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Glycobiology. 2010 May;20(5):500-6. doi: 10.1093/glycob/cwp202. Epub 2010 Jan 5.

The novel proapoptotic activity of nonnatural enantiomer of Lentiginosine.

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Department of Neuroscience, University of Rome Tor Vergata Via Montpellier 1 Rome 00133 and IRCCS S. Lucia, Via Ardeatina 300 00100 Rome, Italy.


D-(-)-Lentiginosine [(-)-4], the nonnatural enantiomer of the iminosugar indolizidine alkaloid L-(+)-lentiginosine, acts as apoptosis inducer on tumor cells of different origin, in contrast to its natural enantiomer. Although D-(-)-4 exhibited a proapoptotic activity towards tumor cells at level lower than the chemotherapeutic agent, SN38, it was less proapoptotic towards normal cells and less cytotoxic. Apoptosis induced by D-(-)-4 was caspase-dependent, as shown by the increased expression and activity of caspase-3 and -8 in treated cells, and by inhibition following treatment with the pan caspase inhibitor, ZVAD-FMK. This study highlighted how a natural iminosugar alkaloid and its synthetic enantiomer, which were simply known for their inhibition against a fungal glucoamylase, could behave in a complete different way when tested towards cell growth and death of cells of different origin.

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