Sugars with nitrogen in the ring isolated from the leaves of Morus bombycis.
It is known that 1-deoxynojirimycin (1) is contained in the leaves and roots of Morus sp. The modified purification procedures of 1 from leaves of Morus bombycis led to the isolation of many polyhydroxylated alkaloids. These include 1, N-methyl-1-deoxynojirimycin (2), 2-O-alpha-D-galactopyranosyl-1-deoxynojirimycin (3), fagomine (4), 1,4-dideoxy-1,4-imino-D-arabinitol (5), 1,4-dideoxy-1,4-imino-(2-O-beta-D-glucopyranosyl)-D-arabinitol (6), and 1 alpha,2 beta,3 alpha,4 beta-tetrahydroxy-nor-tropane (7), designated nortropanoline. The isolation of 2 is the first report of its natural occurrence. Compounds 3 and 6 are the first naturally occurring glycosides of 1 and 5, respectively. Natural alkaloidal glycosidase inhibitors are classified into five structural types: namely polyhydroxylated piperidines, pyrrolidines, pyrrolines, indolizidines, and pyrrolizidines. Nortropanoline is a novel tropane alkaloid and a new type of polyhydroxylated alkaloid.
Asano
N
N
School of Pharmacy, Hokuriku University, Ishikawa, Japan.
Tomioka
E
E
Kizu
H
H
Matsui
K
K
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification*; D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D010946:Plants, Medicinal; D016339:Spectrometry, Mass, Fast Atom Bombardment
D000470:Alkaloids; D017485:1-Deoxynojirimycin