Facile synthesis of de-O-sulfated salacinols: revision of the structure of neosalacinol, a potent alpha-glucosidase inhibitor.
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.
Tanabe
Genzoh
G
School of Pharmacy, Kinki University, Higashi-osaka, Osaka, Japan.
Xie
Weijia
W
Ogawa
Ai
A
Cao
Changnian
C
Minematsu
Toshie
T
Yoshikawa
Masayuki
M
Muraoka
Osamu
O
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
D065089:Glycoside Hydrolase Inhibitors; D010936:Plant Extracts; D013402:Sugar Alcohols; D013431:Sulfates; C427963:salacinol; D000520:alpha-Glucosidases