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.
Publication types
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Research Support, Non-U.S. Gov't
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Review
MeSH terms
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Alkaloids / chemical synthesis*
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Alkaloids / chemistry
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Alkaloids / pharmacology*
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Antineoplastic Agents / chemical synthesis
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / pharmacology*
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Cell Proliferation / drug effects
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Drug Screening Assays, Antitumor
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Enzyme Inhibitors / chemical synthesis*
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Enzyme Inhibitors / chemistry
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Enzyme Inhibitors / pharmacology*
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Glucan 1,4-alpha-Glucosidase / antagonists & inhibitors*
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Glucan 1,4-alpha-Glucosidase / metabolism
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HSP90 Heat-Shock Proteins / antagonists & inhibitors
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Humans
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Molecular Conformation
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Structure-Activity Relationship
Substances
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Alkaloids
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Antineoplastic Agents
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Enzyme Inhibitors
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HSP90 Heat-Shock Proteins
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lentiginosine
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Glucan 1,4-alpha-Glucosidase