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

Appl Microbiol Biotechnol. 2004 May;64(4):497-504. doi: 10.1007/s00253-003-1471-8. Epub 2003 Oct 31.


The marine strain Bacillus pumilus strain AAS3, isolated from the Mediterranean sponge Acanthella acuta, produced a diglucosyl-glycerolipid, 1,2-O-diacyl-3-[beta-glucopyranosyl-(1-6)-beta-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 approximately 1 microg/ml), while the glycerolipids GGL11 and GGL12 were less active or had no effect.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Anticarcinogenic Agents / pharmacology
  • Antineoplastic Agents / pharmacology
  • Bacillus / chemistry*
  • Bacillus / isolation & purification
  • Cell Division / drug effects
  • Cell Line, Tumor
  • DNA, Bacterial / chemistry
  • DNA, Bacterial / isolation & purification
  • DNA, Ribosomal / chemistry
  • DNA, Ribosomal / isolation & purification
  • Fatty Acids / analysis*
  • Fatty Acids, Monounsaturated / metabolism
  • Glycolipids / chemistry*
  • Glycolipids / isolation & purification*
  • Glycolipids / metabolism
  • Glycolipids / pharmacology
  • Humans
  • Kinetics
  • Lipase / metabolism
  • Palmitic Acids / analysis*
  • Porifera / microbiology
  • Sequence Analysis, DNA
  • Surface Tension / drug effects
  • Water Microbiology


  • Anticarcinogenic Agents
  • Antineoplastic Agents
  • DNA, Bacterial
  • DNA, Ribosomal
  • Fatty Acids
  • Fatty Acids, Monounsaturated
  • Glycolipids
  • Palmitic Acids
  • glycerolglycolipids
  • aseanostatin P5
  • 14-methylhexadecanoic acid
  • 4-pentenoic acid
  • Lipase