Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis.

Journal article

Aqueous methanol extracts from the bulbs of Hyacinthusorientalis were subjected to various ion-exchange column chromatographic steps to give 2(R),5(R)-bis(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine (DMDP) (1), 2,5-dideoxy-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-deoxymannojirimycin (6), alpha-homonojirimycin (7), beta-homonojirimycin (8), alpha-homomannojirimycin (9), beta-homomannojirimycin (10), and 7-O-beta-d-glucopyranosyl-alpha-homonojirimycin (MDL 25,637) (11). The structures of the new natural products 3 and 4 were determined by spectroscopic analysis, including extensive 1D and 2D NMR studies. Compound 2 was found to be a potent inhibitor of bacterial beta-glucosidase, mammalian beta-galactosidases, and mammalian trehalases, while 3 was a potent inhibitor of rice alpha-glucosidase and rat intestinal maltase. Compound 4 was observed to be a good inhibitor of alpha-l-fucosidase.

Authors: Asano, N; Kato, A; Miyauchi, M; Kizu, H; Kameda, Y

• Publication status: Published
• Journal: Journal of natural products
• Volume: 61
• Issue: 5
• Pages: 625-628
• Publication date: 1998-05-01
• DOI: 10.1021/np9705726
• EISSN: 1520-6025
• ISSN: 0163-3864
• Language: English
• Keywords: Oryza sativa; Enzyme Inhibitors; Gas Chromatography-Mass Spectrometry; Alkaloids; Plants; Glycoside Hydrolases; Rats; Animals