Title:Recent Syntheses and Biological Activity of Lentiginosine and its Analogues
VOLUME: 14 ISSUE: 10
Author(s):Franca M. Cordero, Donatella Giomi and Alberto Brandi
Affiliation:Dipartimento di Chimica ‘Ugo Schiff’, Università di Firenze, Via della Lastruccia 3-13 I-50019 Sesto Fiorentino (FI), Italy.
Keywords:Alkaloids, apoptosis, azaheterocycles, glycosidase inhibitors, hydroxyindolizidines, iminosugars, organic syntheses.
Abstract:(+)-Lentiginosine, a natural trans-1,2-dihydroxyindolizidine belonging to the class of iminosugars, is a potent
inhibitor of amyloglucosidase, and a good inhibitor of Hsp90. The non-natural enantiomer, (–)-lentiginosine, induces
apoptosis on tumor cells of different origin and is poorly cytotoxic towards non-transformed cells. The significant biological
activity of these compounds has resulted in the development of many synthetic approaches for their preparation. This
review is an update of a previous survey and summarizes the most recent achievements on biological studies as well as total
syntheses of lentiginosine and trans-1,2-dihydroxyindolizidine analogues.
