title: Structure elucidation and characterization of microbial 2-tridecyl sophorosides (biosurfactants).
abstract: To produce novel types of sophorose lipids containing an odd number of carbon atoms in the lipophilic moiety, Candida bombicola ATCC 22214 was grown in 500-ml flask cultures with glucose as main carbon source, and additionally, 2-tridecanone as co-substrate. After solvent extraction, the crude product mixture was separated into pure fractions, and each fraction was analysed via NMR and mass spectroscopy. This effective strategy generated five new glycolipids, 2-tridecyl sophorosides, which differed in the number of glucose units, and acetyl and hydroxy groups, respectively. Based on these compounds, a proposal for the possible biosynthetic pathway was deduced. Two compounds of the mixture, mono- and diacetylated 2-tridecyl sophorosides, respectively, were able to lower the surface tension of water from 72 mN m(-1) to 32 mN m(-1) and the interfacial tension between water and n-hexadecane from 43 mN m(-1) down to 4 and 3 mN m(-1). Thus, both compounds possess a very good surfactant behaviour. Moreover, it was observed that the new products inhibit the growth of particular Gram-positive bacteria, and they indicate potential for antitumour-promoting activity.
authors.affiliation: Braunschweig University of Technology, Institute of Biochemistry, Biotechnology and Bioinformatics, Department of Biotechnology, Spielmannstr. 7, D-38106 Braunschweig, Germany. verena.recke@gmail.com
authors.forename: Verena K
authors.initials: VK
authors.lastname: Recke
authors.affiliation: Braunschweig University of Technology, Institute of Biochemistry, Biotechnology and Bioinformatics, Department of Biotechnology, Spielmannstr. 7, D-38106 Braunschweig, Germany.
authors.forename: Jun B
authors.initials: JB
authors.lastname: Park
authors.affiliation: Karlsruhe Institute of Technology (KIT), Institute of Process Engineering in Life Sciences, Section II: Technical Biology, Engler-Bunte-Ring 1, D-76131 Karlsruhe, Germany.
authors.forename: Melanie
authors.initials: M
authors.lastname: Gerlitzki
authors.affiliation: Hohenheim University, Institute of Food Science and Biotechnology, Department of Bioprocess Engineering, Fruhwirthstr. 12, D-70599 Stuttgart, Germany.
authors.forename: Rudolf
authors.initials: R
authors.lastname: Hausmann
authors.affiliation: Karlsruhe Institute of Technology (KIT), Institute of Process Engineering in Life Sciences, Section II: Technical Biology, Engler-Bunte-Ring 1, D-76131 Karlsruhe, Germany.
authors.forename: Christoph
authors.initials: C
authors.lastname: Syldatk
authors.affiliation: Helmholtz Centre for Infection Research, Department of Molecular Structural Biology, Inhoffenstr. 7, D-38124 Braunschweig, Germany.
authors.forename: Victor
authors.initials: V
authors.lastname: Wray
authors.affiliation: Kanazawa University, Department of Complementary and Alternative Medicine, Clinical R & D, Graduate School of Medical Science, 13-1 Takara-machi, Kanazawa, Japan.
authors.forename: Harukuni
authors.initials: H
authors.lastname: Tokuda
authors.affiliation: Kanazawa University, Department of Complementary and Alternative Medicine, Clinical R & D, Graduate School of Medical Science, 13-1 Takara-machi, Kanazawa, Japan.
authors.forename: Nobutaka
authors.initials: N
authors.lastname: Suzuki
authors.affiliation: Braunschweig University of Technology, Institute of Biochemistry, Biotechnology and Bioinformatics, Department of Biotechnology, Spielmannstr. 7, D-38106 Braunschweig, Germany.
authors.forename: Siegmund
authors.initials: S
authors.lastname: Lang
mesh_terms: D002175:Candida / Q000737:chemistry*; D002240:Carbohydrate Sequence; D002855:Chromatography, Thin Layer; D005936:Glucans / Q000737:chemistry*; D013058:Mass Spectrometry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013501:Surface-Active Agents / Q000737:chemistry*
chemical_list: D005936:Glucans; D013501:Surface-Active Agents; C003328:sophorose