Formation and Identification of Interfacial-Active Glycolipids from Resting Microbial Cells

Resting cells of Arthrobacter sp. strain DSM2567 incubated in the presence of various mono-, di-, or trisaccharides biosynthesized different glycolipids. All eight glycolipids, containing the corresponding carbohydrate moiety and one, two, or three α-branched β-hydroxy fatty acids, were produced when mannose, glucose, cellobiose, maltose, and maltotriose were used as carbon sources in a simple phosphate buffer. The structures of the compounds were elucidated by means of ¹H and ¹³C nuclear magnetic resonance spectroscopy and by chemical ionization mass spectroscopy. In high-salinity solution, the substances showed different surfactant properties. Cellobiose and maltose monocorynomycolates reduced the interfacial tension from 42 to 1 mN/m at critical micelle concentrations below 20 mg/liter.