A Madagascar Sponge Batzella sp. as a source of alkylated iminosugars.
Three new C-alkylated iminosugars, batzellasides A (3), B (4), and C (5), along with the known halitoxin (2) polymer were isolated from a Batzella sp. sponge, collected off the west coast of Madagascar. Although this class of azasugars is well known from terrestrial sources, our report represents the first examples of iminosugars from a marine organism. Comparison with the properties of known natural and synthetic iminosugars assisted in the structure determinations. Compounds 3-5 inhibited the growth of Staphylococcus epidermidis with MICs of < or =6.3 microg/mL.
Segraves
Nathaniel L
NL
Department of Chemistry and Biochemistry, Institute of Marine Sciences, University of California, Santa Cruz, California 95064, USA.
Crews
Phillip
P
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives; D000606:Amino Sugars / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000737:chemistry; D008270:Madagascar; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D011726:Pyridinium Compounds / Q000737:chemistry / Q000302:isolation & purification; D013212:Staphylococcus epidermidis / Q000187:drug effects*
D000606:Amino Sugars; D000900:Anti-Bacterial Agents; D011726:Pyridinium Compounds; C498136:batzellaside A; C498137:batzellaside B; C498138:batzellaside C; C112488:halitoxin; D017485:1-Deoxynojirimycin; D005944:Glucosamine; C013626:nojirimycin