Diglucosyl-glycerolipids from the marine sponge-associated Bacillus pumilus strain AAS3: their production, enzymatic modification and properties

• Published in: Applied microbiology and biotechnology 2004-05, Vol.64 (4), p.497-504
• Main Authors: Ramm, W, Schatton, W, Wagner-Döbler, I, Wray, V, Nimtz, M, Tokuda, H, Enjyo, F, Nishino, H, Beil, W, Heckmann, R, Lurtz, V, Lang, S
• Format: Article
• Language: English
• Subjects: Acanthella acuta; Animals; Anticarcinogenic Agents - pharmacology; Antineoplastic Agents - pharmacology; Artificial seawater; Bacillus - chemistry; Bacillus - isolation & purification; Bacillus pumilus; Bacteria; Biological and medical sciences; Biotechnology; Cell Division - drug effects; Cell Line, Tumor; DNA, Bacterial - chemistry; DNA, Bacterial - isolation & purification; DNA, Ribosomal - chemistry; DNA, Ribosomal - isolation & purification; fatty acids; Fatty Acids - analysis; Fatty Acids, Monounsaturated - metabolism; Fundamental and applied biological sciences. Psychology; glucose; Glycerol; Glycolipids - chemistry; Glycolipids - isolation & purification; Glycolipids - metabolism; Glycolipids - pharmacology; growth retardation; Humans; Kinetics; Lipase - metabolism; neoplasm cells; nitrogen; Palmitic Acids - analysis; phosphates; Porifera - microbiology; Seawater; Sequence Analysis, DNA; Surface tension; Surface Tension - drug effects; Tumors; Water Microbiology; yeast extract; Yeasts
• ISSN: 0175-7598; 1432-0614
• DOI: 10.1007/s00253-003-1471-8

The marine strain Bacillus pumilus strain AAS3, isolated from the Mediterranean sponge Acanthella acuta, produced a diglucosyl-glycerolipid, 1,2-O-diacyl-3-[β-glucopyranosyl-(1–6)-β-glucopyranosyl)]glycerol, with 14-methylhexadecanoic acid and 12-methyltetradecanoic acid as the main fatty acid moieties (GGL11). On a 30 l scale, using artificial seawater supplemented with glucose (20 g/l), yeast extract (10 g/l), and suitable nitrogen/phosphate sources, growth-associated glycoglycerolipid production reached its maximum yield of 90 mg/l after 11 h. Lipase-catalyzed modification of the native substance led to the deacylated parent compound (GG11), which could be reacylated using the same enzyme system to afford a new dipentenoyl-diglucosylglycerol (GGL12) as the major product upon addition of 4-pentenoic acid to the medium. GGL11 decreased the surface tension of water from 72 mN/m to 29 mN/m and the interfacial tension of the water/n-hexadecane system from 44 to 5 mN/m. Anti-tumor-promoting studies on this class of diglucosyl glycerol products showed that the carbohydrate/glycerol backbone (GG11) has a more potent inhibitory activity than the acylated compounds. The diglucosyl-glycerol GG11 strongly inhibited growth of the tumor cell lines HM02 and Hep G2 (50% inhibition at ~1 μg/ml), while the glycerolipids GGL11 and GGL12 were less active or had no effect.