title: Facile synthesis of de-O-sulfated salacinols: revision of the structure of neosalacinol, a potent alpha-glucosidase inhibitor.
abstract: Facile synthesis of de-O-sulfated salacinols (3) was developed by employing the coupling reaction of an epoxide, 1,2-anhydro-3,4-di-O-benzyl-D-erythritol (9) with 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol (10) as the key reaction. The reported structure of a potent alpha-glucosidase inhibitor named neosalacinol (8), isolated recently from Ayurvedic medicine Salacia oblonga, was proved incorrect, and revised to be de-O-sulfated salacinol formate (3c) by comparison of the spectroscopic properties with those of the authentic specimen synthesized. Discrepancies and confusion in the literature concerning the NMR spectroscopic properties of salacinol (1) have also been clarified.
authors.affiliation: School of Pharmacy, Kinki University, Higashi-osaka, Osaka, Japan.
authors.forename: Genzoh
authors.initials: G
authors.lastname: Tanabe
authors.forename: Weijia
authors.initials: W
authors.lastname: Xie
authors.forename: Ai
authors.initials: A
authors.lastname: Ogawa
authors.forename: Changnian
authors.initials: C
authors.lastname: Cao
authors.forename: Toshie
authors.initials: T
authors.lastname: Minematsu
authors.forename: Masayuki
authors.initials: M
authors.lastname: Yoshikawa
authors.forename: Osamu
authors.initials: O
authors.lastname: Muraoka
mesh_terms: D065089:Glycoside Hydrolase Inhibitors; D008515:Medicine, Ayurvedic; D010936:Plant Extracts / Q000138:chemical synthesis / Q000302:isolation & purification / Q000494:pharmacology; D018517:Plant Roots / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry; D049918:Salacia; D013402:Sugar Alcohols / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D013431:Sulfates / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D000520:alpha-Glucosidases / Q000378:metabolism
chemical_list: D065089:Glycoside Hydrolase Inhibitors; D010936:Plant Extracts; D013402:Sugar Alcohols; D013431:Sulfates; C427963:salacinol; D000520:alpha-Glucosidases