ABSTRACT
AIM: To investigate more efficient synthetic method of the nitrogen analogue 4 of salacinol (1) for searching new antidiabetic agents. METHODS: The synthesis of the key intermediate 2, 4-O-isopropylidene-L-erythritol 1,3-cyclic sulfate (2a) was accomplished by modification of reports from D-glucose via seven steps in much more less expensive. Using this method, an efficient synthesis of 4 was carried out. The glycosidase inhibitory activity of 4 was tested for the intestinal alpha-glucosidase in vitro and compared with that of salacinol. RESULTS: A nitrogen analogue 4 of salacinol (1) was synthesized by the coupling reaction between the cyclic sulfate 2a and an azasugar 3b. CONCLUSION: Substitution of the sulfur atom in 1 with a nitrogen reduced the activity considerably.
Subject(s)
Glycoside Hydrolase Inhibitors , Nitrogen Compounds/chemical synthesis , Sugar Alcohols/chemical synthesis , Sulfates/chemical synthesis , Animals , Enzyme Inhibitors/chemical synthesis , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/pharmacology , Intestinal Mucosa/drug effects , Intestinal Mucosa/enzymology , Molecular Structure , Nitrogen Compounds/pharmacology , Rats , Structure-Activity Relationship , Sugar Alcohols/chemistry , Sugar Alcohols/pharmacology , Sulfates/chemistry , Sulfates/pharmacology , alpha-Glucosidases/metabolismABSTRACT
<p><b>OBJECTIVE</b>To study the chemical composition of Opuntia dillenii.</p><p><b>METHOD</b>Many kinds of chromatography methods were used in the isolation procedure, while the structures of isolated compounds were determined on the aids of NMR and MS spectral analysis.</p><p><b>RESULT</b>A new compound, together with five known compounds, was isolated form the 80% ethanolic extract of its stems.</p><p><b>CONCLUSION</b>The new compound was characterized as opuntioside. Four compounds were obtained for the first from the genus Opuntia, and they were daucosterol, p-hydroxybenzoicacid, L-(-)-malic acid, (E)-ferulic acid. Opuntiol was also separated for the first from the plant.</p>
Subject(s)
Coumaric Acids , Chemistry , Molecular Structure , Monosaccharides , Chemistry , Opuntia , Chemistry , Plant Stems , Chemistry , Plants, Medicinal , Chemistry , Sitosterols , ChemistryABSTRACT
<p><b>AIM</b>To study the chemical composition of Opuntia dillenii Haw.</p><p><b>METHODS</b>Many kinds of chromatography methods were used to separate the chemical constituents. Their structures were determined by NMR and MS spectral analysis.</p><p><b>RESULTS</b>A new compound, together with five known compounds, were isolated from the 80% ethanolic extract of the stems.</p><p><b>CONCLUSION</b>The new compound was identified as 4-ethoxyl-6-hydroxymethyl-alpha-pyrone. Compounds 1, 3, 4 and 5 were obtained for the first time from the genus of Opuntia, and they were: 3-O-methyl isorhamnein, 1-heptanecanol, vanillic acid, isorhamnetin-3-O-beta-D-rutinoside. Ruin was isolated from this plant for the first time.</p>
