Novel glycosidase inhibitors, nojirimycin B and D-mannonic-delta-lactam. Isolation, structure determination and biological property.
A new aminosugar named nojirimycin B (1) has been isolated as its bisulfite adduct from the culture broth of Streptomyces lavendulae SF-425, together with nojirimycin. Microbiological oxidation of 1 with Gluconobacter suboxydans IAM 1829 gave a delta-lactam (2). The structures of 1 and 2 were determined to be 5-amino-5-deoxy-D-mannopyranose and D-mannonic-delta-lactam, respectively, on the basis of 1H NMR spectroscopy and X-ray structural analysis. Both 1 and 2 exhibited powerful inhibitory activity against rat epididymal alpha-mannosidase and apricot beta-glucosidase.
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives; D055598:Chemical Phenomena; D002621:Chemistry; D005944:Glucosamine / Q000302:isolation & purification* / Q000494:pharmacology; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D007769:Lactams / Q000302:isolation & purification* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D013302:Streptomyces / Q000378:metabolism*
D007769:Lactams; D017485:1-Deoxynojirimycin; C044532:mannonic-delta-lactam; D006026:Glycoside Hydrolases; D005944:Glucosamine; C013626:nojirimycin