title: Role of the side chain stereochemistry in the α-glucosidase inhibitory activity of kotalanol, a potent natural α-glucosidase inhibitor.
abstract: Synthesis and evaluation of four diastereomers (9a, 9b, 9c and 9d) of kotalanol, a potent α-glucosidase inhibitor isolated from an Ayurvedic medicinal plant Salacia species, are described. Stereo-inversion at C-3' and C-4' of kotalanol (2) caused significant decrease of the inhibitory activities against maltase and sucrase, whereas inhibitory activity against isomaltase sustained, thus resulted in exerting selectivity against isomaltase.
authors.affiliation: School of Pharmacy, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan.
authors.forename: Weijia
authors.initials: W
authors.lastname: Xie
authors.forename: Genzoh
authors.initials: G
authors.lastname: Tanabe
authors.forename: Kanjyun
authors.initials: K
authors.lastname: Matsuoka
authors.forename: Mumen F A
authors.initials: MF
authors.lastname: Amer
authors.forename: Toshie
authors.initials: T
authors.lastname: Minematsu
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Wu
authors.forename: Masayuki
authors.initials: M
authors.lastname: Yoshikawa
authors.forename: Osamu
authors.initials: O
authors.lastname: Muraoka
mesh_terms: D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000494:pharmacology*; D065089:Glycoside Hydrolase Inhibitors; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry* / Q000494:pharmacology*; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013431:Sulfates / Q000737:chemistry* / Q000494:pharmacology*; D000520:alpha-Glucosidases / Q000737:chemistry* / Q000378:metabolism
chemical_list: D004791:Enzyme Inhibitors; D065089:Glycoside Hydrolase Inhibitors; C114502:Kotalanol; D009005:Monosaccharides; D010936:Plant Extracts; D013431:Sulfates; D000520:alpha-Glucosidases