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Synthesis of C-Analogues of β-Glucogallin and Aldose Reductase Inhibition Studies
Date Issued
29-12-2017
Author(s)
Reddy, Mannem Rajeswara
Indian Institute of Technology, Madras
Shruthi, Karnam
Reddy, Geereddy Bhanuprakash
Abstract
β-Glucogallin 1 (BGG), a major component isolated from the Indian gooseberry (Emblica officinalis) medicinal plant, is a potent and selective inhibitor of aldose reductase (AKR1B1). Structurally, BGG is a glucosyl-1-ester, wherein gallic acid is linked to the β-d-glucose ring through an ester functionality. Susceptibility of the easily hydrolysable ester functional group in aqueous solution has been a cause of concern. Isosteric replacement of glucosyl-O- with –NH– has offered the more stable and potent analogue 2; however, the C-analogue 3, wherein a –CH2– unit replaces the glucosyl-O, remains unexplored. Synthesis of C-analogues 3 and 4 and their aldose reductase inhibition (ARI) constitutes the work presented herein.
Volume
2017