Isolation and structure assignment of an iminotetrasaccharide from a cultured filamentous cyanobacterium Anabaena sp.
In search of bioactive metabolites in cultured microalgae, a novel acylated iminopseudotetrasaccharide was isolated from a filamentous cyanobacterium Anabaena sp., and its structure was established by NMR, chemical degradation, and X-ray crystallography. The compound consists of glucose, glucuronic acid, arabinose, and 1,4,6-trideoxy-1,4-imino-D-allitol, which is closely related to potent glucosidase inhibitors such as nojirimycin. The tetrasaccharide itself showed moderate inhibitory activity against beta-D-glucuronidase.
Thammana
Sudhakararao
S
Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island, Kingston, 02881, USA.
Suzuki
Hideharu
H
Lobkovsky
Emil
E
Clardy
Jon
J
Shimizu
Yuzuru
Y
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives; D017033:Anabaena / Q000737:chemistry*; D001315:Australia; D018360:Crystallography, X-Ray; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005944:Glucosamine / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology; D005966:Glucuronidase / Q000037:antagonists & inhibitors*; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009844:Oligosaccharides / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology
D004791:Enzyme Inhibitors; D009844:Oligosaccharides; D017485:1-Deoxynojirimycin; D005966:Glucuronidase; D005944:Glucosamine; C013626:nojirimycin