NOVEL GLYCOSIDASE INHIBITORS, NOJIRIMYCIN B AND D-MANNONIC-δ-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 δ-lactam (2). The structures of 1and 2 were determined...

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Veröffentlicht in:	Journal of antibiotics 1984, Vol.37(12), pp.1579-1586
Hauptverfasser:	NIWA, TOMIZO, TSURUOKA, TAKASHI, GOI, HITOSHI, KODAMA, YOSHIO, ITOH, JIRO, INOUYE, SHIGEHARU, YAMADA, YUJIRO, NIIDA, TARO, NOBE, MISAO, OGAWA, YASUAKI
Format:	Artikel
Sprache:	eng
Schlagworte:	1-Deoxynojirimycin - analogs & derivatives Biological and medical sciences Biotechnology Chemical Phenomena Chemistry D-mannonic- delta -lactam Fundamental and applied biological sciences. Psychology General pharmacology Glucosamine - isolation & purification Glucosamine - pharmacology glycosidase Glycoside Hydrolases - antagonists & inhibitors Health. Pharmaceutical industry Industrial applications and implications. Economical aspects Lactams - isolation & purification Lactams - pharmacology Magnetic Resonance Spectroscopy Medical sciences Molecular Conformation nojirimycin B Other active biomolecules Pharmacology. Drug treatments Physicochemical properties. Structure-activity relationships Production of active biomolecules Streptomyces - metabolism Streptomyces lavendulae
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Beschreibung
Zusammenfassung:	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 δ-lactam (2). The structures of 1and 2 were determined to be 5-amino-5-deoxy-D-mannopyranose and D-mannonic-δ-lactam, respectively, on the basis of 1H NMR spectroscopy and X-ray structural analysis. Both 1 and2 exhibited powerful inhibitory activity against rat epididymal α-mannosidase and apricot β-glucosidase.
ISSN:	0021-8820 1881-1469
DOI:	10.7164/antibiotics.37.1579