title: Isolation, structure identification and SAR studies on thiosugar sulfonium salts, neosalaprinol and neoponkoranol, as potent α-glucosidase inhibitors.
abstract: Two hitherto missing members of sulfonium salts family in Salacia genus plants as a new class of α-glucosidase inhibitors, neoponkoranol (7) and neosalaprinol (8), were isolated from the water extracts, and their structures were unambiguously identified. For further SAR studies on this series of sulfonium salts, several epimers of 7 and 8 were synthesized, and their inhibitory activities against rat small intestinal α-glucosidases were evaluated. Among them, 3'-epimer of 7 was found most potent in this class of molecules, and revealed as potent as currently used antidiabetics, voglibose and acarbose.
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: Junji
authors.initials: J
authors.lastname: Akaki
authors.forename: Toshio
authors.initials: T
authors.lastname: Morikawa
authors.forename: Kiyofumi
authors.initials: K
authors.lastname: Ninomiya
authors.forename: Toshie
authors.initials: T
authors.lastname: Minematsu
authors.forename: Masayuki
authors.initials: M
authors.lastname: Yoshikawa
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Wu
authors.forename: Osamu
authors.initials: O
authors.lastname: Muraoka
mesh_terms: D000818:Animals; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D065089:Glycoside Hydrolase Inhibitors; D007004:Hypoglycemic Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D051381:Rats; D049918:Salacia / Q000737:chemistry; D013329:Structure-Activity Relationship; D013402:Sugar Alcohols / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D013876:Thiophenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D054330:Thiosugars / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D000520:alpha-Glucosidases / Q000378:metabolism
chemical_list: C559081:1,4-dideoxy-1,4-((2,3,4,5,6-pentahydroxyhexyl)episulfoniumylidene)arabinitol; C559082:1,4-dideoxy-1,4-((2,3-dihydroxypropyl)episulfoniumylidene)arabinitol; D004791:Enzyme Inhibitors; D065089:Glycoside Hydrolase Inhibitors; D007004:Hypoglycemic Agents; D013402:Sugar Alcohols; D013876:Thiophenes; D054330:Thiosugars; D000520:alpha-Glucosidases