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- W1974879097 abstract "2,5-Dideoxy-2,5-imino-d-glycero-d-manno-heptitol (homoDMDP) is widely distributed in Hyacinthaceae plants and can also be regarded as the α-1-C-(1,2-dihydroxyethyl) derivative of 1,4-dideoxy-1,4-imino-d-arabinitol (d-AB1). In a search for glycosidase inhibitors in this family of plants, we isolated three new d-AB1 derivatives bearing the 2-hydroxypropyl (1), 1,2-dihydroxypropyl (2), and 1,5,7,12,13-pentahydroxytridecyl (3) side chains at the C-1α position, respectively, from the bulbs of Scilla peruviana. Alkaloid 3 was a powerful inhibitor of bacterial β-glucosidase (IC50 = 80 nM) and bovine liver β-galactosidase (IC50 = 90 nM). This plant coproduced four new pyrrolizidine alkaloids, α-5-C-(3-hydroxybutyl)-7-epi-australine (4), α-5-C-(3-hydroxybutyl)hyacinthacine A1 (5), α-5-C-(1,3-dihydroxybutyl)hyacinthacine A1 (6), and α-5-C-(1,3,4-trihydroxybutyl)hyacinthacine A1 (7). Alkaloids 4 and 6 were potent inhibitors of yeast α-glucosidase, with IC50 values of 6.6 and 6.3 μM, respectively, and alkaloid 6 was also a potent inhibitor of bacterial β-glucosidase with an IC50 value of 5.1 μM." @default.
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- W1974879097 date "2004-04-29" @default.
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- W1974879097 title "Glycosidase-Inhibiting Pyrrolidines and Pyrrolizidines with a Long Side Chain in <i>Scilla </i><i>p</i><i>eruviana</i>" @default.
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- W1974879097 doi "https://doi.org/10.1021/np0499721" @default.
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