Glycosidase Inhibitory Activity

The polyhydroxindolizidine alkaloids, whose most important examples are castanospermine, swainsonine, and lentiginosine, are noted for their potent glycosidase inhibitory activity <2000TA1645, 1998CC1161,... 

Preparation of penta-substituted C8-glycomimetics (e.g. 72) and their glycosidase inhibitory activity was recently studied (Fig. 25).38... 

Fig. 3. Position of the nitrogen atom in various basic sugar analogues of proven glycosidase inhibitory activity (disregarding conformational freedom as well as other ring sizes).

N. Asano, K. Oseki, E. Kaneko, and K. Matsui, Enzymic synthesis of a- and p-D-glucosides of 1-deoxynojirimycin and their glycosidase inhibitory activities, Carbohydr. Res., 258 (1994) 255-266. 

S. M. Andersen, M. Ebner, C. W. Ekhart, G. Gradnig, G. Legler, I. Lundt, A. E. Stiitz, S. G. Withers, and T. Wrodnigg, Two isosteric fluorinated derivatives of the powerful glucosidase inhibitors, 1-deoxynojirimycin and 2,5-dideoxy-2,5-imino-D-mannitol Syntheses and glycosidase inhibitory activities of l,2,5-trideoxy-2-fluoro-l,5-imino-D-glucitol and of l,2,5-trideoxy-l-fluoro-2,5-imino-D-mannitol, Carbohydr. Res., 301 (1997) 155-166. 

Ogawa, S. et al. Synthesis and Glycosidase Inhibitory Activity of 5a-Carba-a-DL-fucopyranosylamine and -galactopyranosylamine. 3.4.1 2000 [162]... 

Glycosidase-inhibiting alkaloids from plants are classified into five structural classes polyhydroxylated pyrrolidines, piperidines, indolizidines, pyrrolizidines, and nortropanes. Furthermore, they also occur as the glycosides. This review describes recent studies on isolation, characterization, glycosidase inhibitory activity, and therapeutic application of the sugar-mimicking alkaloids from plants. 

Biological Activities and Applications 9.3.2.1 Glycosidase Inhibitory Activities... 

Randell, K D, Frandsen, T P, Stoffer, B, Johnson, M A, Svensson, B, Pinto, B M, Synthesis and glycosidase inhibitory activity of 5-thioglucopyranosylamines. Molecular modeling of complexes with glucoamylase, Carbohydr. Res., 321, 143-156, 1999. 

As shown in O Table 1, glycosidase inhibitory activities of these cyclophelitol-related compounds were evaluated [19]. 

The weak glycosidase inhibitory activities usually observed for monosaccharides with sulfur in the ring when compared to the corresponding natural substrates have frequently also been found with di- and oligosaccharides. 

The methanol extract of Sophora flavescens showed potent glycosidase inhibitory activity. Active components were identified as well-known flavonoid antioxidants including kurarinol (3), maackian (6), isoxanthohumol (7), kuraridin (8), sophoraflavanone G (10), 2/-methoxykurarinone (23), kushenol A (26), 8-prenylkaempferol (63), and (-)-kurarinone (68). All of the flavonoids were effective inhibitors of a-glucosidase and /(-amylase. Interestingly, la-... 

Guanidinium and isothiourea derivatives such as 46 and 47 were also reported that exhibited potent and selective (3-glycosidase inhibitory activity, in contradiction with the previous castanospermine analogues depicted above. Noteworthy, sulfamide-type indolizidines such as 48, in which the thiourea moiety has been replaced by a sulfamide group, were also described and found to be modest a-mannosidase inhibitors... 

Asano N, Oseki K, Tomioka E, Kizu H, Matsui K (1994) N-containing sugars from Morus alba and their glycosidase inhibitory activities. Carbohydr Res 259 (Copyright (C) 2012 U.S. National Library of Medicine.) 243-255... 

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