NITROGEN-CONTAINING FURANOSE AND PYRANOSE ANALOGS FROM HYACINTHUS-ORIENTALIS

Aqueous methanol extracts from the bulbs of Hyacinthus orientalis were subjected to various ion-exchange column chromatographic steps to giv e -bis(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine (DMDP) (1), 2,5-d ideoxy-2,5-imino-DL-glycero-D-manno-heptitol (homoDMDP) (2), 2,5-imino -2,5,6-trideoxy-D-manno-heptitol (6-deoxy-homoDMDP) (3), 2,5-imino-2,5 ,6-trideoxy-D-gulo-heptitol (4), 1-deoxynojirimycin (5), 1-deoxymannoj irimycin (6), alpha-homonojirimycin (7), beta-homonojirimycin (8), alp ha-homomannojirimycin (9), beta-homomannojirimycin (10), and 7-O-beta- D-glucopyranosyl-alpha-homonojirimycin (MDL 25,637) (11). The structur es of the new natural products 3 and 4 were determined by spectroscopi c analysis, including extensive 1D and 2D NMR studies. Compound 2 was found to be a potent inhibitor of bacterial beta-glucosidase, mammalia n beta-galactosidases, and mammalian trehalases, while 3 was a potent inhibitor of rice alpha-glucosidase and rat intestinal maltase. Compou nd 4 was observed to be a good inhibitor of alpha-L-fucosidase.