1988) Biosurfactant as food additives. In: Applewhite ThH (ed) Proceedings of the World Conference on Biotechnology for the Fats and Oils Industry, American Oil Chemists' Society, pp 195–201

  • Lancini G, Parenti F (1982) Antibiotics. An integrated view. Springer, Berlin Heidelberg New York, pp 13–28

    Google Scholar 

  • Lang S, Wagner F (1987) Structures and properties of biosurfactants. In: Kosaric N, Cairns WL, Gray NCC (eds) Surfactant sciences series: biosurfactants and biotechnology, vol 25. Dekker, Basel, pp 21–45

    Google Scholar 

  • Layman PL (1985) Industrial surfactants set for strong growth. Chem Eng News 63:23–48

    Google Scholar 

  • MacDonald CR, Cooper DG, Zajic JE (1981) Surface-active lipids from Nocardia erythropolis grown on hydrocarbons. Appl Environ Microbiol 41:117–123

    Google Scholar 

  • McCloscey JA (1970) Mass spectrometry of fatty acid derivatives. In: Gunstone FD (ed) Topics in lipid chemistry, vol 1. Logos Press, London, pp 369–446

    Google Scholar 

  • McInerney MJ, Javaheri M, Nagle DP Jr (1990) Properties of the biosurfactant produced by Bacillus licheniformis strain JF-2. J Ind Microbiol 5:95–102

    Google Scholar 

  • Mulligan C, Chow TY-K, Gibbs BF (1989) Enhanced biosurfactant production by a mutant Bacillus subtilis strain. Appl Microbiol Biotechnol 31:486–489

    Google Scholar 

  • Neu TR, Poralla K (1990) Surface active properties of viscosin: a peptidolipid antibiotic. Appl Microbiol Biotechnol 32:518–520

    Google Scholar 

  • Rouser G, Kritchersky G, Yamamoto A (1976) Lipid chromatographic analyses, 2nd edn. Dekker, New York, pp 713–776

    Google Scholar 

  • Segré A, Bachmann A, Ballio A, Bossa F, Girgurina I, Iacobellis NS, Marino G, Pucci P, Simmaco M, Takemoto JY (1989) The structure of syringomycins A1, E and G. FEBS 255:27–31

    Google Scholar 

  • Shennan JL, Levi JD (1987) In situ microbial enhanced oil recovery. In: Kosaric N, Cairns WL, Gray NCC (eds) Surfactant sciences series: biosurfactants and biotechnology, vol 25. Dekker, Basel, pp 163–181

    Google Scholar 

  • Takahara Y, Hirose Y, Yasuda N, Mitsugi K, Murao S (1976) Effect of peptidolipids produced by Bacillus on the enzymatic lysis of Gram-negative bacterial cells. Agric Biol Chem 40:1901–1903

    Google Scholar 

  • Thomas DW, Ito T (1969) The revised structure of the peptide antibiotic esperin, established by mass spectrometry. Tetrahedron 25:1985–1990

    Google Scholar 

  • Troy FA (1982) Chemistry and biosynthesis of the poly(γ-D-glutamyl) capsule in Bacillus licheniformis. In: Kleinkauf H, Döhren H von (eds) Peptide antibiotics. Walter de Gruyter, Berlin, pp 49–83

    Google Scholar 

  • Umezawa H, Takita T, Shiba T (1978) Bioactive peptides produced by microorganisms. Holsted Press, Tokyo

    Google Scholar 

  • Zajic JE, Mahomedy AY (1984) Biosurfactants: intermediates in the biosynthesis of amphiphatic molecules in microbes. In: Atlas RM (ed) Petroleum microbiology. Macmillan, London, pp 221–297

    Google Scholar 

  • Zajic JE, Seffens W (1983) Biosurfactants. CRC Crit Rev Biotechnol 1:87–107

    Google Scholar 

Download references

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Authors and Affiliations

  1. Institut für Biotechnologie, ETH-Hönggerberg, CH-8093, Zürich, Switzerland

    Katharina Jenny & Armin Fiechter

  2. Bideco AG, Im Schörli, CH-8600, Dübendorf, Switzerland

    Othmar Käppeli

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  1. Katharina Jenny
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  2. Othmar Käppeli
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  3. Armin Fiechter
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Jenny, K., Käppeli, O. & Fiechter, A. Biosurfactants from Bacillus licheniformis: structural analysis and characterization. Appl Microbiol Biotechnol 36, 5–13 (1991). https://doi.org/10.1007/BF00164690

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  • DOI: https://doi.org/10.1007/BF00164690

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