Potent glucosidase inhibitors: de-O-sulfonated ponkoranol and its stereoisomer.
Ponkoranol, a glucosidase inhibitor isolated from the plant Salacia reticulata, comprises a sulfonium ion with an internal sulfate counterion. An efficient synthetic route to de-O-sulfonated ponkoranol and its 5'-stereoisomer is reported, and it is shown that these compounds are potent glucosidase inhibitors that inhibit a key intestinal human glucosidase, the N-terminal catalytic domain of maltase glucoamylase, with K(i) values of 43 +/- 3 and 15 +/- 1 nM, respectively.
Eskandari
Razieh
R
Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, Canada V5A 1S6.
Kuntz
Douglas A
DA
Rose
David R
DR
Pinto
B Mario
BM
D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D065089:Glycoside Hydrolase Inhibitors; D006801:Humans; D008968:Molecular Conformation; D013237:Stereoisomerism; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000520:alpha-Glucosidases / Q000378:metabolism
D004791:Enzyme Inhibitors; D065089:Glycoside Hydrolase Inhibitors; D013876:Thiophenes; C550268:ponkoranol; D000520:alpha-Glucosidases