title: Lipase-catalyzed acylation of microbial mannosylerythritol lipids (biosurfactants) and their characterization.
abstract: 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.
authors.affiliation: Braunschweig University of Technology, Institute of Biochemistry, Biotechnology and Bioinformatics, Department of Biotechnology, Braunschweig, Germany.
authors.forename: Verena K
authors.initials: VK
authors.lastname: Recke
authors.forename: Catharina
authors.initials: C
authors.lastname: Beyrle
authors.forename: Melanie
authors.initials: M
authors.lastname: Gerlitzki
authors.forename: Rudolf
authors.initials: R
authors.lastname: Hausmann
authors.forename: Christoph
authors.initials: C
authors.lastname: Syldatk
authors.forename: Victor
authors.initials: V
authors.lastname: Wray
authors.forename: Harukuni
authors.initials: H
authors.lastname: Tokuda
authors.forename: Nobutaka
authors.initials: N
authors.lastname: Suzuki
authors.forename: Siegmund
authors.initials: S
authors.lastname: Lang
mesh_terms: D000215:Acylation; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology; D002853:Chromatography, Liquid; D003652:Decanoic Acids / Q000737:chemistry; D004354:Drug Screening Assays, Antitumor / Q000379:methods; D006001:Glycoconjugates / Q000737:chemistry; D006017:Glycolipids / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006801:Humans; D008049:Lipase / Q000737:chemistry / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013024:Soybean Oil / Q000737:chemistry / Q000378:metabolism; D013229:Stearic Acids / Q000737:chemistry; D013500:Surface Tension; D013501:Surface-Active Agents / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D014587:Ustilaginales / Q000254:growth & development / Q000378:metabolism
chemical_list: D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D003652:Decanoic Acids; D006001:Glycoconjugates; D006017:Glycolipids; D013229:Stearic Acids; D013501:Surface-Active Agents; C439671:mannosylerythritol lipid; C418382:rhamnolipid; D013024:Soybean Oil; D008049:Lipase; C017552:myrmicacin