title: Biological evaluation of de-O-sulfonated analogs of salacinol, the role of sulfate anion in the side chain on the alpha-glucosidase inhibitory activity.
abstract: De-O-sulfonated analogs (10a, Y(-)=CH(3)OSO(3) and 10b, Y(-)=Cl) of salacinol, a naturally occurring glycosidase inhibitor, and its diastereomer (12a, Y(-)=CH(3)OSO(3)) with L-thiosugar moiety (1,4-dideoxy-1,4-epithio-L-arabinitol) were prepared. Their inhibitory activities against intestinal maltase and sucrase were examined and compared with those of the parent alpha-glycosidase inhibitor, salacinol (1a). Compounds 10a and 10b showed a potent inhibitory activity equal to that of 1a against both enzymes, although 12a was a weak inhibitor against sucrase and maltase. These results indicated that the O-sulfonate anion moiety of 1a is not essential for the inhibitory activity.
authors.affiliation: School of Pharmaceutical Sciences, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan.
authors.forename: Genzoh
authors.initials: G
authors.lastname: Tanabe
authors.forename: Kazuya
authors.initials: K
authors.lastname: Yoshikai
authors.forename: Takanori
authors.initials: T
authors.lastname: Hatanaka
authors.forename: Mizuho
authors.initials: M
authors.lastname: Yamamoto
authors.forename: Ying
authors.initials: Y
authors.lastname: Shao
authors.forename: Toshie
authors.initials: T
authors.lastname: Minematsu
authors.forename: Osamu
authors.initials: O
authors.lastname: Muraoka
authors.forename: Tao
authors.initials: T
authors.lastname: Wang
authors.forename: Hisashi
authors.initials: H
authors.lastname: Matsuda
authors.forename: Masayuki
authors.initials: M
authors.lastname: Yoshikawa
mesh_terms: D000818:Animals; D000838:Anions / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D065089:Glycoside Hydrolase Inhibitors; D051381:Rats; D013329:Structure-Activity Relationship; D013402:Sugar Alcohols / Q000737:chemistry*; D013431:Sulfates / Q000737:chemistry*
chemical_list: D000838:Anions; D004791:Enzyme Inhibitors; D065089:Glycoside Hydrolase Inhibitors; D013402:Sugar Alcohols; D013431:Sulfates; C427963:salacinol