Lipase-catalyzed acylation of microbial mannosylerythritol lipids (biosurfactants) and their characterization
2013
Recke, Verena K. | Beyrle, Catharina | Gerlitzki, Melanie | Hausmann, Rudolf | Syldatk, Christoph | Wray, Victor | Tokuda, Harukuni | Suzuki, Nobutaka | Lang, Siegmund
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 ¹H and ¹³C nuclear magnetic resonance spectroscopy and mass spectrometry. In physicochemical characterization experiments two of the three new glycoconjugates lowered the surface tension of water from 72mNm⁻¹ to 27–38mNm⁻¹. Moreover the novel compounds inhibited the growth of gram-positive bacteria and showed a potential for anti-tumor-promoting activity.
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