HOMONOJIRIMYCIN ISOMERS AND GLYCOSIDES FROM AGLAONEMA-TREUBII

A 50% aqueous EtOH extract of Aglaonema treubii found to potently inhi bit alpha-glucosidase was subjected to various ion-exchange column chr omatographic steps to give bis-(hydroxymethyl)-3(R),4(R)-dihydroxypyrr olidine (1), alpha-homonojirimycin (2), beta-homonojirimycin (3), alph a-homomannojirimycin (4), beta-homomannojirimycin (5), alpha-3,4-di-ep i-homonojirimycin (6), 7-O-beta-D-glucopyranosyl-alpha-homonojirimycin (7), and 5-O-alpha-D-galactopyranosyl-alpha-homonojirimycin (8). Comp ounds 1 and 2 are known inhibitors of various alpha-glucosidases. Comp ounds 6 and 8 are new natural products. Compounds 3-5 and 7 have been chemically synthesized previously, but this is the first report of the ir natural occurrence.