Culturing Pseudozyma aphidis on glucose as main carbon source and soybean oil as co-substrate the mannosylerythritol lipids MEL-A and MEL-B were produced. Based on their excellent surface/interfacial active behavior they possess a high potential among all known biosurfactants. The components of a microbial MEL mixture were purified by medium pressure liquid chromatography (MPLC) and were used as substrates for in vitro enzymatic modifications. Lipase-catalyzed acylations of MEL-A and MEL-B with uncommon fatty acids from other microbial glycolipids-3-hydroxydecanoic acid from rhamnolipids and 17-hydroxyoctadecanoic acid from classical sophorolipids-yielded functionalized products at the C-1 position of the erythritol. The novel products were purified by MPLC and their structures elucidated by (1)H and (13)C nuclear magnetic resonance spectroscopy and mass spectrometry. In physicochemical characterization experiments two of the three new glycoconjugates lowered the surface tension of water from 72 mN m(-1) to 27-38 mN m(-1). Moreover the novel compounds inhibited the growth of gram-positive bacteria and showed a potential for anti-tumor-promoting activity.
enzymatic modification, surface tension, mannosylerythritol lipids, biosurfactants, Pseudozyma aphidis
NCBI PubMed ID: 23584591Publication DOI: 10.1016/j.carres.2013.03.013Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: Lang S
Institutions: Braunschweig University of Technology, Institute of Biochemistry, Biotechnology and Bioinformatics, Department of Biotechnology, Braunschweig, Germany, Karlsruhe Institute of Technology (KIT), Institute of Process Engineering in Life Sciences, Section II: Technical Biology, Karlsruhe, Germany, Hohenheim University, Institute of Food Science and Biotechnology, Department of Bioprocess Engineering, Stuttgart, Germany, Helmholtz Centre for Infection Research, Department of Molecular Structural Biology,Braunschweig, Germany, Kanazawa University, Department of Complementary and Alternative Medicine, Clinical R&D, Graduate School of Medical Science,Kanazawa, Japan
Methods: TLC, antibacterial assay, antitumor activity assay, COSY, MPLC, Agar diffusion test
Found