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α-Glucosidase-inhibitory iminosugars from the leaves of Suregada glomerulata.
- Source :
-
Bioorganic & medicinal chemistry [Bioorg Med Chem] 2013 Nov 01; Vol. 21 (21), pp. 6796-803. Date of Electronic Publication: 2013 Aug 06. - Publication Year :
- 2013
-
Abstract
- A water extract of the leaves of Suregada glomerulata (Euphorbiaceae) was found to inhibit rat small intestinal α-glucosidase. An examination of the extract afforded 20 iminosugars including one pyrrolidine and 19 piperidines. The structures of the 10 new compounds (11-20) were determined by NMR, and MS spectroscopic data analyses, and chemical correlations. The novelty of the identified compounds mainly stems from the loss of a hydroxy at C-4 and the presence of an 8-hydroxyoctyl side chain. Nine N-alkyl derivatives including N-methyl (1a, 8a, and 13a), N-butyl (1b, 2b, and 9b) and N,N-dimethyl (1c, 2c, and 9c) were synthesized. The compounds were tested for rat small intestinal α-glucosidase inhibitory activity. In total, 15 compounds, including compounds 11, 12, 15, and 19 and the three derivatives 8a, 9b, and 13a, showed inhibitory activity with IC50 values less than 40μM. In vivo results showed that total alkaloids of S. glomerulata (10mg/kg) and four major iminosugars 1, 2, 3, and 9 (10mg/kg) can lower the postprandial blood glucose level after sucrose and starch load in healthy male ICR mice.<br /> (Copyright © 2013 Elsevier Ltd. All rights reserved.)
- Subjects :
- Animals
Blood Glucose analysis
Enzyme Inhibitors metabolism
Enzyme Inhibitors therapeutic use
Hyperglycemia drug therapy
Hypoglycemic Agents metabolism
Hypoglycemic Agents therapeutic use
Imino Sugars isolation & purification
Imino Sugars metabolism
Intestine, Small enzymology
Magnetic Resonance Spectroscopy
Male
Mice
Mice, Inbred ICR
Molecular Conformation
Plant Leaves chemistry
Plant Leaves metabolism
Protein Binding
Rats
Suregada metabolism
alpha-Glucosidases metabolism
Enzyme Inhibitors chemistry
Glycoside Hydrolase Inhibitors
Hypoglycemic Agents chemistry
Imino Sugars chemistry
Suregada chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1464-3391
- Volume :
- 21
- Issue :
- 21
- Database :
- MEDLINE
- Journal :
- Bioorganic & medicinal chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 23993676
- Full Text :
- https://doi.org/10.1016/j.bmc.2013.07.048