Production and structure elucidation of glycoglycerolipids from a marine sponge-associated microbacterium species.
The bacterium Microbacterium sp., isolated from the sponge Halichondria panicea, produced four unusual cell-associated glycoglycerolipids and one diphosphatidylglycerol when grown on marine broth and on artificial seawater media. The lipids were isolated by chromatography on silica columns and their structures elucidated using a combination of multidimensional NMR and MS techniques. The main compound was 1-O-acyl-3-[alpha-glucopyranosyl-(1-3)-(6-O-acyl-alpha-mannopyranosyl )]glycerol (GGL.2) with 14-methyl-hexadecanoic acid and 12-methyl-tetradecanoic acid positioned at C-6 of the mannose unit and at the glycerol moiety. Glycolipid production was correlated with growth and reached a maximum value of 200 mg/L when grown on artificial seawater medium with 20 g/L glucose. The main compound decreased the surface tension of water down to 33 mN/m and the interfacial tension of the water/n-hexadecane system down to 5 mN/m. In addition to this good surface-active behavior, the main glycoglycerolipid showed antitumor activities.
Wicke
C
C
Institut für Biochemie und Biotechnologie, Technische Universität Braunschweig, Abt. Biotechnologie, Spielmannstrasse 7, D-38106 Braunschweig, Germany.
Hüners
M
M
Wray
V
V
Nimtz
M
M
Bilitewski
U
U
Lang
S
S
D000192:Actinomycetales / Q000254:growth & development / Q000378:metabolism*; D000818:Animals; D018533:Biomass; D002241:Carbohydrates / Q000737:chemistry; D002245:Carbon Dioxide / Q000378:metabolism; D002308:Cardiolipins / Q000096:biosynthesis / Q000737:chemistry; D002855:Chromatography, Thin Layer; D003470:Culture Media; D005990:Glycerol / Q000737:chemistry; D006017:Glycolipids / Q000096:biosynthesis* / Q000737:chemistry; D013058:Mass Spectrometry; D010101:Oxygen Consumption / Q000502:physiology; D011161:Porifera / Q000382:microbiology*; D013501:Surface-Active Agents / Q000737:chemistry
D002241:Carbohydrates; D002308:Cardiolipins; D003470:Culture Media; D006017:Glycolipids; D013501:Surface-Active Agents; D002245:Carbon Dioxide; D005990:Glycerol