Facile synthesis of de-O-sulfated salacinols: Revision of the structure of neosalacinol, a potent α-glucosidase inhibitor

Quantitative determination of potent α-glucosidase inhibitors, salacinol and kotalanol, in Salacia species using liquid chromatography–mass spectrometry

“…Among the several samples tested in the present study, the roots' extract of S. reticulata gave the best score with respect to the contents of 1 and 2. Recently, their desulfonated analogs, neosalacinol [6,10,11] and neokotalanol [6,8,12] have also been reported as another sulfoniums responsible for the activity. Attempts to develop the quantitative analyses of these highly polar constituents for more precise evaluation of Salacia species are in progress.…”

“…1. Because of their intriguing structure and high ␣-glucosidase inhibitory activities, intensive structure-activity relationship (SAR) studies have also been reported [1,[7][8][9][10].…”

Practical Route to Neokotalanol and Its Natural Analogues: Sulfonium Sugars with Antidiabetic Activities

“…[1c] Tosylation of 24 was conducted in as tandard procedure to give the tosylate 25 in 72 %y ield, and it was subsequently treated with BnBr in the presence of sodium hydride (NaH) in DMF to give the desired benzyl ether 26 in 90 %yield. Coupling reaction between 12 and 13 as the key step for the total synthesis of neosalaprinol (5). [15] Tosylation of 30 provided the corresponding tosylate 31 in good yield and was then treated with KSAc in DMF to give the thioester 32 in 84 %yield.…”

An updated review on the phytochemistry, pharmacology, and clinical trials of Salacia oblonga

“…[7] S. oblonga hot water extract of root contains 1.4% of mangiferin (MA),[6] which was identified and quantified by high-performance liquid chromatography method. Apart from these unique constituents, the extract of S. oblonga has also been reported to contain neokotalanol,[18] ponkoranol,[19] neosalacinol, neoponkoranol,[18] 26-hydroxy-1,3-friedelanedione, 3 β,22α-dihydroxyolean-12-en-29-oic acid,[20] (-)-4-O-methylepigallocatechin,[21] salasol A,[22] salasol B, salasones A, salasones B, salasones C, salasones D, salasones E, salaquinone A, salaquinone B,[2223] and 25,26-oxidofriedelane-1,3-dione. [24] All the chemical components of S. oblonga with their chemical structures are given in Figure 1.…”