α‐Rhamnosidase Inhibitory Activities of Polyhydroxylated Pyrrolidine.

Abstract

Carbohydrates U 0500 α-Rhamnosidase Inhibitory Activities of Polyhydroxylated Pyrrolidine. -Design, synthesis, and α-rhamnosidase inhibitory activities of a series of polyhydroxylated pyrrolidines (I) (12 examples) are described. Pyrrolidine (Ib) shows the best inhibitory activity because it possesses the same stereoconfiguration at C1 and C2 as α-L-rhamnopyranoside. -(KIM, J. H.; CURTIS-LONG, M. J.; SEO, W. D.; LEE, J. H.; LEE, B. W.; YOON, Y. J.; KANG, K. Y.; PARK*, K. H.; Bioorg. Med. Chem. Lett. 15 (2005) 19, 4282-4285; Dep. Agric. Chem., Gyeongsang Natl. Univ., Chinju 660-701, S. Korea; Eng.) -R. Staver 51-175

Polyphenols from Broussonetia papyrifera Displaying Potent α-Glucosidase Inhibition

“…The extracts from five different polar solvents were tested for their enzymatic inhibitory activities against α-glucosidase and α-mannosidase. The enzyme was assayed according to a standard literature procedure by following the hydrolysis of nitrophenyl glycoside spectrophotometrically − . As shown in Table , all extracts investigated apart from the water extract exhibited a significant degree of α-glucosidase inhibition with IC 50 of around 10 μg/mL and a moderate degree of α-mannosidase (IC 50 > 150 μg/mL) inhibition.…”

“…α-Glucosidase (EC 3.2.1.20) and α- l -rhamnosidase (EC 3.2.1.40) activities were assayed according to the methods described by Seo and Kim , with some minor modifications. The reaction mixture consisted of the enzyme solution (0.02 unit of α-glucosidase, 50 μL; 0.2 unit of α- l -rhamnosidase, 50 μL), substrate (1 mM p -nitrophenyl-α- d -glucopyranoside, 50 μL; 2.5 mM p -nitrophenol-α- d -rhamnopyranoside, 100 μL) in 50 mM potassium phosphate buffer (pH 6.8), and test sample in 5% DMSO (10 μL).…”

“…Papyriflavonol A (10): amorphous yellow powder; mp 202-204 °C; EIMS, m/z 438 [M] þ ; HREIMS, m/z 438.1647 (calcd for C 25 H 26 O 7 ,Enzyme Assay. r-Glucosidase and r-L-Rhamnosidase Activity.R-Glucosidase (EC 3.2.1.20) and R-L-rhamnosidase (EC 3.2.1.40) activities were assayed according to the methods described by Seo and Kim(22,23) with some minor modifications. The reaction mixture consisted of the enzyme solution (0.02 unit of R-glucosidase, 50 μL;…”

Piperidine azasugars displaying competitive α-rhamnosidase inhibition and their kinetic mechanism

“…For example, D-deoxymannojirimycin and homologues functionalized at C1 are generally weak inhibitors of Dmannosidase, but are potent inhibitors of L-fucosidase [Evans et al, 1985;Bruce et al, 1989;Winchester et al, 1990;Bruce et al, 1992]. After synthesis of Ldeoxyrhamnojirimycin (LRJ) [Fairbanks et al, 1992], 5-epi-LRJ and several other iminosugar analogues were developed to target the α-rhamnosidase [Shilvock et al, 1996;Kim et al, 2005]. The aim of the present study was to investigate the inhibitory activities and kinetic details of a range of piperidine-derived inhibitors against α-rhamnosidase.…”