Abstract
Chromatographic separation of the 50% aqueous EtOH extract of the leaves of the African medicinal tree Baphia nitida resulted in isolation of 10 iminosugars. The plant contained 2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine (DMDP) as a major alkaloid. The structure of a new alkaloid was also elucidated by spectroscopic methods as the 1-O-beta-D-fructofuranoside of DMDP, and this plant produced 3-O-beta-D-glucopyranosyl-DMDP as well. DMDP is a potent inhibitor of beta-glucosidase and beta-galactosidase, whereas the other two derivatives lowered inhibition toward both of these enzymes and improved inhibitory activities toward rice alpha-glucosidase and rat intestinal maltase.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkaloids / chemistry*
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Alkaloids / isolation & purification
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Alkaloids / pharmacology
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Animals
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Candida / enzymology
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Carbohydrate Conformation
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Cattle
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Dose-Response Relationship, Drug
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Enzyme Activation / drug effects
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Enzyme Inhibitors / chemistry*
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Enzyme Inhibitors / isolation & purification
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Enzyme Inhibitors / pharmacology
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Fabaceae / chemistry*
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Glycoside Hydrolase Inhibitors
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Imino Furanoses / chemistry
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Imino Furanoses / isolation & purification
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Imino Furanoses / pharmacology
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Imino Sugars / chemistry*
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Imino Sugars / isolation & purification
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Imino Sugars / pharmacology
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Intestines / enzymology
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Liver / enzymology
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Mannitol / analogs & derivatives*
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Mannitol / chemistry
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Mannitol / isolation & purification
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Mannitol / pharmacology
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Oryza / enzymology
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Plant Extracts / chemistry*
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Plant Extracts / isolation & purification
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Plant Extracts / pharmacology
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Plant Leaves / chemistry
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Rats
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Stereoisomerism
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Sucrase / antagonists & inhibitors
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Swine
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beta-Galactosidase / antagonists & inhibitors
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beta-Glucosidase / antagonists & inhibitors
Substances
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1-O-beta-D-fructofuranoside-2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine
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3-O-beta-D-glucopyranosyl-2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine
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Alkaloids
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Enzyme Inhibitors
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Glycoside Hydrolase Inhibitors
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Imino Furanoses
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Imino Sugars
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Plant Extracts
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Mannitol
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2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine
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beta-Glucosidase
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beta-Galactosidase
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Sucrase