Summary
During screening for biosurfactants among marine, n-alkane-utilizing bacteria, low- and high-molecular surface-active substances were detected. The marine bacterial strain MM1 was found to synthesize a novel glycolipid that has not so far been cited in the literature. Both 1H, 13C-nuclear magnetic resonance spectroscopic and positive ion fast atom bombardment mass spectrometer studies led to the identification of a glucose lipid consisting of four 3-OH-decanoic acids, which are linked together by ester bonds. The lipophilic moiety is coupled glycosidically with C-1 of glucose. The glucolipid reduced the surface tension from 72 mN/m to 30 mN/m while the minimum interfacial tension towards n-hexadecane was lowered to values smaller than 5 mN/m.
Similar content being viewed by others
References
Baginsky ES, Foa PP, Zak B (1967) Glucose-6-phosphatase. Anal Biochem 21:909–913
Barnes EM, Swindell AC, Wakil SJ (1970) Purifications and properties of a palmityl thioesterase II from E. coli. J Biol Chem 245:3122–3128
Beilsteins Handbuch der Organischen Chemie (1977), 4. Ergänzungswerk, vol. 3 (editor: Beilstein-Institut für Literatur der Organischen Chemie, Frankfurt/Main, FRG). Springer, Berlin Heidelberg New York, pp 873–894
Bernem KH van (1984) Experimentelle Untersuchungen zur Wirkung von Rohöl und Rohöl-Tensidgemischen im Ökosystem Wattenmeer. II. Eindringverhalten und Persistenz von Rohöl-KWS in Sedimenten nach experimenteller Kontamination. Senkenb Marit 16:13–30
Blecher M (1981) Synthesis of long chain fatty acyl CoA thioesters using N-hydroxysuccinimide esters. Methods Enzymol 72:403–407
Boyce SG, Lueking DR (1984) Purification and characterization of a long chain acyl CoA thioesterase from Rhodopseudomonas sphaeroides. Biochemistry 23:141–147
Burger MM, Glaser L, Burton RM (1963) The enzymatic synthesis of a rhamnose-containing glycolipid by extracts of Pseudomonas aeruginosa. J Biol Chem 238:2595–2601
Cirigliano MC, Carman GM (1984) Isolation of a bioemulsifier from Candida lipolytica. Appl Environ Microbiol 48:747–750
Ellman GL (1959) Tissue sulfhydryl groups. Arch Biochem Biophys 82:72–77
Frautz B, Lang S, Wagner F (1986) Formation of cellobiose lipids by growing and resting cells of Ustilago maydis. Biotechnol Lett 8:757–762
Gutnik DL, Bayer EA, Rubinowitz C, Pines O, Shabtai Y, Goldmann S, Rosenberg E (1981) Emulsan production in Acinetbacter RAG-1. Adv Biotechnol 3:455–459
Haferburg D, Hommel R, Claus R, Kleber HP (1986) Extracellular microbial lipids as biosurfactants. Adv Biochem Eng Biotechnol 33:53–93
Hauser G, Karnovsky ML (1957) Rhamnose and rhamnolipid biosynthesis by Pseudomonas aeruginosa. J Biol Chem 229:91–105
Hisatsuka K, Nakahara T, Sano N, Yamada K (1971) Formation of rhamnolipid by Pseudomonas aeruginosa and its function in hydrocarbon fermentation. Agric Biol Chem 35:686–692
Itoh S, Suzuki T (1972) Effect of rhamnolipids on growth of Pseudomonas aeruginosa mutant deficient in n-paraffin-utilizing ability. Agric Biol Chem 36:2233–2235
Kosaric N, Cairns WL, Gray NCC (eds) (1987) Biosurfactants and biotechnology. Surfactant science series, vol 25. Dekker, New York
Kretschmer A, Bock H, Wagner F (1982) Chemical and physical characterization of interfacial active lipids from Rhodococcus erythropolis grown on n-alkanes. Appl Environ Microbiol 44:864–870
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. EK1. Z Naturforsch 46c:204–209
Poremba K, Gunkel W, Lang S, Wagner F (1989) Mikrobieller Ölabbau im Meer. Biol Unserer Zeit 5:145–148
Poremba K, Gunkel W, Lang S, Wagner F (1991) Marine biosurfactants. III. Toxicity testing with marine microorganisms and comparison with synthetic detergents. Z Naturforsch 46c:210–216
Rosen OM, Rosen SM, Horecker BL (1966) Fructose-1,6-diphosphatase. Methods Enzymol 9:632–636
Schulz D, Passeri A, Schmidt M, Lang S, Wagner F, Wray V, Gunkel W (1991) Marine biosurfactants. I. Screening for biosurfactants among crude oil degrading marine microorganism from the North Sea. Z Naturforsch 46c:197–203
Seay T, Lueking DR (1986) Purification and properties of acyl coenzyme A thioesterase II from Rhodopseudomonas sphaeroides. Biochemistry 25:2480–2485
Seubert W, Weicker H (1969) Pyruvate carboxylase from Pseudomonas. Methods Enzymol 13:258–262
Smith J (ed) (1968) Torrey Canyon — pollution and marine life. Report by the Plymouth Laboratory of the Marine Biological Association of the United Kingdom, London. Cambridge University Press, London, pp 1906
Smith S, Mikkelsen J, Witkowski A, Libertini LJ (1986) Thioesterase II: structure-function relationships. Biochem Soc Trans 14:583–584
Syldatk C, Matulovic U, Wagner F (1984) Biotenside — Neue Verfahren zur mikrobiellen Herstellung grenzflächenaktiver, anionischer Glykolipide. Biotechforum (BTF) 3/4:58–66
Takeshima H, Kitao C, Omura S (1977) Inhibition of the biosynthesis of leucomycin by cerulenin. J Biochem 81:1127–1132
Thijsse GJE (1964) Fatty acid accumulation by acrylate inhibition in an alkane oxidizing Pseudomonas. Biochem Biophys Acta 84:195–197
Volpe JV, Vagelos PR (1973) Saturated fatty acid biosynthesis and its regulation. Annu Rev Biochem 42:21–60
Wagner F (1987) Strategies for biosurfactant production. Fat Sci Technol 89:586–591
Wood HG, Davis JJ, Willard JM (1969) Phosphoenolpyruvate carboxytransphosphorylase from Propionibacterium shermanii. Methods Enzymol 13:357–369
Author information
Authors and Affiliations
Additional information
Correspondence to: S. Lang
Rights and permissions
About this article
Cite this article
Passeri, A., Schmidt, M., Haffner, T. et al. Marine biosurfactants. IV. Production, characterization and biosynthesis of an anionic glucose lipid from the marine bacterial strain MM1. Appl Microbiol Biotechnol 37, 281–286 (1992). https://doi.org/10.1007/BF00210978
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00210978