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: Genzoh Tanabe, Weijia Xie, Ai Ogawa, Changnian Cao, Toshie Minematsu, Masayuki Yoshikawa, Osamu Muraoka
• Journal: Bioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 19 Issue 8 Pg. 2195-8 (Apr 15 2009) ISSN: 1464-3405 [Electronic] England
• PMID: 19307117 (Publication Type: Comparative Study, Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Glycoside Hydrolase Inhibitors
• Plant Extracts
• Sugar Alcohols
• Sulfates
• salacinol
• alpha-Glucosidases

Topics

• Glycoside Hydrolase Inhibitors
• Medicine, Ayurvedic
• Plant Extracts (chemical synthesis, isolation & purification, pharmacology)
• Plant Roots (chemistry)
• Plant Stems (chemistry)
• Salacia
• Sugar Alcohols (chemical synthesis, isolation & purification, pharmacology)
• Sulfates (chemical synthesis, isolation & purification, pharmacology)
• alpha-Glucosidases (metabolism)