Diglucosyl-glycerolipids from the marine sponge-associated Bacillus pumilus strain AAS3: their production, enzymatic modification and properties.
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.
Ramm
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W
Institute of Biochemistry and Biotechnology, Biotechnology Group, Technical University of Braunschweig, Spielmannstrasse 7, 38106 Braunschweig, Germany.
Schatton
W
W
Wagner-Döbler
I
I
Wray
V
V
Nimtz
M
M
Tokuda
H
H
Enjyo
F
F
Nishino
H
H
Beil
W
W
Heckmann
R
R
Lurtz
V
V
Lang
S
S
D000818:Animals; D016588:Anticarcinogenic Agents / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000494:pharmacology; D001407:Bacillus / Q000737:chemistry* / Q000302:isolation & purification; D002455:Cell Division / Q000187:drug effects; D045744:Cell Line, Tumor; D004269:DNA, Bacterial / Q000737:chemistry / Q000302:isolation & purification; D004275:DNA, Ribosomal / Q000737:chemistry / Q000302:isolation & purification; D005227:Fatty Acids / Q000032:analysis*; D005229:Fatty Acids, Monounsaturated / Q000378:metabolism; D006017:Glycolipids / Q000737:chemistry* / Q000302:isolation & purification* / Q000378:metabolism / Q000494:pharmacology; D006801:Humans; D007700:Kinetics; D008049:Lipase / Q000378:metabolism; D010169:Palmitic Acids / Q000032:analysis*; D011161:Porifera / Q000382:microbiology; D017422:Sequence Analysis, DNA; D013500:Surface Tension / Q000187:drug effects; D014871:Water Microbiology
D016588:Anticarcinogenic Agents; D000970:Antineoplastic Agents; D004269:DNA, Bacterial; D004275:DNA, Ribosomal; D005227:Fatty Acids; D005229:Fatty Acids, Monounsaturated; D006017:Glycolipids; D010169:Palmitic Acids; C015903:glycerolglycolipids; C069642:aseanostatin P5; C046143:14-methylhexadecanoic acid; C009785:4-pentenoic acid; D008049:Lipase