Marine biosurfactants. IV. Production, characterization and biosynthesis of an anionic glucose lipid from the marine bacterial strain MM1

During screening for biosurfactants among marine, n-alkane-utilizing bacteria, low- and high-molecular surface-active substances were detected. The marine bacterial strain MM1 was found to synthesize a novel glycolipid that has not so far been cited in the literature. Both 1H, 13C-nuclear magnetic resonance spectroscopic and positive ion fast atom bombardment mass spectrometer studies led to the identification of a glucose lipid consisting of four 3-OH-decanoic acids, which are linked together by ester bonds. The lipophilic moiety is coupled glycosidically with C-1 of glucose. The glucolipid reduced the surface tension from 72 mN/m to 30mN/m while the minimum interfacial tension towards n-hexadecane was lowered to values smaller than 5 mN/m. and liposan (Gutnik et al. 1981; Cirigliano and Carman 1984). In contrast to chemical dispersants, which caused ecological damage after application for abatement of spilled oil in marine ecosystems (Smith 1968), biosurfactants from soil or freshwater microorganisms are less toxic and partially biodegradable (van Bernem 1984; Poremba et al. 1991). Concerning our own investigations, we had a special interest in finding surface active compounds produced by marine microorganisms in the expectation of improved environmental ompatibility. In this paper we present the results of the formation, isolation, structural elucidation and investigations of the biosynthesis of a novel glucose lipid from the marine bacterial strain MM1.