Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis.
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.
Asano
N
N
Faculty of Pharmaceutical Sciences, Hokuriku University, Kanazawa 920-11, Japan. naoki22@po.incl.or.jp
Kato
A
A
Miyauchi
M
M
Kizu
H
H
Kameda
Y
Y
Watson
A A
AA
Nash
R J
RJ
Fleet
G W
GW
D000470:Alkaloids / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D004791:Enzyme Inhibitors / Q000302:isolation & purification / Q000494:pharmacology; D008401:Gas Chromatography-Mass Spectrometry; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D012275:Oryza / Q000201:enzymology; D010944:Plants / Q000737:chemistry*; D051381:Rats
D000470:Alkaloids; D004791:Enzyme Inhibitors; D006026:Glycoside Hydrolases