Iminosugars from Baphia nitida Lodd.
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.
Kato
Atsushi
A
Department of Hospital Pharmacy, University of Toyama, Toyama 930-0194, Japan. kato@med.u-toyama.ac.jp
Kato
Noriko
N
Miyauchi
Saori
S
Minoshima
Yuka
Y
Adachi
Isao
I
Ikeda
Kyoko
K
Asano
Naoki
N
Watson
Alison A
AA
Nash
Robert J
RJ
D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D002175:Candida / Q000201:enzymology; D002236:Carbohydrate Conformation; D002417:Cattle; D004305:Dose-Response Relationship, Drug; D004789:Enzyme Activation / Q000187:drug effects; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D007887:Fabaceae / Q000737:chemistry*; D065089:Glycoside Hydrolase Inhibitors; D050113:Imino Furanoses / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D050111:Imino Sugars / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D007422:Intestines / Q000201:enzymology; D008099:Liver / Q000201:enzymology; D008353:Mannitol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D012275:Oryza / Q000201:enzymology; D010936:Plant Extracts / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D018515:Plant Leaves / Q000737:chemistry; D051381:Rats; D013237:Stereoisomerism; D013393:Sucrase / Q000037:antagonists & inhibitors; D013552:Swine; D001616:beta-Galactosidase / Q000037:antagonists & inhibitors; D001617:beta-Glucosidase / Q000037:antagonists & inhibitors
C530582:1-O-beta-D-fructofuranoside-2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine; C530583:3-O-beta-D-glucopyranosyl-2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine; D000470:Alkaloids; D004791:Enzyme Inhibitors; D065089:Glycoside Hydrolase Inhibitors; D050113:Imino Furanoses; D050111:Imino Sugars; D010936:Plant Extracts; D008353:Mannitol; C043121:2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine; D001617:beta-Glucosidase; D001616:beta-Galactosidase; D013393:Sucrase